ChemFOnt: Showing chemical card for Cubebin (CFc000011888)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:59:47 UTC

Chemfont ID

CFc000011888

Molecule Identification

Common Name

Cubebin

Definition

Cubebin is found in herbs and spices. Cubebin is isolated from unripe fruit of Piper cubeba (cubeb pepper) About 15% of a volatile oil is obtained by distilling cubebs with water. Cubebene, the liquid portion, has the formula C15H24. It is a pale green or blue-yellow viscous liquid with a warm woody, slightly camphoraceous odor. After rectification with water, or on keeping, this deposits rhombic crystals of camphor of cubebs. Cubeb (Piper cubeba), or tailed pepper, is a plant in genus Piper, cultivated for its fruit and essential oil. It is mostly grown in Java and Sumatra, hence sometimes called Java pepper. The fruits are gathered before they are ripe, and carefully dried. Commercial cubebs consist of the dried berries, similar in appearance to black pepper, but with stalks attached the "tails" in "tailed pepper". The dried pericarp is wrinkled, its color ranges from grayish-brown to black. The seed is hard, white and oily. The odor of cubebs is described as agreeable and aromatic. The taste, pungent, acrid, slightly bitter and persistent. It has been described as tasting like allspice, or like a cross between allspice and black pepper. Cubebin (C10H10O3) is a crystalline substance existing in cubebs, discovered by Eugene Soubeiran and Capitaine in 1839. It may be prepared from cubebene, or from the pulp left after the distillation of the oil. The drug, along with gum, fatty oils, and malates of magnesium and calcium, contains also about 1% of cubebic acid, and about 6% of a resin. The dose of the fruit is 30 to 60 grains, and the British Pharmacopoeia contains a tincture with a dose of 4 to 1 dram. In Europe, cubeb was one of the valuable spices during the Middle Ages. It was ground as a seasoning for meat or used in sauces. Cubebin is a medieval recipe includes cubeb in making sauce sarcenes, which consists of almond milk and several spices. As an aromatic confectionery, cubeb was often candied and eaten whole. In traditional Chinese medicine cubeb is used for its alleged warming property. In Tibetan medicine, cubeb (ka ko la in Tibetan) is one of bzang po drug, six fine herbs beneficial to specific organs in the body, with cubeb assigned to the spleen

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Cubebin	HMDB
3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol	HMDB
3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol, 9ci	HMDB
9-Hydroxy-3,4:3',4'-bis(methylenedioxy)-9,9'-epoxylignan	HMDB
b-Cubebin	HMDB
Cubebine	HMDB
tetrahydro-3,4-Dipiperonyl-2-furanol	HMDB
tetrahydro-3,4-Dipiperonylfuran-2-ol	HMDB

Chemical Formula

C₂₀H₂₀O₆

Average Molecular Weight

356.3692

Monoisotopic Molecular Weight

356.125988372

IUPAC Name

3,4-bis(2H-1,3-benzodioxol-5-ylmethyl)oxolan-2-ol

Traditional Name

3,4-bis(2H-1,3-benzodioxol-5-ylmethyl)oxolan-2-ol

CAS Registry Number

18423-69-3

SMILES

OC1OCC(CC2=CC3=C(OCO3)C=C2)C1CC1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C20H20O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15,20-21H,5-6,9-11H2

InChI Key

DIYWRNLYKJKHAM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactols. These are lignan compounds containing a 3,4-dibenzyloxolan-2-ol moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactols

Alternative Parents

Substituents

Dibenzylbutyrolactol
Benzodioxole
Benzenoid
Tetrahydrofuran
Hemiacetal
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030682)
Cell membrane (HMDB: HMDB0030682)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030682)

Source

Endogenous

Endogenous (HMDB: HMDB0030682)

Plant

Plant (HMDB: HMDB0030682)

Exogenous

Food

Food (HMDB: HMDB0030682)

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0030682)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Febrifuge (HMDB: HMDB0030682)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.047 g/L	ALOGPS
logP	2.54	ALOGPS
logP	3.18	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.51 m³·mol⁻¹	ChemAxon
Polarizability	36.44 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

External Links

HMDB ID

HMDB0030682

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002600

KNApSAcK ID

C00002591

Chemspider ID

253695

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piper cubeba

METLIN ID

Not Available

PubChem Compound

287685

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Cubebin (CFc000011888)

MOL for CFc000011888 (Cubebin)

3D MOL for CFc000011888 (Cubebin)

3D SDF for CFc000011888 (Cubebin)

3D-SDF for CFc000011888 (Cubebin)

PDB for CFc000011888 (Cubebin)

3D PDB for CFc000011888 (Cubebin)

SMILES for CFc000011888 (Cubebin)

INCHI for CFc000011888 (Cubebin)

Structure for CFc000011888 (Cubebin)

3D Structure for CFc000011888 (Cubebin)