4-[[(1R,2R,3S,4aR,8aR)-3-hydroxy-1-[(3S)-5-hydroxy-3-methylpentyl]-1,4a,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-2-yl]methoxy]-4-oxobutanoic acid

Details

• Internal ID: b50b1e84-70ea-482f-8b9d-ae8ccad31da3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: 4-[[(1R,2R,3S,4aR,8aR)-3-hydroxy-1-[(3S)-5-hydroxy-3-methylpentyl]-1,4a,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-2-yl]methoxy]-4-oxobutanoic acid
• SMILES (Canonical): CC1=CCCC2C1(CC(C(C2(C)CCC(C)CCO)COC(=O)CCC(=O)O)O)C
• SMILES (Isomeric): CC1=CCC[C@H]2[C@]1(C[C@@H]([C@H]([C@]2(C)CC[C@H](C)CCO)COC(=O)CCC(=O)O)O)C
• InChI: InChI=1S/C24H40O6/c1-16(11-13-25)10-12-23(3)18(15-30-22(29)9-8-21(27)28)19(26)14-24(4)17(2)6-5-7-20(23)24/h6,16,18-20,25-26H,5,7-15H2,1-4H3,(H,27,28)/t16-,18+,19-,20+,23-,24-/m0/s1
• InChI Key: DQBYZULBDHLLAH-TXIYWMGPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₀O₆
• Molecular Weight: 424.60 g/mol
• Exact Mass: 424.28248899 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.94
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9778	97.78%
Caco-2	-	0.5722	57.22%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8652	86.52%
OATP2B1 inhibitior	-	0.7134	71.34%
OATP1B1 inhibitior	+	0.8878	88.78%
OATP1B3 inhibitior	+	0.8453	84.53%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6140	61.40%
BSEP inhibitior	+	0.7776	77.76%
P-glycoprotein inhibitior	-	0.5592	55.92%
P-glycoprotein substrate	-	0.5829	58.29%
CYP3A4 substrate	+	0.6554	65.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8717	87.17%
CYP3A4 inhibition	-	0.6695	66.95%
CYP2C9 inhibition	-	0.8930	89.30%
CYP2C19 inhibition	-	0.8982	89.82%
CYP2D6 inhibition	-	0.9434	94.34%
CYP1A2 inhibition	-	0.8399	83.99%
CYP2C8 inhibition	-	0.6712	67.12%
CYP inhibitory promiscuity	-	0.9291	92.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6616	66.16%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9584	95.84%
Skin irritation	-	0.5470	54.70%
Skin corrosion	-	0.9717	97.17%
Ames mutagenesis	-	0.8548	85.48%
Human Ether-a-go-go-Related Gene inhibition	+	0.6772	67.72%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6198	61.98%
skin sensitisation	-	0.8982	89.82%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8057	80.57%
Acute Oral Toxicity (c)	III	0.6292	62.92%
Estrogen receptor binding	+	0.7843	78.43%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6531	65.31%
Glucocorticoid receptor binding	+	0.8646	86.46%
Aromatase binding	+	0.7482	74.82%
PPAR gamma	-	0.5208	52.08%
Honey bee toxicity	-	0.8374	83.74%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7755	77.55%
Fish aquatic toxicity	+	0.9893	98.93%

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	98.60%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	95.59%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.26%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.84%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	92.36%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.32%	97.25%
CHEMBL2581	P07339	Cathepsin D	91.79%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.71%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	89.68%	91.19%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.48%	94.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.26%	93.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.20%	93.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.90%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	84.60%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.20%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.20%	100.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.03%	94.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.03%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.55%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.19%	100.00%
CHEMBL1871	P10275	Androgen Receptor	80.15%	96.43%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.04%	94.23%

Plants that contains it

• Baccharis pteronioides

Cross-Links

• PubChem: 163070801
• LOTUS: LTS0058403
• wikiData: Q104986851