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Record Information
Version2.0
Created at2022-09-12 04:28:15 UTC
Updated at2022-09-12 04:28:15 UTC
NP-MRD IDNP0324409
Secondary Accession NumbersNone
Natural Product Identification
Common Nameamarouciaxanthin b/ sidnyaxanthin
DescriptionAmarouciaxanthin b belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, amarouciaxanthin b is considered to be an isoprenoid. amarouciaxanthin b/ sidnyaxanthin is found in Aplidium pliciferum and Mytilus edulis. amarouciaxanthin b/ sidnyaxanthin was first documented in 2011 (PMID: 21323331). Based on a literature review very few articles have been published on Amarouciaxanthin b.
Structure
Thumb
Synonyms
ValueSource
(6S,3'r)-6,3'-Dihydroxy-4,5,7',8'-tetradehydro-7,8-dihydro-beta,beta-carotene-3,8-dioneMeSH
Chemical FormulaC40H52O4
Average Mass596.8520 Da
Monoisotopic Mass596.38656 Da
IUPAC Name(4S)-4-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15-heptaen-17-yn-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
Traditional Name(4S)-4-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15-heptaen-17-yn-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
CAS Registry NumberNot Available
SMILES
C\C(\C=C\C=C(/C)C#CC1=C(C)C[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)C(=O)C[C@@]1(O)C(C)=CC(=O)CC1(C)C
InChI Identifier
InChI=1S/C40H52O4/c1-28(17-13-18-30(3)21-22-36-32(5)23-34(41)25-38(36,7)8)15-11-12-16-29(2)19-14-20-31(4)37(43)27-40(44)33(6)24-35(42)26-39(40,9)10/h11-20,24,34,41,44H,23,25-27H2,1-10H3/b12-11+,17-13+,19-14+,28-15+,29-16+,30-18+,31-20+/t34-,40-/m1/s1
InChI KeyXUKJTNSSWNXSQU-OMEVNMJGSA-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
Aplidium pliciferumLOTUS Database
Mytilus edulisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclohexenone
  • B'-hydroxy-alpha,beta-unsaturated-ketone
  • Beta-hydroxy ketone
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Acryloyl-group
  • Enone
  • Tertiary alcohol
  • Alpha,beta-unsaturated ketone
  • Secondary alcohol
  • Ketone
  • Cyclic ketone
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP7.76ChemAxon
pKa (Strongest Acidic)13.59ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity193.21 m³·mol⁻¹ChemAxon
Polarizability73.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00023052
Chemspider ID10272733
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061221
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yim MJ, Hosokawa M, Mizushina Y, Yoshida H, Saito Y, Miyashita K: Suppressive effects of Amarouciaxanthin A on 3T3-L1 adipocyte differentiation through down-regulation of PPARgamma and C/EBPalpha mRNA expression. J Agric Food Chem. 2011 Mar 9;59(5):1646-52. doi: 10.1021/jf103290f. Epub 2011 Feb 16. [PubMed:21323331 ]
  2. LOTUS database [Link]