MiMeDB: Showing metabocard for Aspulvinone E (MMDBc0002416)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 20:48:41 UTC

Update Date

2022-08-31 06:19:24 UTC

Metabolite ID

MMDBc0002416

Metabolite Identification

Common Name

Aspulvinone E

Description

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1533006081518322D          
 
 22 24  0  0  0  0            999 V2000
    7.9613  -11.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9613  -12.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6757  -12.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3902  -12.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3902  -11.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6757  -10.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2468  -12.6225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1125  -10.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9311  -10.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2071  -10.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5591   -9.7153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8826  -10.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0946   -9.8948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0120   -9.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0120   -9.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7195   -8.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7194   -7.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0050   -7.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975   -7.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975   -8.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0049   -6.6825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3894  -11.6585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 10 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 18 21  1  0  0  0  0
  9 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0002416

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=C(C(=O)O\C1=C/C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O5/c18-12-5-1-10(2-6-12)9-14-16(20)15(17(21)22-14)11-3-7-13(19)8-4-11/h1-9,18-20H/b14-9-

> <INCHI_KEY>
BNNVVTQUWNGKPH-ZROIWOOFSA-N

> <FORMULA>
C17H12O5

> <MOLECULAR_WEIGHT>
296.278

> <EXACT_MASS>
296.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
30.546671401816205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-4-hydroxy-3-(4-hydroxyphenyl)-5-[(4-hydroxyphenyl)methylidene]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
2.750070631

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.049963355135368

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.711012682024281

> <JCHEM_PKA_STRONGEST_BASIC>
-5.968920354112705

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
82.08480000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aspulvinone E

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUN-15         0                                  
HETATM    1  C   UNK     0      14.861 -21.252   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.861 -22.792   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.195 -23.562   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.528 -22.792   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.528 -21.252   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.195 -20.482   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.527 -23.562   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      18.877 -20.464   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.405 -20.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.920 -19.070   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      19.710 -18.135   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      18.447 -18.997   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      16.977 -18.470   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      22.422 -18.631   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.422 -17.091   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.743 -16.328   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.743 -14.788   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.409 -14.018   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.089 -14.781   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.089 -16.321   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      22.409 -12.474   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      21.260 -21.763   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1                                                       
CONECT    7    2                                                            
CONECT    8    5    9   12                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   18                                                            
CONECT   22    9                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

Synonyms

Value	Source
(5Z)-4-Hydroxy-3-(4-hydroxyphenyl)-5-[(4-hydroxyphenyl)methylene]-2(5H)-furanone	Kegg

Molecular Formula

C₁₇H₁₂O₅

Average Mass

296.278

Monoisotopic Mass

296.068473486

IUPAC Name

(5Z)-4-hydroxy-3-(4-hydroxyphenyl)-5-[(4-hydroxyphenyl)methylidene]-2,5-dihydrofuran-2-one

Traditional Name

aspulvinone E

CAS Registry Number

Not Available

SMILES

OC1=C(C(=O)O\C1=C/C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C17H12O5/c18-12-5-1-10(2-6-12)9-14-16(20)15(17(21)22-14)11-3-7-13(19)8-4-11/h1-9,18-20H/b14-9-

InChI Key

BNNVVTQUWNGKPH-ZROIWOOFSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as phenols. These are compounds containing a phenol moiety, which is a benzene bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenols

Direct Parent

Phenols

Alternative Parents

Substituents

Phenol
2-furanone
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enol ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Enol
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aspulvinone (CHEBI:17704 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.16	ALOGPS
logP	2.75	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	6.71	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.08 m³·mol⁻¹	ChemAxon
Polarizability	30.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0017367	3-(4-hydroxyphenyl)pyruvic acid	Aspulvinone E	Nonribosomal peptide synthetase apvA	Synthesis	RHEA	34755880
MMDBr0017368	3-(4-hydroxyphenyl)pyruvic acid	Aspulvinone E	Nonribosomal peptide synthetase apvA	Synthesis	RHEA	34755880

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	2	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	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

20117948

KEGG Compound ID

C02006

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54675753

PDB ID

Not Available

ChEBI ID

17704

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Aspulvinone E (MMDBc0002416)

MOL for #<Metabolite:0x00007fa4d80238a0>

3D MOL for #<Metabolite:0x00007fa4d80238a0>

3D SDF for #<Metabolite:0x00007fa4d80238a0>

3D-SDF for #<Metabolite:0x00007fa4d80238a0>

PDB for #<Metabolite:0x00007fa4d80238a0>

3D PDB for #<Metabolite:0x00007fa4d80238a0>

SMILES for #<Metabolite:0x00007fa4d80238a0>

INCHI for #<Metabolite:0x00007fa4d80238a0>

Structure for #<Metabolite:0x00007fa4d80238a0>

3D Structure for #<Metabolite:0x00007fa4d80238a0>