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Record Information
Version1.0
Created at2021-06-22 17:25:23 UTC
Updated at2021-06-22 17:25:23 UTC
NP-MRD IDNP0043843
Secondary Accession NumbersNone
Natural Product Identification
Common NameAstraeusin D
DescriptionAstraeusin D belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Astraeusin D is found in Astraeus odoratus. It was first documented in 2021 (PMID: 34610616). Based on a literature review a significant number of articles have been published on Astraeusin D (PMID: 34610566) (PMID: 34610527) (PMID: 34610525) (PMID: 34610470).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H48O3
Average Mass456.7110 Da
Monoisotopic Mass456.36035 Da
IUPAC Name(2S,7R,11R,14R,15R)-14-[(2S,3S,5E)-3,7-dihydroxy-6-methylhept-5-en-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-one
Traditional Name(2S,7R,11R,14R,15R)-14-[(2S,3S,5E)-3,7-dihydroxy-6-methylhept-5-en-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-one
CAS Registry NumberNot Available
SMILES
C[C@H]([C@@H](O)C\C=C(/C)CO)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3
InChI Identifier
InChI=1S/C30H48O3/c1-19(18-31)8-10-24(32)20(2)21-12-16-30(7)23-9-11-25-27(3,4)26(33)14-15-28(25,5)22(23)13-17-29(21,30)6/h8,20-21,24-25,31-32H,9-18H2,1-7H3/b19-8+/t20-,21+,24-,25-,28+,29+,30-/m0/s1
InChI KeyGEDRJURLYBVEGS-OABDCZROSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Astraeus odoratusLinigton's dataset
    • Masahiko Isaka, Somporn Palasarn, Prasert Srikitikulchai, Vanicha Vichai, Somjit Komwijit. Astrae...
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
  • 26-hydroxysteroid
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • 22-hydroxysteroid
  • Bile acid, alcohol, or derivatives
  • 14-alpha-methylsteroid
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • Steroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP5.79ALOGPS
logP5.68ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)16.64ChemAxon
pKa (Strongest Basic)-0.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity137.09 m³·mol⁻¹ChemAxon
Polarizability56.31 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
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 IDNot Available
Chemspider ID78436385
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139583436
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Tanaka T, Iwamoto K, Wada M, Yano E, Suzuki T, Kawaguchi N, Shirasaka N, Moriyama T, Homma Y: Dietary syringic acid reduces fat mass in an ovariectomy-induced mouse model of obesity. Menopause. 2021 Oct 4. pii: 00042192-900000000-96887. doi: 10.1097/GME.0000000000001853. [PubMed:34610616 ]
  2. Venasse M, Gauthier A, Giroux I, Pilutti LA: Dietary intake and characteristics in persons with multiple sclerosis. Mult Scler Relat Disord. 2021 Sep 9;56:103237. doi: 10.1016/j.msard.2021.103237. [PubMed:34610566 ]
  3. Zhang CL, Zhang JJ, Zhu QF, Guan HY, Yang YX, He X, Fu Y, Chen TX, Dong L, Yang XS, Tang KF, Xu GB, Liao SG: Antihyperuricemia and antigouty arthritis effects of Persicaria capitata herba in mice. Phytomedicine. 2021 Sep 23;93:153765. doi: 10.1016/j.phymed.2021.153765. [PubMed:34610527 ]
  4. Koloski CW, Cassone BJ: Transcriptional profiling of Dermacentor variabilis (Acari: Ixodidae) provides insights into the role of the Haller's organ in spatial DEET recognition. Ticks Tick Borne Dis. 2021 Sep 24;13(1):101827. doi: 10.1016/j.ttbdis.2021.101827. [PubMed:34610525 ]
  5. Cai M, Wang Z, Luu TTT, Zhang D, Finke B, He J, Tay LWR, Di Paolo G, Du G: PLD1 Promotes Reactive Oxygen Species Production in Vascular Smooth Muscle Cells and Injury-Induced Neointima Formation. Biochim Biophys Acta Mol Cell Biol Lipids. 2021 Oct 2:159062. doi: 10.1016/j.bbalip.2021.159062. [PubMed:34610470 ]
  6. Masahiko Isaka, Somporn Palasarn, Prasert Srikitikulchai, Vanicha Vichai, Somjit Komwijit (2016). Masahiko Isaka, Somporn Palasarn, Prasert Srikitikulchai, Vanicha Vichai, Somjit Komwijit. Astraeusins A–L, lanostane triterpenoids from the edible mushroom Astraeus odoratus. Tetrahedron Volume 72, Issue 23, 9 June 2016, Pages 3288-3295 DOI: 10.1016/j.tet.2016.04.057. Tetrahedron.