(1R,2R,4aR,5S,8aR)-2-hydroxy-1,4a-dimethyl-6-methylidene-5-(3-oxobutyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: 6acf97b1-97e2-41ed-bc32-d26613bc2108
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1R,2R,4aR,5S,8aR)-2-hydroxy-1,4a-dimethyl-6-methylidene-5-(3-oxobutyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• InChI: InChI=1S/C18H28O4/c1-11-5-8-14-17(3,13(11)7-6-12(2)19)10-9-15(20)18(14,4)16(21)22/h13-15,20H,1,5-10H2,2-4H3,(H,21,22)/t13-,14+,15+,17+,18+/m0/s1
• InChI Key: KGMMKUZTYZGQQY-DBXHJTGRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₈O₄
• Molecular Weight: 308.40 g/mol
• Exact Mass: 308.19875937 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9714	97.14%
Caco-2	+	0.8289	82.89%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7266	72.66%
OATP2B1 inhibitior	-	0.8614	86.14%
OATP1B1 inhibitior	+	0.9075	90.75%
OATP1B3 inhibitior	-	0.3230	32.30%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	-	0.5837	58.37%
P-glycoprotein inhibitior	-	0.7836	78.36%
P-glycoprotein substrate	-	0.7870	78.70%
CYP3A4 substrate	+	0.6160	61.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8538	85.38%
CYP3A4 inhibition	-	0.6166	61.66%
CYP2C9 inhibition	-	0.9099	90.99%
CYP2C19 inhibition	-	0.9014	90.14%
CYP2D6 inhibition	-	0.9581	95.81%
CYP1A2 inhibition	-	0.9308	93.08%
CYP2C8 inhibition	-	0.7833	78.33%
CYP inhibitory promiscuity	-	0.9406	94.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7051	70.51%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.6255	62.55%
Skin irritation	+	0.6441	64.41%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.8154	81.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4364	43.64%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6726	67.26%
skin sensitisation	-	0.7241	72.41%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6858	68.58%
Acute Oral Toxicity (c)	I	0.6189	61.89%
Estrogen receptor binding	+	0.5851	58.51%
Androgen receptor binding	+	0.5303	53.03%
Thyroid receptor binding	+	0.6276	62.76%
Glucocorticoid receptor binding	+	0.7219	72.19%
Aromatase binding	-	0.5838	58.38%
PPAR gamma	-	0.6256	62.56%
Honey bee toxicity	-	0.9041	90.41%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9974	99.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	94.57%	90.17%
CHEMBL4040	P28482	MAP kinase ERK2	92.41%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.86%	91.11%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.84%	96.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.01%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.51%	96.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.52%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.50%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	83.71%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.91%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.49%	95.56%
CHEMBL2581	P07339	Cathepsin D	81.18%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.62%	100.00%

Plants that contains it

• Juniperus thurifera

Cross-Links

• PubChem: 162900458
• LOTUS: LTS0116266
• wikiData: Q105140843