ChemFOnt: Showing chemical card for 6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000167240)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 00:01:03 UTC

Chemfont ID

CFc000167240

Molecule Identification

Common Name

Definition

6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Based on a literature review very few articles have been published on 6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0,.0,.0,]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator
6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₃₄H₄₆O₁₂

Average Molecular Weight

646.73

Monoisotopic Molecular Weight

646.298926921

IUPAC Name

Traditional Name

6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@]3([H])[C@@]4([H])CC[C@@]([H])([C@](C)(O)[C@@]5([H])CC(C)=C(C)C(=O)O5)[C@]4(C)CC[C@@]3([H])[C@]3(C)C(=O)C=CC([H])(OC4([H])OC([H])(C(O)=O)C([H])(O)C([H])(O)C4([H])O)C13O2

InChI Identifier

InChI=1S/C34H46O12/c1-14-12-22(43-29(41)15(14)2)33(5,42)19-7-6-17-16-13-23-34(46-23)21(44-30-26(38)24(36)25(37)27(45-30)28(39)40)9-8-20(35)32(34,4)18(16)10-11-31(17,19)3/h8-9,16-19,21-27,30,36-38,42H,6-7,10-13H2,1-5H3,(H,39,40)/t16-,17-,18-,19-,21?,22-,23+,24?,25?,26?,27?,30?,31-,32-,33+,34?/m1/s1

InChI Key

WUFIKMWVDKIJLX-RVBNLGCQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Diterpene glycoside
Withanolide-skeleton
Steroidal glycoside
Diterpene lactone
Diterpenoid
5,6-epoxysteroid
Terpene glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Cyclohexenone
Beta-hydroxy acid
Dihydropyranone
Oxepane
Hydroxy acid
Monosaccharide
Pyran
Dicarboxylic acid or derivatives
Oxane
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Enoate ester
Secondary alcohol
Ketone
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Carboxylic acid
Dialkyl ether
Acetal
Ether
Oxirane
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2	ALOGPS
logP	2.33	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.35	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	192.58 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	159.15 m³·mol⁻¹	ChemAxon
Polarizability	67.9 Å³	ChemAxon
Number of Rings	7	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

HMDB0186975

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000167240)

MOL for CFc000167240 (6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000167240 (6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000167240 (6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000167240 (6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000167240 (6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000167240 (6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000167240 (6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000167240 (6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000167240 (6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000167240 (6-{[(1R,2S,9S,11R,12R,15R,16R)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)