Details of the Drug

General Information of Drug (ID: DMR8HKC)

• Drug Name: Chebulinic acid
• Synonyms: Chebulinic acid; 18942-26-2; UNII-HVC8VQJ6EK; HVC8VQJ6EK; AC1L2HS1; CHEMBL501154; NSC69862; NSC 69862; CHEBI:3584; ZINC195763592; FT-0697896; C10215; Q-100932; beta-D-Glucopyranose, cyclic 2,4-ester with 3-(6-carboxy-2,3,4-trihydroxyphenyl)-4-hydroxy-1,2,4-butanetricarboxylic acid, 1,3,6-tris(3,4,5-trihydroxybenzoate)

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 4:
  Molecular Weight (mw); 956.7
  Logarithm of the Partition Coefficient (xlogp); 0.7
  Rotatable Bond Count (rotbonds); 12
  Hydrogen Bond Donor Count (hbonddonor); 13
  Hydrogen Bond Acceptor Count (hbondacc); 27
• Chemical Identifiers:
  Formula: C41H32O27
  IUPAC Name: 2-[(4R,5S,7R,8R,11S,12S,13S,21S)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis[(3,4,5-trihydroxybenzoyl)oxy]-7-[(3,4,5-trihydroxybenzoyl)oxymethyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.14,8.016,20]henicosa-1(19),16(20),17-trien-11-yl]acetic acid
  Canonical SMILES: C1=C(C=C(C(=C1O)O)O)C(=O)OC[C@@H]2[C@@H]3[C@@H]([C@H]([C@@H](O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5[C@H]([C@@H](C(=O)O3)CC(=O)O)[C@@H](C(=O)O6)O)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O
  InChI: InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30-,31+,33-,34+,41-/m0/s1
  InChIKey: YGVHOSGNOYKRIH-FJPMMHPYSA-N
• Cross-matching ID:
  PubChem CID: 72284
  ChEBI ID: CHEMBL3584
  TTD ID: D0Z9YK

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Squalene monooxygenase (SQLE)	TTE14XG	ERG1_HUMAN	Inhibitor	[1]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Endothelial transcription factor GATA-2 (GATA2)	OTBP2QQ2	GATA2_HUMAN	Gene/Protein Processing	[2]
Erythroid transcription factor (GATA1)	OTX1R7O1	GATA1_HUMAN	Gene/Protein Processing	[2]
Transcription factor NF-E2 45 kDa subunit (NFE2)	OTLM94BI	NFE2_HUMAN	Gene/Protein Processing	[2]

Molecular Expression Atlas of This Drug

• The Studied Disease: Discovery agent
• ICD Disease Classification: N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Squalene monooxygenase (SQLE)	DTT	SQLE	7.14E-03	0.45	2.51

References

• [1] Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase. J Nat Prod. 2001 Aug;64(8):1010-4.
• [2] Effects of chebulinic acid on differentiation of human leukemia K562 cells. Acta Pharmacol Sin. 2004 Feb;25(2):231-8.