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Entry
CA00190                                                            

Classification
Carotenoid Name
Torulene
IUPAC name 3',4'-Didehydro-beta,psi-carotene
Formula
C40H54
Molecular Weight 
534.832 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Provitamin A activity - 50% of that of all-trans-β-carotene (Ref.468).
  • Number of
    conjugated double bonds 
    13
    Number of
    conjugated multiple bonds 
    13
    Isomers 
  • Constitutional isomer: CA00042, CA00196, CA00307, CA00710, CA00315, CA00316, CA00588
  • Cis/trans isomer: CA00951
  • InChI
    InChI=1S/C40H54/c1-32(2)18-13-21-35(5)24-15-26-36(6)25-14-22-33(3)19-11-12-20-34(4)23-16-27-37(7)29-30-39-38(8)28-17-31-40(39,9)10/h11-16,18-27,29-30H,17,28,31H2,1-10H3/b12-11+,21-13+,22-14+,23-16+,26-15+,30-29+,33-19+,34-20+,35-24+,36-25+,37-27+
    InChIKey
    AIBOHNYYKWYQMM-MXBSLTGDSA-N
    Canonical SMILES
    C/C(=C\C=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=C(C)C)\C)\C
    XLogP
    14.618
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    0
    LipinskiFailures
    2
    Complexity of molecule
    0.064
    Number of heavy atoms
    40
    TPSA
    (Topological Polar Surface Area) 
    0.000 Å2
    Source organisms
    Nostoc sp. PCC 7120 (Ref.72) - Cyanobacteria: same as Anabaena sp. PCC 7120
    Sitobion avenae (Ref.114) - Insect: aphid
    Coccinella septempunctata (Ref.116) - Insect: seven-spotted ladybird
    Macrosiphum liriodendri (Ref.118) - Insect: aphid
    Rhodotorula minuta (Ref.506) - Fungi: red yeast
    Neurospora crassa (Ref.556) - Fungi: red bread mold
    References
  • Ref.72 : Heo, Jinsol; Kim, Se Hyeuk; Lee, Pyung Cheon, Applied and Environmental Microbiology (2013), 79(11), 3336-3345., "New insight into the cleavage reaction of Nostoc sp. strain PCC 7120 carotenoid cleavage dioxygenase in natural and nonnatural carotenoids".
  • Ref.114 : Jenkins, R. L.; Loxdale, H. D.; Brookes, C. P.; Dixon, A. F. G., Physiological Entomology (1999), 24(2), 171-178., "The major carotenoid pigments of the grain aphid, Sitobion avenae (F.) (Hemiptera: Aphididae)".
  • Ref.116 : Britton, George; Lockley, William J. S.; Harriman, Garry A.; Goodwin, Trevor W., Nature (London, United Kingdom) (1977), 266(5597), 49-50., "Pigmentation of the ladybird beetle Coccinella septempunctata by carotenoids not of plant origin".
  • Ref.118 : Andrewes, A. G.; Kjoesen, H.; Liaaen-Jensen, S.; Weisgraber, K. H.; Lousberg, R. J. J. C.; Weiss, U., Acta Chemica Scandinavica (1947-1973) (1971), 25(10), 3878-80., "Animal carotenoids. 7. Carotenes of two color variants of the aphid Macrosiphum liriodendri. Identification of natural γ,​γ-​carotene".
  • Ref.506 : K. Shivalkar Yada and R. Prabha, Indian Journal of Science and Technology, Vol 7(12), 1973–1977, December 2014, ISSN (Print) : 0974-6846 , ISSN (Online) : 0974-5645, "Extraction of Pigments from Rhodotorula Species of Dairy Environment".
  • Ref.556 : Saelices L, Youssar L, Holdermann I, Al-Babili S, Avalos J., Mol Genet Genomics. 2007 Nov;278(5):527-37. Epub 2007 Jul 4., PMID: 17610084 DOI: 10.1007/s00438-007-0269-2, "Identification of the gene responsible for torulene cleavage in the Neurospora carotenoid pathway.".
  • Ref.468 : Gerard P. Moss, Herbert Baxter, J.B. Harborne, Gerald P. Moss, CRC Press; 1 edition (February 15, 1993), ISBN-10: 0850667364, ISBN-13: 978-0850667363, "Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants".
  • CAS
    547-23-9
    Links to other DB
    KEGG COMPOUND: C08613
    KNApSAcK: C00003786
    LipidBank: VCA1006
    ProCarDB: C0662

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