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Record Information
Version2.0
Created at2022-04-28 09:52:54 UTC
Updated at2022-04-28 09:52:54 UTC
NP-MRD IDNP0065681
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,2-Dihydro-1-hydroxy-psi,psi-carotene
Description1-Hydroxylycopene, also known as rhodopin, belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes 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. Xanthophylls arise by oxygenation of the carotene backbone. Thus, 1-hydroxylycopene is considered to be an isoprenoid lipid molecule. 1,2-Dihydro-1-hydroxy-psi,psi-carotene is found in Afifella marina, Rhodomicrobium vannielii and Rhodopseudomonas acidophila str. 7050. 1,2-Dihydro-1-hydroxy-psi,psi-carotene was first documented in 2008 (PMID: 18339744). 1-Hydroxylycopene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 20495036).
Structure
Thumb
Synonyms
ValueSource
(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-Octamethyldotriaconta-6,8,10,12,14,16,18,20,22,24,26,30-dodecaen-2-olChEBI
1,2-Dihydro-1-hydroxy-psi,psi-caroteneChEBI
1,2-Dihydro-1-hydroxylycopeneChEBI
1-Hydroxy-1,2-dihydrolycopeneChEBI
all-trans-2,6,10,14,19,23,27,31-Octamethyldotriaconta-6,8,10,12,14,16,18,20,22,24,26,30-dodecaen-2-olChEBI
RhodopinKegg
1,2-Dihydro-psi,psi-caroten-1-olMeSH
1-HydroxylycopeneChEBI
Chemical FormulaC40H58O
Average Mass554.9030 Da
Monoisotopic Mass554.44877 Da
IUPAC Name(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-6,8,10,12,14,16,18,20,22,24,26,30-dodecaen-2-ol
Traditional Namerhodopin
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C=C(/C)CCCC(C)(C)O
InChI Identifier
InChI=1S/C40H58O/c1-33(2)19-13-22-36(5)25-16-28-37(6)26-14-23-34(3)20-11-12-21-35(4)24-15-27-38(7)29-17-30-39(8)31-18-32-40(9,10)41/h11-12,14-17,19-21,23-30,41H,13,18,22,31-32H2,1-10H3/b12-11+,23-14+,24-15+,28-16+,29-17+,34-20+,35-21+,36-25+,37-26+,38-27+,39-30+
InChI KeyCNYVJTJLUKKCGM-RGGGOQHISA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Afifella marinaLOTUS Database
Rhodomicrobium vannieliiLOTUS Database
Rhodopseudomonas acidophila str. 7050--
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes 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. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.07ALOGPS
logP10.87ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)18.61ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity198.79 m³·mol⁻¹ChemAxon
Polarizability74.43 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030248
KNApSAcK IDC00022854
Chemspider IDNot Available
KEGG Compound IDC19795
BioCyc IDCPD-11447
BiGG IDNot Available
Wikipedia LinkRhodopin
METLIN IDNot Available
PubChem Compound5365880
PDB IDNot Available
ChEBI ID35331
Good Scents IDNot Available
References
General References
  1. Theiss C, Leupold D, Moskalenko AA, Razjivin AP, Eichler HJ, Lokstein H: Femtosecond spectroscopy of native and carotenoidless purple-bacterial LH2 clarifies functions of carotenoids. Biophys J. 2008 Jun;94(12):4808-11. doi: 10.1529/biophysj.107.121681. Epub 2008 Mar 13. [PubMed:18339744 ]
  2. Lakshmi KVNS, Sasikala C, Ashok Kumar GV, Chandrasekaran R, Ramana CV: Phaeovibrio sulfidiphilus gen. nov., sp. nov., phototrophic alphaproteobacteria isolated from brackish water. Int J Syst Evol Microbiol. 2011 Apr;61(Pt 4):828-833. doi: 10.1099/ijs.0.018911-0. Epub 2010 May 21. [PubMed:20495036 ]