Aubergenone

Details

• Internal ID: a5e11f1c-2a72-4a00-864e-186cbfe88c5c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: (1R,4aS,7R,8aS)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one
• SMILES (Canonical): CC1C2CC(CCC2(C=CC1=O)C)C(C)(C)O
• SMILES (Isomeric): C[C@@H]1[C@@H]2C[C@@H](CC[C@]2(C=CC1=O)C)C(C)(C)O
• InChI: InChI=1S/C15H24O2/c1-10-12-9-11(14(2,3)17)5-7-15(12,4)8-6-13(10)16/h6,8,10-12,17H,5,7,9H2,1-4H3/t10-,11-,12+,15+/m1/s1
• InChI Key: MSSWKGZMPUXALD-FJJYHAOUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.35 g/mol
• Exact Mass: 236.177630004 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.95
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Mangeudesmenone
• CD0897RFK3
• 69427-35-6
• UNII-CD0897RFK3
• (1R,4aS,7R,8aS)-4a,5,6,7,8,8a-Hexahydro-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-2(1H)-naphthalenone
• 2(1H)-Naphthalenone, 4a,5,6,7,8,8a-hexahydro-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-, (1R-(1alpha,4aalpha,7alpha,8abeta))-
• CHEBI:173713
• DTXSID701112873
• (1R,4aS,7R,8aS)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one
• 2(1H)-NAPHTHALENONE, 4A,5,6,7,8,8A-HEXAHYDRO-7-(1-HYDROXY-1-METHYLETHYL)-1,4A-DIMETHYL-, (1R-(1.ALPHA.,4A.ALPHA.,7.ALPHA.,8A.BETA.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7048	70.48%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7296	72.96%
OATP2B1 inhibitior	-	0.8521	85.21%
OATP1B1 inhibitior	+	0.8778	87.78%
OATP1B3 inhibitior	+	0.9494	94.94%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.8501	85.01%
P-glycoprotein inhibitior	-	0.9393	93.93%
P-glycoprotein substrate	-	0.8880	88.80%
CYP3A4 substrate	+	0.6233	62.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8881	88.81%
CYP3A4 inhibition	-	0.8095	80.95%
CYP2C9 inhibition	-	0.7081	70.81%
CYP2C19 inhibition	-	0.6209	62.09%
CYP2D6 inhibition	-	0.9572	95.72%
CYP1A2 inhibition	-	0.6225	62.25%
CYP2C8 inhibition	-	0.8223	82.23%
CYP inhibitory promiscuity	-	0.8728	87.28%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6183	61.83%
Eye corrosion	-	0.9756	97.56%
Eye irritation	-	0.9544	95.44%
Skin irritation	+	0.5590	55.90%
Skin corrosion	-	0.9655	96.55%
Ames mutagenesis	-	0.7770	77.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6215	62.15%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.6835	68.35%
skin sensitisation	+	0.6712	67.12%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7119	71.19%
Acute Oral Toxicity (c)	III	0.8132	81.32%
Estrogen receptor binding	-	0.5201	52.01%
Androgen receptor binding	-	0.6194	61.94%
Thyroid receptor binding	-	0.5444	54.44%
Glucocorticoid receptor binding	+	0.5449	54.49%
Aromatase binding	-	0.7866	78.66%
PPAR gamma	-	0.7397	73.97%
Honey bee toxicity	-	0.8790	87.90%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.99%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.39%	91.11%
CHEMBL1871	P10275	Androgen Receptor	91.50%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.86%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.02%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.52%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.66%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.23%	93.04%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.16%	85.14%
CHEMBL2581	P07339	Cathepsin D	84.99%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.43%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.04%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.37%	94.75%
CHEMBL2996	Q05655	Protein kinase C delta	82.24%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.18%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.50%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.37%	95.89%

Plants that contains it

• Aconitum burnatii
• Alseodaphne paludosa
• Annona impressivenia
• Bersama yangambiensis
• Caloncoba echinata
• Castanopsis sclerophylla
• Conocephalum japonicum
• Cordylanthus kingii
• Croton cascarilloides
• Disynaphia halimifolia
• Eragrostis viscosa
• Forsteronia refracta
• Fridericia chica
• Grewia mollis
• Gymnocarpium robertianum
• Heliotropium floridum
• Heterotheca grandiflora
• Hovenia acerba
• Juglans nigra
• Kaempferia marginata
• Kaunia saltensis
• Mangifera indica
• Nauclea officinalis
• Nicotiana undulata
• Ruta pinnata
• Salvia dorrii
• Solanum melongena
• Sophora flavescens var. flavescens
• Stevia polycephala
• Teucrium cubense
• Thymus piperella
• Trichilia rubescens
• Uraria picta

Cross-Links

• PubChem: 15601418
• NPASS: NPC296572
• LOTUS: LTS0238917
• wikiData: Q105171383