NP-MRD: Showing NP-Card for (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate (NP0334618)

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Record Information

Version

2.0

Created at

2024-09-10 19:09:54 UTC

Updated at

2024-09-10 19:09:54 UTC

NP-MRD ID

NP0334618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate

Description

(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate 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. Based on a literature review very few articles have been published on (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate.

Structure

MOL SDF PDB SMILES InChI

IGP
  Mrv2104 05252321422D          

 21 22  0  0  0  0            999 V2000
   -1.4809   -0.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9098   -0.1139    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6243   -0.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -0.8284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3223    0.6006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1953    0.2986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7664    0.2986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7664    1.1236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0519   -0.1139    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0519   -0.9389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625    0.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4162   -0.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9682    0.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6712   -0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488    1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5557    1.2906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7752    0.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781   -0.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0302   -0.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721    0.5906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5576   -0.4059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  7 20  1  6  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  9 21  1  1  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 16  1  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)C1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1/C11H14NO6P/c13-10(6-18-19(15,16)17)11(14)8-5-12-9-4-2-1-3-7(8)9/h1-5,10-14H,6H2,(H2,15,16,17)/t10-,11+/s2

> <INCHI_KEY>
NQEQTYPJSIEPHW-WIBLRKLZNA-N

> <FORMULA>
C11H14NO6P

> <MOLECULAR_WEIGHT>
287.208

> <EXACT_MASS>
287.055874173

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.16299478309461

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3S)-2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acid

> <JCHEM_LOGP>
-0.07957787366666655

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.512307194345705

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.486485478838181

> <JCHEM_PKA_STRONGEST_BASIC>
-3.449835539932993

> <JCHEM_POLAR_SURFACE_AREA>
123.01000000000002

> <JCHEM_REFRACTIVITY>
66.7583

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
indole-3-glycerol phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: IGP                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      -2.764  -0.213   0.000  0.00  0.00           C+0
HETATM    2  P   UNK     0      -5.432  -0.213   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0      -6.765  -0.983   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -4.662  -1.546   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -6.202   1.121   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -4.098   0.557   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.431   0.557   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.431   2.097   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.097  -0.213   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.097  -1.753   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.237   0.557   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.644  -0.069   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.674   1.075   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.120  -1.534   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.398   2.089   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       2.904   2.409   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.180   0.755   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.626  -1.854   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.656  -0.709   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -2.375   1.102   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.041  -0.758   0.000  0.00  0.00           H+0
CONECT    1    6    7                                                       
CONECT    2    3    4    5    6                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    1    2                                                       
CONECT    7    1    8    9   20                                             
CONECT    8    7                                                            
CONECT    9    7   10   11   21                                             
CONECT   10    9                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   16   17                                                  
CONECT   14   12   18                                                       
CONECT   15   11   16                                                       
CONECT   16   13   15                                                       
CONECT   17   13   19                                                       
CONECT   18   14   19                                                       
CONECT   19   17   18                                                       
CONECT   20    7                                                            
CONECT   21    9                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R)-1-C-(indol-3-yl)Glycerol 3-phosphoric acid	Generator

Chemical Formula

C₁₁H₁₄NO₆P

Average Mass

287.2080 Da

Monoisotopic Mass

287.05587 Da

IUPAC Name

[(2R,3S)-2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acid

Traditional Name

indole-3-glycerol phosphate

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)C1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1/C11H14NO6P/c13-10(6-18-19(15,16)17)11(14)8-5-12-9-4-2-1-3-7(8)9/h1-5,10-14H,6H2,(H2,15,16,17)/t10-,11+/s2

InChI Key

NQEQTYPJSIEPHW-WIBLRKLZNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 3-alkylindoles. These 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
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Substituted pyrrole
Alkyl phosphate
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary alcohol
1,2-diol
Azacycle
Hydrocarbon derivative
Organic oxide
Aromatic alcohol
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-C-(indol-3-yl)glycerol 3-phosphate (CHEBI:51793 )

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	-0.08	ChemAxon
pKa (Strongest Acidic)	1.49	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	123.01 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	66.76 m³·mol⁻¹	ChemAxon
Polarizability	26.16 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

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 (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate (NP0334618)

MOL for NP0334618 ((1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate)

3D MOL for NP0334618 ((1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate)

3D SDF for NP0334618 ((1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate)

3D-SDF for NP0334618 ((1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate)

PDB for NP0334618 ((1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate)

3D PDB for NP0334618 ((1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate)

SMILES for NP0334618 ((1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate)

INCHI for NP0334618 ((1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate)

Structure for NP0334618 ((1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate)

3D Structure for NP0334618 ((1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate)