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Record Information
Version1.0
Created at2022-09-05 21:52:35 UTC
Updated at2022-09-05 21:52:35 UTC
NP-MRD IDNP0220536
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,2s,3r,5s,8r,9r,10r,11s,12s)-2,9,10-tris(acetyloxy)-1-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadecan-5-yl (2e)-3-phenylprop-2-enoate
Description1-Hydroxytaxuspine C belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system. (1s,2s,3r,5s,8r,9r,10r,11s,12s)-2,9,10-tris(acetyloxy)-1-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadecan-5-yl (2e)-3-phenylprop-2-enoate is found in Taxus baccata and Taxus cuspidata. It was first documented in 2022 (PMID: 36116040). Based on a literature review a significant number of articles have been published on 1-Hydroxytaxuspine C (PMID: 36116039) (PMID: 36116037) (PMID: 36116005) (PMID: 36115991).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC35H44O10
Average Mass624.7270 Da
Monoisotopic Mass624.29345 Da
IUPAC Name(1S,2S,3R,5S,8R,9R,10R,11S,12S)-2,9,10-tris(acetyloxy)-1-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0^{3,8}]pentadecan-5-yl (2E)-3-phenylprop-2-enoate
Traditional Name(1S,2S,3R,5S,8R,9R,10R,11S,12S)-2,9,10-tris(acetyloxy)-1-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0^{3,8}]pentadecan-5-yl (2E)-3-phenylprop-2-enoate
CAS Registry NumberNot Available
SMILES
C[C@H]1[C@@H]2[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@]3(C)CC[C@H](OC(=O)\C=C\C4=CC=CC=C4)C(=C)[C@H]3[C@H](OC(C)=O)[C@](O)(CC1=O)C2(C)C
InChI Identifier
InChI=1S/C35H44O10/c1-19-25(39)18-35(41)31(43-22(4)37)29-20(2)26(45-27(40)15-14-24-12-10-9-11-13-24)16-17-34(29,8)32(44-23(5)38)30(42-21(3)36)28(19)33(35,6)7/h9-15,19,26,28-32,41H,2,16-18H2,1,3-8H3/b15-14+/t19-,26+,28-,29+,30-,31+,32+,34-,35-/m1/s1
InChI KeyXGQJTMGCTWAMED-UEDUNPOGSA-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
Taxus baccataLOTUS Database
Taxus cuspidataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentTaxanes and derivatives
Alternative Parents
Substituents
  • Taxane diterpenoid
  • Tetracarboxylic acid or derivatives
  • Cinnamic acid ester
  • Cinnamic acid or derivatives
  • Styrene
  • Fatty acid ester
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic 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
logP4.2ChemAxon
pKa (Strongest Acidic)13.23ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area142.5 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity162.24 m³·mol⁻¹ChemAxon
Polarizability65.58 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound100969634
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ranta-Aho J, Olive M, Vandroux M, Roticiani G, Dominguez C, Johari M, Torella A, Bohm J, Turon J, Nigro V, Hackman P, Laporte J, Udd B, Savarese M: Mutation update for the ACTN2 gene. Hum Mutat. 2022 Sep 18. doi: 10.1002/humu.24470. [PubMed:36116040 ]
  2. Treimer E, Kalayci T, Schumann S, Suer I, Greco S, Schanze D, Schmeisser MJ, Kuhl SJ, Zenker M: Functional characterization of a novel TP53RK mutation identified in a family with Galloway-Mowat syndrome. Hum Mutat. 2022 Sep 18. doi: 10.1002/humu.24472. [PubMed:36116039 ]
  3. Savage SA, Jones K, Teshome K, Lori A, McReynolds LJ, Niewisch MR: Next-generation sequencing errors due to genetic variation in WRAP53 encoding TCAB1 on chromosome 17. Hum Mutat. 2022 Sep 18. doi: 10.1002/humu.24469. [PubMed:36116037 ]
  4. Alsheikh S, Alghamdi R, Alqatari A, Alfareed A, AlSaleh M: Combined Factor V and VIII Deficiency with LMAN1 Mutation: A Report of 3 Saudi Siblings. Am J Case Rep. 2022 Sep 18;23:e937312. doi: 10.12659/AJCR.937312. [PubMed:36116005 ]
  5. Salman M, Verma A, Chaurasia S, Prasad D, Kannabiran C, Singh V, Ramappa M: Identification and in silico analysis of a spectrum of SLC4A11 variations in Indian familial and sporadic cases of congenital hereditary endothelial dystrophy. Orphanet J Rare Dis. 2022 Sep 17;17(1):361. doi: 10.1186/s13023-022-02521-4. [PubMed:36115991 ]
  6. LOTUS database [Link]