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Record Information
Version2.0
Created at2022-09-07 14:17:43 UTC
Updated at2022-09-07 14:17:43 UTC
NP-MRD IDNP0251176
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,12-dimethyl (2s,5r,7s,8r,12s,15r,17s,18r,19s,24s)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2⁸,¹¹.0⁴,⁹.0⁵,⁷.0¹⁵,¹⁷.0¹⁸,²²]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate
DescriptionCycloshizukaol A belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 2,12-dimethyl (2s,5r,7s,8r,12s,15r,17s,18r,19s,24s)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2⁸,¹¹.0⁴,⁹.0⁵,⁷.0¹⁵,¹⁷.0¹⁸,²²]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate is found in Chloranthus serratus. 2,12-dimethyl (2s,5r,7s,8r,12s,15r,17s,18r,19s,24s)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2⁸,¹¹.0⁴,⁹.0⁵,⁷.0¹⁵,¹⁷.0¹⁸,²²]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate was first documented in 2006 (PMID: 16229979). Based on a literature review a small amount of articles have been published on Cycloshizukaol A (PMID: 21963639) (PMID: 29243431) (PMID: 18855217) (PMID: 35579502).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC32H36O8
Average Mass548.6320 Da
Monoisotopic Mass548.24102 Da
IUPAC Name2,12-dimethyl (2S,5R,7S,8R,12S,15R,17S,18R,19S,24S)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2^{8,11}.0^{4,9}.0^{5,7}.0^{15,17}.0^{18,22}]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate
Traditional Name2,12-dimethyl (2S,5R,7S,8R,12S,15R,17S,18R,19S,24S)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2^{8,11}.0^{4,9}.0^{5,7}.0^{15,17}.0^{18,22}]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)[C@@]1(C)CC2=C3C=C(C(=O)[C@@H](O)[C@]3(C)[C@H]3C[C@@H]23)[C@](C)(CC2=C3C=C1C(=O)[C@@H](O)[C@]3(C)[C@H]1C[C@@H]21)C(=O)OC
InChI Identifier
InChI=1S/C32H36O8/c1-29(27(37)39-5)11-15-13-7-17(13)32(4)20(15)10-22(24(34)26(32)36)30(2,28(38)40-6)12-16-14-8-18(14)31(3)19(16)9-21(29)23(33)25(31)35/h9-10,13-14,17-18,25-26,35-36H,7-8,11-12H2,1-6H3/t13-,14-,17-,18-,25+,26+,29-,30-,31+,32+/m0/s1
InChI KeyYSPXFYFVBVEVBW-IREBYWDYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Chloranthus serratusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Dicarboxylic acid or derivatives
  • Methyl ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • 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
logP1.97ChemAxon
pKa (Strongest Acidic)12.57ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area127.2 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity145.88 m³·mol⁻¹ChemAxon
Polarizability56.41 ųChemAxon
Number of Rings7ChemAxon
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 IDC00038897
Chemspider ID113601294
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound133561951
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kim SY, Kashiwada Y, Kawazoe K, Murakami K, Sun HD, Li SL, Takaishi Y: Spicachlorantins G-J, new lindenane sesquiterpenoid dimers from the roots of Chloranthus spicatus. Chem Pharm Bull (Tokyo). 2011;59(10):1281-4. doi: 10.1248/cpb.59.1281. [PubMed:21963639 ]
  2. Zhang SS, Fu JJ, Chen HY, Tu LF, Xiao CR, Zhang RZ, Liu DP, Luo YM: [Sesquiterpenes with anti-metastasis breast cancer activity from Chloranthus henryi]. Zhongguo Zhong Yao Za Zhi. 2017 Oct;42(20):3938-3944. doi: 10.19540/j.cnki.cjcmm.2017.0159. [PubMed:29243431 ]
  3. Yang SP, Yue JM: Terpenoids from Chloranthus multistachys. Nat Prod Res. 2008;22(13):1163-8. doi: 10.1080/14786410601133434. [PubMed:18855217 ]
  4. Huang Z, Huang G, Wang X, Qin S, Fu S, Liu B: Asymmetric Total Synthesis of Natural Lindenane Sesquiterpenoid Oligomers via a Triene as a Potential Biosynthetic Intermediate. Angew Chem Int Ed Engl. 2022 Jul 18;61(29):e202204303. doi: 10.1002/anie.202204303. Epub 2022 Jun 1. [PubMed:35579502 ]
  5. Kwon OE, Lee HS, Lee SW, Bae K, Kim K, Hayashi M, Rho MC, Kim YK: Dimeric sesquiterpenoids isolated from Chloranthus japonicus inhibited the expression of cell adhesion molecules. J Ethnopharmacol. 2006 Mar 8;104(1-2):270-7. doi: 10.1016/j.jep.2005.09.018. Epub 2005 Oct 17. [PubMed:16229979 ]
  6. LOTUS database [Link]