Turkesterone

Details

• Internal ID: a6f19d99-00ba-41b8-8847-acdaa86d9771
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives
• IUPAC Name: (2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC12CC(C3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O)O
• SMILES (Isomeric): C[C@]12C[C@H]([C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)O
• InChI: InChI=1S/C27H44O8/c1-23(2,33)8-7-21(32)26(5,34)20-6-9-27(35)15-11-16(28)14-10-17(29)18(30)12-24(14,3)22(15)19(31)13-25(20,27)4/h11,14,17-22,29-35H,6-10,12-13H2,1-5H3/t14-,17+,18-,19+,20-,21+,22+,24-,25+,26+,27+/m0/s1
• InChI Key: WSBAGDDNVWTLOM-XHZKDPLLSA-N
• Popularity: 18 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₈
• Molecular Weight: 496.60 g/mol
• Exact Mass: 496.30361836 g/mol
• Topological Polar Surface Area (TPSA): 159.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): 0.82
• H-Bond Acceptor: 8
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• 41451-87-0
• UNII-53E6Z3F8ZG
• 53E6Z3F8ZG
• (2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• 2,3,11,14,20,22,25-Heptahydroxycholestenone
• SCHEMBL140174
• CHEMBL2087140
• (2beta,3beta,5beta,11alpha,22R)-2,3,11,14,20,22,25-Heptahydroxycholest-7-en-6-one
• CHEBI:191170
• WSBAGDDNVWTLOM-XHZKDPLLSA-N
• HY-N2548
• AC-35148
• MS-29224
• CS-0022820
• Q27261101
• (2.BETA.,3.BETA.,5.BETA.,11.ALPHA.,22R)-2,3,11,14,20,22,25-HEPTAHYDROXYCHOLEST-7-EN-6-ONE
• CHOLEST-7-EN-6-ONE, 2,3,11,14,20,22,25-HEPTAHYDROXY-, (2.BETA.,3.BETA.,5.BETA.,11.ALPHA.,22R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	-	0.6147	61.47%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8310	83.10%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.9193	91.93%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6906	69.06%
P-glycoprotein inhibitior	-	0.6003	60.03%
P-glycoprotein substrate	+	0.5582	55.82%
CYP3A4 substrate	+	0.6982	69.82%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8690	86.90%
CYP2C19 inhibition	-	0.8364	83.64%
CYP2D6 inhibition	-	0.9516	95.16%
CYP1A2 inhibition	-	0.9278	92.78%
CYP2C8 inhibition	-	0.6338	63.38%
CYP inhibitory promiscuity	-	0.8761	87.61%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6900	69.00%
Eye corrosion	-	0.9944	99.44%
Eye irritation	-	0.9396	93.96%
Skin irritation	+	0.6543	65.43%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6746	67.46%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5732	57.32%
skin sensitisation	-	0.7034	70.34%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8795	87.95%
Acute Oral Toxicity (c)	III	0.5365	53.65%
Estrogen receptor binding	+	0.7767	77.67%
Androgen receptor binding	+	0.7475	74.75%
Thyroid receptor binding	+	0.5869	58.69%
Glucocorticoid receptor binding	+	0.7623	76.23%
Aromatase binding	+	0.6728	67.28%
PPAR gamma	-	0.5316	53.16%
Honey bee toxicity	-	0.8017	80.17%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9934	99.34%

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	99.08%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.44%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.80%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.71%	97.09%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	94.36%	94.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.61%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.52%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.57%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.07%	82.69%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.59%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.13%	100.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.43%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.97%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.68%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.90%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.65%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.60%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.14%	86.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.12%	93.04%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.17%	90.24%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.03%	96.90%

Plants that contains it

• Ajuga turkestancia
• Blandfordia punicea
• Cyanotis arachnoidea
• Paris polyphylla
• Rhaponticum carthamoides subsp. carthamoides
• Sida spinosa
• Silene linicola
• Vitex canescens
• Vitex pinnata
• Vitex polygama
• Vitex scabra

Cross-Links

• PubChem: 14376672
• NPASS: NPC11710
• ChEMBL: CHEMBL2087140
• LOTUS: LTS0000020
• wikiData: Q4466094