ChemFOnt: Showing chemical card for 3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid (CFc000129211)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:58:03 UTC

Chemfont ID

CFc000129211

Molecule Identification

Common Name

Definition

3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. Based on a literature review very few articles have been published on 3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4,5-Trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0,.0,.0,]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylate	Generator
3,4,5-Trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylate	Generator

Chemical Formula

C₂₉H₃₀O₁₄

Average Molecular Weight

602.545

Monoisotopic Molecular Weight

602.163555646

IUPAC Name

3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]C1(CC2=C(O1)C=CC1=C2OC2([H])COC3=CC(OC)=C(OC)C=C3[C@@]2(OC2([H])OC([H])(C(O)=O)C([H])(O)C([H])(O)C2([H])O)C1=O)C(=C)CO

InChI Identifier

InChI=1S/C29H30O14/c1-11(9-30)16-6-13-15(40-16)5-4-12-24(13)41-20-10-39-17-8-19(38-3)18(37-2)7-14(17)29(20,26(12)34)43-28-23(33)21(31)22(32)25(42-28)27(35)36/h4-5,7-8,16,20-23,25,28,30-33H,1,6,9-10H2,2-3H3,(H,35,36)/t16?,20?,21?,22?,23?,25?,28?,29-/m0/s1

InChI Key

JAPKQKPWOOVARM-OPUNCXBRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Rotenoids

Direct Parent

Rotenones

Alternative Parents

Substituents

Rotenone or derivatives
8-prenylated isoflavanone
Isoflavanone
Isoflavan
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Chromone
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Coumaran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Beta-hydroxy acid
Monosaccharide
Oxane
Hydroxy acid
Benzenoid
Pyran
Ketone
Secondary alcohol
Polyol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Ether
Acetal
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Primary alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0148802)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.24 g/L	ALOGPS
logP	0.32	ALOGPS
logP	-0.0027	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	199.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	141.01 m³·mol⁻¹	ChemAxon
Polarizability	59.21 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0148802

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 3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid (CFc000129211)

MOL for CFc000129211 (3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid)

3D MOL for CFc000129211 (3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid)

3D SDF for CFc000129211 (3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for CFc000129211 (3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid)

PDB for CFc000129211 (3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid)

3D PDB for CFc000129211 (3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid)

SMILES for CFc000129211 (3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid)

INCHI for CFc000129211 (3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid)

Structure for CFc000129211 (3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid)

3D Structure for CFc000129211 (3,4,5-trihydroxy-6-{[(13S)-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-12-oxo-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-13-yl]oxy}oxane-2-carboxylic acid)