(5S,8R,9S,10R,13R,14S,16S,17R)-16-hydroxy-17-[(E,2S,5R)-2-hydroxy-5,6-dimethylhept-3-en-2-yl]-13-(hydroxymethyl)-10-methyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

Details

• Internal ID: d5bf6597-49a9-40a9-9e76-8997aa033bf6
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Ergostane steroids > Ergosterols and derivatives
• IUPAC Name: (5S,8R,9S,10R,13R,14S,16S,17R)-16-hydroxy-17-[(E,2S,5R)-2-hydroxy-5,6-dimethylhept-3-en-2-yl]-13-(hydroxymethyl)-10-methyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• SMILES (Canonical): CC(C)C(C)C=CC(C)(C1C(CC2C1(CCC3C2CCC4C3(C=CC(=O)C4)C)CO)O)O
• SMILES (Isomeric): C[C@@H](/C=C/[C@@](C)([C@H]1[C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(C=CC(=O)C4)C)CO)O)O)C(C)C
• InChI: InChI=1S/C28H44O4/c1-17(2)18(3)8-12-27(5,32)25-24(31)15-23-21-7-6-19-14-20(30)9-11-26(19,4)22(21)10-13-28(23,25)16-29/h8-9,11-12,17-19,21-25,29,31-32H,6-7,10,13-16H2,1-5H3/b12-8+/t18-,19-,21+,22-,23-,24-,25+,26-,27-,28+/m0/s1
• InChI Key: NYXIHJMIRFLNCA-LDGOKLABSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₄O₄
• Molecular Weight: 444.60 g/mol
• Exact Mass: 444.32395988 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.53
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9869	98.69%
Caco-2	-	0.7115	71.15%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7404	74.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8254	82.54%
OATP1B3 inhibitior	+	0.9176	91.76%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6663	66.63%
BSEP inhibitior	+	0.8527	85.27%
P-glycoprotein inhibitior	-	0.5964	59.64%
P-glycoprotein substrate	+	0.5298	52.98%
CYP3A4 substrate	+	0.7268	72.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8883	88.83%
CYP3A4 inhibition	-	0.8802	88.02%
CYP2C9 inhibition	-	0.8180	81.80%
CYP2C19 inhibition	-	0.8805	88.05%
CYP2D6 inhibition	-	0.9465	94.65%
CYP1A2 inhibition	-	0.8354	83.54%
CYP2C8 inhibition	+	0.4544	45.44%
CYP inhibitory promiscuity	-	0.8594	85.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7345	73.45%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9682	96.82%
Skin irritation	-	0.5675	56.75%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	-	0.8148	81.48%
Human Ether-a-go-go-Related Gene inhibition	-	0.3928	39.28%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.5485	54.85%
skin sensitisation	-	0.8420	84.20%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7695	76.95%
Acute Oral Toxicity (c)	III	0.5819	58.19%
Estrogen receptor binding	+	0.8678	86.78%
Androgen receptor binding	+	0.7585	75.85%
Thyroid receptor binding	+	0.6173	61.73%
Glucocorticoid receptor binding	+	0.7028	70.28%
Aromatase binding	+	0.6311	63.11%
PPAR gamma	+	0.5573	55.73%
Honey bee toxicity	-	0.6799	67.99%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9453	94.53%

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	98.97%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.96%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.54%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.45%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	93.85%	97.79%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.17%	82.69%
CHEMBL299	P17252	Protein kinase C alpha	92.99%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.51%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.21%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	91.47%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.53%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.99%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.87%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.46%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.34%	91.07%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.08%	93.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.91%	96.77%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.00%	97.14%
CHEMBL1902	P62942	FK506-binding protein 1A	83.45%	97.05%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.67%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.58%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.07%	89.00%

Plants that contains it

• Acorus calamus
• Pluchea dioscoridis
• Taiwania cryptomerioides

Cross-Links

• PubChem: 163025135
• LOTUS: LTS0254923
• wikiData: Q105345830