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

Details

• Internal ID: 786caf34-d1d7-4d89-ac40-4ced104e2e24
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: [(1S,2R,4aS,5S,8aS)-1-[2-(furan-3-yl)ethyl]-1-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-2-yl] acetate
• SMILES (Canonical): CC(=O)OC1(C(=O)CC2C(CCCC2(C1(CCC3=COC=C3)O)C)(C)CO)C
• SMILES (Isomeric): CC(=O)O[C@]1(C(=O)C[C@H]2[C@@](CCC[C@@]2([C@]1(CCC3=COC=C3)O)C)(C)CO)C
• InChI: InChI=1S/C22H32O6/c1-15(24)28-21(4)18(25)12-17-19(2,14-23)8-5-9-20(17,3)22(21,26)10-6-16-7-11-27-13-16/h7,11,13,17,23,26H,5-6,8-10,12,14H2,1-4H3/t17-,19+,20-,21-,22-/m0/s1
• InChI Key: CJAPKANNYVSMFT-KVEDYDLGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₆
• Molecular Weight: 392.50 g/mol
• Exact Mass: 392.21988874 g/mol
• Topological Polar Surface Area (TPSA): 97.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.04
• H-Bond Acceptor: 6
• 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	+	0.9694	96.94%
Caco-2	+	0.5621	56.21%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7889	78.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3962	39.62%
OATP1B3 inhibitior	+	0.9116	91.16%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6907	69.07%
BSEP inhibitior	+	0.7262	72.62%
P-glycoprotein inhibitior	-	0.5125	51.25%
P-glycoprotein substrate	-	0.6137	61.37%
CYP3A4 substrate	+	0.6607	66.07%
CYP2C9 substrate	-	0.6116	61.16%
CYP2D6 substrate	-	0.8373	83.73%
CYP3A4 inhibition	+	0.6930	69.30%
CYP2C9 inhibition	-	0.7812	78.12%
CYP2C19 inhibition	-	0.8327	83.27%
CYP2D6 inhibition	-	0.9623	96.23%
CYP1A2 inhibition	-	0.7427	74.27%
CYP2C8 inhibition	+	0.6057	60.57%
CYP inhibitory promiscuity	-	0.8805	88.05%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6019	60.19%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.9315	93.15%
Skin irritation	-	0.5633	56.33%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	-	0.6756	67.56%
Human Ether-a-go-go-Related Gene inhibition	+	0.7178	71.78%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5340	53.40%
skin sensitisation	-	0.9560	95.60%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4764	47.64%
Acute Oral Toxicity (c)	III	0.3510	35.10%
Estrogen receptor binding	+	0.7574	75.74%
Androgen receptor binding	+	0.7734	77.34%
Thyroid receptor binding	+	0.5983	59.83%
Glucocorticoid receptor binding	+	0.7480	74.80%
Aromatase binding	+	0.8140	81.40%
PPAR gamma	-	0.5564	55.64%
Honey bee toxicity	-	0.8352	83.52%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5050	50.50%
Fish aquatic toxicity	+	0.9799	97.99%

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	97.75%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.33%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.04%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.21%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.09%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.97%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.85%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.66%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.17%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.26%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.94%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	84.86%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.35%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.83%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.31%	93.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.77%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.61%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.93%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.47%	94.80%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.34%	100.00%

Plants that contains it

• Leonurus cardiaca
• Leonurus persicus

Cross-Links

• PubChem: 10691916
• LOTUS: LTS0155724
• wikiData: Q104960744