NP-MRD: Showing NP-Card for (2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid (NP0146180)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 01:31:51 UTC

Updated at

2022-09-02 01:31:51 UTC

NP-MRD ID

NP0146180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid

Description

CHEBI:80546 Belongs to the class of organic compounds known as s-alkyl-thiohydroximates. These are organosulfur compounds with the general structure RC(S)=NOH, where R =alkyl group. CHEBI:80546 Is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid is found in Apis cerana. Based on a literature review very few articles have been published on CHEBI:80546.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.0022   -1.3718    0.2446 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0017    0.0950    0.2166 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9293    0.4882   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2952   -0.0568   -0.3920 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4767    0.6821    0.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8321    0.0609    1.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066    0.1238    0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6544    0.6406   -0.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037    0.4753   -1.6577 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7182   -0.1437   -0.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298   -0.5296   -1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7078   -1.1488   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1043   -1.3815    1.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8022   -0.9883    1.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895   -0.3636    0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8346    1.7167    1.6142 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9675    2.3604    1.2699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3177    0.5502   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5605    1.7668   -0.4021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2962   -0.3612   -0.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9412   -1.6950   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8814   -1.6663    0.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408    0.4665    1.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243    1.5703   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2295   -0.0181   -1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832   -1.0027    1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351    0.5254    2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7513    1.1077   -1.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9898    0.7703   -2.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5121   -0.3468   -2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7380   -1.4578   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6511   -1.8728    1.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911   -1.1580    2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9954    3.0928    0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7062   -0.9301    0.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  2  0
 16 17  1  0
  2 18  1  0
 18 20  1  0
 18 19  2  0
 15  7  1  0
 15 10  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 17 34  1  0
 20 35  1  0
M  END


  Mrv1652309022203312D          

 20 21  0  0  1  0            999 V2000
    5.1774    1.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1774    0.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4630   -0.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7485    0.3750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0340   -0.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0340   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3195   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2333   -2.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4263   -2.2670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0138   -1.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069   -1.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0481   -0.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    0.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3109   -0.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5659   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3195    0.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3195    1.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8919   -0.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6064    0.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8919   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
 10 15  1  0  0  0  0
  5 16  2  0  0  0  0
 16 17  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CS\C(CC1=CNC2=CC=CC=C12)=N/O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H15N3O3S/c14-10(13(17)18)7-20-12(16-19)5-8-6-15-11-4-2-1-3-9(8)11/h1-4,6,10,15,19H,5,7,14H2,(H,17,18)/b16-12-/t10-/m0/s1

> <INCHI_KEY>
GREVXYZKHGJYAU-HPCMQXCGSA-N

> <FORMULA>
C13H15N3O3S

> <MOLECULAR_WEIGHT>
293.34

> <EXACT_MASS>
293.083412529

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.66214351981354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-{[(1Z)-1-(hydroxyimino)-2-(1H-indol-3-yl)ethyl]sulfanyl}propanoic acid

> <ALOGPS_LOGP>
-0.82

> <JCHEM_LOGP>
-1.0093643803560204

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.722238063728167

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.11998228496221

> <JCHEM_PKA_STRONGEST_BASIC>
8.822696369744111

> <JCHEM_POLAR_SURFACE_AREA>
111.7

> <JCHEM_REFRACTIVITY>
77.32149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-amino-3-{[(1Z)-1-(hydroxyimino)-2-(1H-indol-3-yl)ethyl]sulfanyl}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  N   UNK     0       9.665   2.240   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       9.665   0.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.331  -0.070   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       6.997   0.700   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       5.663  -0.070   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.663  -1.610   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.330  -2.380   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.169  -3.911   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.662  -4.232   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.892  -2.898   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.386  -2.578   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.090  -1.113   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.941   0.031   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.447  -0.289   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.923  -1.754   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.330   0.700   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       4.330   2.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.998  -0.070   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.332   0.700   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.998  -1.610   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   10                                                  
CONECT   16    5   17                                                       
CONECT   17   16                                                            
CONECT   18    2   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₅N₃O₃S

Average Mass

293.3400 Da

Monoisotopic Mass

293.08341 Da

IUPAC Name

(2R)-2-amino-3-{[(1Z)-1-(hydroxyimino)-2-(1H-indol-3-yl)ethyl]sulfanyl}propanoic acid

Traditional Name

(2R)-2-amino-3-{[(1Z)-1-(hydroxyimino)-2-(1H-indol-3-yl)ethyl]sulfanyl}propanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CS\C(CC1=CNC2=CC=CC=C12)=N/O)C(O)=O

InChI Identifier

InChI=1S/C13H15N3O3S/c14-10(13(17)18)7-20-12(16-19)5-8-6-15-11-4-2-1-3-9(8)11/h1-4,6,10,15,19H,5,7,14H2,(H,17,18)/b16-12-/t10-/m0/s1

InChI Key

GREVXYZKHGJYAU-HPCMQXCGSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as s-alkyl-thiohydroximates. These are organosulfur compounds with the general structure RC(S)=NOH, where R =alkyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Thiohydroximic acids and derivatives

Sub Class

Thiohydroximic acids

Direct Parent

S-alkyl-thiohydroximates

Alternative Parents

Substituents

S-alkyl-thiohydroximate
L-cysteine-s-conjugate
Cysteine or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
L-alpha-amino acid
Indole
Indole or derivatives
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid
Amino acid or derivatives
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Sulfenyl compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organooxygen compound
Organosulfur compound
Primary amine
Organopnictogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:80546 )

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	-0.82	ALOGPS
logP	-1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.12	ChemAxon
pKa (Strongest Basic)	8.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	111.7 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	77.32 m³·mol⁻¹	ChemAxon
Polarizability	29.66 Å³	ChemAxon
Number of Rings	2	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30791791

KEGG Compound ID

C16518

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25245902

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid (NP0146180)

MOL for NP0146180 ((2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid)

3D MOL for NP0146180 ((2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid)

3D SDF for NP0146180 ((2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid)

3D-SDF for NP0146180 ((2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid)

PDB for NP0146180 ((2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid)

3D PDB for NP0146180 ((2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid)

SMILES for NP0146180 ((2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid)

INCHI for NP0146180 ((2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid)

Structure for NP0146180 ((2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid)

3D Structure for NP0146180 ((2r)-2-amino-3-{[(1z)-1-(hydroxyimino)-2-(1h-indol-3-yl)ethyl]sulfanyl}propanoic acid)