Gambierol

Details

• Internal ID: 7abecf73-27af-44c0-89d4-ba695a810aee
• Taxonomy: Organoheterocyclic compounds > Oxepanes
• IUPAC Name: (1S,3R,5S,7R,10S,11R,13S,15R,17S,20R,22S,24R,26S,27S,29S,31R,33S,35R)-11-[(1Z,3Z)-hepta-1,3,6-trienyl]-29-(3-hydroxypropyl)-3,5,10,24,26-pentamethyl-2,6,12,16,21,25,30,34-octaoxaoctacyclo[18.16.0.03,17.05,15.07,13.022,35.024,33.026,31]hexatriacont-8-ene-10,27-diol
• SMILES (Canonical): CC12CC3C(CC4C(O3)CCC5C(O4)(CC6(C(O5)CC7C(O6)C=CC(C(O7)C=CC=CCC=C)(C)O)C)C)OC1CC8C(O2)(C(CC(O8)CCCO)O)C
• SMILES (Isomeric): C[C@@]12C[C@H]3[C@@H](C[C@H]4[C@H](O3)CC[C@H]5[C@](O4)(C[C@]6([C@H](O5)C[C@H]7[C@H](O6)C=C[C@]([C@H](O7)/C=C\C=C/CC=C)(C)O)C)C)O[C@H]1C[C@@H]8[C@@](O2)([C@H](C[C@@H](O8)CCCO)O)C
• InChI: InChI=1S/C43H64O11/c1-7-8-9-10-11-14-34-39(2,46)18-17-28-30(49-34)22-36-42(5,52-28)25-41(4)35(51-36)16-15-27-31(53-41)21-29-32(48-27)24-40(3)37(50-29)23-38-43(6,54-40)33(45)20-26(47-38)13-12-19-44/h7,9-11,14,17-18,26-38,44-46H,1,8,12-13,15-16,19-25H2,2-6H3/b10-9-,14-11-/t26-,27+,28+,29+,30-,31-,32-,33-,34+,35-,36+,37-,38+,39-,40+,41+,42-,43-/m0/s1
• InChI Key: GKLILONDTZZKRF-IDJCTBPMSA-N
• Popularity: 48 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₄O₁₁
• Molecular Weight: 757.00 g/mol
• Exact Mass: 756.44486285 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 4.94
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• (-)-Gambierol
• 146763-62-4
• 844Q8WC5F6
• (1S,3R,5S,7R,10S,11R,13S,15R,17S,20R,22S,24R,26S,27S,29S,31R,33S,35R)-11-[(1Z,3Z)-hepta-1,3,6-trienyl]-29-(3-hydroxypropyl)-3,5,10,24,26-pentamethyl-2,6,12,16,21,25,30,34-octaoxaoctacyclo[18.16.0.03,17.05,15.07,13.022,35.024,33.026,31]hexatriacont-8-ene-10,27-diol
• UNII-844Q8WC5F6
• CHEMBL266438
• DTXSID30880110

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9119	91.19%
Caco-2	-	0.8586	85.86%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5291	52.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8240	82.40%
OATP1B3 inhibitior	+	0.9005	90.05%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6102	61.02%
BSEP inhibitior	+	0.8140	81.40%
P-glycoprotein inhibitior	+	0.7468	74.68%
P-glycoprotein substrate	+	0.7445	74.45%
CYP3A4 substrate	+	0.7363	73.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7861	78.61%
CYP3A4 inhibition	-	0.7491	74.91%
CYP2C9 inhibition	-	0.8964	89.64%
CYP2C19 inhibition	-	0.8494	84.94%
CYP2D6 inhibition	-	0.9581	95.81%
CYP1A2 inhibition	-	0.8040	80.40%
CYP2C8 inhibition	+	0.7976	79.76%
CYP inhibitory promiscuity	-	0.9632	96.32%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6887	68.87%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9113	91.13%
Skin irritation	-	0.6190	61.90%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7811	78.11%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	+	0.5303	53.03%
skin sensitisation	-	0.8854	88.54%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.7564	75.64%
Acute Oral Toxicity (c)	III	0.5287	52.87%
Estrogen receptor binding	+	0.7657	76.57%
Androgen receptor binding	+	0.7320	73.20%
Thyroid receptor binding	-	0.4897	48.97%
Glucocorticoid receptor binding	+	0.6790	67.90%
Aromatase binding	+	0.5876	58.76%
PPAR gamma	+	0.7013	70.13%
Honey bee toxicity	-	0.7151	71.51%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6030	60.30%
Fish aquatic toxicity	+	0.8908	89.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.73%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.23%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.94%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.72%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	90.07%	95.83%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	90.03%	91.03%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.75%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.32%	91.24%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	88.98%	90.24%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.32%	92.94%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.63%	91.07%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	87.53%	97.50%
CHEMBL226	P30542	Adenosine A1 receptor	87.28%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.17%	100.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	86.29%	92.88%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.20%	97.09%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.79%	82.38%
CHEMBL1951	P21397	Monoamine oxidase A	85.39%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.28%	89.00%
CHEMBL3055	P50613	Cyclin-dependent kinase 7	84.75%	81.88%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	83.54%	92.95%
CHEMBL2885	P07451	Carbonic anhydrase III	83.26%	87.45%
CHEMBL4588	P22894	Matrix metalloproteinase 8	82.96%	94.66%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	82.61%	95.52%
CHEMBL1871	P10275	Androgen Receptor	82.56%	96.43%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.82%	98.33%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.09%	97.50%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	80.50%	92.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.45%	94.45%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	80.37%	95.36%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.15%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6442244
• LOTUS: LTS0250518
• wikiData: Q30594796