2-[(4aS,4bS,8aS,10aR)-4b,8,8-trimethyl-1-methylidene-4-oxo-4a,5,6,7,8a,9,10,10a-octahydrophenanthren-2-yl]ethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: d24ce4e6-1c89-432d-9263-4f49221ed9ed
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(4aS,4bS,8aS,10aR)-4b,8,8-trimethyl-1-methylidene-4-oxo-4a,5,6,7,8a,9,10,10a-octahydrophenanthren-2-yl]ethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1(CCCC2(C1CCC3C2C(=O)C=C(C3=C)CCOC(=O)C=CC4=CC(=C(C=C4)O)O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CC[C@@H]3[C@@H]2C(=O)C=C(C3=C)CCOC(=O)/C=C/C4=CC(=C(C=C4)O)O)(C)C
• InChI: InChI=1S/C29H36O5/c1-18-20(12-15-34-26(33)11-7-19-6-9-22(30)23(31)16-19)17-24(32)27-21(18)8-10-25-28(2,3)13-5-14-29(25,27)4/h6-7,9,11,16-17,21,25,27,30-31H,1,5,8,10,12-15H2,2-4H3/b11-7+/t21-,25-,27+,29-/m0/s1
• InChI Key: NUXCVQJWVRCNMX-CYELNHJYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₅
• Molecular Weight: 464.60 g/mol
• Exact Mass: 464.25627424 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 5.97
• H-Bond Acceptor: 5
• 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	+	0.9862	98.62%
Caco-2	-	0.7721	77.21%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.9157	91.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8354	83.54%
OATP1B3 inhibitior	+	0.8102	81.02%
MATE1 inhibitior	-	0.5200	52.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9901	99.01%
P-glycoprotein inhibitior	+	0.7434	74.34%
P-glycoprotein substrate	-	0.6686	66.86%
CYP3A4 substrate	+	0.6945	69.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8902	89.02%
CYP3A4 inhibition	-	0.6470	64.70%
CYP2C9 inhibition	-	0.6360	63.60%
CYP2C19 inhibition	-	0.5758	57.58%
CYP2D6 inhibition	-	0.8906	89.06%
CYP1A2 inhibition	+	0.6077	60.77%
CYP2C8 inhibition	+	0.8296	82.96%
CYP inhibitory promiscuity	-	0.8309	83.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6752	67.52%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9480	94.80%
Skin irritation	-	0.7080	70.80%
Skin corrosion	-	0.9627	96.27%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4550	45.50%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5967	59.67%
skin sensitisation	-	0.7392	73.92%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.9215	92.15%
Acute Oral Toxicity (c)	III	0.6095	60.95%
Estrogen receptor binding	+	0.7432	74.32%
Androgen receptor binding	+	0.8599	85.99%
Thyroid receptor binding	+	0.5682	56.82%
Glucocorticoid receptor binding	+	0.7321	73.21%
Aromatase binding	+	0.7147	71.47%
PPAR gamma	+	0.6280	62.80%
Honey bee toxicity	-	0.7743	77.43%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
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	99.75%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.87%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	97.38%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.27%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.32%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.57%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.22%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	92.99%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.48%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.88%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.23%	89.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.10%	96.38%
CHEMBL1929	P47989	Xanthine dehydrogenase	89.32%	96.12%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.24%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.13%	90.71%
CHEMBL3194	P02766	Transthyretin	87.28%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.03%	92.94%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.73%	94.62%
CHEMBL4208	P20618	Proteasome component C5	83.40%	90.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.67%	91.07%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.91%	97.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.66%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.20%	92.62%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.17%	94.00%

Plants that contains it

• Guilandina volkensii

Cross-Links

• PubChem: 71615304
• NPASS: NPC471152
• ChEMBL: CHEMBL2381685