(1S,4aS,5R,8aS)-5-[(Z)-5-hydroxy-3-(hydroxymethyl)pent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: 70fe90a6-b536-4b6e-8705-3d940667db5a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,4aS,5R,8aS)-5-[(Z)-5-hydroxy-3-(hydroxymethyl)pent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC12CCCC(C1CCC(=C)C2CCC(=CCO)CO)(C)C(=O)O
• SMILES (Isomeric): C[C@@]12CCC[C@]([C@H]1CCC(=C)[C@H]2CC/C(=C/CO)/CO)(C)C(=O)O
• InChI: InChI=1S/C20H32O4/c1-14-5-8-17-19(2,10-4-11-20(17,3)18(23)24)16(14)7-6-15(13-22)9-12-21/h9,16-17,21-22H,1,4-8,10-13H2,2-3H3,(H,23,24)/b15-9-/t16-,17+,19+,20+/m1/s1
• InChI Key: UTBCORIJXVSSBE-ZYGAUNNZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.54
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9651	96.51%
Caco-2	+	0.7554	75.54%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6880	68.80%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.8003	80.03%
OATP1B3 inhibitior	+	0.8291	82.91%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5605	56.05%
BSEP inhibitior	+	0.6663	66.63%
P-glycoprotein inhibitior	-	0.7999	79.99%
P-glycoprotein substrate	-	0.7474	74.74%
CYP3A4 substrate	+	0.6278	62.78%
CYP2C9 substrate	-	0.6197	61.97%
CYP2D6 substrate	-	0.8732	87.32%
CYP3A4 inhibition	-	0.7040	70.40%
CYP2C9 inhibition	-	0.8044	80.44%
CYP2C19 inhibition	-	0.8451	84.51%
CYP2D6 inhibition	-	0.8935	89.35%
CYP1A2 inhibition	-	0.8357	83.57%
CYP2C8 inhibition	-	0.6383	63.83%
CYP inhibitory promiscuity	-	0.7900	79.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6670	66.70%
Eye corrosion	-	0.9800	98.00%
Eye irritation	-	0.8131	81.31%
Skin irritation	-	0.7760	77.60%
Skin corrosion	-	0.9787	97.87%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4028	40.28%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.7694	76.94%
skin sensitisation	-	0.5892	58.92%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7059	70.59%
Acute Oral Toxicity (c)	III	0.5952	59.52%
Estrogen receptor binding	+	0.6506	65.06%
Androgen receptor binding	+	0.5789	57.89%
Thyroid receptor binding	+	0.6735	67.35%
Glucocorticoid receptor binding	+	0.7874	78.74%
Aromatase binding	+	0.6812	68.12%
PPAR gamma	+	0.5233	52.33%
Honey bee toxicity	-	0.9032	90.32%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
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	92.62%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.02%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.75%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.80%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.16%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.42%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.65%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.30%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.87%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.96%	96.38%

Plants that contains it

• Brickellia lemmonii

Cross-Links

• PubChem: 14845499
• LOTUS: LTS0053515
• wikiData: Q105278661