NP-MRD: Showing NP-Card for Isatan B (NP0050716)

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Record Information

Version

2.0

Created at

2022-04-27 22:03:17 UTC

Updated at

2022-04-27 22:03:17 UTC

NP-MRD ID

NP0050716

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isatan B

Description

1H-indol-3-yl (2S,3R,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylate belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. Isatan B is found in Isatis indigotica . Based on a literature review very few articles have been published on 1H-indol-3-yl (2S,3R,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200032D          

 22 24  0  0  1  0            999 V2000
    3.3523    1.9354    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    0.6979    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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    2.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    3.9312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9628    4.1861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9628    5.0111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1781    5.2660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3068    4.5986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1318    4.5986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    6.0507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823    5.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3062    5.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275    5.8389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  1  0  0  0
 15 20  1  1  0  0  0
 15 21  1  6  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@]1(O)O[C@@H]([C@H](O)[C@@H]1O)C(=O)OC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C14H15NO7/c16-6-14(20)12(18)10(17)11(22-14)13(19)21-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-12,15-18,20H,6H2/t10-,11-,12-,14+/m0/s1

> <INCHI_KEY>
KGXOHVOUKNLUNP-ZJQBRPOHSA-N

> <FORMULA>
C14H15NO7

> <MOLECULAR_WEIGHT>
309.274

> <EXACT_MASS>
309.084851827

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.7394512056237

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-indol-3-yl (2S,3R,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylate

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
-0.5351102823333334

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.628656812121154

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.274102848038757

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4512936448794225

> <JCHEM_POLAR_SURFACE_AREA>
132.24

> <JCHEM_REFRACTIVITY>
71.8614

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1H-indol-3-yl (2S,3R,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.143   5.874   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.887   4.729   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.333   7.338   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.797   7.814   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.797   9.354   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.333   9.830   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.573   8.584   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.113   8.584   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.143  11.295   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.327   9.531   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.438  10.754   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.971  10.899   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20   21                                             
CONECT   16   15   17   19                                                  
CONECT   17   16   13   18                                                  
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21   15   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
1H-indol-3-yl (2S,3R,4S,5R)-3,4,5-Trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylic acid	Generator

Chemical Formula

C₁₄H₁₅NO₇

Average Mass

309.2740 Da

Monoisotopic Mass

309.08485 Da

IUPAC Name

1H-indol-3-yl (2S,3R,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylate

Traditional Name

1H-indol-3-yl (2S,3R,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylate

CAS Registry Number

Not Available

SMILES

OC[C@@]1(O)O[C@@H]([C@H](O)[C@@H]1O)C(=O)OC1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C14H15NO7/c16-6-14(20)12(18)10(17)11(22-14)13(19)21-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-12,15-18,20H,6H2/t10-,11-,12-,14+/m0/s1

InChI Key

KGXOHVOUKNLUNP-ZJQBRPOHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isatis tinctoria	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Pentose monosaccharide
Indole or derivatives
Indole
Sugar acid
Beta-hydroxy acid
Benzenoid
Substituted pyrrole
Monosaccharide
Hydroxy acid
Heteroaromatic compound
Tetrahydrofuran
Pyrrole
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Carbonyl group
Alcohol
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	0.1	ALOGPS
logP	-0.54	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	132.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.86 m³·mol⁻¹	ChemAxon
Polarizability	29.74 Å³	ChemAxon
Number of Rings	3	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

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

154496773

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isatan B (NP0050716)

MOL for NP0050716 (Isatan B)

3D MOL for NP0050716 (Isatan B)

3D SDF for NP0050716 (Isatan B)

3D-SDF for NP0050716 (Isatan B)

PDB for NP0050716 (Isatan B)

3D PDB for NP0050716 (Isatan B)

SMILES for NP0050716 (Isatan B)

INCHI for NP0050716 (Isatan B)

Structure for NP0050716 (Isatan B)

3D Structure for NP0050716 (Isatan B)