[(1S,2R,4aS,8S,8aR)-5-(3,5-dihydroxy-3-methylpentyl)-8-hydroxy-1-(hydroxymethyl)-1,4a,6-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-2-yl] acetate

Details

• Internal ID: 80b6ebf8-7e8b-414b-bc62-16b06e83def7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(1S,2R,4aS,8S,8aR)-5-(3,5-dihydroxy-3-methylpentyl)-8-hydroxy-1-(hydroxymethyl)-1,4a,6-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-2-yl] acetate
• SMILES (Canonical): CC1=C(C2(CCC(C(C2C(C1=O)O)(C)CO)OC(=O)C)C)CCC(C)(CCO)O
• SMILES (Isomeric): CC1=C([C@]2(CC[C@H]([C@]([C@@H]2[C@@H](C1=O)O)(C)CO)OC(=O)C)C)CCC(C)(CCO)O
• InChI: InChI=1S/C22H36O7/c1-13-15(6-8-20(3,28)10-11-23)21(4)9-7-16(29-14(2)25)22(5,12-24)19(21)18(27)17(13)26/h16,18-19,23-24,27-28H,6-12H2,1-5H3/t16-,18-,19-,20?,21-,22+/m1/s1
• InChI Key: JXTGVDBHDXFAJS-PZYGZVTGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆O₇
• Molecular Weight: 412.50 g/mol
• Exact Mass: 412.24610348 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.51
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9374	93.74%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8329	83.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8520	85.20%
OATP1B3 inhibitior	+	0.8089	80.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5890	58.90%
BSEP inhibitior	-	0.4819	48.19%
P-glycoprotein inhibitior	-	0.6947	69.47%
P-glycoprotein substrate	-	0.6547	65.47%
CYP3A4 substrate	+	0.6804	68.04%
CYP2C9 substrate	-	0.8151	81.51%
CYP2D6 substrate	-	0.9121	91.21%
CYP3A4 inhibition	-	0.8268	82.68%
CYP2C9 inhibition	-	0.8677	86.77%
CYP2C19 inhibition	-	0.8891	88.91%
CYP2D6 inhibition	-	0.9423	94.23%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	-	0.6112	61.12%
CYP inhibitory promiscuity	-	0.9424	94.24%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7207	72.07%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9123	91.23%
Skin irritation	-	0.5216	52.16%
Skin corrosion	-	0.9666	96.66%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4709	47.09%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5842	58.42%
skin sensitisation	-	0.9202	92.02%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5770	57.70%
Acute Oral Toxicity (c)	III	0.6811	68.11%
Estrogen receptor binding	+	0.8577	85.77%
Androgen receptor binding	+	0.6643	66.43%
Thyroid receptor binding	+	0.5635	56.35%
Glucocorticoid receptor binding	+	0.8425	84.25%
Aromatase binding	+	0.6297	62.97%
PPAR gamma	+	0.6778	67.78%
Honey bee toxicity	-	0.8572	85.72%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9814	98.14%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.65%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	95.13%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.19%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.43%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.86%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.41%	97.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.97%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.14%	94.75%
CHEMBL2996	Q05655	Protein kinase C delta	84.98%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.74%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.70%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.86%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.64%	93.04%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.40%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.22%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.91%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.80%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.52%	97.33%
CHEMBL5028	O14672	ADAM10	81.45%	97.50%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.10%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.09%	97.14%

Plants that contains it

• Leonurus macranthus
• Vismia japurensis

Cross-Links

• PubChem: 122187010
• LOTUS: LTS0014913
• wikiData: Q105034587