MiMeDB: Showing metabocard for AI-77-F (MMDBc0019221)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 09:19:00 UTC

Update Date

2022-08-31 06:45:00 UTC

Metabolite ID

MMDBc0019221

Metabolite Identification

Common Name

AI-77-F

Description

2-hydroxy-N-[1-(8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl)-3-methylbutyl]-2-(5-oxo-2,5-dihydrofuran-2-yl)ethanimidic acid belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. 2-hydroxy-N-[1-(8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl)-3-methylbutyl]-2-(5-oxo-2,5-dihydrofuran-2-yl)ethanimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251508522D          

 28 30  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4694   -2.9644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0215   -3.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8420   -3.4913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6090   -4.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8020   -4.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 17 28  1  0  0  0  0
M  END


  Mrv1533004251508522D          

 28 30  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4694   -2.9644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0215   -3.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8420   -3.4913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6090   -4.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8020   -4.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 17 28  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0019221

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)CC(NC(=O)C(O)C1OC(=O)C=C1)C1CC2=CC=CC(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO7/c1-10(2)8-12(21-19(25)18(24)14-6-7-16(23)27-14)15-9-11-4-3-5-13(22)17(11)20(26)28-15/h3-7,10,12,14-15,18,22,24H,8-9H2,1-2H3,(H,21,25)

> <INCHI_KEY>
MXZNZZJLGOWQFM-UHFFFAOYSA-N

> <FORMULA>
C20H23NO7

> <MOLECULAR_WEIGHT>
389.404

> <EXACT_MASS>
389.147452085

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.29476272053418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-N-[1-(8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl)-3-methylbutyl]-2-(5-oxo-2,5-dihydrofuran-2-yl)acetamide

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
2.734926967000001

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.647778804484851

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.854597229428782

> <JCHEM_PKA_STRONGEST_BASIC>
-4.059412837066243

> <JCHEM_POLAR_SURFACE_AREA>
122.16000000000001

> <JCHEM_REFRACTIVITY>
98.92609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-N-[1-(8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl)-3-methylbutyl]-2-(5-oxo-2H-furan-2-yl)acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.076  -5.534   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.107  -6.678   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.638  -6.517   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.337  -8.012   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.830  -7.692   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001 -13.090   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667 -10.780   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.001  -8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   11                                                       
CONECT   17    5   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   19   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   17                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

Synonyms

Value	Source
2-Hydroxy-N-[1-(8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl)-3-methylbutyl]-2-(5-oxo-2,5-dihydrofuran-2-yl)ethanimidate	Generator

Molecular Formula

C₂₀H₂₃NO₇

Average Mass

389.404

Monoisotopic Mass

389.147452085

IUPAC Name

2-hydroxy-N-[1-(8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl)-3-methylbutyl]-2-(5-oxo-2,5-dihydrofuran-2-yl)acetamide

Traditional Name

2-hydroxy-N-[1-(8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl)-3-methylbutyl]-2-(5-oxo-2H-furan-2-yl)acetamide

CAS Registry Number

Not Available

SMILES

CC(C)CC(NC(=O)C(O)C1OC(=O)C=C1)C1CC2=CC=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C20H23NO7/c1-10(2)8-12(21-19(25)18(24)14-6-7-16(23)27-14)15-9-11-4-3-5-13(22)17(11)20(26)28-15/h3-7,10,12,14-15,18,22,24H,8-9H2,1-2H3,(H,21,25)

InChI Key

MXZNZZJLGOWQFM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
2-furanone
Dicarboxylic acid or derivatives
Benzenoid
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Carboxamide group
Carboxylic acid ester
Lactone
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
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	0.6 g/L	ALOGPS
logP	1.51	ALOGPS
logP	2.73	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.16 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	98.93 m³·mol⁻¹	ChemAxon
Polarizability	39.29 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	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

Not Available

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
Bacteria	Firmicutes	1		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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12806480

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 AI-77-F (MMDBc0019221)

MOL for #<Metabolite:0x00005634c28de468>

3D MOL for #<Metabolite:0x00005634c28de468>

3D SDF for #<Metabolite:0x00005634c28de468>

3D-SDF for #<Metabolite:0x00005634c28de468>

PDB for #<Metabolite:0x00005634c28de468>

3D PDB for #<Metabolite:0x00005634c28de468>

SMILES for #<Metabolite:0x00005634c28de468>

INCHI for #<Metabolite:0x00005634c28de468>

Structure for #<Metabolite:0x00005634c28de468>

3D Structure for #<Metabolite:0x00005634c28de468>