Natural Product (NP) Details

General Information of the NP (ID: NP4536)
Name
Calcipotriol
Synonyms
Calcipotriol; calcipotriene; Dovonex; Daivonex; Psorcutan; Sorilux; 112965-21-6; Calcitrene; MC 903; MC-903; Calcipotriol hydrate; UNII-143NQ3779B; CHEBI:50749; Dovonex (TN); 143NQ3779B; (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol; 112828-00-9; NCGC00167465-01; Calciptriol; DSSTox_CID_26648; DSSTox_RID_81793; DSSTox_GSID_46648; Divonex; (22E)-(24S)-1alpha,24-dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22E)-(24S)-1alpha,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol / Calcipotriol; (5Z,7E,22E)-(1S,3R,24S)-26,27-cyclo-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol; SMR000466353; CAS-112965-21-6; Calcipotriene [USAN]; SR-01000762910; CCRIS 7700; MFCD10567086; (5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1alpha,3beta,24-triol; PRI 2201; Calcipotriol (JAN); Calcipotriol [INN]; Calcipotriene (USP); BMS-181161; PubChem18810; PubChem19334; Epitope ID:114242; SCHEMBL2853; MLS000759467; MLS001424130; GTPL2778; CHEMBL1200666; DTXSID0046648; AMY2864; 1s19; HMS2051N11; HMS2089J08; HMS3269P03; HMS3413D04; HMS3677D04; HMS3713K08; MC903; EX-A4430; PRI-2201; ZINC3921872; Tox21_112469; BDBM50369964; LMST03020106; s3739; AKOS015855239; Tox21_112469_1; CCG-100949; CS-0387; DB02300; NC00199; STF-115469; NCGC00167465-02; AS-56390; CPD000466353; HY-10001; O763; D01125; U-0267; W-5148; 24207-EP2275420A1; 24207-EP2295055A2; 24207-EP2295416A2; 24207-EP2298748A2; 24207-EP2298764A1; 24207-EP2298765A1; 24207-EP2305640A2; 24207-EP2305642A2; 24207-EP2308861A1; 24207-EP2311453A1; 24207-EP2314590A1; AB00698343-05; 828C009; Q155683; SR-01000762910-3; SR-01000762910-4; (1?,3?,5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1,3,24-triol; (1S,3R,5Z,7E,14beta,17alpha,22E,24S)-26,27-cyclo-9,10-secocholesta-5,7,10,22-tetraene-1,3,24-triol; (5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1alpha,3beta,24-triol hydrate; (5Z,7E,24S)-26,27-Cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1alpha,3beta,24-triol; 9,10-Secochola-5,7,10(19),22-tetraene-1,3,24-triol, 24-cyclopropyl-, (1alpha,3beta,5Z,7E,22E,24S)-
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Plaque psoriasis [ICD-11: EA90] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.272
 
MDCK Permeability
 -5.009
 
PAMPA
 ++
 
HIA
 - - -
 
Distribution
VDss
 -0.447
 
PPB
 80.1%
 
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
 9.14
 
T1/2
 1.528
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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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C27H40O3
PubChem CID
5288783
Canonical SMILES
CC(C=CC(C1CC1)O)C2CCC3C2(CCCC3=CC=C4CC(CC(C4=C)O)O)C
InChI
1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1
InChIKey
LWQQLNNNIPYSNX-UROSTWAQSA-N
CAS Number
CAS 112965-21-6
ChEBI ID
CHEBI:50749
TTD Drug ID
D01QUS
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Betamethasone dipropionate      Psoriasis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     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
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 The fixed combination treatment improves quality of life to a significantly greater extent than calcipotriol, with the once daily regimen most appreciated by patients, in both active disease and recurrency.
Target and Pathway
Target(s) Vitamin D3 receptor (VDR)  Molecule Info  [3]
KEGG Pathway Endocrine and other factor-regulated calcium reabsorption Click to Show/Hide
2 Mineral absorption
3 Tuberculosis
NetPath Pathway IL4 Signaling Pathway Click to Show/Hide
Panther Pathway Vitamin D metabolism and pathway Click to Show/Hide
Pathway Interaction Database Regulation of nuclear SMAD2/3 signaling Click to Show/Hide
2 Direct p53 effectors
3 RXR and RAR heterodimerization with other nuclear receptor
4 Retinoic acid receptors-mediated signaling
5 Validated transcriptional targets of deltaNp63 isoforms
6 Validated transcriptional targets of TAp63 isoforms
Reactome Nuclear Receptor transcription pathway Click to Show/Hide
WikiPathways Ovarian Infertility Genes Click to Show/Hide
2 Nuclear Receptors in Lipid Metabolism and Toxicity
3 Nuclear Receptors Meta-Pathway
4 Vitamin D Receptor Pathway
5 Drug Induction of Bile Acid Pathway
6 Nuclear Receptors
7 Vitamin D Metabolism
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2778).
Reference 2 Consensus on the use of the fixed combination calcipotriol/betamethasone dipropionate in the treatment of plaque psoriasis. G Ital Dermatol Venereol. 2012 Dec;147(6):609-24.
Reference 3 Cellular and molecular mechanisms involved in the action of vitamin D analogs targeting vitiligo depigmentation. Curr Drug Targets. 2008 Apr;9(4):345-59.
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