Macrophyllicin

Details

• Internal ID: 125c7a8b-2902-4b0c-8737-b9b325ce212a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(5S,6aR,6bS,8S,8aS,12aR,14bR)-5,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl] (2S,3S,4S,5R,6R)-3-hydroxy-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O)C(=O)OC5CCC6(C7CC=C8C9CC(CCC9(C(CC8(C7(CC(C6C5(C)C)O)C)C)O)CO)(C)C)C)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H](O[C@@H]([C@@H]2O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O[C@@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)C(=O)OC5CC[C@@]6(C7CC=C8[C@H]9CC(CC[C@@]9([C@H](C[C@]8([C@@]7(C[C@@H](C6C5(C)C)O)C)C)O)CO)(C)C)C)O)O)O)O
• InChI: InChI=1S/C54H88O24/c1-21-30(60)33(63)36(66)45(71-21)75-40-39(69)41(76-48(78-47-38(68)35(65)32(62)26(19-56)73-47)42(40)77-46-37(67)34(64)31(61)25(18-55)72-46)44(70)74-29-11-12-51(6)27-10-9-22-23-15-49(2,3)13-14-54(23,20-57)28(59)17-52(22,7)53(27,8)16-24(58)43(51)50(29,4)5/h9,21,23-43,45-48,55-69H,10-20H2,1-8H3/t21-,23+,24-,25+,26+,27?,28-,29?,30-,31+,32-,33+,34-,35-,36+,37+,38+,39-,40-,41-,42+,43?,45-,46+,47+,48+,51+,52+,53+,54+/m0/s1
• InChI Key: CDYAORBMMPRWHL-XOJINRSKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₈O₂₄
• Molecular Weight: 1121.30 g/mol
• Exact Mass: 1120.56655367 g/mol
• Topological Polar Surface Area (TPSA): 394.00 Ų
• XlogP: -0.20

Synonyms

• 149474-93-1
• 3-O-(alpha-L-Rhamnopyranosyl(1-2)-beta-D-glucopyranosyl-(1-2)-beta-D-galactopyranosyl-(1-2)-beta-D-glucuronopyranosyl)-6beta,16alpha,28-trihydroxyolean-12-ene
• beta-D-Glucopyranosiduronic acid, (3beta,6beta,16alpha)-6,16,28-trihydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-beta-D-glucopyranosyl-(1-2)-O-beta-D-galactopyranosyl-(1-2)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

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	97.39%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.38%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.02%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	92.07%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.91%	96.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.85%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.33%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.30%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.68%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.23%	94.00%
CHEMBL2581	P07339	Cathepsin D	85.16%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.59%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.52%	96.61%
CHEMBL5255	O00206	Toll-like receptor 4	82.22%	92.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.02%	97.36%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.84%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.65%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	81.46%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.14%	97.25%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.89%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.29%	96.77%

Plants that contains it

• Primula macrophylla

Cross-Links

• PubChem: 44150651
• LOTUS: LTS0136580
• wikiData: Q104955313