NP-MRD: Showing NP-Card for Ovothiol A (NP0022724)

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Record Information

Version

1.0

Created at

2021-01-06 07:54:21 UTC

Updated at

2021-07-15 17:39:48 UTC

NP-MRD ID

NP0022724

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ovothiol A

Provided By

NPAtlas

Description

SCHEMBL13201930 belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Ovothiol A is found in Crithidia fasciculata, Leishmania donovani, Leishmania donovni, Mycobacterium and Platynereis dumerilii. It was first documented in 1994 (PMID: 8076641). Based on a literature review very few articles have been published on SCHEMBL13201930.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105373D          

 24 24  0  0  0  0            999 V2000
    1.9183   -0.7792   -1.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7788    0.1678   -0.4369 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7187    1.0940   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3113    1.8114    0.9267 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1247    1.3451    1.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727    1.8991    2.6521 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914    0.3207    0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300   -0.5003    0.4548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6483    0.1670   -0.0943 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5516    0.5869   -1.4469 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7689   -0.7998    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4327   -1.0963   -0.9837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1107   -1.3888    1.2553 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7571   -1.4812   -1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403   -0.2533   -2.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9773   -1.3483   -1.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6594    1.2611   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7364    1.7392    3.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -0.7085    1.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2433   -1.4823   -0.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984    1.0001    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758   -0.0701   -2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    0.7095   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5628   -2.1941    1.5912 H   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7  2  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  3 17  1  0  0  0  0
  6 18  1  0  0  0  0
  8 19  1  0  0  0  0
  8 20  1  0  0  0  0
  9 21  1  1  0  0  0
 10 22  1  0  0  0  0
 10 23  1  0  0  0  0
 13 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022724

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(N([H])[H])C([H])([H])C1=C(S[H])N=C([H])N1C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C7H11N3O2S/c1-10-3-9-6(13)5(10)2-4(8)7(11)12/h3-4,13H,2,8H2,1H3,(H,11,12)/t4-/m1/s1

> <INCHI_KEY>
XWKKYVJREGXHFO-UHFFFAOYSA-N

> <FORMULA>
C7H11N3O2S

> <MOLECULAR_WEIGHT>
201.24

> <EXACT_MASS>
201.05719778

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.8855374230686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-(1-methyl-4-sulfanyl-1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-1.84

> <JCHEM_LOGP>
-2.7330268401482547

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.733267014358527

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7592584986637956

> <JCHEM_PKA_STRONGEST_BASIC>
9.520794098549782

> <JCHEM_POLAR_SURFACE_AREA>
81.14

> <JCHEM_REFRACTIVITY>
51.279

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-amino-3-(3-methyl-5-sulfanylimidazol-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       1.918  -0.779  -1.548  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.779   0.168  -0.437  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.719   1.094  -0.134  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.311   1.811   0.927  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.125   1.345   1.294  0.00  0.00           C+0
HETATM    6  S   UNK     0       0.073   1.899   2.652  0.00  0.00           S+0
HETATM    7  C   UNK     0       0.791   0.321   0.444  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.430  -0.500   0.455  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.648   0.167  -0.094  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.552   0.587  -1.447  0.00  0.00           N+0
HETATM   11  C   UNK     0      -2.769  -0.800   0.040  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.433  -1.096  -0.984  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.111  -1.389   1.255  0.00  0.00           O+0
HETATM   14  H   UNK     0       2.757  -1.481  -1.369  0.00  0.00           H+0
HETATM   15  H   UNK     0       2.140  -0.253  -2.491  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.977  -1.348  -1.638  0.00  0.00           H+0
HETATM   17  H   UNK     0       3.659   1.261  -0.640  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.736   1.739   3.881  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.656  -0.709   1.540  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.243  -1.482  -0.020  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.898   1.000   0.614  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.076  -0.070  -2.061  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.608   0.710  -1.831  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.563  -2.194   1.591  0.00  0.00           H+0
CONECT    1    2   14   15   16                                             
CONECT    2    1    3    7                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5   18                                                       
CONECT    7    5    8    2                                                  
CONECT    8    7    9   19   20                                             
CONECT    9    8   10   11   21                                             
CONECT   10    9   22   23                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   24                                                       
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    3                                                            
CONECT   18    6                                                            
CONECT   19    8                                                            
CONECT   20    8                                                            
CONECT   21    9                                                            
CONECT   22   10                                                            
CONECT   23   10                                                            
CONECT   24   13                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-Amino-3-(1-methyl-4-sulfanyl-1H-imidazol-5-yl)propanoate	Generator
2-Amino-3-(1-methyl-4-sulphanyl-1H-imidazol-5-yl)propanoate	Generator
2-Amino-3-(1-methyl-4-sulphanyl-1H-imidazol-5-yl)propanoic acid	Generator

Chemical Formula

C₇H₁₁N₃O₂S

Average Mass

201.2400 Da

Monoisotopic Mass

201.05720 Da

IUPAC Name

(2R)-2-amino-3-(1-methyl-4-sulfanyl-1H-imidazol-5-yl)propanoic acid

Traditional Name

(2R)-2-amino-3-(3-methyl-5-sulfanylimidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

CN1C=NC(S)=C1CC(N)C(O)=O

InChI Identifier

InChI=1S/C7H11N3O2S/c1-10-3-9-6(13)5(10)2-4(8)7(11)12/h3-4,13H,2,8H2,1H3,(H,11,12)

InChI Key

XWKKYVJREGXHFO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Crithidia fasciculata	-	KNApSAcK
Leishmania donovani	LOTUS Database	35616633
Leishmania donovni	-	KNApSAcK
Mycobacterium	NPAtlas	8076641
Platynereis dumerilii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Amino acid
Azacycle
Organoheterocyclic compound
Arylthiol
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organosulfur compound
Primary aliphatic amine
Organic oxygen compound
Amine
Primary amine
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-1.8	ALOGPS
logP	-2.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.76	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.28 m³·mol⁻¹	ChemAxon
Polarizability	19.89 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

External Links

NPAtlas ID

NPA009446

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7969993

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9794226

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Spies HS, Steenkamp DJ: Thiols of intracellular pathogens. Identification of ovothiol A in Leishmania donovani and structural analysis of a novel thiol from Mycobacterium bovis. Eur J Biochem. 1994 Aug 15;224(1):203-13. doi: 10.1111/j.1432-1033.1994.tb20013.x. [PubMed:8076641 ]

Showing NP-Card for Ovothiol A (NP0022724)

MOL for NP0022724 (Ovothiol A)

3D MOL for NP0022724 (Ovothiol A)

3D SDF for NP0022724 (Ovothiol A)

3D-SDF for NP0022724 (Ovothiol A)

PDB for NP0022724 (Ovothiol A)

3D PDB for NP0022724 (Ovothiol A)

SMILES for NP0022724 (Ovothiol A)

INCHI for NP0022724 (Ovothiol A)

Structure for NP0022724 (Ovothiol A)

3D Structure for NP0022724 (Ovothiol A)