ChemFOnt: Showing chemical card for 3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid (CFc000129165)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:57:59 UTC

Chemfont ID

CFc000129165

Molecule Identification

Common Name

3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid

Definition

3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-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-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4,5-Trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0,.0,.0,]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylate	Generator
3,4,5-Trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylate	Generator

Chemical Formula

C₂₆H₂₆O₁₃

Average Molecular Weight

546.481

Monoisotopic Molecular Weight

546.137340897

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C(OCC3OC4=C(C=C5C=COC5=C4)C(O)C23OC2OC(C(O)C(O)C2O)C(O)=O)=C1

InChI Identifier

InChI=1S/C26H26O13/c1-33-16-6-12-15(8-17(16)34-2)36-9-18-26(12,39-25-21(29)19(27)20(28)22(38-25)24(31)32)23(30)11-5-10-3-4-35-13(10)7-14(11)37-18/h3-8,18-23,25,27-30H,9H2,1-2H3,(H,31,32)

InChI Key

KHIRCRXYJKCQNP-UHFFFAOYSA-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
Isoflavan
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Benzofuran
Anisole
Beta-hydroxy acid
Alkyl aryl ether
Pyran
Oxane
Hydroxy acid
Monosaccharide
Benzenoid
Furan
Heteroaromatic compound
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0148756)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.38 g/L	ALOGPS
logP	1.25	ALOGPS
logP	0.078	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.85	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	186.74 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.72 m³·mol⁻¹	ChemAxon
Polarizability	52.18 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	No	ChemAxon

External Links

HMDB ID

HMDB0148756

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-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid (CFc000129165)

MOL for CFc000129165 (3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid)

3D MOL for CFc000129165 (3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid)

3D SDF for CFc000129165 (3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid)

3D-SDF for CFc000129165 (3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid)

PDB for CFc000129165 (3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid)

3D PDB for CFc000129165 (3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid)

SMILES for CFc000129165 (3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid)

INCHI for CFc000129165 (3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid)

Structure for CFc000129165 (3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid)

3D Structure for CFc000129165 (3,4,5-trihydroxy-6-({12-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-13-yl}oxy)oxane-2-carboxylic acid)