Macarangioside A

Details

• Internal ID: 53748e1e-ff3e-45f4-8501-c4abc0135667
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R)-4-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]butan-2-yl]oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• SMILES (Canonical): CC1=CC(=O)CC(C1(CCC(C)OC2C(C(C(C(O2)COC(=O)C3=CC(=C(C(=C3)O)O)O)O)O)O)O)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC([C@]1(CC[C@@H](C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C3=CC(=C(C(=C3)O)O)O)O)O)O)O)(C)C
• InChI: InChI=1S/C26H36O12/c1-12-7-15(27)10-25(3,4)26(12,35)6-5-13(2)37-24-22(33)21(32)20(31)18(38-24)11-36-23(34)14-8-16(28)19(30)17(29)9-14/h7-9,13,18,20-22,24,28-33,35H,5-6,10-11H2,1-4H3/t13-,18-,20-,21+,22-,24-,26-/m1/s1
• InChI Key: YTTZYTOMXNRFMJ-AVSPSPHWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₆O₁₂
• Molecular Weight: 540.60 g/mol
• Exact Mass: 540.22067658 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.63
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R)-4-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]butan-2-yl]oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8497	84.97%
Caco-2	-	0.8509	85.09%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8609	86.09%
OATP2B1 inhibitior	-	0.7194	71.94%
OATP1B1 inhibitior	+	0.7560	75.60%
OATP1B3 inhibitior	+	0.8135	81.35%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6818	68.18%
BSEP inhibitior	-	0.6516	65.16%
P-glycoprotein inhibitior	-	0.4760	47.60%
P-glycoprotein substrate	-	0.5837	58.37%
CYP3A4 substrate	+	0.6916	69.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8837	88.37%
CYP3A4 inhibition	-	0.6938	69.38%
CYP2C9 inhibition	-	0.5927	59.27%
CYP2C19 inhibition	-	0.6160	61.60%
CYP2D6 inhibition	-	0.8937	89.37%
CYP1A2 inhibition	+	0.5577	55.77%
CYP2C8 inhibition	-	0.6252	62.52%
CYP inhibitory promiscuity	-	0.8964	89.64%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7294	72.94%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9203	92.03%
Skin irritation	-	0.7281	72.81%
Skin corrosion	-	0.9537	95.37%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4553	45.53%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8196	81.96%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.9218	92.18%
Acute Oral Toxicity (c)	III	0.5091	50.91%
Estrogen receptor binding	+	0.6726	67.26%
Androgen receptor binding	+	0.7031	70.31%
Thyroid receptor binding	+	0.5756	57.56%
Glucocorticoid receptor binding	+	0.6480	64.80%
Aromatase binding	+	0.6874	68.74%
PPAR gamma	+	0.6278	62.78%
Honey bee toxicity	-	0.8520	85.20%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.9958	99.58%

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	99.58%	91.11%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	98.50%	83.57%
CHEMBL220	P22303	Acetylcholinesterase	96.86%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.70%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.07%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.52%	90.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.96%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.89%	89.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.88%	95.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.53%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.15%	86.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.14%	96.47%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.34%	83.00%
CHEMBL5255	O00206	Toll-like receptor 4	87.05%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.25%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.07%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	85.99%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.14%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.13%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.57%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.68%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	83.68%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.33%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.26%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.07%	97.09%
CHEMBL2535	P11166	Glucose transporter	82.96%	98.75%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.72%	94.80%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.68%	93.04%
CHEMBL4208	P20618	Proteasome component C5	82.29%	90.00%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	81.81%	80.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.46%	94.75%
CHEMBL4581	P52732	Kinesin-like protein 1	81.10%	93.18%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.31%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.25%	96.00%

Plants that contains it

• Bobgunnia madagascariensis
• Calodendrum capense
• Croton caudatus
• Elaeocarpus fuscoides
• Jacobaea adonidifolia
• Macaranga tanarius
• Meconopsis horridula
• Oxera splendida
• Stevia eupatoria
• Vitex pinnata

Cross-Links

• PubChem: 16062725
• NPASS: NPC201093
• LOTUS: LTS0010219
• wikiData: Q105362043