Details of the Drug

General Information of Drug (ID: DMZWTY7)

• Drug Name: Phorbol 12,13-butyrate
• Synonyms: Phorbol 12,13-dibutyrate; PDBU; Phorbol dibutyrate; 37558-16-0; Phorbol 12,13-dibutanoate; UNII-67MX82CL58; Phorbol-12,13-dibutyrate; NSC 622507; CHEBI:17598; 67MX82CL58; (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulene-9,9a-diyl dibutanoate; Butanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9aH-cyclopropa[3,4]be

Indication

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

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 1:
  Molecular Weight (mw); 504.6
  Topological Polar Surface Area (xlogp); 2
  Rotatable Bond Count (rotbonds); 9
  Hydrogen Bond Donor Count (hbonddonor); 3
  Hydrogen Bond Acceptor Count (hbondacc); 8
• Chemical Identifiers:
  Formula: C28H40O8
  IUPAC Name: [(1S,2S,6R,10S,11R,13S,14R,15R)-13-butanoyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] butanoate
  Canonical SMILES: CCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)CCC)O)C
  InChI: InChI=1S/C28H40O8/c1-7-9-20(30)35-24-16(4)27(34)18(22-25(5,6)28(22,24)36-21(31)10-8-2)12-17(14-29)13-26(33)19(27)11-15(3)23(26)32/h11-12,16,18-19,22,24,29,33-34H,7-10,13-14H2,1-6H3/t16-,18+,19-,22-,24-,26-,27-,28-/m1/s1
  InChIKey: BQJRUJTZSGYBEZ-YVQNUNKESA-N
• Cross-matching ID:
  PubChem CID: 37783
  ChEBI ID: CHEBI:17598
  CAS Number: 37558-16-0
  TTD ID: D02KPV

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Protein kinase C delta (PRKCD)	TT9WJ8U	KPCD_HUMAN	Inhibitor	[1]

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
Protein kinase C delta (PRKCD)	DTT	PRKCD	1.25E-22	0.59	0.82

References

• [1] Conformationally constrained analogues of diacylglycerol (DAG). 28. DAG-dioxolanones reveal a new additional interaction site in the C1b domain of ... J Med Chem. 2007 Jul 26;50(15):3465-81.
• [2] PKC delta and epsilon in drug targeting and therapeutics. Recent Pat DNA Gene Seq. 2009;3(2):96-101.
• [3] Bisindolylmaleimide inhibitors of protein kinase C. Further conformational restriction of a tertiary amine side chain, Bioorg. Med. Chem. Lett. 4(11):1303-1308 (1994).
• [4] Synthesis of bisindolylmaleimide macrocycles, Bioorg. Med. Chem. Lett. 5(18):2093-2096 (1995).
• [5] Novel extranuclear-targeted anthracyclines override the antiapoptotic functions of Bcl-2 and target protein kinase C pathways to induce apoptosis. Mol Cancer Ther. 2002 May;1(7):469-81.
• [6] Inhibitors of protein kinase C. 1. 2,3-Bisarylmaleimides. J Med Chem. 1992 Jan;35(1):177-84.
• [7] (S)-13-[(dimethylamino)methyl]-10,11,14,15-tetrahydro-4,9:16, 21-dimetheno-1H, 13H-dibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecene-1,3(2H... J Med Chem. 1996 Jul 5;39(14):2664-71.
• [8] A nonpromoting phorbol from the samoan medicinal plant Homalanthus nutans inhibits cell killing by HIV-1. J Med Chem. 1992 May 29;35(11):1978-86.
• [9] Novel protein kinase C inhibitors: synthesis and PKC inhibition of beta-substituted polythiophene derivatives. Bioorg Med Chem Lett. 1999 Aug 2;9(15):2279-82.
• [10] Multivariate analysis by the minimum spanning tree method of the structural determinants of diphenylethylenes and triphenylacrylonitriles implicate... J Med Chem. 1992 Feb 7;35(3):573-83.