Glaucolide B

Details

• Internal ID: 83646afc-cf70-4fc4-a283-089f5a82284a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1S,2R,4R,8R,10S)-8,10-diacetyloxy-4,8-dimethyl-7,13-dioxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-11-en-12-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1=C2C(CC(C(=O)CCC3(C(C2OC1=O)O3)C)(C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): CC(=O)OCC1=C2[C@H](C[C@@](C(=O)CC[C@@]3([C@@H]([C@H]2OC1=O)O3)C)(C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C21H26O10/c1-10(22)27-9-13-16-14(28-11(2)23)8-21(5,30-12(3)24)15(25)6-7-20(4)18(31-20)17(16)29-19(13)26/h14,17-18H,6-9H2,1-5H3/t14-,17-,18+,20+,21+/m0/s1
• InChI Key: JNLNEIIZZQABDP-ZBWGKUOUSA-N
• Popularity: 18 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₁₀
• Molecular Weight: 438.40 g/mol
• Exact Mass: 438.15259702 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.94
• H-Bond Acceptor: 10
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• CHEMBL4278902
• C09465
• CHEBI:5375
• DTXSID50911894
• BDBM50466096
• Q27106740
• 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-5,7-diyl diacetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9869	98.69%
Caco-2	-	0.5453	54.53%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7882	78.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8773	87.73%
OATP1B3 inhibitior	+	0.9497	94.97%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9067	90.67%
P-glycoprotein inhibitior	+	0.8097	80.97%
P-glycoprotein substrate	-	0.7096	70.96%
CYP3A4 substrate	+	0.6589	65.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8947	89.47%
CYP3A4 inhibition	-	0.7922	79.22%
CYP2C9 inhibition	-	0.7775	77.75%
CYP2C19 inhibition	-	0.8889	88.89%
CYP2D6 inhibition	-	0.9371	93.71%
CYP1A2 inhibition	-	0.6523	65.23%
CYP2C8 inhibition	+	0.4501	45.01%
CYP inhibitory promiscuity	-	0.8975	89.75%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4726	47.26%
Eye corrosion	-	0.9791	97.91%
Eye irritation	-	0.8715	87.15%
Skin irritation	-	0.5249	52.49%
Skin corrosion	-	0.9235	92.35%
Ames mutagenesis	-	0.5654	56.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6469	64.69%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6395	63.95%
skin sensitisation	-	0.8428	84.28%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.6878	68.78%
Acute Oral Toxicity (c)	III	0.5503	55.03%
Estrogen receptor binding	+	0.7577	75.77%
Androgen receptor binding	+	0.6824	68.24%
Thyroid receptor binding	+	0.5731	57.31%
Glucocorticoid receptor binding	+	0.8330	83.30%
Aromatase binding	+	0.5711	57.11%
PPAR gamma	+	0.7207	72.07%
Honey bee toxicity	-	0.6604	66.04%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9822	98.22%

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	96.79%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.28%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.00%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.94%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.06%	86.33%
CHEMBL299	P17252	Protein kinase C alpha	89.02%	98.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.92%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.43%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.08%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.77%	94.00%
CHEMBL2996	Q05655	Protein kinase C delta	84.36%	97.79%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.72%	82.69%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.31%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	81.73%	91.19%

Plants that contains it

• Chrysolaena platensis
• Chrysolaena propinqua
• Cuatrecasanthus flexipappus
• Eirmocephala megaphylla
• Lepidaploa chalybaea
• Lepidaploa remotiflora
• Lepidaploa rufogrisea
• Lepidaploa tortuosa
• Pseudelephantopus spicatus
• Quechualia fulta
• Stramentopappus pooleae
• Tarlmounia elliptica
• Vernonia greggii

Cross-Links

• PubChem: 442250
• LOTUS: LTS0228373
• wikiData: Q27106740