MiMeDB: Showing metabocard for (5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxyate (MMDBc0054070)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:51:02 UTC

Update Date

2022-09-01 02:26:56 UTC

Metabolite ID

MMDBc0054070

Metabolite Identification

Common Name

(5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxyate

Description

(2s,3s)-Trans-2,3-Dihydro-3-Hydroxyanthranilic Acid, also known as trans-2,3-dihydro-3-hydroxyanthranilate or (2S,3S)-2-amino-2,3-dihydro-3-hydroxybenzoic acid, belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl) (2s,3s)-Trans-2,3-Dihydro-3-Hydroxyanthranilic Acid is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05041405132D          

 13 13  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    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
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  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
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  6  8  1  1  0  0  0
  5  9  1  6  0  0  0
 10  7  1  0  0  0  0
 11  7  2  0  0  0  0
  5 12  1  1  0  0  0
  6 13  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054070

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H9NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,5-6,9H,8H2,(H,10,11)/t5-,6-/m0/s1

> <INCHI_KEY>
XBTXTLKLSHACSS-WDSKDSINSA-N

> <FORMULA>
C7H9NO3

> <MOLECULAR_WEIGHT>
155.1513

> <EXACT_MASS>
155.058243159

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
14.614557038622872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid

> <ALOGPS_LOGP>
-2.38

> <JCHEM_LOGP>
-3.1421392202788847

> <ALOGPS_LOGS>
-0.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.16827400260302

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.770027125264067

> <JCHEM_PKA_STRONGEST_BASIC>
9.384726129676254

> <JCHEM_POLAR_SURFACE_AREA>
83.55000000000001

> <JCHEM_REFRACTIVITY>
40.2189

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.54e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6    7                                                  
CONECT    5    3    6    9   12                                             
CONECT    6    4    5    8   13                                             
CONECT    7    4   10   11                                                  
CONECT    8    6                                                            
CONECT    9    5                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    5                                                            
CONECT   13    6                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Synonyms

Value	Source
(2S,3S)-2-Amino-2,3-dihydro-3-hydroxybenzoic acid	ChEBI
trans-2,3-Dihydro-3-hydroxyanthranilate	Kegg
trans-2,3-Dihydro-3-hydroxyanthranilic acid	Kegg
DHHA	Kegg
(2S,3S)-2-Amino-2,3-dihydro-3-hydroxybenzoate	Generator
(2S,3S)-trans-2,3-Dihydro-3-hydroxyanthranilate	Generator
(2S,3S)-trans-2,3-dihydro-3-HYDROXYANTHRANILIC ACID	ChEBI
(2S,3S)-2,3-dihydro-3-Hydroxyanthranilate	Generator

Molecular Formula

C₇H₉NO₃

Average Mass

155.1513

Monoisotopic Mass

155.058243159

IUPAC Name

(5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid

Traditional Name

(5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C7H9NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,5-6,9H,8H2,(H,10,11)/t5-,6-/m0/s1

InChI Key

XBTXTLKLSHACSS-WDSKDSINSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Secondary alcohols

Alternative Parents

Substituents

Amino acid or derivatives
Secondary alcohol
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Primary amine
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Amine
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

2,3-dihydro-3-hydroxyanthranilic acid (CHEBI:60844 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	65.4 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3.1	ChemAxon
logS	-0.38	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40.22 m³·mol⁻¹	ChemAxon
Polarizability	14.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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 (Non-derivatized) - 70eV, Positive	splash10-052s-9500000000-3907264e67cd3eb0e54f	2017-08-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1900000000-1ef1fa0de1103ecaf1c4	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-007c-4900000000-512e05cd64066441665c	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ktf-9000000000-2f2c2454277f4337a8b5	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0w2c-2900000000-6024111918a83f22d32f	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-9800000000-8ef91534cc11aa934a6e	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-9400000000-ada9123fd1482a9d0d2b	2017-07-26	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

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
Bacteria	Proteobacteria	3	Human ; Human subgingival plaque

Exposure Sources

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

DB02124

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C19830

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

448825

PDB ID

Not Available

ChEBI ID

60844

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 (5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxyate (MMDBc0054070)

MOL for #<Metabolite:0x00007fdb3909f120>

3D MOL for #<Metabolite:0x00007fdb3909f120>

3D SDF for #<Metabolite:0x00007fdb3909f120>

3D-SDF for #<Metabolite:0x00007fdb3909f120>

PDB for #<Metabolite:0x00007fdb3909f120>

3D PDB for #<Metabolite:0x00007fdb3909f120>

SMILES for #<Metabolite:0x00007fdb3909f120>

INCHI for #<Metabolite:0x00007fdb3909f120>

Structure for #<Metabolite:0x00007fdb3909f120>

3D Structure for #<Metabolite:0x00007fdb3909f120>