MiMeDB: Showing metabocard for 8'-Phosphoamicoumacin A (MMDBc0009905)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 02:16:42 UTC

Update Date

2022-08-31 06:30:55 UTC

Metabolite ID

MMDBc0009905

Metabolite Identification

Common Name

8'-Phosphoamicoumacin A

Description

8'-Phosphoamicoumacin A belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. Based on a literature review very few articles have been published on 8'-Phosphoamicoumacin A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152104162D          

 34 35  0  0  0  0            999 V2000
   -2.8579    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    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
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    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
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   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
   -3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    2.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 13  5  2  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 16  1  0  0  0  0
 21 11  1  0  0  0  0
 22 15  2  0  0  0  0
 23 12  1  4  0  0  0
 23 19  2  0  0  0  0
 24 13  1  0  0  0  0
 25 15  1  0  0  0  0
 26 17  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  2  0  0  0  0
 32 14  1  0  0  0  0
 32 20  1  0  0  0  0
 33 18  1  0  0  0  0
 34 29  1  0  0  0  0
 34 30  1  0  0  0  0
 34 31  2  0  0  0  0
 34 33  1  0  0  0  0
M  END


  Mrv1652305152104162D          

 34 35  0  0  0  0            999 V2000
   -2.8579    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    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
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    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
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   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
   -3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    2.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 13  5  2  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 16  1  0  0  0  0
 21 11  1  0  0  0  0
 22 15  2  0  0  0  0
 23 12  1  4  0  0  0
 23 19  2  0  0  0  0
 24 13  1  0  0  0  0
 25 15  1  0  0  0  0
 26 17  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  2  0  0  0  0
 32 14  1  0  0  0  0
 32 20  1  0  0  0  0
 33 18  1  0  0  0  0
 34 29  1  0  0  0  0
 34 30  1  0  0  0  0
 34 31  2  0  0  0  0
 34 33  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0009905

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)CC(N=C(O)C(OP(O)(O)=O)C(O)C(N)CC(O)=N)C1CC2=C(C(O)=CC=C2)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H30N3O10P/c1-9(2)6-12(14-7-10-4-3-5-13(24)16(10)20(28)32-14)23-19(27)18(33-34(29,30)31)17(26)11(21)8-15(22)25/h3-5,9,11-12,14,17-18,24,26H,6-8,21H2,1-2H3,(H2,22,25)(H,23,27)(H2,29,30,31)

> <INCHI_KEY>
HOJHDNFGPGIISV-UHFFFAOYSA-N

> <FORMULA>
C20H30N3O10P

> <MOLECULAR_WEIGHT>
503.445

> <EXACT_MASS>
503.166881176

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.49755114345453

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-3-hydroxy-N-[1-(8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl)-3-methylbutyl]-2-(phosphonooxy)hexanediimidic acid

> <ALOGPS_LOGP>
-0.11

> <JCHEM_LOGP>
-5.845632583646028

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
0.9122543945403327

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.114807028501283

> <JCHEM_PKA_STRONGEST_BASIC>
12.652930623894493

> <JCHEM_POLAR_SURFACE_AREA>
236.20999999999995

> <JCHEM_REFRACTIVITY>
128.49739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-amino-3-hydroxy-N-[1-(8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl)-3-methylbutyl]-2-(phosphonooxy)hexanediimidic 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      -5.335  15.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.337  10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.003  11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.337   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -12.003   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -1.334   6.930   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       2.667   9.240   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      -5.335  10.780   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0     -12.003   6.930   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.668   8.470   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -9.336   6.930   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -6.105   7.494   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.565   4.826   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.668   5.390   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -8.002   9.240   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   34  P   UNK     0      -5.335   6.160   0.000  0.00  0.00           P+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    4    5                                                       
CONECT    4    3   10                                                       
CONECT    5    3   13                                                       
CONECT    6    9   12                                                       
CONECT    7   10   14                                                       
CONECT    8   11   15                                                       
CONECT    9    1    2    6                                                  
CONECT   10    4    7   16                                                  
CONECT   11    8   17   21                                                  
CONECT   12    6   14   23                                                  
CONECT   13    5   16   24                                                  
CONECT   14    7   12   32                                                  
CONECT   15    8   22   25                                                  
CONECT   16   10   13   20                                                  
CONECT   17   11   18   26                                                  
CONECT   18   17   19   33                                                  
CONECT   19   18   23   27                                                  
CONECT   20   16   28   32                                                  
CONECT   21   11                                                            
CONECT   22   15                                                            
CONECT   23   12   19                                                       
CONECT   24   13                                                            
CONECT   25   15                                                            
CONECT   26   17                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29   34                                                            
CONECT   30   34                                                            
CONECT   31   34                                                            
CONECT   32   14   20                                                       
CONECT   33   18   34                                                       
CONECT   34   29   30   31   33                                             
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

Synonyms

Not Available

Molecular Formula

C₂₀H₃₀N₃O₁₀P

Average Mass

503.445

Monoisotopic Mass

503.166881176

IUPAC Name

4-amino-3-hydroxy-N-[1-(8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl)-3-methylbutyl]-2-(phosphonooxy)hexanediimidic acid

Traditional Name

4-amino-3-hydroxy-N-[1-(8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl)-3-methylbutyl]-2-(phosphonooxy)hexanediimidic acid

CAS Registry Number

Not Available

SMILES

CC(C)CC(N=C(O)C(OP(O)(O)=O)C(O)C(N)CC(O)=N)C1CC2=C(C(O)=CC=C2)C(=O)O1

InChI Identifier

InChI=1S/C20H30N3O10P/c1-9(2)6-12(14-7-10-4-3-5-13(24)16(10)20(28)32-14)23-19(27)18(33-34(29,30)31)17(26)11(21)8-15(22)25/h3-5,9,11-12,14,17-18,24,26H,6-8,21H2,1-2H3,(H2,22,25)(H,23,27)(H2,29,30,31)

InChI Key

HOJHDNFGPGIISV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Beta amino acids and derivatives

Alternative Parents

Substituents

Beta amino acid or derivatives
Benzopyran
Isochromane
2-benzopyran
Phosphoethanolamine
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monoalkyl phosphate
Fatty amide
Monosaccharide
N-acyl-amine
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Benzenoid
Vinylogous acid
Secondary carboxylic acid amide
Secondary alcohol
Primary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
1,2-aminoalcohol
Lactone
Organoheterocyclic compound
Oxacycle
Alcohol
Primary aliphatic amine
Carbonyl group
Primary amine
Organic oxygen compound
Organic oxide
Amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
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	0.17 g/L	ALOGPS
logP	-0.11	ALOGPS
logP	-5.8	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	-1.1	ChemAxon
pKa (Strongest Basic)	12.65	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	236.21 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	128.5 m³·mol⁻¹	ChemAxon
Polarizability	47.5 Å³	ChemAxon
Number of Rings	2	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

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

78444137

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24770476

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 8'-Phosphoamicoumacin A (MMDBc0009905)

MOL for #<Metabolite:0x00007feccc97f660>

3D MOL for #<Metabolite:0x00007feccc97f660>

3D SDF for #<Metabolite:0x00007feccc97f660>

3D-SDF for #<Metabolite:0x00007feccc97f660>

PDB for #<Metabolite:0x00007feccc97f660>

3D PDB for #<Metabolite:0x00007feccc97f660>

SMILES for #<Metabolite:0x00007feccc97f660>

INCHI for #<Metabolite:0x00007feccc97f660>

Structure for #<Metabolite:0x00007feccc97f660>

3D Structure for #<Metabolite:0x00007feccc97f660>