Hardwickic acid methyl ester

Details

• Internal ID: ef68f089-f5dd-4def-a270-d6be1d8dfade
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: methyl (4aR,5S,6R,8aR)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC3=COC=C3)CCC=C2C(=O)OC)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CCC3=COC=C3)CCC=C2C(=O)OC)C
• InChI: InChI=1S/C21H30O3/c1-15-8-11-21(3)17(19(22)23-4)6-5-7-18(21)20(15,2)12-9-16-10-13-24-14-16/h6,10,13-15,18H,5,7-9,11-12H2,1-4H3/t15-,18-,20+,21+/m1/s1
• InChI Key: QDSWHJNTSPBQME-NXXWWENFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.50 g/mol
• Exact Mass: 330.21949481 g/mol
• Topological Polar Surface Area (TPSA): 39.40 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 5.16
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• CHEMBL483650

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.8758	87.58%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Plasma membrane	0.4771	47.71%
OATP2B1 inhibitior	-	0.8665	86.65%
OATP1B1 inhibitior	+	0.7203	72.03%
OATP1B3 inhibitior	+	0.8922	89.22%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.7468	74.68%
P-glycoprotein inhibitior	-	0.4807	48.07%
P-glycoprotein substrate	-	0.6477	64.77%
CYP3A4 substrate	+	0.6720	67.20%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.5994	59.94%
CYP2C19 inhibition	+	0.6175	61.75%
CYP2D6 inhibition	-	0.8873	88.73%
CYP1A2 inhibition	+	0.5188	51.88%
CYP2C8 inhibition	+	0.6979	69.79%
CYP inhibitory promiscuity	+	0.7587	75.87%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5811	58.11%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9439	94.39%
Skin irritation	-	0.7446	74.46%
Skin corrosion	-	0.9756	97.56%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.9472	94.72%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.6938	69.38%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4672	46.72%
Acute Oral Toxicity (c)	III	0.6227	62.27%
Estrogen receptor binding	+	0.7464	74.64%
Androgen receptor binding	+	0.6016	60.16%
Thyroid receptor binding	+	0.6871	68.71%
Glucocorticoid receptor binding	+	0.6069	60.69%
Aromatase binding	+	0.6846	68.46%
PPAR gamma	-	0.5304	53.04%
Honey bee toxicity	-	0.8405	84.05%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
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	97.77%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.17%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.17%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.68%	97.25%
CHEMBL240	Q12809	HERG	92.41%	89.76%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.55%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	91.11%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.86%	94.45%
CHEMBL4072	P07858	Cathepsin B	88.07%	93.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.44%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	84.86%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.49%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.07%	97.14%
CHEMBL5028	O14672	ADAM10	81.03%	97.50%

Plants that contains it

• Croton megistocarpus
• Grangea maderaspatana

Cross-Links

• PubChem: 14037445
• LOTUS: LTS0230797
• wikiData: Q105218955