(4aR,7R,8R,8aR)-7,8-dihydroxy-4,4,7,8a-tetramethyl-8-(3-methylidenepent-4-enyl)-3,4a,5,6-tetrahydro-2H-naphthalen-1-one

Details

• Internal ID: d58f6e94-4ac8-420d-abea-6d7bb2ffe9b2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (4aR,7R,8R,8aR)-7,8-dihydroxy-4,4,7,8a-tetramethyl-8-(3-methylidenepent-4-enyl)-3,4a,5,6-tetrahydro-2H-naphthalen-1-one
• SMILES (Canonical): CC1(CCC(=O)C2(C1CCC(C2(CCC(=C)C=C)O)(C)O)C)C
• SMILES (Isomeric): C[C@]1(CC[C@H]2[C@]([C@@]1(CCC(=C)C=C)O)(C(=O)CCC2(C)C)C)O
• InChI: InChI=1S/C20H32O3/c1-7-14(2)8-13-20(23)18(5,22)12-9-15-17(3,4)11-10-16(21)19(15,20)6/h7,15,22-23H,1-2,8-13H2,3-6H3/t15-,18-,19+,20+/m1/s1
• InChI Key: MFXMFYDAHORRBV-XCLNPWKQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.80
• 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	+	0.9939	99.39%
Caco-2	+	0.6866	68.66%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7608	76.08%
OATP2B1 inhibitior	-	0.8553	85.53%
OATP1B1 inhibitior	+	0.9102	91.02%
OATP1B3 inhibitior	+	0.9290	92.90%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5500	55.00%
P-glycoprotein inhibitior	-	0.8509	85.09%
P-glycoprotein substrate	-	0.8611	86.11%
CYP3A4 substrate	+	0.5984	59.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8451	84.51%
CYP3A4 inhibition	-	0.7141	71.41%
CYP2C9 inhibition	-	0.8010	80.10%
CYP2C19 inhibition	-	0.6367	63.67%
CYP2D6 inhibition	-	0.9507	95.07%
CYP1A2 inhibition	-	0.8718	87.18%
CYP2C8 inhibition	-	0.7516	75.16%
CYP inhibitory promiscuity	-	0.9059	90.59%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6427	64.27%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.7936	79.36%
Skin irritation	+	0.5432	54.32%
Skin corrosion	-	0.9424	94.24%
Ames mutagenesis	-	0.7454	74.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4553	45.53%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.5044	50.44%
skin sensitisation	-	0.5970	59.70%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6532	65.32%
Acute Oral Toxicity (c)	I	0.4537	45.37%
Estrogen receptor binding	+	0.6775	67.75%
Androgen receptor binding	+	0.6225	62.25%
Thyroid receptor binding	+	0.5229	52.29%
Glucocorticoid receptor binding	+	0.7541	75.41%
Aromatase binding	+	0.7365	73.65%
PPAR gamma	+	0.5859	58.59%
Honey bee toxicity	-	0.8476	84.76%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9946	99.46%

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	96.17%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.52%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	93.20%	94.75%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.04%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.75%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.70%	100.00%
CHEMBL3524	P56524	Histone deacetylase 4	86.92%	92.97%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.09%	96.09%
CHEMBL2581	P07339	Cathepsin D	83.63%	98.95%
CHEMBL1871	P10275	Androgen Receptor	80.41%	96.43%

Plants that contains it

• Blepharostoma trichophyllum

Cross-Links

• PubChem: 21579294
• LOTUS: LTS0119890
• wikiData: Q105163073