(4aR,5S,8aS)-5-[(3R)-3-hydroxy-3-methylpent-4-enyl]-1,1,4a,6-tetramethyl-4,5,8,8a-tetrahydro-3H-naphthalen-2-one

Details

• Internal ID: 09340703-6f44-46dc-b002-f0e048a50721
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (4aR,5S,8aS)-5-[(3R)-3-hydroxy-3-methylpent-4-enyl]-1,1,4a,6-tetramethyl-4,5,8,8a-tetrahydro-3H-naphthalen-2-one
• SMILES (Canonical): CC1=CCC2C(C(=O)CCC2(C1CCC(C)(C=C)O)C)(C)C
• SMILES (Isomeric): CC1=CC[C@H]2[C@@]([C@H]1CC[C@](C)(C=C)O)(CCC(=O)C2(C)C)C
• InChI: InChI=1S/C20H32O2/c1-7-19(5,22)12-10-15-14(2)8-9-16-18(3,4)17(21)11-13-20(15,16)6/h7-8,15-16,22H,1,9-13H2,2-6H3/t15-,16+,19-,20+/m0/s1
• InChI Key: WDRYHWJSXGKQDU-ACZWYYKOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₂
• Molecular Weight: 304.50 g/mol
• Exact Mass: 304.240230259 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.68
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8024	80.24%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6937	69.37%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8855	88.55%
OATP1B3 inhibitior	+	0.9250	92.50%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.4652	46.52%
P-glycoprotein inhibitior	-	0.7802	78.02%
P-glycoprotein substrate	-	0.8429	84.29%
CYP3A4 substrate	+	0.5993	59.93%
CYP2C9 substrate	-	0.8375	83.75%
CYP2D6 substrate	-	0.8168	81.68%
CYP3A4 inhibition	-	0.6462	64.62%
CYP2C9 inhibition	-	0.8948	89.48%
CYP2C19 inhibition	-	0.8276	82.76%
CYP2D6 inhibition	-	0.9552	95.52%
CYP1A2 inhibition	-	0.9132	91.32%
CYP2C8 inhibition	-	0.6314	63.14%
CYP inhibitory promiscuity	-	0.8577	85.77%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6312	63.12%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9391	93.91%
Skin irritation	+	0.5185	51.85%
Skin corrosion	-	0.9680	96.80%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3757	37.57%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.6717	67.17%
skin sensitisation	+	0.6965	69.65%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6649	66.49%
Acute Oral Toxicity (c)	III	0.4355	43.55%
Estrogen receptor binding	+	0.5618	56.18%
Androgen receptor binding	-	0.5128	51.28%
Thyroid receptor binding	+	0.6038	60.38%
Glucocorticoid receptor binding	+	0.6846	68.46%
Aromatase binding	-	0.5377	53.77%
PPAR gamma	+	0.6261	62.61%
Honey bee toxicity	-	0.8669	86.69%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9932	99.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.12%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.89%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.31%	98.95%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	90.59%	90.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.33%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	88.87%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.30%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.20%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.05%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.26%	96.09%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.06%	98.00%

Plants that contains it

• Helichrysum albirosulatum

Cross-Links

• PubChem: 162871352
• LOTUS: LTS0054262
• wikiData: Q105302612