Penicisteroid H

Details

• Internal ID: ab26144a-751f-48cf-94ec-96f8d54e15a3
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Ergostane steroids > Ergosterols and derivatives
• IUPAC Name: [(3S,5S,6S,7R,8R,9S,10R,13S,14S,16S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,6,7-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl] acetate
• SMILES (Canonical): CC(C)C(C)C=CC(C)C1C(CC2C1(CCC3C2C(C(C4C3(CCC(C4)O)C)O)O)C)OC(=O)C
• SMILES (Isomeric): C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1[C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H]([C@H]([C@@H]4[C@@]3(CC[C@@H](C4)O)C)O)O)C)OC(=O)C
• InChI: InChI=1S/C30H50O5/c1-16(2)17(3)8-9-18(4)26-24(35-19(5)31)15-22-25-21(11-13-30(22,26)7)29(6)12-10-20(32)14-23(29)27(33)28(25)34/h8-9,16-18,20-28,32-34H,10-15H2,1-7H3/b9-8+/t17-,18+,20-,21-,22-,23+,24-,25+,26-,27-,28+,29+,30-/m0/s1
• InChI Key: XGCBEJNSJGKYKN-WIJDSFKRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₀O₅
• Molecular Weight: 490.70 g/mol
• Exact Mass: 490.36582469 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 4.97
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• [(3S,5S,6S,7R,8R,9S,10R,13S,14S,16S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,6,7-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl] acetate
• ((3S,5S,6S,7R,8R,9S,10R,13S,14S,16S,17R)-17-((E,2R,5R)-5,6-dimethylhept-3-en-2-yl)-3,6,7-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-16-yl) acetate
• RefChem:171028
• 16beta-acetoxy-5alpha-ergosta-22E-en-3beta,,6beta,7beta,triol
• 16beta-acetoxy-3beta,,6beta,7beta-trihydroxy-5alpha-ergost-22E-ene
• CHEBI:207871

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9838	98.38%
Caco-2	-	0.6826	68.26%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8371	83.71%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	+	0.8694	86.94%
OATP1B3 inhibitior	+	0.8384	83.84%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8571	85.71%
BSEP inhibitior	+	0.6843	68.43%
P-glycoprotein inhibitior	-	0.5071	50.71%
P-glycoprotein substrate	-	0.6410	64.10%
CYP3A4 substrate	+	0.7242	72.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8624	86.24%
CYP3A4 inhibition	-	0.8082	80.82%
CYP2C9 inhibition	-	0.8794	87.94%
CYP2C19 inhibition	-	0.7983	79.83%
CYP2D6 inhibition	-	0.9652	96.52%
CYP1A2 inhibition	-	0.7636	76.36%
CYP2C8 inhibition	-	0.5650	56.50%
CYP inhibitory promiscuity	-	0.9619	96.19%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6769	67.69%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.9585	95.85%
Skin irritation	+	0.6491	64.91%
Skin corrosion	-	0.9436	94.36%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6771	67.71%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.6412	64.12%
skin sensitisation	-	0.7436	74.36%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.5568	55.68%
Acute Oral Toxicity (c)	III	0.5187	51.87%
Estrogen receptor binding	+	0.7357	73.57%
Androgen receptor binding	+	0.5830	58.30%
Thyroid receptor binding	-	0.5135	51.35%
Glucocorticoid receptor binding	+	0.5645	56.45%
Aromatase binding	+	0.5524	55.24%
PPAR gamma	+	0.5746	57.46%
Honey bee toxicity	-	0.5832	58.32%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9946	99.46%

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	95.90%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.98%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	94.30%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.38%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.39%	91.11%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.86%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	90.11%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.39%	85.14%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	89.34%	95.71%
CHEMBL2179	P04062	Beta-glucocerebrosidase	89.28%	85.31%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.16%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.99%	97.25%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.95%	98.75%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	87.35%	97.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.26%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.63%	97.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.49%	96.38%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.82%	91.07%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.10%	94.23%
CHEMBL2581	P07339	Cathepsin D	84.92%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.49%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.07%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.48%	89.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.47%	91.03%
CHEMBL5028	O14672	ADAM10	82.66%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.18%	91.19%
CHEMBL238	Q01959	Dopamine transporter	81.75%	95.88%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.75%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.30%	100.00%
CHEMBL2535	P11166	Glucose transporter	80.98%	98.75%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 146682904
• LOTUS: LTS0104307
• wikiData: Q105327492