(1S,5R,7R)-3-[(3,4-dihydroxyphenyl)-hydroxymethylidene]-1,7-bis[(2E)-3,7-dimethylocta-2,6-dienyl]-6,6-dimethyl-5-(3-methylbut-2-enyl)bicyclo[3.3.1]nonane-2,4,9-trione

Details

• Internal ID: 58ff9eff-11a7-47d4-9bda-4c6cbd593426
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1S,5R,7R)-3-[(3,4-dihydroxyphenyl)-hydroxymethylidene]-1,7-bis[(2E)-3,7-dimethylocta-2,6-dienyl]-6,6-dimethyl-5-(3-methylbut-2-enyl)bicyclo[3.3.1]nonane-2,4,9-trione
• SMILES (Canonical): CC(=CCCC(=CCC1CC2(C(=O)C(=C(C3=CC(=C(C=C3)O)O)O)C(=O)C(C2=O)(C1(C)C)CC=C(C)C)CC=C(C)CCC=C(C)C)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/C[C@@H]1C[C@@]2(C(=O)C(=C(C3=CC(=C(C=C3)O)O)O)C(=O)[C@@](C2=O)(C1(C)C)CC=C(C)C)C/C=C(\C)/CCC=C(C)C)/C)C
• InChI: InChI=1S/C43H58O6/c1-27(2)13-11-15-30(7)17-19-33-26-42(23-22-31(8)16-12-14-28(3)4)38(47)36(37(46)32-18-20-34(44)35(45)25-32)39(48)43(40(42)49,41(33,9)10)24-21-29(5)6/h13-14,17-18,20-22,25,33,44-46H,11-12,15-16,19,23-24,26H2,1-10H3/b30-17+,31-22+,37-36?/t33-,42-,43+/m1/s1
• InChI Key: AWADGPGGHLGLFD-FQTDFKCZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₅₈O₆
• Molecular Weight: 670.90 g/mol
• Exact Mass: 670.42333957 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 12.10
• Atomic LogP (AlogP): 10.63
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9931	99.31%
Caco-2	-	0.8110	81.10%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8428	84.28%
OATP2B1 inhibitior	+	0.8578	85.78%
OATP1B1 inhibitior	+	0.8759	87.59%
OATP1B3 inhibitior	+	0.8757	87.57%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.8098	80.98%
P-glycoprotein substrate	-	0.5075	50.75%
CYP3A4 substrate	+	0.6294	62.94%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8625	86.25%
CYP3A4 inhibition	-	0.8076	80.76%
CYP2C9 inhibition	-	0.5537	55.37%
CYP2C19 inhibition	-	0.6356	63.56%
CYP2D6 inhibition	-	0.9059	90.59%
CYP1A2 inhibition	+	0.6855	68.55%
CYP2C8 inhibition	+	0.6032	60.32%
CYP inhibitory promiscuity	-	0.7441	74.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6580	65.80%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8991	89.91%
Skin irritation	-	0.6396	63.96%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7480	74.80%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5802	58.02%
skin sensitisation	-	0.6213	62.13%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.4518	45.18%
Acute Oral Toxicity (c)	III	0.6535	65.35%
Estrogen receptor binding	+	0.7450	74.50%
Androgen receptor binding	+	0.7346	73.46%
Thyroid receptor binding	+	0.6201	62.01%
Glucocorticoid receptor binding	+	0.8124	81.24%
Aromatase binding	+	0.6988	69.88%
PPAR gamma	+	0.6844	68.44%
Honey bee toxicity	-	0.7933	79.33%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.26%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.14%	91.49%
CHEMBL2581	P07339	Cathepsin D	92.87%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.82%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.30%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.21%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.59%	94.73%
CHEMBL4208	P20618	Proteasome component C5	87.15%	90.00%
CHEMBL1937	Q92769	Histone deacetylase 2	86.11%	94.75%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.70%	85.30%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	84.60%	92.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.60%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.55%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.34%	90.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.51%	93.99%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.49%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.92%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.31%	100.00%

Plants that contains it

• Garcinia oblongifolia

Cross-Links

• PubChem: 102291451
• LOTUS: LTS0272917
• wikiData: Q104400302