(4aR,5S,6R,8aR)-5-[(3R)-3-(acetyloxymethyl)-5-hydroxypentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: 81173796-66af-4c70-90f6-20a9d322fdb1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (4aR,5S,6R,8aR)-5-[(3R)-3-(acetyloxymethyl)-5-hydroxypentyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
• InChI: InChI=1S/C22H36O5/c1-15-8-11-22(4)18(20(25)26)6-5-7-19(22)21(15,3)12-9-17(10-13-23)14-27-16(2)24/h6,15,17,19,23H,5,7-14H2,1-4H3,(H,25,26)/t15-,17-,19-,21+,22+/m1/s1
• InChI Key: NHICXBFHDXVLOW-VCHDQXCVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆O₅
• Molecular Weight: 380.50 g/mol
• Exact Mass: 380.25627424 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.19
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9563	95.63%
Caco-2	+	0.6480	64.80%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7725	77.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8844	88.44%
OATP1B3 inhibitior	+	0.8661	86.61%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.5364	53.64%
BSEP inhibitior	+	0.9295	92.95%
P-glycoprotein inhibitior	-	0.6725	67.25%
P-glycoprotein substrate	-	0.7037	70.37%
CYP3A4 substrate	+	0.6053	60.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9153	91.53%
CYP3A4 inhibition	-	0.5634	56.34%
CYP2C9 inhibition	-	0.9010	90.10%
CYP2C19 inhibition	-	0.8988	89.88%
CYP2D6 inhibition	-	0.8992	89.92%
CYP1A2 inhibition	-	0.8374	83.74%
CYP2C8 inhibition	-	0.6519	65.19%
CYP inhibitory promiscuity	-	0.7862	78.62%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6721	67.21%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9433	94.33%
Skin irritation	-	0.6536	65.36%
Skin corrosion	-	0.9787	97.87%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6709	67.09%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5763	57.63%
skin sensitisation	-	0.7279	72.79%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6632	66.32%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6457	64.57%
Acute Oral Toxicity (c)	III	0.7176	71.76%
Estrogen receptor binding	+	0.8130	81.30%
Androgen receptor binding	-	0.5529	55.29%
Thyroid receptor binding	+	0.5729	57.29%
Glucocorticoid receptor binding	+	0.7627	76.27%
Aromatase binding	+	0.7234	72.34%
PPAR gamma	-	0.5541	55.41%
Honey bee toxicity	-	0.8111	81.11%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7850	78.50%
Fish aquatic toxicity	+	0.9948	99.48%

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	98.48%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.41%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.21%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.23%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.68%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.05%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.26%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.19%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.69%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.22%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.02%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.03%	95.56%

Plants that contains it

• Baccharis gaudichaudiana

Cross-Links

• PubChem: 162888164
• LOTUS: LTS0040835
• wikiData: Q105179388