MiMeDB: Showing metabocard for Asperlide B (MMDBc0027531)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 17:14:50 UTC

Update Date

2022-08-31 06:52:39 UTC

Metabolite ID

MMDBc0027531

Metabolite Identification

Common Name

Asperlide B

Description

Asperlide B belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. Based on a literature review a significant number of articles have been published on Asperlide B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152119142D          

 32 35  0  0  1  0            999 V2000
   -0.3551    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6085   -2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2093   -1.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2955   -0.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4556   -1.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6281    0.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7882   -1.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8744   -0.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2070    0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2070    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7579   -0.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8744    1.5649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1674    2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5784   -0.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2730   -1.4211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9374    0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9204    1.1476    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  9  2  0  0  0  0
 14  9  1  0  0  0  0
 14 11  2  0  0  0  0
 14 13  1  0  0  0  0
 15  7  2  0  0  0  0
 15  8  1  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  2  0  0  0  0
 18 12  1  0  0  0  0
 19 15  1  0  0  0  0
 20 19  2  0  0  0  0
 21 20  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 23 18  1  0  0  0  0
 24 13  1  1  0  0  0
 24 19  1  0  0  0  0
 24 22  1  6  0  0  0
 25 20  1  0  0  0  0
 26 21  2  0  0  0  0
 27 22  2  0  0  0  0
 28 23  1  0  0  0  0
 29  3  1  0  0  0  0
 29 22  1  0  0  0  0
 30 17  1  0  0  0  0
 30 18  1  0  0  0  0
 31 21  1  0  0  0  0
 31 24  1  0  0  0  0
 32 18  1  0  0  0  0
M  END


  Mrv1652305152119142D          

 32 35  0  0  1  0            999 V2000
   -0.3551    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6085   -2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2093   -1.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2955   -0.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4556   -1.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6281    0.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7882   -1.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8744   -0.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2070    0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2070    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7579   -0.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8744    1.5649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1674    2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5784   -0.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2730   -1.4211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9374    0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9204    1.1476    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  9  2  0  0  0  0
 14  9  1  0  0  0  0
 14 11  2  0  0  0  0
 14 13  1  0  0  0  0
 15  7  2  0  0  0  0
 15  8  1  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  2  0  0  0  0
 18 12  1  0  0  0  0
 19 15  1  0  0  0  0
 20 19  2  0  0  0  0
 21 20  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 23 18  1  0  0  0  0
 24 13  1  1  0  0  0
 24 19  1  0  0  0  0
 24 22  1  6  0  0  0
 25 20  1  0  0  0  0
 26 21  2  0  0  0  0
 27 22  2  0  0  0  0
 28 23  1  0  0  0  0
 29  3  1  0  0  0  0
 29 22  1  0  0  0  0
 30 17  1  0  0  0  0
 30 18  1  0  0  0  0
 31 21  1  0  0  0  0
 31 24  1  0  0  0  0
 32 18  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0027531

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C1(CC2=C(O1)C=CC(C[C@]1(OC(=O)C(O)=C1C1=CC=CC=C1)C(=O)OC)=C2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O7/c1-23(2,28)18-12-16-11-14(9-10-17(16)30-18)13-24(22(27)29-3)19(20(25)21(26)31-24)15-7-5-4-6-8-15/h4-11,18,25,28H,12-13H2,1-3H3/t18?,24-/m1/s1

> <INCHI_KEY>
CTMIBXKMQNCFFO-VCUSLETLSA-N

> <FORMULA>
C24H24O7

> <MOLECULAR_WEIGHT>
424.449

> <EXACT_MASS>
424.152203113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.006988698577615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R)-4-hydroxy-2-{[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl}-5-oxo-3-phenyl-2,5-dihydrofuran-2-carboxylate

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.407816382333333

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.296809383658346

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.748863620128509

> <JCHEM_PKA_STRONGEST_BASIC>
-3.106376113520443

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
112.31539999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-4-hydroxy-2-{[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl}-5-oxo-3-phenylfuran-2-carboxylate

> <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      -0.663   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.877  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.469  -4.060   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.324  -2.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.485  -0.708   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.917  -2.866   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.239   0.197   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.671  -1.961   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.832  -0.429   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.586   0.476   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.586   2.016   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.122   2.492   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.748  -1.407   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.122  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.832   2.921   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.646   3.956   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      12.280  -1.568   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.877   2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.843  -2.653   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.217   1.246   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0       1.718   2.142   0.000  0.00  0.00           H+0
CONECT    1   23                                                            
CONECT    2   23                                                            
CONECT    3   29                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   15                                                       
CONECT    8    6   15                                                       
CONECT    9   10   14                                                       
CONECT   10    9   17                                                       
CONECT   11   14   16                                                       
CONECT   12   16   18                                                       
CONECT   13   14   24                                                       
CONECT   14    9   11   13                                                  
CONECT   15    7    8   19                                                  
CONECT   16   11   12   17                                                  
CONECT   17   10   16   30                                                  
CONECT   18   12   23   30   32                                             
CONECT   19   15   20   24                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   26   31                                                  
CONECT   22   24   27   29                                                  
CONECT   23    1    2   18   28                                             
CONECT   24   13   19   22   31                                             
CONECT   25   20                                                            
CONECT   26   21                                                            
CONECT   27   22                                                            
CONECT   28   23                                                            
CONECT   29    3   22                                                       
CONECT   30   17   18                                                       
CONECT   31   21   24                                                       
CONECT   32   18                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

Synonyms

Not Available

Molecular Formula

C₂₄H₂₄O₇

Average Mass

424.449

Monoisotopic Mass

424.152203113

IUPAC Name

methyl (2R)-4-hydroxy-2-{[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl}-5-oxo-3-phenyl-2,5-dihydrofuran-2-carboxylate

Traditional Name

methyl (2R)-4-hydroxy-2-{[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl}-5-oxo-3-phenylfuran-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H]C1(CC2=C(O1)C=CC(C[C@]1(OC(=O)C(O)=C1C1=CC=CC=C1)C(=O)OC)=C2)C(C)(C)O

InChI Identifier

InChI=1S/C24H24O7/c1-23(2,28)18-12-16-11-14(9-10-17(16)30-18)13-24(22(27)29-3)19(20(25)21(26)31-24)15-7-5-4-6-8-15/h4-11,18,25,28H,12-13H2,1-3H3/t18?,24-/m1/s1

InChI Key

CTMIBXKMQNCFFO-VCUSLETLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
2-furanone
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Ether
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	2.96	ALOGPS
logP	3.41	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.32 m³·mol⁻¹	ChemAxon
Polarizability	43.01 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

Chemspider ID

71048514

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

145992345

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 Asperlide B (MMDBc0027531)

MOL for #<Metabolite:0x00007f9206ecbd60>

3D MOL for #<Metabolite:0x00007f9206ecbd60>

3D SDF for #<Metabolite:0x00007f9206ecbd60>

3D-SDF for #<Metabolite:0x00007f9206ecbd60>

PDB for #<Metabolite:0x00007f9206ecbd60>

3D PDB for #<Metabolite:0x00007f9206ecbd60>

SMILES for #<Metabolite:0x00007f9206ecbd60>

INCHI for #<Metabolite:0x00007f9206ecbd60>

Structure for #<Metabolite:0x00007f9206ecbd60>

3D Structure for #<Metabolite:0x00007f9206ecbd60>