ChemFOnt: Showing chemical card for 3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid (CFc000129215)

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

CFc000129215

Molecule Identification

Common Name

Definition

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

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₂₉H₃₂O₁₃

Average Molecular Weight

588.562

Monoisotopic Molecular Weight

588.18429109

IUPAC Name

3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-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-12-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(O)C1([H])OC1([H])OC([H])(C(O)=O)C([H])(O)C([H])(O)C1([H])O)C(C)=C

InChI Identifier

InChI=1S/C29H32O13/c1-11(2)16-7-13-15(39-16)6-5-12-24(13)40-20-10-38-17-9-19(37-4)18(36-3)8-14(17)29(20,35)26(12)42-28-23(32)21(30)22(31)25(41-28)27(33)34/h5-6,8-9,16,20-23,25-26,28,30-32,35H,1,7,10H2,2-4H3,(H,33,34)/t16?,20?,21?,22?,23?,25?,26?,28?,29-/m1/s1

InChI Key

MXEDUSKHSCICBK-HMSNPJCWSA-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
O-glycosyl compound
Glycosyl compound
1-benzopyran
Benzopyran
Chromane
Coumaran
Anisole
Alkyl aryl ether
Beta-hydroxy acid
Pyran
Hydroxy acid
Oxane
Monosaccharide
Benzenoid
Tertiary alcohol
Secondary alcohol
Polyol
Acetal
Ether
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0148806)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.34 g/L	ALOGPS
logP	1.33	ALOGPS
logP	0.84	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.76 m³·mol⁻¹	ChemAxon
Polarizability	58.46 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

HMDB0148806

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)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid (CFc000129215)

MOL for CFc000129215 (3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid)

3D MOL for CFc000129215 (3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid)

3D SDF for CFc000129215 (3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for CFc000129215 (3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid)

PDB for CFc000129215 (3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid)

3D PDB for CFc000129215 (3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid)

SMILES for CFc000129215 (3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid)

INCHI for CFc000129215 (3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid)

Structure for CFc000129215 (3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid)

3D Structure for CFc000129215 (3,4,5-trihydroxy-6-{[(13S)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14,16,18-hexaen-12-yl]oxy}oxane-2-carboxylic acid)