(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Details

• Internal ID: a7d86598-22ba-4f1e-9981-fbcb109d5c7a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)COC(=O)C=CC6=CC=C(C=C6)O)O)C)C)C2C1)C)C(=O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)COC(=O)C=CC6=CC=C(C=C6)O)O
• InChI: InChI=1S/C39H54O6/c1-34(2)19-21-39(33(43)44)22-20-37(5)27(28(39)23-34)12-13-30-35(3)17-16-31(41)36(4,29(35)15-18-38(30,37)6)24-45-32(42)14-9-25-7-10-26(40)11-8-25/h7-12,14,28-31,40-41H,13,15-24H2,1-6H3,(H,43,44)/t28-,29+,30+,31-,35-,36-,37+,38+,39-/m0/s1
• InChI Key: APFPLZLTXJYXMM-KRAILMGQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₄O₆
• Molecular Weight: 618.80 g/mol
• Exact Mass: 618.39203944 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 8.60
• Atomic LogP (AlogP): 8.18
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	-	0.8068	80.68%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.9219	92.19%
OATP2B1 inhibitior	+	0.5693	56.93%
OATP1B1 inhibitior	+	0.8141	81.41%
OATP1B3 inhibitior	-	0.2870	28.70%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7433	74.33%
BSEP inhibitior	+	0.9821	98.21%
P-glycoprotein inhibitior	+	0.7645	76.45%
P-glycoprotein substrate	-	0.6083	60.83%
CYP3A4 substrate	+	0.7083	70.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8772	87.72%
CYP3A4 inhibition	-	0.7098	70.98%
CYP2C9 inhibition	-	0.6507	65.07%
CYP2C19 inhibition	-	0.7010	70.10%
CYP2D6 inhibition	-	0.9318	93.18%
CYP1A2 inhibition	+	0.5705	57.05%
CYP2C8 inhibition	+	0.8295	82.95%
CYP inhibitory promiscuity	-	0.7985	79.85%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6536	65.36%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.9263	92.63%
Skin irritation	-	0.6171	61.71%
Skin corrosion	-	0.9663	96.63%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7710	77.10%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8273	82.73%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6886	68.86%
Acute Oral Toxicity (c)	III	0.4109	41.09%
Estrogen receptor binding	+	0.7982	79.82%
Androgen receptor binding	+	0.7777	77.77%
Thyroid receptor binding	+	0.5683	56.83%
Glucocorticoid receptor binding	+	0.8143	81.43%
Aromatase binding	+	0.7042	70.42%
PPAR gamma	+	0.7253	72.53%
Honey bee toxicity	-	0.7966	79.66%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	96.40%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.28%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.69%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.41%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.37%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.85%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.59%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.21%	96.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	89.84%	85.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.75%	95.89%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.16%	91.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.12%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.71%	93.00%
CHEMBL206	P03372	Estrogen receptor alpha	83.55%	97.64%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.09%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.44%	100.00%

Plants that contains it

• Bryonia cretica
• Citrullus colocynthis
• Citrullus lanatus
• Iberis amara
• Ludwigia octovalvis

Cross-Links

• PubChem: 162976962
• LOTUS: LTS0027951
• wikiData: Q105152208