(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-[1-(hydroxymethyl)vinyl]-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol

Details

• Internal ID: 8cefbdc0-4e1b-426c-8206-3d04a8a403ae
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1O)C)CCC4C3(CCC5(C4C(CC5)C(=C)CO)CO)C)C)C
• SMILES (Isomeric): C[C@@]12CC[C@]3(CC[C@H]([C@@H]3[C@H]1CC[C@H]4[C@]2(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)C(=C)CO)CO
• InChI: InChI=1S/C30H50O3/c1-19(17-31)20-9-14-30(18-32)16-15-28(5)21(25(20)30)7-8-23-27(4)12-11-24(33)26(2,3)22(27)10-13-29(23,28)6/h20-25,31-33H,1,7-18H2,2-6H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
• InChI Key: XTNACZMKNVUNAA-ROUWMTJPSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₀O₃
• Molecular Weight: 458.70 g/mol
• Exact Mass: 458.37599545 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 7.00
• Atomic LogP (AlogP): 5.97
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 30-Hydroxy-Betulin
• CHEMBL141717
• SCHEMBL13910805
• Lup-20(29)-ene-3beta,28,30-triol
• (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-[1-(hydroxymethyl)vinyl]-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9924	99.24%
Caco-2	-	0.5922	59.22%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5413	54.13%
OATP2B1 inhibitior	-	0.5780	57.80%
OATP1B1 inhibitior	+	0.9358	93.58%
OATP1B3 inhibitior	+	0.9413	94.13%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6134	61.34%
BSEP inhibitior	+	0.5907	59.07%
P-glycoprotein inhibitior	-	0.8250	82.50%
P-glycoprotein substrate	-	0.7555	75.55%
CYP3A4 substrate	+	0.6898	68.98%
CYP2C9 substrate	-	0.6284	62.84%
CYP2D6 substrate	-	0.7222	72.22%
CYP3A4 inhibition	-	0.8138	81.38%
CYP2C9 inhibition	-	0.9041	90.41%
CYP2C19 inhibition	-	0.9093	90.93%
CYP2D6 inhibition	-	0.9257	92.57%
CYP1A2 inhibition	-	0.9419	94.19%
CYP2C8 inhibition	+	0.4767	47.67%
CYP inhibitory promiscuity	-	0.7719	77.19%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6670	66.70%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9210	92.10%
Skin irritation	-	0.6371	63.71%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.7470	74.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3770	37.70%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.7027	70.27%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.4601	46.01%
Acute Oral Toxicity (c)	III	0.6490	64.90%
Estrogen receptor binding	+	0.7700	77.00%
Androgen receptor binding	+	0.7943	79.43%
Thyroid receptor binding	+	0.5853	58.53%
Glucocorticoid receptor binding	+	0.7896	78.96%
Aromatase binding	+	0.7202	72.02%
PPAR gamma	+	0.5705	57.05%
Honey bee toxicity	-	0.7359	73.59%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9852	98.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL204	P00734	Thrombin	97.27%	96.01%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.69%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.46%	96.09%
CHEMBL233	P35372	Mu opioid receptor	89.91%	97.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.48%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.83%	96.38%
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	86.58%	95.42%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.29%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.11%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.97%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	85.86%	97.79%
CHEMBL1937	Q92769	Histone deacetylase 2	85.65%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.63%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.67%	82.69%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	84.66%	85.49%
CHEMBL206	P03372	Estrogen receptor alpha	84.06%	97.64%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.21%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.20%	92.94%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.85%	95.50%
CHEMBL4302	P08183	P-glycoprotein 1	81.75%	92.98%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.94%	95.89%
CHEMBL4040	P28482	MAP kinase ERK2	80.63%	83.82%
CHEMBL2581	P07339	Cathepsin D	80.55%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.25%	96.95%

Plants that contains it

• Gymnosporia cassinoides
• Microtropis fokienensis
• Perrottetia arisanensis

Cross-Links

• PubChem: 473110
• NPASS: NPC119355
• LOTUS: LTS0108358
• wikiData: Q104401484