Showing Compound Card for Carotene (CDB000345)

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Record Information
Version1.0
Created at2020-03-19 00:32:05 UTC
Updated at2020-12-07 19:07:22 UTC
CannabisDB IDCDB000345
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCarotene
DescriptionAlpha carotene belongs to the group of compounds known as carotenoids. More specifically carotenoids are classified as tetraterpenoids, being built from four terpene units (8 isoprene units) each containing 10 carbon atoms. As a result, carotenoids typically have a total of 40 carbon atoms. 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. There are more than 1100 known carotenoids. Carotenoids can be further categorized into two classes, xanthophylls (which contain oxygen) and carotenes (which are purely hydrocarbons and contain no oxygen). Carotenoids are among the most common pigments in nature and are natural lipid soluble antioxidants. Alpha-carotene is one of the primary isomers of carotene, although Beta-carotene is the most abundant. There are six known carotene isomers including α-, β-, γ-, δ-, ε-, and ζ-carotene. These carotene isomers contain unsubstituted beta-ionone rings, which means they can be readily converted to retinol and vitamin A. In other words, they have pro-vitamin A activity. Alpha-carotene has less vitamin A activity than Beta-Carotene. This is because of its structure, as Alpha-carotene it is converted to just one molecule of biologically active retinol after central cleavage, while Beta-carotene is converted to two molecules after cleavage. Plants, fungi, and photosynthetic bacteria synthesize carotenes, while animals must obtain them as a dietary nutrient. In plants carotenes contribute to photosynthesis by transmitting the light energy they absorb to chlorophyll. They also protect plant tissues by helping to absorb the energy from singlet oxygen, an excited form of the oxygen molecule O2 which is formed during photosynthesis. Alpha-carotene is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Alpha-carotene is found in many common orange-, yellow-, and green-colored fruits and vegetables such as carrots, pumpkins, squash, apricots, sweet potatoes, and beans. The concentration of α-Carotene is especially high in orange carrots and high serum concentrations are associated with high carrot intake. Other plants and foods that have high levels of alpha-carotene include cloves, shallots, cumin, wolfberries, cantaloupes, papaya, spinach, broccoli, turnip, avocado, green peas, orange and red peppers, and tomatoes. Alpha-carotene (along with beta-carotene) exhibits numerous beneficial health or pharmacological properties including antioxidant, anti-obesity, anti-cancer, anti-aging, anti-atherosclerotic and anti-sunburn properties as well as hepatoprotective, neuroprotective and improved vision and night blindness prevention ( PMID: 27047317 ). Alpha-carotene is one of a small number of pigments including (beta-carotene and xanthophylls) found in cannabis plants. It was first isolated from hemp leaves and identified as a cannabis constituent in 1969 (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+)-alpha-CaroteneChEBI
alpha-Carotene (natural)ChEBI
(+)-a-CaroteneGenerator
(+)-Α-caroteneGenerator
a-Carotene (natural)Generator
Α-carotene (natural)Generator
a-CaroteneGenerator
Α-caroteneGenerator
alpha-Carotene, (6'r)-isomerMeSH
CarotenesMeSH
CarotenoidsMeSH
alpha-CaroteneMeSH
(6'R)-alpha-CaroteneHMDB
(6'R)-beta,epsilon-CaroteneHMDB
(6'R)-α-CaroteneHMDB
(6'R)-β,ε-CaroteneHMDB
(6’R)-α-CaroteneHMDB
(6’R)-β,ε-CaroteneHMDB
all-trans-alpha-CaroteneHMDB
all-trans-α-CaroteneHMDB
α-Carotene, (6’R)-isomerHMDB
Chemical FormulaC40H56
Average Molecular Weight536.87
Monoisotopic Molecular Weight536.4382
IUPAC Name(6R)-1,5,5-trimethyl-6-[(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 Namehi-α
CAS Registry NumberNot Available
SMILES
C\C(\C=C\C=C(/C)\C=C\[C@H]1C(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/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+/t37-/m0/s1
InChI KeyANVAOWXLWRTKGA-NTXLUARGSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentCarotenes
Alternative Parents
Substituents
  • Carotene
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

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Role

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Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point187.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.79ALOGPS
logP11.17ChemAxon
logS-6.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity191.88 m³·mol⁻¹ChemAxon
Polarizability71.41 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0334190000-e05f79db2e425bfe81862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0769200000-81f1f88961c73bc3943a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-2689700000-a8528456aa6fa28bfb102016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-df0db1851156c1e36da62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000090000-ac5ac3829642d0394d242016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0947360000-b2ba5d2cce5367c8424b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0101090000-e6a413ebb46fe9a97e602021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-0336290000-c736f8dfebfeee67f7c12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0319000000-1e7037ebf4dd84aadb002021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01pa-0269820000-f183b75adeec601193322021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007t-0429400000-232c7e964986bedd5ad62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q0-0229100000-971b11f97635708e01302021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003993
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013716
KNApSAcK IDC00003765
Chemspider ID4925358
KEGG Compound IDC05433
BioCyc IDCPD1F-118
BiGG IDNot Available
Wikipedia LinkAlpha-Carotene
METLIN ID6998
PubChem Compound6419725
PDB IDNot Available
ChEBI ID35147
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Kim JK: An update on the potential health benefits of carotenes. EXCLI J. 2016 Jan 6;15:1-4. doi: 10.17179/excli2015-664. eCollection 2016. [PubMed:27047317 ]
  3. During A, Smith MK, Piper JB, Smith JC: beta-Carotene 15,15'-Dioxygenase activity in human tissues and cells: evidence of an iron dependency. J Nutr Biochem. 2001 Nov;12(11):640-647. doi: 10.1016/s0955-2863(01)00184-x. [PubMed:12031257 ]
  4. dela Sena C, Narayanasamy S, Riedl KM, Curley RW Jr, Schwartz SJ, Harrison EH: Substrate specificity of purified recombinant human beta-carotene 15,15'-oxygenase (BCO1). J Biol Chem. 2013 Dec 27;288(52):37094-103. doi: 10.1074/jbc.M113.507160. Epub 2013 Nov 1. [PubMed:24187135 ]
  5. Fraser PD, Bramley PM: The biosynthesis and nutritional uses of carotenoids. Prog Lipid Res. 2004 May;43(3):228-65. doi: 10.1016/j.plipres.2003.10.002. [PubMed:15003396 ]