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Record Information
Created at2022-09-05 22:38:12 UTC
Updated at2022-09-05 22:38:12 UTC
NP-MRD IDNP0221138
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,3s,5s,12s,13r)-12-hydroxy-5,9,13-trimethyl-16-methylidene-4,14-dioxatricyclo[³,⁵]octadec-8-en-15-one
DescriptionSinulariolide belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (1r,3s,5s,12s,13r)-12-hydroxy-5,9,13-trimethyl-16-methylidene-4,14-dioxatricyclo[³,⁵]octadec-8-en-15-one is found in Sinularia capillosa, Sinularia flexibilis and Sinularia sandensis. It was first documented in 2016 (PMID: 27801783). Based on a literature review a significant number of articles have been published on Sinulariolide (PMID: 31783709) (PMID: 30096866) (PMID: 28901434) (PMID: 28767067).
SynonymsNot Available
Chemical FormulaC20H30O4
Average Mass334.4560 Da
Monoisotopic Mass334.21441 Da
IUPAC Name(1R,3S,5S,12S,13R)-12-hydroxy-5,9,13-trimethyl-16-methylidene-4,14-dioxatricyclo[^{3,5}]octadec-8-en-15-one
Traditional Name(1R,3S,5S,12S,13R)-12-hydroxy-5,9,13-trimethyl-16-methylidene-4,14-dioxatricyclo[^{3,5}]octadec-8-en-15-one
CAS Registry NumberNot Available
InChI Identifier
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species of Origin
Species NameSourceReference
Sinularia capillosaLOTUS Database
Sinularia flexibilisLOTUS Database
Sinularia sandensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
  • Macrolide
  • Caprolactone
  • Oxepane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
pKa (Strongest Acidic)13.97ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.06 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity93.34 m³·mol⁻¹ChemAxon
Polarizability36.54 ųChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00038285
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound134730293
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
General References
  1. Wu YJ, Lin SH, Din ZH, Su JH, Liu CI: Sinulariolide Inhibits Gastric Cancer Cell Migration and Invasion through Downregulation of the EMT Process and Suppression of FAK/PI3K/AKT/mTOR and MAPKs Signaling Pathways. Mar Drugs. 2019 Nov 27;17(12). pii: md17120668. doi: 10.3390/md17120668. [PubMed:31783709 ]
  2. Wu CH, Chao CH, Huang TZ, Huang CY, Hwang TL, Dai CF, Sheu JH: Cembranoid-Related Metabolites and Biological Activities from the Soft Coral Sinularia flexibilis. Mar Drugs. 2018 Aug 9;16(8). pii: md16080278. doi: 10.3390/md16080278. [PubMed:30096866 ]
  3. Chung TW, Li YR, Huang WY, Su JH, Chan HL, Lin SH, Liu CS, Lin SC, Lin CC, Lin CH: Sinulariolide suppresses LPSinduced phenotypic and functional maturation of dendritic cells. Mol Med Rep. 2017 Nov;16(5):6992-7000. doi: 10.3892/mmr.2017.7480. Epub 2017 Sep 13. [PubMed:28901434 ]
  4. Cheng TC, Din ZH, Su JH, Wu YJ, Liu CI: Sinulariolide Suppresses Cell Migration and Invasion by Inhibiting Matrix Metalloproteinase-2/-9 and Urokinase through the PI3K/AKT/mTOR Signaling Pathway in Human Bladder Cancer Cells. Mar Drugs. 2017 Aug 2;15(8). pii: md15080238. doi: 10.3390/md15080238. [PubMed:28767067 ]
  5. Lin JJ, Wang RY, Chen JC, Chiu CC, Liao MH, Wu YJ: Cytotoxicity of 11-epi-Sinulariolide Acetate Isolated from Cultured Soft Corals on HA22T Cells through the Endoplasmic Reticulum Stress Pathway and Mitochondrial Dysfunction. Int J Mol Sci. 2016 Oct 27;17(11). pii: ijms17111787. doi: 10.3390/ijms17111787. [PubMed:27801783 ]
  6. LOTUS database [Link]