NP-MRD: Showing NP-Card for henicosyl 2,3-dihydroxybenzoate (NP0252011)

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Record Information

Version

2.0

Created at

2022-09-07 15:23:33 UTC

Updated at

2022-09-07 15:23:33 UTC

NP-MRD ID

NP0252011

Secondary Accession Numbers

None

Natural Product Identification

Common Name

henicosyl 2,3-dihydroxybenzoate

Description

Gentiside I belongs to the class of organic compounds known as m-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is meta-substituted with a hydroxy group. henicosyl 2,3-dihydroxybenzoate is found in Gentiana rigescens. Gentiside I is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191523452D          

 32 32  0  0  0  0            999 V2000
    6.4302  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.1473  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.4341  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.2920  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775  -16.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
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  9 10  1  0  0  0  0
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 13 14  1  0  0  0  0
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 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 80 80  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004191523452D          

 32 32  0  0  0  0            999 V2000
    6.4302  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.1486  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0252011

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-24-32-28(31)25-22-21-23-26(29)27(25)30/h21-23,29-30H,2-20,24H2,1H3

> <INCHI_KEY>
BFWBTIXVUPMKPV-UHFFFAOYSA-N

> <FORMULA>
C28H48O4

> <MOLECULAR_WEIGHT>
448.688

> <EXACT_MASS>
448.355260026

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
58.49428747606425

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
henicosyl 2,3-dihydroxybenzoate

> <ALOGPS_LOGP>
9.40

> <JCHEM_LOGP>
10.901158456333334

> <ALOGPS_LOGS>
-6.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.82966205665975

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.27326587534443

> <JCHEM_PKA_STRONGEST_BASIC>
-4.614823842648943

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
134.13569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
henicosyl 2,3-dihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      12.003 -25.410   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337 -26.180   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.670 -25.410   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.004 -26.180   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.338 -25.410   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.672 -26.180   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.005 -25.410   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.339 -26.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.673 -25.410   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.006 -26.180   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.340 -25.410   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.674 -26.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.007 -25.410   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.341 -26.180   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.675 -25.410   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.008 -26.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.342 -25.410   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.676 -26.180   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.009 -25.410   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      37.343 -26.180   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      38.677 -25.410   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      40.010 -26.180   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      41.344 -25.410   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      41.344 -23.870   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      42.678 -26.180   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      44.011 -25.410   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      45.345 -26.180   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      45.345 -27.720   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      44.011 -28.490   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      44.011 -30.030   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      42.678 -27.720   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      41.344 -28.490   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   25   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₈O₄

Average Mass

448.6880 Da

Monoisotopic Mass

448.35526 Da

IUPAC Name

henicosyl 2,3-dihydroxybenzoate

Traditional Name

henicosyl 2,3-dihydroxybenzoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC(O)=C1O

InChI Identifier

InChI=1S/C28H48O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-24-32-28(31)25-22-21-23-26(29)27(25)30/h21-23,29-30H,2-20,24H2,1H3

InChI Key

BFWBTIXVUPMKPV-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, 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
Gentiana rigescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is meta-substituted with a hydroxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

m-Hydroxybenzoic acid esters

Alternative Parents

Substituents

M-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Salicylic acid or derivatives
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	9.4	ALOGPS
logP	10.9	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	9.27	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	134.14 m³·mol⁻¹	ChemAxon
Polarizability	58.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

46899164

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for henicosyl 2,3-dihydroxybenzoate (NP0252011)

MOL for NP0252011 (henicosyl 2,3-dihydroxybenzoate)

3D MOL for NP0252011 (henicosyl 2,3-dihydroxybenzoate)

3D SDF for NP0252011 (henicosyl 2,3-dihydroxybenzoate)

3D-SDF for NP0252011 (henicosyl 2,3-dihydroxybenzoate)

PDB for NP0252011 (henicosyl 2,3-dihydroxybenzoate)

3D PDB for NP0252011 (henicosyl 2,3-dihydroxybenzoate)

SMILES for NP0252011 (henicosyl 2,3-dihydroxybenzoate)

INCHI for NP0252011 (henicosyl 2,3-dihydroxybenzoate)

Structure for NP0252011 (henicosyl 2,3-dihydroxybenzoate)

3D Structure for NP0252011 (henicosyl 2,3-dihydroxybenzoate)