Cannabis Compound Database: Showing Compound Card for beta-Carotene (CDB004847)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (2) Show 4 proteins XML

Show more...Show more...Show more...

Record Information

Version

1.0

Created at

2020-04-17 18:42:56 UTC

Updated at

2020-12-07 19:11:06 UTC

CannabisDB ID

CDB004847

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

beta-Carotene

Description

beta-Carotene, also known as b-karotin or β-carotene, belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Thus, beta-carotene is considered to be an isoprenoid lipid molecule. beta-Carotene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. beta-Carotene is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,1'-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohexene)	ChEBI
all-trans-beta-Carotene	ChEBI
beta-Karotin	ChEBI
all-trans-b-Carotene	Generator
all-trans-Β-carotene	Generator
b-Karotin	Generator
Β-karotin	Generator
b-Carotene	Generator
Β-carotene	Generator
(all-e)-1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis	HMDB
(all-e)-1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethyl-cyclohexene	HMDB
all-e-b-Carotene	HMDB
all-epsilon-beta-Carotene	HMDB
Betacarotene	HMDB
BetaVit	HMDB
Carotaben	HMDB
Carotene base 80S	HMDB
FOOD Orange 5	HMDB
KPMK	HMDB
Lucaratin	HMDB
Lucarotin	HMDB
Lurotin	HMDB
Provatene	HMDB
Provatenol	HMDB
Rovimix b-carotene	HMDB
Serlabo	HMDB
Solatene	HMDB
Hermal brand OF betacarotene	HMDB
Max-caro	HMDB
Merck brand OF betacarotene	HMDB
Roche brand OF betacarotene	HMDB
BellaCarotin	HMDB
Betacarotene roche brand	HMDB
Betacarotene solgar brand	HMDB
Marlyn brand OF betacarotene	HMDB
Betacarotene hermal brand	HMDB
Max caro	HMDB
Solgar brand OF betacarotene	HMDB
3m Brand OF betacarotene	HMDB
Betacarotene 3m brand	HMDB
Betacarotene marlyn brand	HMDB
Betacarotene merck brand	HMDB
Carotene, beta	HMDB
MaxCaro	HMDB
Vetoron	HMDB
beta Carotene	HMDB
b Carotene	HMDB
Β carotene	HMDB
beta-Carotene	HMDB

Chemical Formula

C₄₀H₅₆

Average Molecular Weight

536.89

Monoisotopic Molecular Weight

536.4382

IUPAC Name

1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene

Traditional Name

β-carotene

CAS Registry Number

7235-40-7

SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+

InChI Key

OENHQHLEOONYIE-JLTXGRSLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Carotenes

Alternative Parents

Substituents

Carotene
Branched unsaturated hydrocarbon
Cycloalkene
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

cyclic carotene (CHEBI:17579 )
C40 isoprenoids (tetraterpenes) (C02094 )
Carotenoids (C02094 )
C40 isoprenoids (tetraterpenes) (LMPR01070000 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	183 °C	Not Available
Boiling Point	654.7 °C at 760 mmHg	Wikipedia
Water Solubility	0.6 mg/mL	Not Available
logP	14.764	Wikipedia

Predicted Properties

Property	Value	Source
logP	9.72	ALOGPS
logP	11.12	ChemAxon
logS	-6.1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	191.61 m³·mol⁻¹	ChemAxon
Polarizability	72.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-05mx-9810010000-9a261fb8602890c2481e	2015-03-01	View Spectrum
Predicted GC-MS	beta-Carotene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-3211290000-f968c686d39ae0f0fc50	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0016-2794670000-c5bc2a4dbcd0f12cbf7f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-2687970000-782d048d873c21fc6b82	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-05ai-1009510000-585581456b10671692bd	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Positive	splash10-05mx-2920010000-471219f3e66bafb29bee	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-0144900000-2fa7b609c7300ff8aba3	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0434190000-0f2f0f2c4af76e6c3322	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000b-0679100000-6f4450c8ade1963f9201	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000j-1789100000-6f2a7024e42303e7737a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000090000-cdea7c2d939f0c68b905	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0000090000-530c81799c9daabdc9bf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0968170000-ec71ee19e546088e3b05	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-0277960000-5b1eef16ffbc2ccd4b1e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0081-0449400000-e362d306c4b151321fb6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0iki-0149200000-5b858e5700ff1d750a4e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0001090000-b0a4df7c3417e82842d7	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000j-0135090000-fb91b96b3605a056f12f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0apj-0229000000-23e454829ef21fbedf66	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Retinol Metabolism
Vitamin A Deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Beta,beta-carotene 15,15'-monooxygenase	BCMO1	16q23.2	Q9HAY6	details
Beta,beta-carotene 9',10'-oxygenase	BCO2	11q23.1	Q9BYV7	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Beta,beta-carotene 15,15'-monooxygenase	BCMO1	16q23.2	Q9HAY6	details
Beta,beta-carotene 9',10'-oxygenase	BCO2	11q23.1	Q9BYV7	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000561

DrugBank ID

DB06755

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Beta_Carotene

METLIN ID

Not Available

PubChem Compound

5280489

PDB ID

Not Available

ChEBI ID

17579

References

General References

Not Available

Enzymes

Enzyme Details

1. Beta,beta-carotene 15,15'-monooxygenase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Symmetrically cleaves beta-carotene into two molecules of retinal. The reaction proceeds in three stages, epoxidation of the 15,15'-double bond, hydration of the double bond leading to ring opening, and oxidative cleavage of the diol formed.
Gene Name:: BCMO1
Uniprot ID:: Q9HAY6
Molecular weight:: 62636.69

Enzyme Details

2. Beta,beta-carotene 9',10'-oxygenase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Asymmetrically cleaves beta-carotene at the 9',10' double bond resulting in the formation of beta-apo-10'-carotenal and beta-ionone. Besides beta-carotene, lycopene is also oxidatively cleaved. The apocarotenals formed by this enzyme may be the precursors for the biosynthesis of retinoic acid or exert unknown physiological effects.
Gene Name:: BCO2
Uniprot ID:: Q9BYV7
Molecular weight:: 61509.65

Showing Compound Card for beta-Carotene (CDB004847)

Structure for CDB004847 (beta-Carotene)

Enzymes