ChemFOnt: Showing chemical card for Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- (CFc000227267)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:52:11 UTC

Chemfont ID

CFc000227267

Molecule Identification

Common Name

Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-

Definition

Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-, also known as 12-(chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0,]dodeca-2,6-diene-7-carboxylate, belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a significant number of articles have been published on Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
12-(Chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0,]dodeca-2,6-diene-7-carboxylate	HMDB
12-(Chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0¹,⁵]dodeca-2,6-diene-7-carboxylate	HMDB

Chemical Formula

C₁₅H₁₇ClO₅

Average Molecular Weight

312.75

Monoisotopic Molecular Weight

312.0764513

IUPAC Name

12-(chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0¹,⁵]dodeca-2,6-diene-7-carboxylic acid

Traditional Name

12-(chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0¹,⁵]dodeca-2,6-diene-7-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1C2C=C(C3COC(=O)C(O)(CCl)C23C=C1C)C(O)=O

InChI Identifier

InChI=1S/C15H17ClO5/c1-7-4-14-10(8(7)2)3-9(12(17)18)11(14)5-21-13(19)15(14,20)6-16/h3-4,8,10-11,20H,5-6H2,1-2H3,(H,17,18)

InChI Key

JIBVJJZCSYJNBC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Iridoid-skeleton
Monoterpenoid
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Tertiary alcohol
Carboxylic acid ester
Chlorohydrin
Halohydrin
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Alcohol
Organic oxygen compound
Organochloride
Alkyl chloride
Organooxygen compound
Carbonyl group
Organohalogen compound
Organic oxide
Hydrocarbon derivative
Alkyl halide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.45 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.06	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.26 m³·mol⁻¹	ChemAxon
Polarizability	30.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0247731

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

95638843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78174337

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- (CFc000227267)

MOL for CFc000227267 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

3D MOL for CFc000227267 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

3D SDF for CFc000227267 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

3D-SDF for CFc000227267 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

PDB for CFc000227267 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

3D PDB for CFc000227267 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

SMILES for CFc000227267 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

INCHI for CFc000227267 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

Structure for CFc000227267 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

3D Structure for CFc000227267 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)