MiMeDB: Showing metabocard for Asperiamide B (MMDBc0016028)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:44:41 UTC

Update Date

2022-08-31 06:40:16 UTC

Metabolite ID

MMDBc0016028

Metabolite Identification

Common Name

Asperiamide B

Description

Asperiamide B belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported. Based on a literature review very few articles have been published on Asperiamide B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152108442D          

 68 68  0  0  1  0            999 V2000
  -15.0354    3.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0377   12.3443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1056   11.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6113    3.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4274   11.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8653    3.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4952   10.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1872    3.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8171    9.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4412    3.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
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 68 42  1  0  0  0  0
M  END


  Mrv1652305152108442D          

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 68 42  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0016028

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCC)=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)C(O)=N[C@@]([H])(COC1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)[C@]([H])(O)CCCCCCCCCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C42H75NO9/c1-3-5-7-9-11-13-14-15-16-17-18-19-20-21-23-24-26-28-30-35(45)34(33-51-42-40(49)39(48)38(47)37(32-44)52-42)43-41(50)36(46)31-29-27-25-22-12-10-8-6-4-2/h8,10,12,22,25,27,29,31,34-40,42,44-49H,3-7,9,11,13-21,23-24,26,28,30,32-33H2,1-2H3,(H,43,50)/b10-8+,22-12+,27-25+,31-29+/t34-,35+,36+,37+,38+,39-,40+,42?/m0/s1

> <INCHI_KEY>
XYVQIIFHEOOJMH-NZBJCEFGSA-N

> <FORMULA>
C42H75NO9

> <MOLECULAR_WEIGHT>
738.06

> <EXACT_MASS>
737.544182999

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
127

> <JCHEM_AVERAGE_POLARIZABILITY>
92.082925772977

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3E,5E,7E,9E)-2-hydroxy-N-[(2S,3R)-3-hydroxy-1-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricosan-2-yl]trideca-3,5,7,9-tetraenimidic acid

> <ALOGPS_LOGP>
7.27

> <JCHEM_LOGP>
8.846430064333335

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.202338074080451

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.721538484008968

> <JCHEM_PKA_STRONGEST_BASIC>
1.6199571760359721

> <JCHEM_POLAR_SURFACE_AREA>
172.42999999999998

> <JCHEM_REFRACTIVITY>
212.75470000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
32

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3E,5E,7E,9E)-2-hydroxy-N-[(2S,3R)-3-hydroxy-1-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricosan-2-yl]trideca-3,5,7,9-tetraenimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0     -28.066   6.818   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.404  23.043   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -26.674   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.530  21.508   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -25.408   7.037   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.264  20.631   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -24.015   6.379   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.391  19.096   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -22.749   7.256   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.125  18.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -21.357   6.599   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.252  16.684   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -20.091   7.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -18.699   6.818   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -17.433   7.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -16.040   7.037   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -14.774   7.914   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -13.382   7.256   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.116   8.133   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -10.724   7.476   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.458   8.353   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.986  15.807   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.065   7.695   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.799   8.572   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.113  14.272   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.407   7.914   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.847  13.395   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.141   8.791   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.973  11.861   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.749   8.133   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.707  10.984   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.850   1.336   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.036   6.818   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.090   8.353   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.483   9.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.834   9.449   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.416   2.213   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.809   1.556   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.074   2.433   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.948   3.967   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.568   8.572   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.555   4.625   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0       1.176   9.230   0.000  0.00  0.00           N+0
HETATM   44  O   UNK     0      -2.242   1.994   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -1.609  10.545   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       5.226   8.791   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       1.935   0.021   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       4.467   1.775   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       4.214   4.844   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       2.695   7.037   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       1.429   6.160   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       0.289   3.748   0.000  0.00  0.00           O+0
HETATM   53  H   UNK     0       9.784  18.438   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.733  18.877   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       8.644  16.026   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.593  16.465   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       7.505  13.615   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.454  14.053   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       6.366  11.203   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.315  11.641   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.356   7.476   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.217   9.887   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.441  10.107   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.543   0.679   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.201   0.898   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.682   3.090   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0       4.340   3.310   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.821   5.502   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10   53                                                  
CONECT    9    7   11                                                       
CONECT   10    8   12   54                                                  
CONECT   11    9   13                                                       
CONECT   12   10   22   55                                                  
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   23                                                       
CONECT   22   12   25   56                                                  
CONECT   23   21   24                                                       
CONECT   24   23   26                                                       
CONECT   25   22   27   57                                                  
CONECT   26   24   28                                                       
CONECT   27   25   29   58                                                  
CONECT   28   26   30                                                       
CONECT   29   27   31   59                                                  
CONECT   30   28   35                                                       
CONECT   31   29   36   60                                                  
CONECT   32   37   44                                                       
CONECT   33   34   51                                                       
CONECT   34   33   35   43   61                                             
CONECT   35   30   34   45   62                                             
CONECT   36   31   41   46   63                                             
CONECT   37   32   38   52   64                                             
CONECT   38   37   39   47   65                                             
CONECT   39   38   40   48   66                                             
CONECT   40   39   42   49   67                                             
CONECT   41   36   43   50                                                  
CONECT   42   40   51   52   68                                             
CONECT   43   34   41                                                       
CONECT   44   32                                                            
CONECT   45   35                                                            
CONECT   46   36                                                            
CONECT   47   38                                                            
CONECT   48   39                                                            
CONECT   49   40                                                            
CONECT   50   41                                                            
CONECT   51   33   42                                                       
CONECT   52   37   42                                                       
CONECT   53    8                                                            
CONECT   54   10                                                            
CONECT   55   12                                                            
CONECT   56   22                                                            
CONECT   57   25                                                            
CONECT   58   27                                                            
CONECT   59   29                                                            
CONECT   60   31                                                            
CONECT   61   34                                                            
CONECT   62   35                                                            
CONECT   63   36                                                            
CONECT   64   37                                                            
CONECT   65   38                                                            
CONECT   66   39                                                            
CONECT   67   40                                                            
CONECT   68   42                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  136    0
END

Synonyms

Not Available

Molecular Formula

C₄₂H₇₅NO₉

Average Mass

738.06

Monoisotopic Mass

737.544182999

IUPAC Name

(2R,3E,5E,7E,9E)-2-hydroxy-N-[(2S,3R)-3-hydroxy-1-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricosan-2-yl]trideca-3,5,7,9-tetraenimidic acid

Traditional Name

(2R,3E,5E,7E,9E)-2-hydroxy-N-[(2S,3R)-3-hydroxy-1-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricosan-2-yl]trideca-3,5,7,9-tetraenimidic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCC)=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\[H])[C@@]([H])(O)C(O)=N[C@@]([H])(COC1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)[C@]([H])(O)CCCCCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C42H75NO9/c1-3-5-7-9-11-13-14-15-16-17-18-19-20-21-23-24-26-28-30-35(45)34(33-51-42-40(49)39(48)38(47)37(32-44)52-42)43-41(50)36(46)31-29-27-25-22-12-10-8-6-4-2/h8,10,12,22,25,27,29,31,34-40,42,44-49H,3-7,9,11,13-21,23-24,26,28,30,32-33H2,1-2H3,(H,43,50)/b10-8+,22-12+,27-25+,31-29+/t34-,35+,36+,37+,38+,39-,40+,42?/m0/s1

InChI Key

XYVQIIFHEOOJMH-NZBJCEFGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.G. S-,C-, or N-type) has been reported.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosphingolipids

Alternative Parents

Substituents

Glycosphingolipid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acyl
Monosaccharide
N-acyl-amine
Oxane
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	7.27	ALOGPS
logP	8.85	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	1.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	172.43 Å²	ChemAxon
Rotatable Bond Count	32	ChemAxon
Refractivity	212.75 m³·mol⁻¹	ChemAxon
Polarizability	92.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00048618

Chemspider ID

78441374

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587498

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Asperiamide B (MMDBc0016028)

MOL for #<Metabolite:0x00005645ca1a4260>

3D MOL for #<Metabolite:0x00005645ca1a4260>

3D SDF for #<Metabolite:0x00005645ca1a4260>

3D-SDF for #<Metabolite:0x00005645ca1a4260>

PDB for #<Metabolite:0x00005645ca1a4260>

3D PDB for #<Metabolite:0x00005645ca1a4260>

SMILES for #<Metabolite:0x00005645ca1a4260>

INCHI for #<Metabolite:0x00005645ca1a4260>

Structure for #<Metabolite:0x00005645ca1a4260>

3D Structure for #<Metabolite:0x00005645ca1a4260>