Cholesta-8(14)-ene-3beta,5alpha,6alpha,25-tetraol

Details

• Internal ID: b34d9965-5e49-4f25-bdb5-2d07688a03dd
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cholestane steroids > Cholesterols and derivatives
• IUPAC Name: (3S,5R,6S,9S,10R,13R,17R)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,6,7,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,5,6-triol
• SMILES (Canonical): CC(CCCC(C)(C)O)C1CCC2=C3CC(C4(CC(CCC4(C3CCC12C)C)O)O)O
• SMILES (Isomeric): C[C@H](CCCC(C)(C)O)[C@H]1CCC2=C3C[C@@H]([C@]4(C[C@H](CC[C@@]4([C@H]3CC[C@]12C)C)O)O)O
• InChI: InChI=1S/C27H46O4/c1-17(7-6-12-24(2,3)30)20-8-9-21-19-15-23(29)27(31)16-18(28)10-14-26(27,5)22(19)11-13-25(20,21)4/h17-18,20,22-23,28-31H,6-16H2,1-5H3/t17-,18+,20-,22+,23+,25-,26-,27+/m1/s1
• InChI Key: CMHZEZSZYMDGID-PDEFXIAYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₆O₄
• Molecular Weight: 434.70 g/mol
• Exact Mass: 434.33960994 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.73
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9818	98.18%
Caco-2	-	0.5201	52.01%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6239	62.39%
OATP2B1 inhibitior	-	0.5827	58.27%
OATP1B1 inhibitior	+	0.8509	85.09%
OATP1B3 inhibitior	+	0.9099	90.99%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6196	61.96%
P-glycoprotein inhibitior	-	0.6876	68.76%
P-glycoprotein substrate	+	0.6013	60.13%
CYP3A4 substrate	+	0.6699	66.99%
CYP2C9 substrate	-	0.5858	58.58%
CYP2D6 substrate	-	0.7545	75.45%
CYP3A4 inhibition	-	0.8827	88.27%
CYP2C9 inhibition	-	0.8512	85.12%
CYP2C19 inhibition	-	0.7611	76.11%
CYP2D6 inhibition	-	0.9461	94.61%
CYP1A2 inhibition	-	0.8996	89.96%
CYP2C8 inhibition	-	0.5906	59.06%
CYP inhibitory promiscuity	-	0.8451	84.51%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6779	67.79%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9404	94.04%
Skin irritation	+	0.5700	57.00%
Skin corrosion	-	0.9365	93.65%
Ames mutagenesis	-	0.6974	69.74%
Human Ether-a-go-go-Related Gene inhibition	-	0.4107	41.07%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.6758	67.58%
skin sensitisation	-	0.7633	76.33%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8151	81.51%
Acute Oral Toxicity (c)	I	0.6181	61.81%
Estrogen receptor binding	+	0.7968	79.68%
Androgen receptor binding	+	0.7879	78.79%
Thyroid receptor binding	+	0.6550	65.50%
Glucocorticoid receptor binding	+	0.7850	78.50%
Aromatase binding	+	0.6656	66.56%
PPAR gamma	-	0.5299	52.99%
Honey bee toxicity	-	0.8251	82.51%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9872	98.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.94%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.61%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.23%	95.93%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	93.84%	89.05%
CHEMBL2581	P07339	Cathepsin D	93.18%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.68%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	90.30%	97.79%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.39%	93.56%
CHEMBL1977	P11473	Vitamin D receptor	89.34%	99.43%
CHEMBL2094135	Q96BI3	Gamma-secretase	89.26%	98.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.06%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.97%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.97%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.44%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.88%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.30%	100.00%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	84.85%	94.78%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.57%	95.89%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.77%	85.31%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	83.69%	95.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.46%	90.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.74%	97.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.79%	82.69%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.25%	92.62%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.34%	95.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.04%	93.04%

Plants that contains it

• Achillea leptophylla
• Aldama cordifolia
• Cordiera macrophylla
• Dioscorea futschauensis
• Dorstenia barnimiana
• Petrosedum forsterianum
• Rubia yunnanensis
• Uvaria mocoli
• Verbascum georgicum
• Zieria chevalieri

Cross-Links

• PubChem: 11640639
• NPASS: NPC42700
• LOTUS: LTS0046468
• wikiData: Q104964596