(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol

Details

• Internal ID: 9a52fe63-2ab3-40c8-9107-d586fd922d63
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,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-ol
• SMILES (Canonical): CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)CO
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@]2([C@H]1C3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)CO
• InChI: InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21?,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
• InChI Key: FVWJYYTZTCVBKE-MAIYTPNSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₀O₂
• Molecular Weight: 442.70 g/mol
• Exact Mass: 442.381080833 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 8.30
• Atomic LogP (AlogP): 7.00
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• FVWJYYTZTCVBKE-MAIYTPNSSA-N
• AKOS025402304
• AC-7983
• (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9958	99.58%
Caco-2	-	0.5542	55.42%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.4831	48.31%
OATP2B1 inhibitior	-	0.7184	71.84%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6385	63.85%
BSEP inhibitior	+	0.6370	63.70%
P-glycoprotein inhibitior	-	0.8836	88.36%
P-glycoprotein substrate	-	0.7347	73.47%
CYP3A4 substrate	+	0.6751	67.51%
CYP2C9 substrate	-	0.6284	62.84%
CYP2D6 substrate	-	0.7222	72.22%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9297	92.97%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.4753	47.53%
CYP inhibitory promiscuity	-	0.6441	64.41%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6609	66.09%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9008	90.08%
Skin irritation	-	0.6073	60.73%
Skin corrosion	-	0.9611	96.11%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3617	36.17%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.6442	64.42%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7092	70.92%
Acute Oral Toxicity (c)	III	0.7441	74.41%
Estrogen receptor binding	+	0.8036	80.36%
Androgen receptor binding	+	0.7726	77.26%
Thyroid receptor binding	+	0.6121	61.21%
Glucocorticoid receptor binding	+	0.7877	78.77%
Aromatase binding	+	0.6960	69.60%
PPAR gamma	-	0.4879	48.79%
Honey bee toxicity	-	0.7295	72.95%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9839	98.39%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	3.5 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.61%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.60%	96.09%
CHEMBL233	P35372	Mu opioid receptor	91.49%	97.93%
CHEMBL204	P00734	Thrombin	90.36%	96.01%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.83%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	88.72%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.86%	100.00%
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	87.32%	95.42%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.16%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	86.27%	94.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.40%	92.94%
CHEMBL2581	P07339	Cathepsin D	85.28%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.13%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.06%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.33%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.22%	82.69%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.15%	96.38%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	84.07%	92.86%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.71%	95.50%
CHEMBL4040	P28482	MAP kinase ERK2	82.90%	83.82%
CHEMBL3524	P56524	Histone deacetylase 4	82.51%	92.97%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.50%	91.11%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	80.90%	99.17%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.57%	100.00%
CHEMBL206	P03372	Estrogen receptor alpha	80.52%	97.64%
CHEMBL259	P32245	Melanocortin receptor 4	80.20%	95.38%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	80.11%	96.09%
CHEMBL237	P41145	Kappa opioid receptor	80.10%	98.10%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.00%	85.49%

Plants that contains it

• Anemonoides raddeana
• Aucklandia costus
• Betula pendula subsp. mandshurica
• Chaenomeles sinensis
• Diospyros ebenum
• Diospyros kaki
• Dolomiaea souliei
• Eucommia ulmoides
• Euonymus alatus
• Euphorbia lathyris
• Hypoestes purpurea
• Isatis tinctoria
• Juglans regia
• Platycodon grandiflorus
• Rhodomyrtus tomentosa
• Rosmarinus officinalis
• Sambucus williamsii
• Senegalia mellifera
• Sorbaria kirilowii
• Sparganium stoloniferum
• Vicia faba
• Ziziphus jujuba

Cross-Links

• PubChem: 51340201
• NPASS: NPC95615