Showing Compound (-)-cis-Rotenolone (FDB012420)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:09 UTC

Update date

2019-11-26 03:06:44 UTC

Primary ID

FDB012420

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(-)-cis-Rotenolone

Description

(-)-cis-Rotenolone 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 (-)-cis-Rotenolone has been detected, but not quantified in, jicamas (Pachyrhizus erosus) and pulses. This could make (-)-cis-rotenolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (-)-cis-Rotenolone.

CAS Number

509-96-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-cis-12a-Hydroxyrotenone	HMDB
1,2,12,12a-tetrahydro-6a-Hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-(2R,6ar,12ar)-[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one	HMDB
12-Hydroxyrotenone	HMDB
12alpha-Hydroxyrotenone	HMDB
6a-beta,12a-beta-Rotenolone	HMDB
6Ab,12ab-rotenolone	HMDB
Rotenalone	HMDB
Rotenolon I	HMDB
Rotenolone	HMDB
Rotenolone I	HMDB
6 alpha(beta),12 alpha(beta)-Rotenolone	MeSH
Rotenolone, (2R-(2alpha,6aalpha,12aalpha))-isomer	MeSH
Rotenolone, (2R-(2alpha,6abeta,12aalpha))-isomer	MeSH
Rotenolone, (2R-(2alpha,6aalpha,12abeta))-isomer	MeSH
[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aR,12aR)-	manual
1,2,12,12a-Tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-(2R,6ar,12ar)-[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one	HMDB
12a-Hydroxyrotenone	biospider
6ab,12ab-Rotenolone	biospider
Rotenolone; (-)-cis-form	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.056 g/L	ALOGPS
logP	2.4	ALOGPS
logP	2.73	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.08	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.96 m³·mol⁻¹	ChemAxon
Polarizability	42.8 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C23H22O7

IUPAC name

(1R,6R,13R)-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-3,8,10,14(19),15,17-hexaen-12-one

InChI Identifier

InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1

InChI Key

JFVKWCYZKMUTLH-AYPBNUJASA-N

Isomeric SMILES

[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C

Average Molecular Weight

410.4166

Monoisotopic Molecular Weight

410.136553058

Classification

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
Chromone
1-benzopyran
Chromane
Benzopyran
Coumaran
Aryl alkyl ketone
Aryl ketone
Anisole
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Ketone
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic molecular entity (CHEBI:68051 )
rotenones (C10464 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Fabaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 67.31%; H 5.40%; O 27.29%	DFC
Melting Point	Mp 91-92° (88°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -190.1 (CHCl3) (-145)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(-)-cis-Rotenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udj-2898000000-a911918046b993e78796	Spectrum
Predicted GC-MS	(-)-cis-Rotenolone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0v4i-9420700000-d42a2e5be951b642755e	Spectrum
Predicted GC-MS	(-)-cis-Rotenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1223900000-9a1f17cd964abaa81aa8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w29-2394300000-b8d33d58c295207f77a3	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-2930000000-7ebdad6df07b04059cf4	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0011900000-068963a903131042e2de	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0059600000-b085e22dff915ed213c1	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udr-1933000000-acb18ae95eb8c0f59fb9	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-13ca06aa040c9821ae69	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0325900000-33ff0fbbe9523120bd61	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1869100000-793032f9edca87024cfd	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000900000-cc474c0f71581fe9b76f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0115900000-866e3635b32607356e9c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi0-3395000000-409148100e6d88cb50cd	Spectrum