Details of the Drug

General Information of Drug (ID: DMPT74U)

Drug Name

Gramicidin D

Synonyms

Gramicidins; Gramoderm; Gramacidine S; Gramicidin C; Gramicidin Dubos; Gramicidin J; Gramicidin K; Gramicidin P; Gramicidin S; Gramicidin S [INN]; Gramicidina D; Gramicidina S; Gramicidinum S; Neosporin Ophthalmic Solution; Gramicin S 1; Gramacidine S [INN-French]; Gramicidin A(1); Gramicidin [INN:BAN]; Gramicidina S [INN-Spanish]; Gramicidina [INN-Spanish]; Gramicidine [INN-French]; Gramicidinum S [INN-Latin]; Gramicidinum [INN-Latin]; Gramicin S-A; Cyclo(L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl); 1,10-anhydro(L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithine)

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]
Blepharoconjunctivitis	N.A.	Approved	[2]
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Therapeutic Class

Antibiotics

Affected Organisms

Staphylococcus aureusStreptococcus agalactiaeStreptococcus pneumoniaeEscherichia coliHaemophilus influenzaeKlebsiellaEnterobacterNeisseria gonorrhoeaeNeisseria meningitidisPseudomonas aeruginosa

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 5

Molecular Weight (mw)

1811.2

Logarithm of the Partition Coefficient (xlogp)

10.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C96H135N19O16
IUPAC Name: (2R)-2-[[2-[[(2S)-2-formamido-3-methylbutanoyl]amino]acetyl]amino]-N-[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-(2-hydroxyethylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]-4-methylpentanamide
Canonical SMILES: C[C@@H](C(=O)N[C@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC5=CNC6=CC=CC=C65)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC7=CNC8=CC=CC=C87)C(=O)NCCO)NC(=O)[C@@H](CC(C)C)NC(=O)CNC(=O)[C@H](C(C)C)NC=O
InChI: InChI=1S/C96H135N19O16/c1-50(2)36-71(105-79(118)48-102-93(128)80(54(9)10)103-49-117)86(121)104-58(17)84(119)113-82(56(13)14)95(130)115-83(57(15)16)96(131)114-81(55(11)12)94(129)112-78(43-62-47-101-70-33-25-21-29-66(62)70)92(127)108-74(39-53(7)8)89(124)111-77(42-61-46-100-69-32-24-20-28-65(61)69)91(126)107-73(38-52(5)6)88(123)110-76(41-60-45-99-68-31-23-19-27-64(60)68)90(125)106-72(37-51(3)4)87(122)109-75(85(120)97-34-35-116)40-59-44-98-67-30-22-18-26-63(59)67/h18-33,44-47,49-58,71-78,80-83,98-101,116H,34-43,48H2,1-17H3,(H,97,120)(H,102,128)(H,103,117)(H,104,121)(H,105,118)(H,106,125)(H,107,126)(H,108,127)(H,109,122)(H,110,123)(H,111,124)(H,112,129)(H,113,119)(H,114,131)(H,115,130)/t58-,71+,72+,73+,74+,75-,76-,77-,78-,80-,81+,82+,83-/m0/s1
InChIKey: NDAYQJDHGXTBJL-MWWSRJDJSA-N

Cross-matching ID

PubChem CID: 45267103
CAS Number: 1405-97-6
UNII: 5IE62321P4
DrugBank ID: DB00027
TTD ID: D0J7XL
VARIDT ID: DR01276

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Dihydropteroate synthetase (Bact folP)	TT4ILYC	DHPS_ECOLI	Binder	[3]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	Drug information of Gramicidin D, 2008. eduDrugs.
2	A standard database for drug repositioning. Sci Data. 2017 Mar 14;4:170029.
3	Structures of gramicidins A, B, and C incorporated into sodium dodecyl sulfate micelles. Biochemistry. 2001 Oct 2;40(39):11676-86.
4	Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.