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Entry
CA00655                                                            

Classification
Carotenoid Name
Phoenicopterone;
(6'R)-α-Echinenone;
4-Oxo-α-carotene;
4-keto-α-Carotene;
(6'R)-alpha-Echinenone;
4-Oxo-alpha-carotene;
4-keto-alpha-Carotene
IUPAC name beta,epsilon-Caroten-4-one
Formula
C40H54O
Molecular Weight 
550.832 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11 including one ketone (11 in total)
Number of
conjugated multiple bonds 
11 including one ketone (11 in total)
Isomers 
InChI
InChI=1S/C40H54O/c1-30(18-13-20-32(3)23-25-36-34(5)22-15-28-39(36,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-37-35(6)38(41)27-29-40(37,9)10/h11-14,16-26,36H,15,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+
InChIKey
ZRXISZZQHKYPQA-QQGJMDNJSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C(=O)CCC1(C)C)/C)/C)/C=C/C=C(/C=C/C1C(=CCCC1(C)C)C)\C
XLogP
13.214
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
1
LipinskiFailures
1
Complexity of molecule
0.316
Number of heavy atoms
41
TPSA
(Topological Polar Surface Area) 
17.070 Å2
Source organisms
Marine crinoi  - Crinoid
Corbicula japonica (Ref.221) - Shellfish: bivalve
Corbicula sandai (Ref.221) - Shellfish: bivalve
Corbicula clam (Ref.221) - Shellfish: bivalve
Phoenicoparrus ruber (Ref.471) - Bird: American flamingo
Phoenicoparrus ruber (Ref.474) - Bird: American flamingo
References
  • Ref.221 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2005), 53(21), 8357-8364. "Carotenoids in Three Species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam)".
  • Ref.471 : Denis L Fox, Thomas S Hopkins, Comparative Biochemistry and Physiology, Volume 17, Issue 3, March 1966, Pages 841–856, "Comparative metabolic fractionation of carotenoids in three flamingo species".
  • Ref.474 : Denis L Fox, James W McBeth, Gordon Mackinney, Comparative Biochemistry and Physiology, Volume 36, Issue 2, 15 September 1970, Pages 253–262, "Some dietary carotenoids and blood-carotenoid levels in flamingos—II. γ-carotene and α-carotene consumed by the American flamingo".
  • CAS
    3297-23-2
    Links to other DB
    LipidBank: VCA0079
    MassBank: CA000054

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