Details of the Drug

General Information of Drug (ID: DMJZ0AM)

Drug Name

GERANYLGERANYL DIPHOSPHATE

Synonyms

Geranylgeranyl pyrophosphate; Geranylgeranyl diphosphate; GGDP; 6699-20-3; geranylgeranyl-PP; GGPP; UNII-N21T0D88LX; (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl trihydrogen diphosphate; N21T0D88LX; Geranylgeraniol diphosphate; CHEBI:48861; all-trans-Geranylgeranyl pyrophosphate; all-trans-Geranylgeranyl diphosphate; Diphosphoric acid, mono(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl) ester, (E,E,E)-; Geranylgeranyl pyrophosphate ammonium salt; 2-trans,6-trans,10-trans-geranylgeranyl diphosphate

Indication

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

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

450.4

Topological Polar Surface Area (xlogp)

4.4

Rotatable Bond Count (rotbonds)

14

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

7

Chemical Identifiers

Formula: C20H36O7P2
IUPAC Name: phosphono [(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl] hydrogen phosphate
Canonical SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)/C)C
InChI: InChI=1S/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b18-11+,19-13+,20-15+
InChIKey: OINNEUNVOZHBOX-QIRCYJPOSA-N

Cross-matching ID

PubChem CID: 447277
ChEBI ID: CHEBI:48861
CAS Number: 6699-20-3
DrugBank ID: DB07841
TTD ID: D0QX6B

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
CAAX farnesyltransferase beta (FNTB)	TT7WZIJ	FNTB_HUMAN	Inhibitor	[2]
Farnesyl protein transferase (Ftase)	TTXQKM3	FNTA_HUMAN; FNTB_HUMAN	Inhibitor	[2]
Geranyltranstransferase (FDPS)	TTIKWV4	FPPS_HUMAN	Inhibitor	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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
Farnesyl protein transferase (Ftase)	DTT	FNTB; FNTA	5.43E-01	-0.1	-0.4

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3052).
2	The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
3	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
4	Tipifarnib in the treatment of newly diagnosed acute myelogenous leukemia. Biologics. 2008 Sep;2(3):491-500.
5	Preclinical and clinical pharmacodynamic assessment of L-778,123, a dual inhibitor of farnesyl:protein transferase and geranylgeranyl:protein trans... Mol Cancer Ther. 2002 Jul;1(9):747-58.
6	Company report (Prescient)
7	Farnesyltransferase inhibitor BMS-214662 induces apoptosis in B-cell chronic lymphocytic leukemia cells. Leukemia. 2004 Oct;18(10):1599-604.
8	Ras farnesyltransferase: a new therapeutic target. J Med Chem. 1997 Sep 12;40(19):2971-90.
9	Aryl tetrahydropyridine inhibitors of farnesyltransferase: glycine, phenylalanine and histidine derivatives. Bioorg Med Chem Lett. 2003 Apr 7;13(7):1359-62.
10	A novel metal-chelating inhibitor of protein farnesyltransferase. Bioorg Med Chem Lett. 2003 May 5;13(9):1523-6.
11	Tricyclic farnesyl protein transferase inhibitors: crystallographic and calorimetric studies of structure-activity relationships. J Med Chem. 1999 Jun 17;42(12):2125-35.
12	Novel conformationally extended naphthalene-based inhibitors of farnesyltransferase. J Med Chem. 1997 Jun 6;40(12):1763-7.
13	Design and synthesis of o-trifluoromethylbiphenyl substituted 2-amino-nicotinonitriles as inhibitors of farnesyltransferase. Bioorg Med Chem Lett. 2005 Jan 3;15(1):153-8.
14	Modeling of binding modes and inhibition mechanism of some natural ligands of farnesyl transferase using molecular docking. J Med Chem. 2002 Mar 28;45(7):1460-5.
15	Potent farnesyltransferase inhibitor ABT-100 abrogates acute allograft rejection. J Heart Lung Transplant. 2005 Sep;24(9):1403-9.
16	Inhibition of human tumor xenograft growth by treatment with the farnesyl transferase inhibitor B956. Cancer Res. 1995 Nov 15;55(22):5310-4.
17	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
18	Synthesis, chiral high performance liquid chromatographic resolution and enantiospecific activity of a potent new geranylgeranyl transferase inhibitor, 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic acid. J Med Chem. 2010 May 13;53(9):3454-64.
19	Detection of nonsterol isoprenoids by HPLC-MS/MS. Anal Biochem. 2008 Dec 1;383(1):18-24.
20	Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates. J Pharmacol Exp Ther. 2001 Feb;296(2):235-42.
21	Activity of bisphosphonates against Trypanosoma brucei rhodesiense. J Med Chem. 2002 Jul 4;45(14):2904-14.
22	Structure-activity relationships among the nitrogen containing bisphosphonates in clinical use and other analogues: time-dependent inhibition of hu... J Med Chem. 2008 Apr 10;51(7):2187-95.
23	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)