(4aS,8aS)-3,4a,8,8-tetramethyl-4-[(3R)-3-methyl-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxypent-4-enyl]-5,6,7,8a-tetrahydro-1H-naphthalen-2-one

Details

• Internal ID: 4fb39a73-a2fd-4875-8caf-e3a345e85083
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (4aS,8aS)-3,4a,8,8-tetramethyl-4-[(3R)-3-methyl-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxypent-4-enyl]-5,6,7,8a-tetrahydro-1H-naphthalen-2-one
• SMILES (Canonical): CC1=C(C2(CCCC(C2CC1=O)(C)C)C)CCC(C)(C=C)OC3C(C(C(CO3)O)O)O
• SMILES (Isomeric): CC1=C([C@]2(CCCC([C@@H]2CC1=O)(C)C)C)CC[C@](C)(C=C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O
• InChI: InChI=1S/C25H40O6/c1-7-24(5,31-22-21(29)20(28)18(27)14-30-22)12-9-16-15(2)17(26)13-19-23(3,4)10-8-11-25(16,19)6/h7,18-22,27-29H,1,8-14H2,2-6H3/t18-,19-,20-,21+,22-,24-,25+/m0/s1
• InChI Key: TZANJAYUFBSKPK-FQBMDWTRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₀O₆
• Molecular Weight: 436.60 g/mol
• Exact Mass: 436.28248899 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.29
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8573	85.73%
Caco-2	-	0.6456	64.56%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8206	82.06%
OATP2B1 inhibitior	-	0.7161	71.61%
OATP1B1 inhibitior	+	0.8284	82.84%
OATP1B3 inhibitior	+	0.8004	80.04%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7318	73.18%
BSEP inhibitior	+	0.7759	77.59%
P-glycoprotein inhibitior	-	0.5396	53.96%
P-glycoprotein substrate	-	0.6815	68.15%
CYP3A4 substrate	+	0.6872	68.72%
CYP2C9 substrate	-	0.7887	78.87%
CYP2D6 substrate	-	0.8822	88.22%
CYP3A4 inhibition	-	0.7923	79.23%
CYP2C9 inhibition	-	0.7260	72.60%
CYP2C19 inhibition	-	0.7296	72.96%
CYP2D6 inhibition	-	0.9347	93.47%
CYP1A2 inhibition	-	0.7117	71.17%
CYP2C8 inhibition	+	0.5636	56.36%
CYP inhibitory promiscuity	-	0.9343	93.43%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7330	73.30%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9486	94.86%
Skin irritation	-	0.5254	52.54%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4217	42.17%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6549	65.49%
skin sensitisation	-	0.8479	84.79%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7642	76.42%
Acute Oral Toxicity (c)	III	0.6800	68.00%
Estrogen receptor binding	+	0.6129	61.29%
Androgen receptor binding	+	0.6184	61.84%
Thyroid receptor binding	+	0.5608	56.08%
Glucocorticoid receptor binding	+	0.7122	71.22%
Aromatase binding	+	0.7223	72.23%
PPAR gamma	+	0.5358	53.58%
Honey bee toxicity	-	0.6917	69.17%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9878	98.78%

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	98.65%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.88%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.44%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	92.40%	83.82%
CHEMBL325	Q13547	Histone deacetylase 1	91.59%	95.92%
CHEMBL1937	Q92769	Histone deacetylase 2	91.28%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.11%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.73%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.64%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.51%	96.61%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.10%	89.34%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.02%	91.07%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.83%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.43%	96.77%
CHEMBL3401	O75469	Pregnane X receptor	84.40%	94.73%
CHEMBL1902	P62942	FK506-binding protein 1A	84.08%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.93%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.85%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.73%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.98%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.00%	94.45%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.83%	90.93%
CHEMBL5028	O14672	ADAM10	81.49%	97.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.26%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.84%	89.00%

Plants that contains it

• Cassinia subtropica
• Cota palaestina
• Egletes viscosa
• Greenmaniella resinosa
• Inula japonica
• Inula salsoloides
• Jefea phyllocephala
• Tanacetum argenteum
• Tanacetum polycephalum subsp. argyrophyllum

Cross-Links

• PubChem: 162940885
• LOTUS: LTS0218856
• wikiData: Q105250555