Clerosterol

Details

• Internal ID: caf59d11-96c3-4c72-b37d-517201e6e094
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Stigmastanes and derivatives
• IUPAC Name: (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-ethyl-6-methylhept-6-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• SMILES (Canonical): CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(=C)C
• SMILES (Isomeric): CC[C@@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(=C)C
• InChI: InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,20-21,23-27,30H,2,7-9,11-18H2,1,3-6H3/t20-,21+,23+,24+,25-,26+,27+,28+,29-/m1/s1
• InChI Key: GHGKPLPBPGYSOO-FBZNIEFRSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₈O
• Molecular Weight: 412.70 g/mol
• Exact Mass: 412.370516150 g/mol
• Topological Polar Surface Area (TPSA): 20.20 Ų
• XlogP: 9.30
• Atomic LogP (AlogP): 7.94
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 2364-23-0
• Poriferasta-5,25-dien-3beta-ol
• NSC 144945
• (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-ethyl-6-methylhept-6-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 5,25-Stigmastadienol
• Stigmasta-5,25-dien-3-ol, (3beta,24S)-
• NSC144945
• 17-(5-Ethyl-6-methylhept-6-en-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-ol
• 17-(5-Ethyl-6-methylhept-6-en-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• SCHEMBL598225
• CHEMBL252365
• CHEBI:166817
• (24s)stigmasta-5,25-dien-3b-ol
• LMST01040124
• AKOS040761517
• 1H-cyclopenta(a)phenanthren-3-ol, 2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-17-(5-ethyl-6-methylhept-6-en-2-yl)-10,13-dimethyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5075	50.75%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Lysosomes	0.6163	61.63%
OATP2B1 inhibitior	-	0.5822	58.22%
OATP1B1 inhibitior	+	0.9278	92.78%
OATP1B3 inhibitior	+	0.9505	95.05%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7994	79.94%
P-glycoprotein inhibitior	-	0.4743	47.43%
P-glycoprotein substrate	+	0.8341	83.41%
CYP3A4 substrate	+	0.7290	72.90%
CYP2C9 substrate	-	0.6499	64.99%
CYP2D6 substrate	-	0.6843	68.43%
CYP3A4 inhibition	-	0.7586	75.86%
CYP2C9 inhibition	-	0.8882	88.82%
CYP2C19 inhibition	-	0.8557	85.57%
CYP2D6 inhibition	-	0.9320	93.20%
CYP1A2 inhibition	-	0.9036	90.36%
CYP2C8 inhibition	+	0.4739	47.39%
CYP inhibitory promiscuity	-	0.6161	61.61%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5687	56.87%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9584	95.84%
Skin irritation	+	0.5204	52.04%
Skin corrosion	-	0.9433	94.33%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6573	65.73%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.6510	65.10%
skin sensitisation	+	0.5547	55.47%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8173	81.73%
Acute Oral Toxicity (c)	I	0.3975	39.75%
Estrogen receptor binding	+	0.8007	80.07%
Androgen receptor binding	+	0.8057	80.57%
Thyroid receptor binding	+	0.6376	63.76%
Glucocorticoid receptor binding	+	0.7709	77.09%
Aromatase binding	+	0.5473	54.73%
PPAR gamma	-	0.5054	50.54%
Honey bee toxicity	-	0.6913	69.13%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9945	99.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.80%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.73%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	95.80%	95.93%
CHEMBL2581	P07339	Cathepsin D	93.46%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.65%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.97%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	91.49%	90.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.21%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.84%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.76%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.79%	97.09%
CHEMBL1871	P10275	Androgen Receptor	86.63%	96.43%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.55%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.60%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.34%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.51%	93.04%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.35%	82.69%

Plants that contains it

• Aegiphila lhotskiana
• Ajuga reptans
• Balanophora harlandii
• Capparis masaikai
• Carthamus tinctorius
• Citrullus lanatus
• Clerodendrum bungei
• Clerodendrum chinense
• Clerodendrum colebrookianum
• Clerodendrum cyrtophyllum
• Clerodendrum indicum
• Clerodendrum mandarinorum
• Clerodendrum nutans
• Clerodendrum splendens
• Coffea racemosa
• Combretum indicum
• Cucurbita maxima
• Dioscorea polystachya
• Eryngium foetidum
• Fritillaria pallidiflora
• Juglans regia
• Kalanchoe daigremontiana
• Kalanchoe marmorata
• Kalanchoe pinnata
• Koelreuteria paniculata
• Laggera alata
• Momordica charantia
• Nectandra pichurim
• Nicotiana tabacum
• Panax quinquefolius
• Phaseolus vulgaris
• Pityrogramma ebenea
• Prunus zippeliana
• Salvia miltiorrhiza
• Stevia rebaudiana
• Strychnos spinosa
• Symphoricarpos albus
• Teucrium fruticans
• Volkameria inermis
• Wrightia tinctoria
• Zea mays

Cross-Links

• PubChem: 5283638
• NPASS: NPC285893
• LOTUS: LTS0190573
• wikiData: Q104253515