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Record Information
Version2.0
Created at2022-09-05 23:44:07 UTC
Updated at2022-09-05 23:44:07 UTC
NP-MRD IDNP0222011
Secondary Accession NumbersNone
Natural Product Identification
Common Nameneurosporene
DescriptionNeurosporene 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, neurosporene is considered to be an isoprenoid lipid molecule. Neurosporene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Neurosporene exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Neurosporene has been detected, but not quantified in, several different foods, such as wild celeries, common wheats, swamp cabbages, thistles, and moth beans. This could make neurosporene a potential biomarker for the consumption of these foods. neurosporene is found in Averrhoa carambola, Brassica napus, Citrus sinensis, Flavocetraria nivalis, Ipomoea batatas, Pantoea ananatis, Passiflora edulis, Phaffia rhodozyma, Rhodomicrobium vannielii, Rhodopila globiformis, Rhodospirillum rubrum, Rosa villosa, Streptomyces griseus and Zea mays. neurosporene was first documented in 1980 (PMID: 7358679). Neurosporene is a carotenoid pigment (PMID: 1416048) (PMID: 8898919).
Structure
Thumb
Synonyms
ValueSource
(6E,8E,10E,12E,14E,16E,18E,20E,22E,26E)-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,26,30-dodecaeneChEBI
all-trans-NeurosporeneChEBI
7,8-Dihydro-psi,psi-caroteneHMDB
1,2-DihydroneurosporeneHMDB
7,8-Dihydro-ψ,ψ-caroteneHMDB
NeurosporinHMDB
NeurosporeneHMDB
Chemical FormulaC40H58
Average Mass538.8885 Da
Monoisotopic Mass538.45385 Da
IUPAC Name(6E,8E,10E,12E,14E,16E,18E,20E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,26,30-dodecaene
Traditional Nameneurosporene
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C
InChI Identifier
InChI=1S/C40H58/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-17,19-22,25-31H,13-14,18,23-24,32H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
InChI KeyATCICVFRSJQYDV-XILUKMICSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Averrhoa carambolaLOTUS Database
Brassica napusLOTUS Database
Citrus sinensisLOTUS Database
Flavocetraria nivalisLOTUS Database
Ipomoea batatasLOTUS Database
Pantoea ananatisLOTUS Database
Passiflora edulisLOTUS Database
Phaffia rhodozymaLOTUS Database
Rhodomicrobium vannieliiLOTUS Database
Rhodopila globiformisLOTUS Database
Rhodospirillum rubrumLOTUS Database
Rosa villosaLOTUS Database
Streptomyces griseusLOTUS Database
Zea maysLOTUS Database
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
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • 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
logP9.28ALOGPS
logP12.29ChemAxon
logS-6.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity196.69 m³·mol⁻¹ChemAxon
Polarizability74.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003114
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030661
KNApSAcK IDC00000912
Chemspider ID4444347
KEGG Compound IDC05431
BioCyc IDNEUROSPORENE
BiGG IDNot Available
Wikipedia LinkNeurosporene
METLIN ID3591
PubChem Compound5280789
PDB IDNot Available
ChEBI ID16833
Good Scents IDNot Available
References
General References
  1. Khachik F, Beecher GR, Goli MB, Lusby WR, Smith JC Jr: Separation and identification of carotenoids and their oxidation products in the extracts of human plasma. Anal Chem. 1992 Sep 15;64(18):2111-22. doi: 10.1021/ac00042a016. [PubMed:1416048 ]
  2. Scolnik PA, Walker MA, Marrs BL: Biosynthesis of carotenoids derived from neurosporene in Rhodopseudomonas capsulata. J Biol Chem. 1980 Mar 25;255(6):2427-32. [PubMed:7358679 ]
  3. Takaichi S, Sandmann G, Schnurr G, Satomi Y, Suzuki A, Misawa N: The carotenoid 7,8-dihydro-psi end group can be cyclized by the lycopene cyclases from the bacterium Erwinia uredovora and the higher plant Capsicum annuum. Eur J Biochem. 1996 Oct 1;241(1):291-6. doi: 10.1111/j.1432-1033.1996.0291t.x. [PubMed:8898919 ]
  4. LOTUS database [Link]