Lupa-20(29)-ene-3beta,28-diol 3-(4-hydroxy-cis-cinnamate)

Details

• Internal ID: e77325cc-8e4d-45b7-8634-c41c3e0931ee
• 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] (Z)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)C=CC6=CC=C(C=C6)O)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\C6=CC=C(C=C6)O)C)CO
• InChI: InChI=1S/C39H56O4/c1-25(2)28-16-21-39(24-40)23-22-37(6)29(34(28)39)13-14-31-36(5)19-18-32(35(3,4)30(36)17-20-38(31,37)7)43-33(42)15-10-26-8-11-27(41)12-9-26/h8-12,15,28-32,34,40-41H,1,13-14,16-24H2,2-7H3/b15-10-/t28-,29+,30-,31+,32-,34+,36-,37+,38+,39+/m0/s1
• InChI Key: FKTQBZHKUPHHSC-SDUJRMPFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₆O₄
• Molecular Weight: 588.90 g/mol
• Exact Mass: 588.41786026 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 10.60
• Atomic LogP (AlogP): 8.97
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9934	99.34%
Caco-2	-	0.8153	81.53%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8826	88.26%
OATP2B1 inhibitior	-	0.5678	56.78%
OATP1B1 inhibitior	+	0.8415	84.15%
OATP1B3 inhibitior	-	0.3698	36.98%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7026	70.26%
BSEP inhibitior	+	0.9526	95.26%
P-glycoprotein inhibitior	+	0.6808	68.08%
P-glycoprotein substrate	+	0.5283	52.83%
CYP3A4 substrate	+	0.7239	72.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8761	87.61%
CYP3A4 inhibition	-	0.5705	57.05%
CYP2C9 inhibition	-	0.6272	62.72%
CYP2C19 inhibition	-	0.6696	66.96%
CYP2D6 inhibition	-	0.9120	91.20%
CYP1A2 inhibition	-	0.5160	51.60%
CYP2C8 inhibition	+	0.8695	86.95%
CYP inhibitory promiscuity	-	0.5109	51.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6672	66.72%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.9338	93.38%
Skin irritation	-	0.6346	63.46%
Skin corrosion	-	0.9665	96.65%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8039	80.39%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7794	77.94%
skin sensitisation	-	0.8425	84.25%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7516	75.16%
Acute Oral Toxicity (c)	III	0.6602	66.02%
Estrogen receptor binding	+	0.7513	75.13%
Androgen receptor binding	+	0.8193	81.93%
Thyroid receptor binding	+	0.5373	53.73%
Glucocorticoid receptor binding	+	0.7214	72.14%
Aromatase binding	+	0.7299	72.99%
PPAR gamma	+	0.7422	74.22%
Honey bee toxicity	-	0.7150	71.50%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
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	96.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.59%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.77%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.10%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.41%	95.56%
CHEMBL206	P03372	Estrogen receptor alpha	91.86%	97.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.93%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.74%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.46%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	87.40%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.16%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.77%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.42%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	84.60%	83.82%
CHEMBL2996	Q05655	Protein kinase C delta	84.37%	97.79%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	84.08%	96.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.55%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.83%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.82%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	82.36%	91.19%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.17%	90.93%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.85%	97.28%
CHEMBL233	P35372	Mu opioid receptor	80.80%	97.93%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.52%	89.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.41%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.21%	99.17%

Plants that contains it

• Barbarea verna
• Chaenomeles sinensis
• Chenopodium foliosum
• Diospyros maritima
• Orthocaulis attenuatus
• Scabiosa pyrenaica

Cross-Links

• PubChem: 101756120
• NPASS: NPC127683
• LOTUS: LTS0231777
• wikiData: Q104996786