(Z)-5-[(1S,4aR,5R,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-6-oxo-1,3,4,4a,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: 902d00e3-d65f-47f5-bf01-a86fedb0ccfb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (Z)-5-[(1S,4aR,5R,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-6-oxo-1,3,4,4a,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid
• InChI: InChI=1S/C20H30O4/c1-13(11-18(23)24)5-7-15-14(2)6-8-16-19(15,3)10-9-17(22)20(16,4)12-21/h11,15-16,21H,2,5-10,12H2,1,3-4H3,(H,23,24)/b13-11-/t15-,16+,19+,20-/m0/s1
• InChI Key: HWJYPRVKHDNDKE-FNGUMRJLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.75
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9705	97.05%
Caco-2	+	0.7578	75.78%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8131	81.31%
OATP2B1 inhibitior	-	0.8677	86.77%
OATP1B1 inhibitior	+	0.8671	86.71%
OATP1B3 inhibitior	+	0.8182	81.82%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5245	52.45%
BSEP inhibitior	+	0.7044	70.44%
P-glycoprotein inhibitior	-	0.7220	72.20%
P-glycoprotein substrate	-	0.7770	77.70%
CYP3A4 substrate	+	0.6176	61.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9132	91.32%
CYP3A4 inhibition	-	0.5789	57.89%
CYP2C9 inhibition	-	0.9118	91.18%
CYP2C19 inhibition	-	0.9211	92.11%
CYP2D6 inhibition	-	0.9374	93.74%
CYP1A2 inhibition	-	0.7398	73.98%
CYP2C8 inhibition	-	0.6602	66.02%
CYP inhibitory promiscuity	-	0.9098	90.98%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6644	66.44%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.7197	71.97%
Skin irritation	+	0.5901	59.01%
Skin corrosion	-	0.9640	96.40%
Ames mutagenesis	-	0.7954	79.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7582	75.82%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7101	71.01%
skin sensitisation	-	0.8521	85.21%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6197	61.97%
Acute Oral Toxicity (c)	III	0.7711	77.11%
Estrogen receptor binding	+	0.7020	70.20%
Androgen receptor binding	+	0.6794	67.94%
Thyroid receptor binding	+	0.6835	68.35%
Glucocorticoid receptor binding	+	0.7768	77.68%
Aromatase binding	+	0.5893	58.93%
PPAR gamma	+	0.5822	58.22%
Honey bee toxicity	-	0.8897	88.97%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9965	99.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.33%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.73%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.27%	97.25%
CHEMBL2581	P07339	Cathepsin D	86.16%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.51%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.19%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	82.93%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.93%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.76%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.63%	95.56%

Plants that contains it

• Nolana rostrata

Cross-Links

• PubChem: 162878804
• LOTUS: LTS0071071
• wikiData: Q105034678