(5beta,9alpha,10alpha,13S)-15-[(3,4-Dihydroxy-trans-cinnamoyl)oxy]labd-8(20)-en-19-oic acid

Details

• Internal ID: f5a82899-0003-4269-9154-3921fc6e4411
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,4aS,5R,8aS)-5-[(3S)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-methylpentyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC(CCC1C(=C)CCC2C1(CCCC2(C)C(=O)O)C)CCOC(=O)C=CC3=CC(=C(C=C3)O)O
• SMILES (Isomeric): C[C@@H](CC[C@@H]1C(=C)CC[C@H]2[C@]1(CCC[C@]2(C)C(=O)O)C)CCOC(=O)/C=C/C3=CC(=C(C=C3)O)O
• InChI: InChI=1S/C29H40O6/c1-19(14-17-35-26(32)13-9-21-8-11-23(30)24(31)18-21)6-10-22-20(2)7-12-25-28(22,3)15-5-16-29(25,4)27(33)34/h8-9,11,13,18-19,22,25,30-31H,2,5-7,10,12,14-17H2,1,3-4H3,(H,33,34)/b13-9+/t19-,22+,25-,28-,29-/m0/s1
• InChI Key: SLUZPAKLAPWHGG-LHLWPZQGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₀O₆
• Molecular Weight: 484.60 g/mol
• Exact Mass: 484.28248899 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 6.80
• Atomic LogP (AlogP): 6.32
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9782	97.82%
Caco-2	-	0.7512	75.12%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.9062	90.62%
OATP2B1 inhibitior	-	0.5716	57.16%
OATP1B1 inhibitior	+	0.8623	86.23%
OATP1B3 inhibitior	+	0.7891	78.91%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.7276	72.76%
BSEP inhibitior	+	0.9768	97.68%
P-glycoprotein inhibitior	+	0.6537	65.37%
P-glycoprotein substrate	-	0.5686	56.86%
CYP3A4 substrate	+	0.6786	67.86%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8847	88.47%
CYP3A4 inhibition	-	0.6664	66.64%
CYP2C9 inhibition	-	0.7384	73.84%
CYP2C19 inhibition	-	0.6561	65.61%
CYP2D6 inhibition	-	0.9151	91.51%
CYP1A2 inhibition	+	0.6719	67.19%
CYP2C8 inhibition	+	0.6730	67.30%
CYP inhibitory promiscuity	-	0.8462	84.62%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6832	68.32%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9321	93.21%
Skin irritation	-	0.6459	64.59%
Skin corrosion	-	0.9590	95.90%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6723	67.23%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6389	63.89%
skin sensitisation	-	0.8479	84.79%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8912	89.12%
Acute Oral Toxicity (c)	III	0.5794	57.94%
Estrogen receptor binding	+	0.7624	76.24%
Androgen receptor binding	+	0.8259	82.59%
Thyroid receptor binding	+	0.6435	64.35%
Glucocorticoid receptor binding	+	0.7243	72.43%
Aromatase binding	+	0.6461	64.61%
PPAR gamma	+	0.6251	62.51%
Honey bee toxicity	-	0.8225	82.25%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
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
CHEMBL1951	P21397	Monoamine oxidase A	99.47%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.16%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.35%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	95.00%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.01%	86.33%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.95%	96.38%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.28%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.47%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.94%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.80%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.44%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.83%	96.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.42%	91.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.96%	89.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.86%	94.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.85%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.02%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.28%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.95%	100.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.21%	99.15%
CHEMBL340	P08684	Cytochrome P450 3A4	80.83%	91.19%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.60%	91.03%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.00%	89.62%

Plants that contains it

• Nuxia sphaerocephala

Cross-Links

• PubChem: 11648747
• LOTUS: LTS0250062
• wikiData: Q105255658