Calcitriol

Details

• Internal ID: ff5abd37-f1d7-43ec-ac92-7e14a93347a2
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Vitamin D and derivatives
• IUPAC Name: (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• SMILES (Canonical): CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
• SMILES (Isomeric): C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C
• InChI: InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1
• InChI Key: GMRQFYUYWCNGIN-NKMMMXOESA-N
• Popularity: 23,393 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₃
• Molecular Weight: 416.60 g/mol
• Exact Mass: 416.32904526 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 5.70
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 32222-06-3
• Rocaltrol
• Calcijex
• Topitriol
• 1alpha,25-Dihydroxyvitamin D3
• Silkis
• 1alpha,25-Dihydroxycholecalciferol
• Soltriol
• Dihydroxyvitamin D3
• Vectical
• 1,25-DHCC
• 1,25-DIHYDROXYCHOLECALCIFEROL
• 1,25-Dihydroxyvitamin D3
• 1,25-Dihydroxyvitamin D
• Calcitriolum
• 1alpha,25(OH)2D3
• Ro 21-5535
• 1alpha,25-Dihydroxyvitamin D
• 1-alpha,25-Dihydroxyvitamin D3
• Calcitriolum [INN-Latin]
• DN-101
• 1,25-Dihydroxycholecaliferol
• CCRIS 5522
• HSDB 3482
• EINECS 250-963-8
• DN 101
• CHEMBL846
• UNII-FXC9231JVH
• Ro 215535
• (1S,3R,5Z,7E)-9,10-secocholesta-5,7,10-triene-1,3,25-triol
• 1-alpha,25-Dihydroxycholecalciferol
• 1a,25-Dihydroxyvitamin D3
• FXC9231JVH
• Ro-21-5535
• 1,25-(OH)2D3
• 1a,25-Dihydroxycholecalciferol
• CHEBI:17823
• 1-alpha-25-dihydroxyvitamin D3
• vit D
• 1alpha 25-dihydroxycholecalciferol
• Calcitriol [USAN:INN:BAN:JAN]
• U 49562
• (1R,3S,Z)-5-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol
• Calcitriol [USAN:USP:INN:BAN:JAN]
• Ro-215535
• Cholecalciferol, 1-alpha,25-dihydroxy-
• (5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1alpha,3beta,25-triol
• 9,10-Seco(5Z,7E)-5,7,10(19)-cholestatriene-1alpha,3beta,25-triol
• (1alpha,3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol
• (5Z,7E)-(1S,3R)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol
• 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, (1a,3b,5Z,7E)-
• 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, (1alpha,3beta,5Z,7E)-
• 1 25-Dihydroxyvitamin D
• 1,25-dihydroxy vitamin D3
• Toptriol
• 1000873-74-4
• 1 25-Dihydroxyvitamin D3
• 1alpha 25-(OH)2D3
• 1 25-Dihydroxycholecalciferol
• Decostriol
• 1alpha 25-Dihydroxyvitamin D3
• MC1288
• (1S,3R,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol
• (5Z,7E)-(1S,3R)-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
• (5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1-alpha,3-beta,25-triol
• Calcitriol [USAN:BAN:INN:JAN]
• MC-1288
• 1alpha,25-dihydroxyvitamin D3 / 1alpha,25-dihydroxycholecalciferol / calcitriol
• SMR000466393
• 1,25 (OH)2 D3
• 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, (1.alpha.,3.beta.,5Z,7E)-
• dihydroxy-vitamin D3
• (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• DTXSID5022722
• Asentar
• Panbonis
• (3beta 5Z7E)-910-Secocholesta-5710(19)-trienetriol
• 1,25 Dihydroxycholecalciferol
• 1,25-(OH)2-D3
• 1.alpha.,25-dihydroxycholecalciferol
• 1 alpha,25-Dihydroxyvitamin D3
• 9,10-Secocholesta-5,6,10(19)-triene-1.alpha.,3.beta.,25-triol
• Rocaltrol (TN)
• NCGC00161327-04
• (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-5-hydroxy-1,5-dimethyl-hexyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexane-1,3-diol
• 1,25(OH)2-20epi-D3
• (1-alpha,3-beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol
• 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol(1.alpha.,3.beta.,5Z,7E)-
• 910-Secocholesta-5710(19)-triene-1325-triol (1alpha 3beta 5Z7E)-(9CI)
• MFCD00867079
• 1,25-dihydroxy-20-epi-Vitamin D3
• 1,3-ciclohexanediol, 4-metileno-5-[(2E)-2-[(1R, 3aS, 7aS)-octahidro-1-[(1R)-5-hidroxi-1,5-dimetilhexil]-7a-metil-4H-inden-4-iliden]etilideno]-, (1R, 3S, 5Z)-
• 9,10-Secocholesta-5, 7,10 (19)-trieno-,3,25-triol 1, (1.alfa., 3.beta., 5Z, 7E)-(9CI)
• 1db1
• starbld0021993
• 20-epi-1alpha,25-dihydroxycholecaliferol
• CALCITRIOL [MI]
• CALCITRIOL [INN]
• CALCITRIOL [JAN]
• Spectrum5_002061
• CALCITRIOL [HSDB]
• CALCITRIOL [USAN]
• CALCITRIOL [VANDF]
• 25-dihydroxycholecalciferol
• D0G2KU
• D0T2PL
• CALCITRIOL [MART.]
• SCHEMBL3245
• CALCITRIOL [USP-RS]
• CALCITRIOL [WHO-DD]
• 1alpha,25(OH)2-D3
• BSPBio_001287
• Calcitriol (JAN/USP/INN)
• MLS000759536
• MLS001424122
• BML2-E03
• GTPL2779
• (1S,3R,5Z,7E)-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
• CALCITRIOL [ORANGE BOOK]
• BCBcMAP01_000160
• CHEBI:93988
• CALCITRIOL [EP MONOGRAPH]
• Cas Number 32222-06-3
• GMRQFYUYWCNGIN-NKMMMXOESA-N
• 1alpha,25 dihydroxyvitamin D(3)
• BCPP000304
• CALCITRIOL [USP MONOGRAPH]
• HMS1361A09
• HMS1791A09
• HMS1989A09
• HMS2051F06
• HMS2089N03
• HMS2232D18
• HMS3402A09
• 1 alpha ,25-Dihydroxyvitamin D3
• 5-{2-[1-(5-HYDROXY-1,5-DIMETHYL-HEXYL)-7A-METHYL-OCTAHYDRO-INDEN-4-YLIDENE]-ETHYLIDENE}-4-METHYLENE-CYCLOHEXANE-1,3-DIOL
• EX-A4435
• 1a,25-(OH)2D3
• BDBM50200182
• LMST03020258
• NSC749776
• s1466
• 1-alpha,-1,25-Dihydroxyvitamin D3
• AKOS015961898
• AC-1859
• BCP9000474
• CCG-101001
• CD-2027
• CS-0388
• CS-O-06153
• DB00136
• NC00251
• NSC-749776
• '1,25 DIHYDROXY VITAMIN D3'
• 1,25(OH2)D3
• IDI1_033757
• 1,25(OH)2D3 & CD4
• Calcitriol (1,25-Dihydroxyvitamin D3)
• Calcitrol 100 microg/mL in Acetonitrile
• NCGC00161327-01
• (1R,3S,Z)-5-(2-((1R,3aS,7aR,E)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methyloctahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol
• 1.alpha.,25-Dihydroxyvitamin D(sub 3)
• Calcitriol (chemotherapy-induced alopecia)
• CPD000466393
• HY-10002
• LS-53093
• RO215535
• C3078
• Vitamin D3-1alpha,25-dihydroxy (Calcitriol)
• 1,25D3
• C01673
• D00129
• AB00639957-06
• AB00639957_07
• 1,25-DIHYDROXYCHOLECALCIFEROL, (1ALPHA)-
• 1alpha,25-Dihydroxyvitamin D3, >=99% (HPLC)
• EN300-22411582
• Q139195
• SR-01000759361
• SR-01000946978
• 1alpha,25-Dihydroxyvitamin D3, >=97.0% (HPLC)
• SR-01000759361-4
• SR-01000946978-1
• 1.Alpha.,25-Dihydroxy-26,27-hexadeuterovitamin D3
• BRD-K27316855-001-06-7
• BRD-K27316855-001-19-0
• Calcitriol (chemotherapy-induced alopecia), Cytotech Labs
• (3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trienetriol
• Calcitriol, European Pharmacopoeia (EP) Reference Standard
• Calcitriol (API-31543, drug-induced alopecia), Cytotech Labs
• (1?,3?,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol
• (5Z,10-secocholesta-5,7,10(19)-triene-1.alpha.,3.beta.,25-triol
• 9,10-seco(5Z,7E)-5,7,10(19)-cholestatriene-1alpha, 3beta, 25-triol
• 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, (1.alpha.,3.beta,.5Z,7E)-
• 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, (1.alpha.,3.beta,.5Z,7E)- & CD4
• '5-{2-[1-(5-HYDROXY-1,5-DIMETHYL-HEXYL)-7A-METHYL-OCTAHYDRO-INDEN-4-YLIDENE]-ETHYLIDENE}-4-METHYLENE-CYCLOHEXANE-1,3-DIOL'
• (1R,3S)-5-{2-[(1R,3aS,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexane-1,3-diol
• (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• 1,3-Cyclohexanediol, 4-methylene-5-[2-[(1R,3aS,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-, (1R,3S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9926	99.26%
Caco-2	+	0.5681	56.81%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.9000	90.00%
Subcellular localzation	Lysosomes	0.5400	54.00%
OATP2B1 inhibitior	-	0.8633	86.33%
OATP1B1 inhibitior	+	0.8176	81.76%
OATP1B3 inhibitior	+	0.8460	84.60%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8148	81.48%
P-glycoprotein inhibitior	-	0.5794	57.94%
P-glycoprotein substrate	+	0.5139	51.39%
CYP3A4 substrate	+	0.6241	62.41%
CYP2C9 substrate	-	0.7968	79.68%
CYP2D6 substrate	-	0.7741	77.41%
CYP3A4 inhibition	-	0.8130	81.30%
CYP2C9 inhibition	-	0.8354	83.54%
CYP2C19 inhibition	-	0.7796	77.96%
CYP2D6 inhibition	-	0.9495	94.95%
CYP1A2 inhibition	-	0.9033	90.33%
CYP2C8 inhibition	-	0.6074	60.74%
CYP inhibitory promiscuity	-	0.6175	61.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6277	62.77%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9540	95.40%
Skin irritation	+	0.5235	52.35%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8130	81.30%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.8322	83.22%
skin sensitisation	-	0.6213	62.13%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8805	88.05%
Acute Oral Toxicity (c)	I	0.8580	85.80%
Estrogen receptor binding	+	0.8907	89.07%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.7957	79.57%
Glucocorticoid receptor binding	+	0.6601	66.01%
Aromatase binding	+	0.5906	59.06%
PPAR gamma	+	0.6618	66.18%
Honey bee toxicity	-	0.7891	78.91%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9931	99.31%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4040	P28482	MAP kinase ERK2	25118.9 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	22387.2 nM	Potency	via CMAUP
CHEMBL1977	P11473	Vitamin D receptor	1.13 nM; 0.01 nM; 0.1 nM; 0.35 nM; 1.13 nM; 0.06 nM; 0.08 nM; 1.24 nM; 0.8 nM; 0.7 nM	IC50; EC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	via Super-PRED; via Super-PRED; PMID: 26613420; PMID: 26613420; PMID: 26562542; PMID: 26515040; PMID: 24742174; PMID: 22989379; PMID: 17924616; PMID: 17149880

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.70%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	96.27%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.11%	91.11%
CHEMBL237	P41145	Kappa opioid receptor	94.70%	98.10%
CHEMBL2581	P07339	Cathepsin D	93.33%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.07%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	93.05%	97.79%
CHEMBL3359	P21462	Formyl peptide receptor 1	92.81%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.31%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.79%	94.45%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	90.55%	95.58%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.59%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	89.50%	100.00%
CHEMBL206	P03372	Estrogen receptor alpha	88.42%	97.64%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.18%	90.71%
CHEMBL1902	P62942	FK506-binding protein 1A	87.84%	97.05%
CHEMBL2179	P04062	Beta-glucocerebrosidase	87.68%	85.31%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.39%	82.69%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.24%	92.88%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.52%	100.00%
CHEMBL299	P17252	Protein kinase C alpha	85.85%	98.03%
CHEMBL233	P35372	Mu opioid receptor	85.02%	97.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.90%	100.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.51%	97.47%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	83.81%	94.78%
CHEMBL221	P23219	Cyclooxygenase-1	83.59%	90.17%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.53%	91.03%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.50%	95.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.12%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.92%	95.56%
CHEMBL236	P41143	Delta opioid receptor	81.85%	99.35%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	81.57%	95.00%
CHEMBL238	Q01959	Dopamine transporter	81.54%	95.88%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.92%	89.50%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.77%	99.18%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.66%	93.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.30%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.25%	86.33%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.01%	98.33%

Plants that contains it

• Erycibe expansa
• Solanum glaucophyllum

Cross-Links

• PubChem: 5280453
• NPASS: NPC324772
• ChEMBL: CHEMBL846
• LOTUS: LTS0173185
• wikiData: Q139195