Aguerin B

Details

• Internal ID: ce9566c3-c1fa-40a9-aab2-56a037a3fd9f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-methylprop-2-enoate
• SMILES (Canonical): CC(=C)C(=O)OC1CC(=C)C2CC(C(=C)C2C3C1C(=C)C(=O)O3)O
• SMILES (Isomeric): CC(=C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@@H](C(=C)[C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)O
• InChI: InChI=1S/C19H22O5/c1-8(2)18(21)23-14-6-9(3)12-7-13(20)10(4)15(12)17-16(14)11(5)19(22)24-17/h12-17,20H,1,3-7H2,2H3/t12-,13-,14-,15-,16+,17+/m0/s1
• InChI Key: ZGDWDAMVZDRRQA-NQLMQOPMSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.14672380 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Arguerin B
• 4'-Deoxycynaropicrin
• 68370-45-6
• [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-methylprop-2-enoate
• 2-Propenoic acid, 2-methyl-, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester
• CHEMBL520721
• DTXSID20987920
• 8-Hydroxy-3,6,9-trimethylidene-2-oxododecahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.6385	63.85%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5963	59.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9048	90.48%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8674	86.74%
P-glycoprotein inhibitior	-	0.8579	85.79%
P-glycoprotein substrate	-	0.6616	66.16%
CYP3A4 substrate	+	0.6392	63.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8451	84.51%
CYP3A4 inhibition	-	0.7961	79.61%
CYP2C9 inhibition	-	0.9089	90.89%
CYP2C19 inhibition	-	0.8295	82.95%
CYP2D6 inhibition	-	0.9489	94.89%
CYP1A2 inhibition	-	0.7890	78.90%
CYP2C8 inhibition	-	0.7958	79.58%
CYP inhibitory promiscuity	-	0.9228	92.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9225	92.25%
Carcinogenicity (trinary)	Non-required	0.4913	49.13%
Eye corrosion	-	0.8851	88.51%
Eye irritation	-	0.6444	64.44%
Skin irritation	-	0.6135	61.35%
Skin corrosion	-	0.8667	86.67%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6599	65.99%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.7190	71.90%
skin sensitisation	-	0.7397	73.97%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.8307	83.07%
Acute Oral Toxicity (c)	III	0.3671	36.71%
Estrogen receptor binding	+	0.6451	64.51%
Androgen receptor binding	+	0.5721	57.21%
Thyroid receptor binding	-	0.5283	52.83%
Glucocorticoid receptor binding	+	0.5981	59.81%
Aromatase binding	-	0.6217	62.17%
PPAR gamma	+	0.5805	58.05%
Honey bee toxicity	-	0.5789	57.89%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9387	93.87%

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	94.43%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	90.41%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.99%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	87.39%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.64%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.98%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.69%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	83.32%	90.17%
CHEMBL2581	P07339	Cathepsin D	83.16%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.49%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.49%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.71%	89.00%

Plants that contains it

• Achillea barrelieri subsp. barrelieri
• Brachylaena huillensis
• Carlina acaulis
• Centaurea behen
• Centaurea deflexa
• Centaurea glastifolia
• Centaurea macrocephala
• Centaurea musimonum
• Centaurea solstitialis
• Cheirolophus canariensis
• Cheirolophus teydis
• Cheirolophus uliginosus
• Colchicum soboliferum
• Cousinia canescens
• Cynara cardunculus
• Cynara humilis
• Pleiotaxis rugosa
• Psorothamnus spinosus
• Saussurea amurensis
• Saussurea candicans
• Saussurea elegans
• Trachelospermum asiaticum
• Vernonanthura montevidensis
• Volutaria tubuliflora

Cross-Links

• PubChem: 155102
• NPASS: NPC207114
• ChEMBL: CHEMBL520721
• LOTUS: LTS0140805
• wikiData: Q82976293