(2R,3S,4aS,8R,8aR)-8-[(E)-5-hydroxy-3-methylpent-3-enyl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalene-2,3-diol

Details

• Internal ID: f9f3811e-b16a-4c8f-add5-cc78c466bd30
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (2R,3S,4aS,8R,8aR)-8-[(E)-5-hydroxy-3-methylpent-3-enyl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalene-2,3-diol
• SMILES (Canonical): CC1=CCC2C(C(C(CC2(C1CCC(=CCO)C)C)O)O)(C)C
• SMILES (Isomeric): CC1=CC[C@H]2[C@@]([C@@H]1CC/C(=C/CO)/C)(C[C@H]([C@H](C2(C)C)O)O)C
• InChI: InChI=1S/C20H34O3/c1-13(10-11-21)6-8-15-14(2)7-9-17-19(3,4)18(23)16(22)12-20(15,17)5/h7,10,15-18,21-23H,6,8-9,11-12H2,1-5H3/b13-10+/t15-,16-,17-,18-,20-/m1/s1
• InChI Key: CIYWZBZTBINQTM-MHBYTKFFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₃
• Molecular Weight: 322.50 g/mol
• Exact Mass: 322.25079494 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.45
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9911	99.11%
Caco-2	+	0.6116	61.16%
Blood Brain Barrier	+	0.7385	73.85%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7441	74.41%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.8928	89.28%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6583	65.83%
BSEP inhibitior	-	0.5853	58.53%
P-glycoprotein inhibitior	-	0.7783	77.83%
P-glycoprotein substrate	-	0.7586	75.86%
CYP3A4 substrate	+	0.5903	59.03%
CYP2C9 substrate	-	0.6197	61.97%
CYP2D6 substrate	-	0.7438	74.38%
CYP3A4 inhibition	-	0.6929	69.29%
CYP2C9 inhibition	-	0.8395	83.95%
CYP2C19 inhibition	-	0.8612	86.12%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.8884	88.84%
CYP2C8 inhibition	-	0.6957	69.57%
CYP inhibitory promiscuity	-	0.8570	85.70%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7123	71.23%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9730	97.30%
Skin irritation	-	0.6320	63.20%
Skin corrosion	-	0.9650	96.50%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6545	65.45%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.7265	72.65%
skin sensitisation	-	0.6870	68.70%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6496	64.96%
Acute Oral Toxicity (c)	III	0.7051	70.51%
Estrogen receptor binding	+	0.6396	63.96%
Androgen receptor binding	-	0.5520	55.20%
Thyroid receptor binding	+	0.6016	60.16%
Glucocorticoid receptor binding	+	0.7645	76.45%
Aromatase binding	-	0.5185	51.85%
PPAR gamma	+	0.6848	68.48%
Honey bee toxicity	-	0.8875	88.75%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9692	96.92%

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	96.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.60%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	90.87%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.62%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.35%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	85.43%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.39%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.90%	82.69%
CHEMBL2581	P07339	Cathepsin D	81.81%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	81.01%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.69%	95.89%

Plants that contains it

• Baccharis gnidiifolia

Cross-Links

• PubChem: 163103667
• LOTUS: LTS0159226
• wikiData: Q104960684