NP-MRD: Showing NP-Card for Dopachrome o-semiquinone (NP0339120)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 19:46:57 UTC

Updated at

2024-09-11 19:46:57 UTC

NP-MRD ID

NP0339120

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dopachrome o-semiquinone

Description

Dopachrome o-semiquinone, also known as DCSQ, belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole. Dopachrome o-semiquinone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

      
  Mrv1652303102016472D          

 14 15  0  0  1  0            999 V2000
   12.9563  -12.4297    0.0000 O   0  0  0  0  0  1  0  0  0  0  0  0
   13.6708  -12.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3854  -12.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0999  -12.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8845  -12.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3689  -11.6047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.8845  -10.9374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0999  -11.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3854  -10.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6708  -11.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9563  -10.7798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1939  -11.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6063  -10.8901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6064  -12.3191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  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
  6 12  1  1  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  1  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339120

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[O]C1=C(O)C=C2N[C@H](CC2=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H8NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10,12H,1H2,(H,13,14)/t6-/m1/s1

> <INCHI_KEY>
YHAPBGUGQAHLME-ZCFIWIBFSA-N

> <FORMULA>
C9H8NO4

> <MOLECULAR_WEIGHT>
194.1641

> <EXACT_MASS>
194.045332749

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.111933224809608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-2-carboxy-6-hydroxy-2,3-dihydro-1H-indol-5-yl]oxidanyl

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
0.6101999999999997

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.150245268106089

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0841756577883355

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2954218802517934

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
59.90340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-carboxy-6-hydroxy-2,3-dihydro-1H-indol-5-yloxidanyl

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  O   UNK     0      24.185 -23.202   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      25.519 -22.432   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.853 -23.202   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.186 -22.432   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.651 -22.908   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.555 -21.662   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      29.651 -20.416   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      28.186 -20.892   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.853 -20.122   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.519 -20.892   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      24.185 -20.122   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      32.095 -21.662   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      32.865 -20.328   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      32.865 -22.996   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    3   10    1                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    4    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    2    9   11                                                  
CONECT   11   10                                                            
CONECT   12    6   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
DCSQ	HMDB
Leukodopachrome O-semiquinone radical	HMDB

Chemical Formula

C₉H₈NO₄

Average Mass

194.1641 Da

Monoisotopic Mass

194.04533 Da

IUPAC Name

[(2R)-2-carboxy-6-hydroxy-2,3-dihydro-1H-indol-5-yl]oxidanyl

Traditional Name

(2R)-2-carboxy-6-hydroxy-2,3-dihydro-1H-indol-5-yloxidanyl

CAS Registry Number

Not Available

SMILES

[O]C1=C(O)C=C2N[C@H](CC2=C1)C(O)=O

InChI Identifier

InChI=1S/C9H8NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10,12H,1H2,(H,13,14)/t6-/m1/s1

InChI Key

YHAPBGUGQAHLME-ZCFIWIBFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids

Alternative Parents

Substituents

Indolecarboxylic acid
Alpha-amino acid
Alpha-amino acid or derivatives
D-alpha-amino acid
Dihydroindole
1-hydroxy-2-unsubstituted benzenoid
Secondary aliphatic/aromatic amine
Aralkylamine
Benzenoid
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Secondary amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	1.1	ALOGPS
logP	0.61	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	59.9 m³·mol⁻¹	ChemAxon
Polarizability	18.11 Å³	ChemAxon
Number of Rings	2	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

HMDB0012931

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029211

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

Not Available

Showing NP-Card for Dopachrome o-semiquinone (NP0339120)

MOL for NP0339120 (Dopachrome o-semiquinone)

3D MOL for NP0339120 (Dopachrome o-semiquinone)

3D SDF for NP0339120 (Dopachrome o-semiquinone)

3D-SDF for NP0339120 (Dopachrome o-semiquinone)

PDB for NP0339120 (Dopachrome o-semiquinone)

3D PDB for NP0339120 (Dopachrome o-semiquinone)

SMILES for NP0339120 (Dopachrome o-semiquinone)

INCHI for NP0339120 (Dopachrome o-semiquinone)

Structure for NP0339120 (Dopachrome o-semiquinone)

3D Structure for NP0339120 (Dopachrome o-semiquinone)