(5Z,7E)-(1S,3R)-18-acetoxy-9,10-seco-5,7,10(19)-cholestatriene-1,3-diol

Details

• Internal ID: 6c830152-0a08-455c-bac9-72b931f15299
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Vitamin D and derivatives
• IUPAC Name: [(3R,3aS,7E,7aS)-7-[(2Z)-2-[(3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene]-3-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7a-hexahydro-1H-inden-3a-yl]methyl acetate
• SMILES (Canonical): CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)COC(=O)C
• SMILES (Isomeric): C[C@H](CCCC(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)COC(=O)C
• InChI: InChI=1S/C29H46O4/c1-19(2)8-6-9-20(3)26-13-14-27-23(10-7-15-29(26,27)18-33-22(5)30)11-12-24-16-25(31)17-28(32)21(24)4/h11-12,19-20,25-28,31-32H,4,6-10,13-18H2,1-3,5H3/b23-11+,24-12-/t20-,25-,26-,27+,28+,29+/m1/s1
• InChI Key: PXVFRWYXTUOPCC-JORAJEIRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₆O₄
• Molecular Weight: 458.70 g/mol
• Exact Mass: 458.33960994 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 6.13
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

• 18-acetoxy-1alpha-hydroxyvitamin D3
• 18-acetoxy-1alpha-hydroxyvitamin D3 / 18-acetoxy-1alpha-hydroxycholecalciferol
• LMST03020409
• CHEBI:73906
• 18-acetoxy-1alpha-hydroxycholecalciferol
• Q27144232
• (1S,3R,5Z,7E)-1,3-dihydroxy-9,10-secocholesta-5,7,10-trien-18-yl acetate
• [(3R,3aS,7E,7aS)-7-[(2Z)-2-[(3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene]-3-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7a-hexahydro-1H-inden-3a-yl]methyl acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9791	97.91%
Caco-2	-	0.5851	58.51%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7184	71.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8647	86.47%
OATP1B3 inhibitior	-	0.2443	24.43%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7385	73.85%
BSEP inhibitior	+	0.9495	94.95%
P-glycoprotein inhibitior	+	0.5870	58.70%
P-glycoprotein substrate	+	0.5554	55.54%
CYP3A4 substrate	+	0.6554	65.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8689	86.89%
CYP3A4 inhibition	-	0.8760	87.60%
CYP2C9 inhibition	-	0.7661	76.61%
CYP2C19 inhibition	-	0.8595	85.95%
CYP2D6 inhibition	-	0.9364	93.64%
CYP1A2 inhibition	-	0.8324	83.24%
CYP2C8 inhibition	+	0.4575	45.75%
CYP inhibitory promiscuity	-	0.7864	78.64%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6722	67.22%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9124	91.24%
Skin irritation	+	0.5951	59.51%
Skin corrosion	-	0.9583	95.83%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7005	70.05%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8009	80.09%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.9107	91.07%
Acute Oral Toxicity (c)	I	0.6741	67.41%
Estrogen receptor binding	+	0.8591	85.91%
Androgen receptor binding	+	0.8021	80.21%
Thyroid receptor binding	+	0.5563	55.63%
Glucocorticoid receptor binding	+	0.6552	65.52%
Aromatase binding	+	0.6439	64.39%
PPAR gamma	-	0.4857	48.57%
Honey bee toxicity	-	0.7578	75.78%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6155	61.55%
Fish aquatic toxicity	+	0.9970	99.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1977	P11473	Vitamin D receptor	97.38%	99.43%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.22%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.88%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.48%	94.45%
CHEMBL299	P17252	Protein kinase C alpha	95.35%	98.03%
CHEMBL226	P30542	Adenosine A1 receptor	95.10%	95.93%
CHEMBL2581	P07339	Cathepsin D	94.32%	98.95%
CHEMBL2179	P04062	Beta-glucocerebrosidase	93.16%	85.31%
CHEMBL3359	P21462	Formyl peptide receptor 1	92.10%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.02%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	90.55%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.23%	90.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.84%	82.69%
CHEMBL237	P41145	Kappa opioid receptor	89.75%	98.10%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.41%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	88.55%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.59%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.41%	95.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.32%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.38%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.00%	89.50%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.85%	97.47%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.77%	93.00%
CHEMBL221	P23219	Cyclooxygenase-1	81.57%	90.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.07%	92.62%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.07%	98.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.01%	95.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.94%	98.75%
CHEMBL3837	P07711	Cathepsin L	80.74%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.63%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.55%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.02%	94.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 9547517
• LOTUS: LTS0002738
• wikiData: Q27144232