(E)-5-[(1R,2S,4R,4aR,8aR)-4-hydroxy-1,2,4a,5-tetramethyl-3-oxo-4,7,8,8a-tetrahydro-2H-naphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: aafab091-1458-46c4-be98-86c8c9b261ad
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (E)-5-[(1R,2S,4R,4aR,8aR)-4-hydroxy-1,2,4a,5-tetramethyl-3-oxo-4,7,8,8a-tetrahydro-2H-naphthalen-1-yl]-3-methylpent-2-enoic acid
• SMILES (Canonical): CC1C(=O)C(C2(C(C1(C)CCC(=CC(=O)O)C)CCC=C2C)C)O
• SMILES (Isomeric): C[C@@H]1C(=O)[C@@H]([C@@]2([C@@H]([C@@]1(C)CC/C(=C/C(=O)O)/C)CCC=C2C)C)O
• InChI: InChI=1S/C20H30O4/c1-12(11-16(21)22)9-10-19(4)14(3)17(23)18(24)20(5)13(2)7-6-8-15(19)20/h7,11,14-15,18,24H,6,8-10H2,1-5H3,(H,21,22)/b12-11+/t14-,15-,18+,19+,20+/m1/s1
• InChI Key: QBTMVLQTZBMTNE-WBJSIRLMSA-N
• Popularity: 0 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: 4.00
• Atomic LogP (AlogP): 3.75
• 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	+	0.9724	97.24%
Caco-2	+	0.6816	68.16%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8050	80.50%
OATP2B1 inhibitior	-	0.8672	86.72%
OATP1B1 inhibitior	+	0.8826	88.26%
OATP1B3 inhibitior	+	0.8516	85.16%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	+	0.7355	73.55%
P-glycoprotein inhibitior	-	0.7065	70.65%
P-glycoprotein substrate	-	0.6820	68.20%
CYP3A4 substrate	+	0.6064	60.64%
CYP2C9 substrate	-	0.7735	77.35%
CYP2D6 substrate	-	0.9031	90.31%
CYP3A4 inhibition	-	0.8033	80.33%
CYP2C9 inhibition	-	0.9173	91.73%
CYP2C19 inhibition	-	0.9366	93.66%
CYP2D6 inhibition	-	0.9004	90.04%
CYP1A2 inhibition	-	0.8167	81.67%
CYP2C8 inhibition	-	0.7529	75.29%
CYP inhibitory promiscuity	-	0.8639	86.39%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6626	66.26%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.9388	93.88%
Skin irritation	+	0.6493	64.93%
Skin corrosion	-	0.9637	96.37%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7855	78.55%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.5429	54.29%
skin sensitisation	-	0.5730	57.30%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6629	66.29%
Acute Oral Toxicity (c)	III	0.6699	66.99%
Estrogen receptor binding	+	0.6039	60.39%
Androgen receptor binding	+	0.6865	68.65%
Thyroid receptor binding	+	0.7079	70.79%
Glucocorticoid receptor binding	+	0.7274	72.74%
Aromatase binding	+	0.7145	71.45%
PPAR gamma	+	0.6039	60.39%
Honey bee toxicity	-	0.8869	88.69%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
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
CHEMBL4040	P28482	MAP kinase ERK2	99.14%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.96%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.57%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.90%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.30%	96.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.99%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.24%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.20%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.07%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.59%	89.00%

Plants that contains it

• Pulicaria aucheri

Cross-Links

• PubChem: 14543725
• LOTUS: LTS0227864
• wikiData: Q105218002