Natural Product (NP) Details

General Information of the NP (ID: NP8268)
Name
Curcumol
Synonyms
(-)-Curcumol; 4871-97-0; UNII-9190RTN07X; 9190RTN07X; MFCD00272163; (3S,3aS,5S,6R,8aS)-Octahydro-3-methyl-8-methylene-5-(1-methylethyl)-6H-3a,6-epoxyazulen-6-ol; 5,8-Epoxy-10(14)-guaien-8-ol; ( -)-Curcumol; CHEMBL4303567; SCHEMBL22404924; HY-N0104; ( -)-Curcumol, analytical standard; s2407; ZINC70466453; AKOS022168205; CCG-266844; NCGC00346607-02; BS-16857; V0174; 871C970; Q-100546; Q27271386; (1S,2S,5S,8R,9S)-2-methyl-6-methylidene-9-propan-2-yl-11-oxatricyclo[6.2.1.01,5]undecan-8-ol; (3S-(3alpha,3aalpha,5alpha,6alpha,8abeta))-Octahydro-3-methyl-8-methylene-5-(1-methylethyl)-6H-3a,6-epoxyazulen-6-ol; 6H-3a,6-Epoxyazulen-6-ol, octahydro-3-methyl-8-methylene-5-(1-methylethyl)-, (3S,3aS,5S,6R,8aS)-
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Species Origin Halicephalobus sp. hali_val ...     Click to Show/Hide
Halicephalobus sp. hali_val
Kingdom: Metazoa
Phylum: Nematoda
Class: Chromadorea
Order: Rhabditida
Family: Panagrolaimidae
Genus: Halicephalobus
Species: Halicephalobus sp. hali_val
Disease Mucositis [ICD-11: CA00] Phase 3 [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.714
 
MDCK Permeability
 -4.648
 
PAMPA
 - - -
 
HIA
 - - -
 
Distribution
VDss
 0.625
 
PPB
 93.2%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 -
CYP2C9 substrate
 - -
CYP2D6 inhibitor
 - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 -
CYP3A4 substrate
 +
CYP2B6 inhibitor
 +
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 -
 
Excretion
CLplasma
 8.895
 
T1/2
 1.78
Toxicity
DILI
 - -
 
Rat Oral Acute Toxicity
 +
 
FDAMDD
 -
 
Respiratory
 +
 
Human Hepatotoxicity
 +
 
Ototoxicity
 +
 
Drug-induced Nephrotoxicity
 -
 
Drug-induced Neurotoxicity
 -
 
Hematotoxicity
 - -
 
Genotoxicity
 - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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Formula
C15H24O2
PubChem CID
14240392
Canonical SMILES
CC1CCC2C13CC(C(O3)(CC2=C)O)C(C)C
InChI
1S/C15H24O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h9,11-13,16H,3,5-8H2,1-2,4H3/t11-,12-,13-,14-,15+/m0/s1
InChIKey
QRMPRVXWPCLVNI-YYFQZIEXSA-N
CAS Number
CAS 4871-97-0
Herb ID
HBIN021990
ETMC ID
3259
SymMap ID
SMIT00084
TCMSP ID
MOL000902
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Resistance can be Reversed by This NP
          TNF-related apoptosis inducing ligand      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Down-regulation Expression NQO2  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
NCI-H1299 CVCL_0060 Lung large cell carcinoma Homo sapiens
NCI-H1975 CVCL_1511 Lung adenocarcinoma Homo sapiens
NCI-H358 CVCL_1559 Lung adenocarcinoma Homo sapiens
NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
                    In-vivo Model BALB/c nude mice (5-week-old) were subcutaneously inoculated with A549 cells (1*106).
                    Experimental
                    Result(s)		 Curcumol overcomes TRAIL resistance of non-small cell lung cancer by targeting NRH:Quinone Oxidoreductase 2 (NQO2).
Target and Pathway
Target(s) Receptor-interacting protein 1 (RIPK1)  Molecule Info  [3]
Receptor-interacting protein 3 (RIPK3)  Molecule Info  [3]
References
Reference 1 ClinicalTrials.gov (NCT00475683) Curcumin for Prevention of Oral Mucositis in Children Chemotherapy
Reference 2 Curcumol Overcomes TRAIL Resistance of Non-Small Cell Lung Cancer by Targeting NRH:Quinone Oxidoreductase 2 (NQO2). Adv Sci (Weinh). 2020 Oct 15;7(22):2002306.
Reference 3 Curcumol induces RIPK1/RIPK3 complex-dependent necroptosis via JNK1/2-ROS signaling in hepatic stellate cells. Redox Biol. 2018 Oct;19:375-387.
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