(4aR,5S,6R,8S,8aR)-5-[(E)-5-acetyloxy-3-methylpent-3-enyl]-8-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: 0d455c76-4aec-4d58-b306-f4db42ca6ee3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (4aR,5S,6R,8S,8aR)-5-[(E)-5-acetyloxy-3-methylpent-3-enyl]-8-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
• InChI: InChI=1S/C22H34O5/c1-14(10-12-27-16(3)23)9-11-21(4)15(2)13-19(24)22(5)17(20(25)26)7-6-8-18(21)22/h7,10,15,18-19,24H,6,8-9,11-13H2,1-5H3,(H,25,26)/b14-10+/t15-,18-,19+,21+,22+/m1/s1
• InChI Key: VESVIOLXNFMXSV-FJRLOJCVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₅
• Molecular Weight: 378.50 g/mol
• Exact Mass: 378.24062418 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.11
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9842	98.42%
Caco-2	+	0.6478	64.78%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8844	88.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8725	87.25%
OATP1B3 inhibitior	+	0.9193	91.93%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5656	56.56%
BSEP inhibitior	+	0.7828	78.28%
P-glycoprotein inhibitior	-	0.6404	64.04%
P-glycoprotein substrate	-	0.6595	65.95%
CYP3A4 substrate	+	0.6071	60.71%
CYP2C9 substrate	-	0.7828	78.28%
CYP2D6 substrate	-	0.9079	90.79%
CYP3A4 inhibition	-	0.6820	68.20%
CYP2C9 inhibition	-	0.9279	92.79%
CYP2C19 inhibition	-	0.9484	94.84%
CYP2D6 inhibition	-	0.9085	90.85%
CYP1A2 inhibition	-	0.8418	84.18%
CYP2C8 inhibition	-	0.5608	56.08%
CYP inhibitory promiscuity	-	0.8645	86.45%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6912	69.12%
Eye corrosion	-	0.9949	99.49%
Eye irritation	-	0.9468	94.68%
Skin irritation	+	0.6129	61.29%
Skin corrosion	-	0.9767	97.67%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5523	55.23%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5713	57.13%
skin sensitisation	-	0.8242	82.42%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5144	51.44%
Acute Oral Toxicity (c)	III	0.8075	80.75%
Estrogen receptor binding	+	0.6297	62.97%
Androgen receptor binding	+	0.5265	52.65%
Thyroid receptor binding	+	0.6349	63.49%
Glucocorticoid receptor binding	+	0.6815	68.15%
Aromatase binding	+	0.6841	68.41%
PPAR gamma	+	0.6098	60.98%
Honey bee toxicity	-	0.8107	81.07%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9954	99.54%

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	97.31%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.13%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.88%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.05%	93.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.87%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.86%	97.25%
CHEMBL2581	P07339	Cathepsin D	85.73%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.46%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	85.45%	91.19%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.92%	94.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.36%	100.00%
CHEMBL5028	O14672	ADAM10	81.63%	97.50%

Plants that contains it

• Pulicaria salviifolia

Cross-Links

• PubChem: 21769480
• LOTUS: LTS0202132
• wikiData: Q105284840