NP-MRD: Showing NP-Card for (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate (NP0336532)

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Record Information

Version

2.0

Created at

2024-09-11 06:44:16 UTC

Updated at

2024-09-11 06:44:16 UTC

NP-MRD ID

NP0336532

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate

Description

It was first documented in 2018 (PMID: 30149503). Based on a literature review very few articles have been published on (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate.

Structure

MOL SDF PDB SMILES InChI

164
  Mrv2104 05262309162D          

 19 19  0  0  0  0            999 V2000
   -2.4034    0.4108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -0.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -0.8267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    0.4108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9744    1.2358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2600    1.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889    1.6483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600   -0.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -1.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545   -1.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -1.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5979   -0.8267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -2.0642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    0.5122    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    1.1344    0.0000 H   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
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 18  1  6  0  0  0
  5  6  1  0  0  0  0
  5  9  1  6  0  0  0
  5 19  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0336532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(O)C=CC=C(C(=O)CCC(O)=O)[C@@]1([H])C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C11H12O6/c12-7(4-5-9(14)15)6-2-1-3-8(13)10(6)11(16)17/h1-3,8,10,13H,4-5H2,(H,14,15)(H,16,17)/t8-,10-/s2

> <INCHI_KEY>
QJYRAJSESKVEAE-CSEYRULYNA-N

> <FORMULA>
C11H12O6

> <MOLECULAR_WEIGHT>
240.211

> <EXACT_MASS>
240.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.355227336156318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,6R)-2-(3-carboxypropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid

> <JCHEM_LOGP>
-0.3190482766666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.340411281613184

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.625212506826645

> <JCHEM_PKA_STRONGEST_BASIC>
-3.135487152589675

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
57.88420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
shchc

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 164                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  O   UNK     0      -4.486   0.767   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.153  -0.003   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.153  -1.543   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.819   0.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.819   2.307   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.485   3.077   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.848   2.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.848   0.767   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.153   3.077   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.485  -0.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.485  -1.543   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.819  -2.313   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.848  -2.313   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.182  -1.543   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.516  -2.313   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.849  -1.543   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.516  -3.853   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0      -2.892   0.956   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.892   2.118   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10   18                                             
CONECT    5    4    6    9   19                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   10                                                       
CONECT    9    5                                                            
CONECT   10    4    8   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    4                                                            
CONECT   19    5                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
(1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylic acid	Generator

Chemical Formula

C₁₁H₁₂O₆

Average Mass

240.2110 Da

Monoisotopic Mass

240.06339 Da

IUPAC Name

(1R,6R)-2-(3-carboxypropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid

Traditional Name

shchc

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)C=CC=C(C(=O)CCC(O)=O)[C@@]1([H])C(O)=O

InChI Identifier

InChI=1/C11H12O6/c12-7(4-5-9(14)15)6-2-1-3-8(13)10(6)11(16)17/h1-3,8,10,13H,4-5H2,(H,14,15)(H,16,17)/t8-,10-/s2

InChI Key

QJYRAJSESKVEAE-CSEYRULYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

Gamma-keto acid
Beta-hydroxy acid
Short-chain keto acid
Dicarboxylic acid or derivatives
Hydroxy acid
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

2-succinyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid (CHEBI:39564 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.32	ChemAxon
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.88 m³·mol⁻¹	ChemAxon
Polarizability	22.36 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dickson L, Tenon M, Svilar L, Fanca-Berthon P, Lugan R, Martin JC, Vaillant F, Rogez H: Main Human Urinary Metabolites after Genipap (Genipa americana L.) Juice Intake. Nutrients. 2018 Aug 24;10(9):1155. doi: 10.3390/nu10091155. [PubMed:30149503 ]

Showing NP-Card for (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate (NP0336532)

MOL for NP0336532 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

3D MOL for NP0336532 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

3D SDF for NP0336532 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

3D-SDF for NP0336532 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

PDB for NP0336532 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

3D PDB for NP0336532 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

SMILES for NP0336532 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

INCHI for NP0336532 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

Structure for NP0336532 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)

3D Structure for NP0336532 ((1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate)