MiMeDB: Showing metabocard for Aspernolide A (MMDBc0009416)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:56:05 UTC

Update Date

2022-08-31 06:30:01 UTC

Metabolite ID

MMDBc0009416

Metabolite Identification

Common Name

Aspernolide A

Description

Aspernolide A belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Based on a literature review a small amount of articles have been published on Aspernolide A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152103562D          

 31 34  0  0  1  0            999 V2000
    2.9559    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256    2.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3296   -0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3491    1.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5092    0.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166    0.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1767   -0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5955    1.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9304    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9280    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9280    2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4790    0.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5978   -0.4473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5955    2.8024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8885    3.3570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995    0.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9940   -0.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585    1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  2  0  0  0  0
 11 10  1  0  0  0  0
 14  4  1  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15  5  2  0  0  0  0
 15  6  1  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  2  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 18 16  2  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 11  1  0  0  0  0
 24 13  1  6  0  0  0
 24 19  1  0  0  0  0
 24 22  1  1  0  0  0
 25 17  1  0  0  0  0
 26 20  1  0  0  0  0
 27 21  2  0  0  0  0
 28 22  2  0  0  0  0
 29  3  1  0  0  0  0
 29 22  1  0  0  0  0
 30 18  1  0  0  0  0
 30 23  1  0  0  0  0
 31 21  1  0  0  0  0
 31 24  1  0  0  0  0
M  END


  Mrv1652305152103562D          

 31 34  0  0  1  0            999 V2000
    2.9559    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256    2.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3296   -0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3491    1.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5092    0.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166    0.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1767   -0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5955    1.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9304    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9280    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9280    2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4790    0.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5978   -0.4473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5955    2.8024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8885    3.3570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995    0.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9940   -0.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585    1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  2  0  0  0  0
 11 10  1  0  0  0  0
 14  4  1  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15  5  2  0  0  0  0
 15  6  1  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  2  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 18 16  2  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 11  1  0  0  0  0
 24 13  1  6  0  0  0
 24 19  1  0  0  0  0
 24 22  1  1  0  0  0
 25 17  1  0  0  0  0
 26 20  1  0  0  0  0
 27 21  2  0  0  0  0
 28 22  2  0  0  0  0
 29  3  1  0  0  0  0
 29 22  1  0  0  0  0
 30 18  1  0  0  0  0
 30 23  1  0  0  0  0
 31 21  1  0  0  0  0
 31 24  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0009416

> <DATABASE_NAME>
MIME

> <SMILES>
COC(=O)[C@]1(CC2=CC3=C(OC(C)(C)CC3)C=C2)OC(=O)C(O)=C1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O7/c1-23(2)11-10-16-12-14(4-9-18(16)30-23)13-24(22(28)29-3)19(20(26)21(27)31-24)15-5-7-17(25)8-6-15/h4-9,12,25-26H,10-11,13H2,1-3H3/t24-/m1/s1

> <INCHI_KEY>
YCHNFUWRXHTAFK-XMMPIXPASA-N

> <FORMULA>
C24H24O7

> <MOLECULAR_WEIGHT>
424.449

> <EXACT_MASS>
424.152203113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.4262878269116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R)-2-[(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)methyl]-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
4.179154667666667

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.751981458500305

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.53489727860715

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3023026461774965

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
112.93479999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.13e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-2-[(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)methyl]-4-hydroxy-3-(4-hydroxyphenyl)-5-oxofuran-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       5.518   3.583   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.528   5.297   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.349  -1.750   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.118   2.507   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.551   0.349   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.364   1.602   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.796  -0.556   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.712   1.881   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.203   0.070   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.466   2.786   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.466   4.326   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001   4.802   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.627   0.903   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -10.449  -0.835   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -6.712   5.231   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -3.525   6.266   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -6.159   0.742   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -3.722  -0.343   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -3.096   3.556   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   23                                                            
CONECT    3   29                                                            
CONECT    4    9   14                                                       
CONECT    5    7   15                                                       
CONECT    6    8   15                                                       
CONECT    7    5   17                                                       
CONECT    8    6   17                                                       
CONECT    9    4   18                                                       
CONECT   10   11   16                                                       
CONECT   11   10   23                                                       
CONECT   12   14   16                                                       
CONECT   13   14   24                                                       
CONECT   14    4   12   13                                                  
CONECT   15    5    6   19                                                  
CONECT   16   10   12   18                                                  
CONECT   17    7    8   25                                                  
CONECT   18    9   16   30                                                  
CONECT   19   15   20   24                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   27   31                                                  
CONECT   22   24   28   29                                                  
CONECT   23    1    2   11   30                                             
CONECT   24   13   19   22   31                                             
CONECT   25   17                                                            
CONECT   26   20                                                            
CONECT   27   21                                                            
CONECT   28   22                                                            
CONECT   29    3   22                                                       
CONECT   30   18   23                                                       
CONECT   31   21   24                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

Synonyms

Not Available

Molecular Formula

C₂₄H₂₄O₇

Average Mass

424.449

Monoisotopic Mass

424.152203113

IUPAC Name

methyl (2R)-2-[(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)methyl]-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate

Traditional Name

methyl (2R)-2-[(2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl)methyl]-4-hydroxy-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(CC2=CC3=C(OC(C)(C)CC3)C=C2)OC(=O)C(O)=C1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C24H24O7/c1-23(2)11-10-16-12-14(4-9-18(16)30-23)13-24(22(28)29-3)19(20(26)21(27)31-24)15-5-7-17(25)8-6-15/h4-9,12,25-26H,10-11,13H2,1-3H3/t24-/m1/s1

InChI Key

YCHNFUWRXHTAFK-XMMPIXPASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Fatty acid ester
Monocyclic benzene moiety
2-furanone
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Dihydrofuran
Carboxylic acid ester
Lactone
Enol
Oxacycle
Carboxylic acid derivative
Ether
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	0.0071 g/L	ALOGPS
logP	4.09	ALOGPS
logP	4.18	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.53	ChemAxon
pKa (Strongest Basic)	-3.3	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	5	ChemAxon
Refractivity	112.93 m³·mol⁻¹	ChemAxon
Polarizability	43.43 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	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

Not Available

Chemspider ID

27023983

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25265784

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 Aspernolide A (MMDBc0009416)

MOL for #<Metabolite:0x00007f922c099f28>

3D MOL for #<Metabolite:0x00007f922c099f28>

3D SDF for #<Metabolite:0x00007f922c099f28>

3D-SDF for #<Metabolite:0x00007f922c099f28>

PDB for #<Metabolite:0x00007f922c099f28>

3D PDB for #<Metabolite:0x00007f922c099f28>

SMILES for #<Metabolite:0x00007f922c099f28>

INCHI for #<Metabolite:0x00007f922c099f28>

Structure for #<Metabolite:0x00007f922c099f28>

3D Structure for #<Metabolite:0x00007f922c099f28>