NP-MRD: Showing NP-Card for n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid (NP0176333)

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Record Information

Version

2.0

Created at

2022-09-03 13:58:27 UTC

Updated at

2022-09-03 13:58:27 UTC

NP-MRD ID

NP0176333

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid

Description

N-acetyl-l-tryptophanol belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid is found in Streptomyces blastmyceticus. Based on a literature review very few articles have been published on N-acetyl-l-tryptophanol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.9687    1.2422   -0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6104    0.7314    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6104    0.7787    1.6113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5024    0.2629    0.9465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2874    0.0517    0.2661 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3629   -0.5243   -1.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9836   -1.7800   -1.1164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878   -0.7643    1.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9788   -0.9619    0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3916   -2.1221   -0.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807   -1.8855   -0.8916 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9413   -0.6233   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0759    0.1186   -0.9601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1821    1.4115   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2011    1.9953    0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801    1.2979    0.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599   -0.0204    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9757    1.7282   -0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0928    0.3713   -1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2110    1.9296   -1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8297   -0.0782    2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7928    1.0630    0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595    0.1805   -1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2882   -0.7015   -1.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4564   -2.4746   -1.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101   -0.2825    2.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7007   -1.7736    1.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8003   -3.0414   -0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588   -2.5453   -1.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8527   -0.3413   -1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0609    2.0031   -0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891    3.0256    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2773    1.7286    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  9  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  6
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
M  END


  Mrv1652309032215582D          

 17 18  0  0  1  0            999 V2000
   -1.2400   -4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0176333

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O2/c1-9(17)15-11(8-16)6-10-7-14-13-5-3-2-4-12(10)13/h2-5,7,11,14,16H,6,8H2,1H3,(H,15,17)/t11-/m0/s1

> <INCHI_KEY>
VCJZLHSIECUOIT-NSHDSACASA-N

> <FORMULA>
C13H16N2O2

> <MOLECULAR_WEIGHT>
232.283

> <EXACT_MASS>
232.121177763

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.779457765892122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(2S)-1-hydroxy-3-(1H-indol-3-yl)propan-2-yl]ethanimidic acid

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
1.4945532380000002

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.050907808921608

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.4257599742791705

> <JCHEM_PKA_STRONGEST_BASIC>
3.9516533708893626

> <JCHEM_POLAR_SURFACE_AREA>
68.61000000000001

> <JCHEM_REFRACTIVITY>
66.3009

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2S)-1-hydroxy-3-(1H-indol-3-yl)propan-2-yl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.869  -4.974   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.411  -1.724   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   12                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₆N₂O₂

Average Mass

232.2830 Da

Monoisotopic Mass

232.12118 Da

IUPAC Name

N-[(2S)-1-hydroxy-3-(1H-indol-3-yl)propan-2-yl]ethanimidic acid

Traditional Name

N-[(2S)-1-hydroxy-3-(1H-indol-3-yl)propan-2-yl]ethanimidic acid

CAS Registry Number

Not Available

SMILES

CC(O)=N[C@H](CO)CC1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C13H16N2O2/c1-9(17)15-11(8-16)6-10-7-14-13-5-3-2-4-12(10)13/h2-5,7,11,14,16H,6,8H2,1H3,(H,15,17)/t11-/m0/s1

InChI Key

VCJZLHSIECUOIT-NSHDSACASA-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
Streptomyces blastmyceticus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Substituted pyrrole
Benzenoid
Pyrrole
Acetamide
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Azacycle
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Alcohol
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
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	1.33	ALOGPS
logP	1.49	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	3.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	68.61 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.3 m³·mol⁻¹	ChemAxon
Polarizability	24.78 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23992878

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

38354785

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid (NP0176333)

MOL for NP0176333 (n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid)

3D MOL for NP0176333 (n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid)

3D SDF for NP0176333 (n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid)

3D-SDF for NP0176333 (n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid)

PDB for NP0176333 (n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid)

3D PDB for NP0176333 (n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid)

SMILES for NP0176333 (n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid)

INCHI for NP0176333 (n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid)

Structure for NP0176333 (n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid)

3D Structure for NP0176333 (n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]ethanimidic acid)