Glaucolide A

Details

• Internal ID: 3bb3a67e-35d0-4400-b7ef-35235107b2b0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1S,2R,4R,8R,10S)-8-acetyloxy-12-(acetyloxymethyl)-4,8-dimethyl-7,13-dioxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-11-en-10-yl] 2-methylprop-2-enoate
• SMILES (Canonical): CC(=C)C(=O)OC1CC(C(=O)CCC2(C(O2)C3C1=C(C(=O)O3)COC(=O)C)C)(C)OC(=O)C
• SMILES (Isomeric): CC(=C)C(=O)O[C@H]1C[C@@](C(=O)CC[C@@]2([C@H](O2)[C@@H]3C1=C(C(=O)O3)COC(=O)C)C)(C)OC(=O)C
• InChI: InChI=1S/C23H28O10/c1-11(2)20(27)30-15-9-23(6,32-13(4)25)16(26)7-8-22(5)19(33-22)18-17(15)14(21(28)31-18)10-29-12(3)24/h15,18-19H,1,7-10H2,2-6H3/t15-,18-,19+,22+,23+/m0/s1
• InChI Key: DDRDDFBLSIAXPP-WMFJGPPASA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₁₀
• Molecular Weight: 464.50 g/mol
• Exact Mass: 464.16824709 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 10
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 11091-29-5
• 2-Propenoic acid, 2-methyl-, 5-(acetyloxy)-8-((acetyloxy)methyl)-1a,2,3,4,5,6,7,9,10a,10b-decahydro-1a,5-dimethyl-4,9-dioxooxireno(9,10)cyclodeca(1,2-b)furan-7-yl ester, (1aR-(1aR*,5R*,7S*,10aS*,10bR*))-
• Glaucolid-A
• C09463
• CHEBI:5374
• DTXSID10911895
• Q27106739
• [(1S,2R,4R,8R,10S)-8-acetyloxy-12-(acetyloxymethyl)-4,8-dimethyl-7,13-dioxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-11-en-10-yl] 2-methylprop-2-enoate
• 2-Methylpropenoic acid (1aR,5R,7S,10aS,10bR)-5-acetoxy-8-acetoxymethyl-1a,2,3,4,5,6,7,9,10a,10b-deca
• 5-(Acetyloxy)-8-[(acetyloxy)methyl]-1a,5-dimethyl-4,9-dioxo-1a,2,3,4,5,6,7,9,10a,10b-decahydrooxireno[9,10]cyclodeca[1,2-b]furan-7-yl 2-methylprop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9841	98.41%
Caco-2	-	0.5928	59.28%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7560	75.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8718	87.18%
OATP1B3 inhibitior	+	0.9304	93.04%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.8894	88.94%
P-glycoprotein inhibitior	+	0.8118	81.18%
P-glycoprotein substrate	-	0.6436	64.36%
CYP3A4 substrate	+	0.6834	68.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8947	89.47%
CYP3A4 inhibition	-	0.7087	70.87%
CYP2C9 inhibition	-	0.7677	76.77%
CYP2C19 inhibition	-	0.8664	86.64%
CYP2D6 inhibition	-	0.9367	93.67%
CYP1A2 inhibition	-	0.5861	58.61%
CYP2C8 inhibition	+	0.5194	51.94%
CYP inhibitory promiscuity	-	0.9053	90.53%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5112	51.12%
Eye corrosion	-	0.9773	97.73%
Eye irritation	-	0.8566	85.66%
Skin irritation	-	0.5141	51.41%
Skin corrosion	-	0.9161	91.61%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5403	54.03%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6770	67.70%
skin sensitisation	-	0.8207	82.07%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.7907	79.07%
Acute Oral Toxicity (c)	III	0.5918	59.18%
Estrogen receptor binding	+	0.7378	73.78%
Androgen receptor binding	+	0.6791	67.91%
Thyroid receptor binding	+	0.6053	60.53%
Glucocorticoid receptor binding	+	0.8279	82.79%
Aromatase binding	+	0.6480	64.80%
PPAR gamma	+	0.7452	74.52%
Honey bee toxicity	-	0.6139	61.39%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9912	99.12%

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	96.45%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.69%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.55%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.20%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.69%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.63%	86.33%
CHEMBL299	P17252	Protein kinase C alpha	88.15%	98.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.68%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	85.55%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	85.27%	91.49%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.24%	82.69%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.21%	94.00%
CHEMBL2581	P07339	Cathepsin D	83.63%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.35%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.82%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	80.80%	97.79%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.01%	91.07%

Plants that contains it

• Brenandendron frondosum
• Cyrtocymura scorpioides
• Lepidaploa pineticola
• Pseudelephantopus spicatus
• Tarlmounia elliptica
• Vernonanthura cordata
• Vernonanthura nudiflora
• Vernonanthura squamulosa
• Vernonia incana
• Vernonia syringifolia

Cross-Links

• PubChem: 442248
• LOTUS: LTS0066679
• wikiData: Q27106739