Macrocliniside A

Details

• Internal ID: d310f04f-025f-4170-b2c1-f3cb09cb0673
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,5R,6aR,8S,9aR,9bS)-5-hydroxy-3,6,9-trimethylidene-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): C=C1C2CC(C(=C)C2C3C(CC1O)C(=C)C(=O)O3)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C=C1[C@@H]2C[C@@H](C(=C)[C@@H]2[C@@H]3[C@@H](C[C@H]1O)C(=C)C(=O)O3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C21H28O9/c1-7-10-5-13(28-21-18(26)17(25)16(24)14(6-22)29-21)9(3)15(10)19-11(4-12(7)23)8(2)20(27)30-19/h10-19,21-26H,1-6H2/t10-,11-,12+,13-,14+,15-,16+,17-,18+,19-,21+/m0/s1
• InChI Key: ARJUJAMZTUUZNZ-NJQUUYHGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₉
• Molecular Weight: 424.40 g/mol
• Exact Mass: 424.17333247 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.22
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• CHEMBL3622760
• 94474-61-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6652	66.52%
Caco-2	-	0.8239	82.39%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6210	62.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8356	83.56%
OATP1B3 inhibitior	+	0.9527	95.27%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7652	76.52%
P-glycoprotein inhibitior	-	0.7842	78.42%
P-glycoprotein substrate	-	0.8128	81.28%
CYP3A4 substrate	+	0.6080	60.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8596	85.96%
CYP3A4 inhibition	-	0.8911	89.11%
CYP2C9 inhibition	-	0.9202	92.02%
CYP2C19 inhibition	-	0.8559	85.59%
CYP2D6 inhibition	-	0.8966	89.66%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	-	0.7243	72.43%
CYP inhibitory promiscuity	-	0.9173	91.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7650	76.50%
Eye corrosion	-	0.9847	98.47%
Eye irritation	-	0.8979	89.79%
Skin irritation	-	0.7751	77.51%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4593	45.93%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8491	84.91%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6604	66.04%
Acute Oral Toxicity (c)	III	0.4004	40.04%
Estrogen receptor binding	+	0.6464	64.64%
Androgen receptor binding	+	0.5884	58.84%
Thyroid receptor binding	+	0.5732	57.32%
Glucocorticoid receptor binding	-	0.4632	46.32%
Aromatase binding	+	0.6683	66.83%
PPAR gamma	+	0.5297	52.97%
Honey bee toxicity	-	0.5930	59.30%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7151	71.51%

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	95.63%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.74%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.45%	96.61%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.43%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.32%	97.36%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.54%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.40%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.90%	89.34%
CHEMBL2581	P07339	Cathepsin D	80.23%	98.95%

Plants that contains it

• Callitris drummondii
• Capuronianthus mahafalensis
• Cardiospermum grandiflorum
• Crepidiastrum sonchifolium subsp. sonchifolium
• Crepis pyrenaica
• Euryale ferox
• Ixeris repens
• Ixeris stolonifera
• Lactuca quercina
• Lactuca saligna
• Lactuca sativa
• Lactuca serriola
• Lactuca tatarica
• Lactuca virosa
• Launaea arborescens
• Pertya triloba
• Solanum villosum
• Sonchus oleraceus
• Taraxacum udum

Cross-Links

• PubChem: 10455028
• NPASS: NPC80144
• LOTUS: LTS0266397
• wikiData: Q104402655