(4aR,5R,6S,7R,8aR)-7-acetyloxy-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: f03160dc-220d-4add-9d05-8901c9c6842c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (4aR,5R,6S,7R,8aR)-7-acetyloxy-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1C(CC2(C(C1(C)CCC3=COC=C3)CCC=C2C(=O)O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1[C@@H](C[C@@]2([C@@H]([C@@]1(C)CCC3=COC=C3)CCC=C2C(=O)O)C)OC(=O)C
• InChI: InChI=1S/C22H30O5/c1-14-18(27-15(2)23)12-22(4)17(20(24)25)6-5-7-19(22)21(14,3)10-8-16-9-11-26-13-16/h6,9,11,13-14,18-19H,5,7-8,10,12H2,1-4H3,(H,24,25)/t14-,18-,19-,21+,22+/m1/s1
• InChI Key: WVFCUDNKYBYAQX-HRLOXLBDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₅
• Molecular Weight: 374.50 g/mol
• Exact Mass: 374.20932405 g/mol
• Topological Polar Surface Area (TPSA): 76.70 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.62
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9886	98.86%
Caco-2	+	0.6388	63.88%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7442	74.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7678	76.78%
OATP1B3 inhibitior	-	0.3304	33.04%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6021	60.21%
BSEP inhibitior	+	0.7819	78.19%
P-glycoprotein inhibitior	-	0.4560	45.60%
P-glycoprotein substrate	-	0.6341	63.41%
CYP3A4 substrate	+	0.6363	63.63%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	+	0.7273	72.73%
CYP2C9 inhibition	-	0.7925	79.25%
CYP2C19 inhibition	-	0.7298	72.98%
CYP2D6 inhibition	-	0.8949	89.49%
CYP1A2 inhibition	+	0.6205	62.05%
CYP2C8 inhibition	+	0.5298	52.98%
CYP inhibitory promiscuity	-	0.5995	59.95%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6014	60.14%
Eye corrosion	-	0.9955	99.55%
Eye irritation	-	0.9527	95.27%
Skin irritation	+	0.5407	54.07%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7451	74.51%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5338	53.38%
skin sensitisation	-	0.8443	84.43%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6036	60.36%
Acute Oral Toxicity (c)	III	0.6109	61.09%
Estrogen receptor binding	+	0.7558	75.58%
Androgen receptor binding	+	0.5642	56.42%
Thyroid receptor binding	+	0.5904	59.04%
Glucocorticoid receptor binding	+	0.7526	75.26%
Aromatase binding	+	0.6650	66.50%
PPAR gamma	+	0.5280	52.80%
Honey bee toxicity	-	0.7958	79.58%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5950	59.50%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.87%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.84%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.85%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.71%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	92.16%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.79%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.47%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.62%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	86.77%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.57%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.63%	94.80%

Plants that contains it

• Sindora sumatrana

Cross-Links

• PubChem: 162874223
• LOTUS: LTS0055226
• wikiData: Q105313497