(Z)-5-[(1S,2R,4aR,8aR)-5-formyl-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-(hydroxymethyl)pent-2-enoic acid

Details

• Internal ID: 796c41e0-8d4a-44a2-bc69-8df36fd5ecc9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (Z)-5-[(1S,2R,4aR,8aR)-5-formyl-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-(hydroxymethyl)pent-2-enoic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC(=CC(=O)O)CO)CCC=C2C=O)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CC/C(=C/C(=O)O)/CO)CCC=C2C=O)C
• InChI: InChI=1S/C20H30O4/c1-14-7-9-20(3)16(13-22)5-4-6-17(20)19(14,2)10-8-15(12-21)11-18(23)24/h5,11,13-14,17,21H,4,6-10,12H2,1-3H3,(H,23,24)/b15-11-/t14-,17-,19+,20+/m1/s1
• InChI Key: AVRIRMRRWLLLDT-CBYQQGIISA-N
• Popularity: 1 reference 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: 4.20
• Atomic LogP (AlogP): 3.75
• H-Bond Acceptor: 3
• 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	+	0.9785	97.85%
Caco-2	+	0.6876	68.76%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7870	78.70%
OATP2B1 inhibitior	-	0.8693	86.93%
OATP1B1 inhibitior	+	0.8425	84.25%
OATP1B3 inhibitior	-	0.2601	26.01%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5329	53.29%
BSEP inhibitior	-	0.4516	45.16%
P-glycoprotein inhibitior	-	0.6113	61.13%
P-glycoprotein substrate	-	0.7183	71.83%
CYP3A4 substrate	+	0.5874	58.74%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.9097	90.97%
CYP3A4 inhibition	-	0.6181	61.81%
CYP2C9 inhibition	-	0.8240	82.40%
CYP2C19 inhibition	-	0.8879	88.79%
CYP2D6 inhibition	-	0.9112	91.12%
CYP1A2 inhibition	-	0.8357	83.57%
CYP2C8 inhibition	+	0.4650	46.50%
CYP inhibitory promiscuity	-	0.7639	76.39%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6816	68.16%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9191	91.91%
Skin irritation	-	0.7064	70.64%
Skin corrosion	-	0.9810	98.10%
Ames mutagenesis	-	0.5370	53.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6622	66.22%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5839	58.39%
skin sensitisation	+	0.4730	47.30%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6521	65.21%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6076	60.76%
Acute Oral Toxicity (c)	III	0.6242	62.42%
Estrogen receptor binding	+	0.9244	92.44%
Androgen receptor binding	+	0.6065	60.65%
Thyroid receptor binding	+	0.7538	75.38%
Glucocorticoid receptor binding	+	0.8565	85.65%
Aromatase binding	+	0.8709	87.09%
PPAR gamma	+	0.6327	63.27%
Honey bee toxicity	-	0.9031	90.31%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.46%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.29%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.25%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.33%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.91%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.70%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.49%	91.11%
CHEMBL233	P35372	Mu opioid receptor	85.24%	97.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.87%	97.09%
CHEMBL5028	O14672	ADAM10	82.11%	97.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.50%	95.50%

Plants that contains it

• Acritopappus heterolepis

Cross-Links

• PubChem: 38355618
• LOTUS: LTS0238125
• wikiData: Q104919758