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

Details

• Internal ID: 2b0f450c-3aab-48a7-8475-e2ee6cd89841
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate
• SMILES (Canonical): CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)C)C)CO
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)C)C)CO
• InChI: InChI=1S/C32H52O3/c1-20(2)22-11-16-32(19-33)18-17-30(7)23(27(22)32)9-10-25-29(6)14-13-26(35-21(3)34)28(4,5)24(29)12-15-31(25,30)8/h22-27,33H,1,9-19H2,2-8H3/t22-,23+,24-,25+,26-,27+,29-,30+,31+,32+/m0/s1
• InChI Key: XUDTWJGGQFHXCR-VFUWXHBOSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₅₂O₃
• Molecular Weight: 484.80 g/mol
• Exact Mass: 484.39164552 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 8.90
• Atomic LogP (AlogP): 7.57
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 3-Acetylbetulin
• Betulin 3-acetate
• Betulin-3-acetate
• [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate
• 3-O-Acetylbetulin
• Betulin monoacetate
• SCHEMBL214200
• CHEMBL1087415
• DTXSID801339991
• MFCD08459609
• PD143238
• Lup-20(29)-ene-3.beta.,28-diol, 3-acetate
• Lup-20(29)-ene-3,28-diol, 3-acetate, (3.beta.)-
• (5S,17S,1R,2R,8R,14R)-5-(Hydroxymethyl)-1,2,14,18,18-pentamethyl-8-(1-methylvinyl)pentacyclo[11.8.0.0<2,10>.0<5,9>.0<14,19>]henicos-17-yl acetate
• [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-1-isopropenyl-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-yl] acetate
• [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	-	0.6537	65.37%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8480	84.80%
OATP2B1 inhibitior	-	0.7095	70.95%
OATP1B1 inhibitior	+	0.8862	88.62%
OATP1B3 inhibitior	-	0.2197	21.97%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.5977	59.77%
P-glycoprotein inhibitior	-	0.6284	62.84%
P-glycoprotein substrate	-	0.7089	70.89%
CYP3A4 substrate	+	0.7069	70.69%
CYP2C9 substrate	-	0.8092	80.92%
CYP2D6 substrate	-	0.8657	86.57%
CYP3A4 inhibition	-	0.7454	74.54%
CYP2C9 inhibition	-	0.6358	63.58%
CYP2C19 inhibition	-	0.7739	77.39%
CYP2D6 inhibition	-	0.9363	93.63%
CYP1A2 inhibition	-	0.8497	84.97%
CYP2C8 inhibition	+	0.6004	60.04%
CYP inhibitory promiscuity	-	0.7104	71.04%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5959	59.59%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.8837	88.37%
Skin irritation	-	0.5585	55.85%
Skin corrosion	-	0.9698	96.98%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3933	39.33%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.8473	84.73%
skin sensitisation	-	0.7643	76.43%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.4544	45.44%
Acute Oral Toxicity (c)	III	0.7787	77.87%
Estrogen receptor binding	+	0.7404	74.04%
Androgen receptor binding	+	0.7634	76.34%
Thyroid receptor binding	+	0.5397	53.97%
Glucocorticoid receptor binding	+	0.7122	71.22%
Aromatase binding	+	0.7032	70.32%
PPAR gamma	+	0.6239	62.39%
Honey bee toxicity	-	0.6898	68.98%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9972	99.72%

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	97.41%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.48%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.50%	97.25%
CHEMBL233	P35372	Mu opioid receptor	89.30%	97.93%
CHEMBL340	P08684	Cytochrome P450 3A4	88.50%	91.19%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.24%	96.61%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	87.30%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.24%	82.69%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.78%	96.95%
CHEMBL2581	P07339	Cathepsin D	85.55%	98.95%
CHEMBL204	P00734	Thrombin	85.37%	96.01%
CHEMBL4040	P28482	MAP kinase ERK2	84.33%	83.82%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.30%	92.94%
CHEMBL2996	Q05655	Protein kinase C delta	84.17%	97.79%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.92%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.52%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.00%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.98%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.87%	91.11%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.40%	95.50%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.35%	96.38%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.04%	82.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.98%	95.89%
CHEMBL202	P00374	Dihydrofolate reductase	81.47%	89.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.24%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.75%	94.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.56%	93.04%

Plants that contains it

• Acacia sparsiflora
• Achyranthes bidentata
• Agave shawii
• Ambrosia grayi
• Astrantia major
• Camellia sasanqua
• Carpinus cordata
• Cassia javanica subsp. agnes
• Convallaria keiskei
• Diospyros maritima
• Dirca occidentalis
• Dolichandrone atrovirens
• Drypetes littoralis
• Edgeworthia gardneri
• Eucalyptus regnans
• Euphorbia iberica
• Grindelia hirsutula
• Helicteres angustifolia
• Hopea jucunda
• Khaya grandifoliola
• Plumbago pulchella
• Plumeria alba
• Polygala ruwenzoriensis
• Rhododendron formosanum
• Rhodomyrtus tomentosa
• Rumex conglomeratus
• Senecio glaucus subsp. coronopifolius
• Silene vulgaris
• Syzygium jambos
• Tainia latifolia
• Thesium humile
• Tilia europaea
• Xenophyllum decorum

Cross-Links

• PubChem: 479957
• NPASS: NPC5280
• ChEMBL: CHEMBL1087415
• LOTUS: LTS0145696
• wikiData: Q105342148