(1R,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2-(hydroxymethyl)-10-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-1,6a,6b,9,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

Details

• Internal ID: c2d8a7bb-c6e7-44d7-ba56-253b761703ff
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2-(hydroxymethyl)-10-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-1,6a,6b,9,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• SMILES (Canonical): CC1C(CCC2(C1C3=CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)C=CC6=CC=C(C=C6)O)C)C(=O)O)CO
• SMILES (Isomeric): C[C@H]1[C@@H](CC[C@]2([C@@H]1C3=CC[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/C6=CC=C(C=C6)O)C)C(=O)O)CO
• InChI: InChI=1S/C39H54O6/c1-24-26(23-40)15-20-39(34(43)44)22-21-37(5)28(33(24)39)12-13-30-36(4)18-17-31(35(2,3)29(36)16-19-38(30,37)6)45-32(42)14-9-25-7-10-27(41)11-8-25/h7-12,14,24,26,29-31,33,40-41H,13,15-23H2,1-6H3,(H,43,44)/b14-9+/t24-,26-,29-,30+,31-,33-,36-,37+,38+,39-/m0/s1
• InChI Key: WENIKWFUTBDGAV-BFDBMYDBSA-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: 8.20
• Atomic LogP (AlogP): 8.03
• 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	+	0.9935	99.35%
Caco-2	-	0.8191	81.91%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.9351	93.51%
OATP2B1 inhibitior	-	0.5719	57.19%
OATP1B1 inhibitior	+	0.7334	73.34%
OATP1B3 inhibitior	-	0.5163	51.63%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6391	63.91%
BSEP inhibitior	+	0.9638	96.38%
P-glycoprotein inhibitior	+	0.7738	77.38%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7075	70.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8863	88.63%
CYP3A4 inhibition	-	0.5793	57.93%
CYP2C9 inhibition	-	0.6964	69.64%
CYP2C19 inhibition	-	0.7471	74.71%
CYP2D6 inhibition	-	0.9171	91.71%
CYP1A2 inhibition	+	0.5253	52.53%
CYP2C8 inhibition	+	0.8675	86.75%
CYP inhibitory promiscuity	-	0.6504	65.04%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6874	68.74%
Eye corrosion	-	0.9944	99.44%
Eye irritation	-	0.9354	93.54%
Skin irritation	-	0.6676	66.76%
Skin corrosion	-	0.9711	97.11%
Ames mutagenesis	-	0.7470	74.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3886	38.86%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7059	70.59%
skin sensitisation	-	0.8403	84.03%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6576	65.76%
Acute Oral Toxicity (c)	III	0.7446	74.46%
Estrogen receptor binding	+	0.7778	77.78%
Androgen receptor binding	+	0.7906	79.06%
Thyroid receptor binding	+	0.5455	54.55%
Glucocorticoid receptor binding	+	0.8380	83.80%
Aromatase binding	+	0.7260	72.60%
PPAR gamma	+	0.7556	75.56%
Honey bee toxicity	-	0.7640	76.40%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5445	54.45%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.90%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.04%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.51%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.43%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.15%	86.33%
CHEMBL206	P03372	Estrogen receptor alpha	93.42%	97.64%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.10%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.47%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.31%	98.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.26%	91.71%
CHEMBL242	Q92731	Estrogen receptor beta	86.44%	98.35%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.22%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.72%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.00%	91.19%
CHEMBL1937	Q92769	Histone deacetylase 2	82.64%	94.75%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.39%	93.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.08%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.00%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.71%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.56%	95.89%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.33%	89.67%

Plants that contains it

• Rubia cordifolia
• Sphaeranthus suaveolens

Cross-Links

• PubChem: 20056275
• LOTUS: LTS0151908
• wikiData: Q105347396