Basic information

CPKB ID	CP00038
IUPAC Name	(3R,6S,9S,12S,15S,21R,24S,27S,30S,33S)-9,27-bis(3-aminopropyl)-3,21-dibenzyl-6,24-bis(2-methylpropyl)-12,30-di(propan-2-yl)-1,4,7,10,13,19,22,25,28,31-decazatricyclo[31.3.0.015,19]hexatriacontane-2,5,8,11,14,20,23,26,29,32-decone
Synonyms	(3R,6S,9S,12S,15S,21R,24S,27S,30S,33S)-9,27-Bis(3-Aminopropyl)-3,21-Dibenzyl-6,24-Bis(2-Methylpropyl)-12,30-Di(Propan-2-Yl)-1,4,7,10,13,19,22,25,28,31-Decazatricyclo[31.3.0.015,19]Hexatriacontane-2,5,8,11,14,20,23,26,29,32-Decone 1,10-Anhydro(L-Leucyl-D-Phenylalanyl-L-Prolyl-L-Valyl-L-Ornithyl-L-Leucyl-D-Phenylalanyl-L-Prolyl-L-Valyl-L-Ornithine) 113-73-5 Bis(3-Aminopropyl)-Dibenzyl-Diisobutyl-Diisopropyl-[?]Decone Brn-0605227 Cas-113-73-5 Chebi:5530 Chembl373496 Cyclo(L-Leucyl-D-Phenylalanyl-L-Prolyl-L-Valyl-L-Ornithyl-L-Leucyl-D-Phenylalanyl-L-Prolyl-L-Valyl-L-Ornithyl) Cyclo(L-Valyl-L-Ornithyl-L-Leucyl-D-Phenylalanyl-L-Prolyl-L-Valyl-L-Ornithyl-L-Leucyl-D-Phenylalanyl-L-Prolyl) Dtxsid6046008 Gramacidine-S Gramacidine-S-[Inn-French] Gramicidin-A-S Gramicidin-S Gramicidin-S-[Inn] Gramicidin-S-[Mart.] Gramicidin-S-[Mi] Gramicidin-S-[Who-Dd] Gramicidin-S-1 Gramicidin-S-A Gramicidina-S Gramicidina-S-[Inn-Spanish] Gramicidinum-S Gramicidinum-S-[Inn-Latin] Gramicin-S-1 Gramicin-S-A Grammidin Ncgc00095992-01 Ncgc00095992-05 Q4147636 Schembl135010 Tox21_111543 Unii-Whm29Qa23F Whm29Qa23F
Family	Gramicidin Norine
Function	Anti-Microbial Norine
Information	Gramicidin S is a homodetic cyclic peptide. A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN. PubChem\|73357 Norine\|NOR00249

Legend

Structure

Molecular Formula	C60H92N12O10
Molecular Weight	1140.705937 g/mol
SMILES RUN SEA Predictions	CC(C)C[C@@H]1NC(=O)[C@H](CCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC1=O PubChem\|73357
InChI	InChI=1S/C60H92N12O10/c1-35(2)31-43-53(75)67-45(33-39-19-11-9-12-20-39)59(81)71-29-17-25-47(71)55(77)70-50(38(7)8)58(80)64-42(24-16-28-62)52(74)66-44(32-36(3)4)54(76)68-46(34-40-21-13-10-14-22-40)60(82)72-30-18-26-48(72)56(78)69-49(37(5)6)57(79)63-41(23-15-27-61)51(73)65-43/h9-14,19-22,35-38,41-50H,15-18,23-34,61-62H2,1-8H3,(H,63,79)(H,64,80)(H,65,73)(H,66,74)(H,67,75)(H,68,76)(H,69,78)(H,70,77)/t41-,42-,43-,44-,45+,46+,47-,48-,49-,50-/m0/s1
InChIKey	IUAYMJGZBVDSGL-AXYZPTJPNA-N

2D Structure PubChem\|73357

Sequence

IUPAC Condensed	cyclo[Leu-D-Phe-Pro-Val-Orn-Leu-D-Phe-Pro-Val-Orn] PubChem\|73357
Amino acid chain	Leu(1)--D-Phe--Pro--Val--Orn--Leu--D-Phe--Pro--Val--Orn(1) CyclicPepedia\|PP
Graph representation	Leu,D-Phe,Pro,Val,Orn,Leu,D-Phe,Pro,Val,Orn @0,9 CyclicPepedia\|PP
One letter code from Structure	LFPVALFPVA CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Leu(1)--Phe--Pro--Val--Orn--Leu--Phe--Pro--Val--Orn(1) CyclicPepedia\|Struct2seq
Description of the conversion sequence	The one letter code and Amino acid chain derived from the structural transformation may be inconsistent, with the Amino acid chain containing Essential Amino acid and the one letter code not.
svg Image PubChem\|73357

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name	Property Value
Exact Mass	1140.705937
Number of Rings	5.0
Complexity	0.414634146
XlogP3 AA	1.2278
Heavy Atom Count	82.0
Hydrogen Bond Donor Count	10.0
Hydrogen Bond Acceptor Count	12.0
Rotatable Bond Count	16.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	310.3704
Rule_of_Five	0.0
Number of Atoms	82.0
Topological Polar Surface Area	325.46
Refractivity	310.3704
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01000010101000100100100011011000010000100111010000100010000000100010101111101100100110000010110010000101000001001010001000110010010001001000110000001111000110010101001010000110000110011111100100100000101001001000000000000000010100000101011110001110011100101111000110001000000010001001000000000010011010010011101011000001010100000010111011010110101000000010011000000001100010000000000000000010010100000100000110001100000010000000101000110011110011100000000100010010111000010000000000001010001010010100100000101100110000000100101110010101100110000100100010010110001000000100010010000000000010111000101000110001001010011000100000001001100100100100000010100110000001000110001010000000000101011100011100010010100101100000000100110011001001011000101010001010001110101010001110010010000001100001001010001000001000001000100000001001111010110000010011101101000000110010011101100001000100000100111000000011001101000010111000010110011110011010000001011110101000001000011001010000011000010100001010000011010100000000000000101101001101110011110110001010100000001010000000001010101001100001000001001001110110000001001001010010000000101000000110001001010000000000101000001000101110100110100111001000010010001110000001000000100001001101010010100000011100010111010010010000100101000010001000100000100000111000110001001001011010100000000001100001100001000011111110000001010110110001010000010000100101011000001000000001000001001100000001000101100011001000010011111110001001001011000100000110010000100001110000111011011000000000100100100111000001100000001000010000010110100100010010100000000100100111001001000101100010000001000010000001000000100010110000000100000000000000010000000001000011000100001010000001000000010001011110000100100101000001010110001000100000100011011000010100010010010110100000000000100001010010000000000011111001101100000010110000011110100111110010000000100000000000100011100000010000001101101100000100101101000001010000010101010010000111110110000011111001011011001000000001001001100110000101000000100010000000001001101110000100000000111000000011
Morgan Fingerprint	0100110000100000000100000000100001000000001000000000000000000000100000000000000010000000001000000000000000000000000100000000000000000000000000000001000000000000000000000000000100000000000000000000000000000000000000001000000000000001000000000000000000000100000000000000000000000000000100001000000000000100000000000010000001000000000000010000100000000100000110000000000000000000000000000000010000000000000000000000000000000000000000001001000000000010000000001010000000000000000000000010000000001100000000000001000000000001000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000010000000000000010000000000000000001000000000100000000000000000000000000000001000100000000000000000000000000000000000000000000000000000000000000000000000000000000100001000000100000000100000000000000001001000000000000000000000000000000000010000000000000000000000000000000000000010000000010000000000000000000001000000000000000000000001000000000000000000000000100100000000010000
MACCS Keys	00000000000000000000000000000000000000000000000000000010000000000000000000100001001111000011100110001000110000110001011011100101110100001110111101111111011110111111110

Sequence Properties

Property Name	Property Value
Boman Index	-2.75
Instability	86.04
Charge	-0.00201570060725275
Aliphatic Index	156.0

Binding Target

Other evidence

Property Name	Property ID
TTD	D0J7XL
DrugMAP	DMPT74U

Manufacturers

Manufacturers Name	Value
CreativePeptides	Gramicidin S
Bayer healthcare pharmaceuticals	Gramicidin S
Upsher smith laboratories	Gramicidin S
Merck	Gramicidin S

Manufacturers Name	Value
Apotex	Gramicidin S
Baxter Healthcare Corp	Gramicidin S
Pharmasources	Gramicidin S
Novartis	Gramicidin S
AstraZeneca	Gramicidin S

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CC(C)C[C@@H]1NC(=O)[C@H](CCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC1=O
Structure Properties	CC(C)C[C@@H]1NC(=O)[C@H](CCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC1=O
Sequence to Structure	LFPVALFPVA
Sequence Properties	LFPVALFPVA
Expasy ProtParam Tool	LFPVALFPVA
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	IUAYMJGZBVDSGL-AXYZPTJPNA-N
pubchem	73357
Drugbank	Gramicidin S
DRAMP3	Gramicidin S
Uniprot	Gramicidin S
Cybase	Gramicidin S
NORINE	NOR00249
CONOSERVER	Gramicidin S
BindingDB	CC(C)C[C@@H]1NC(=O)[C@H](CCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC1=O
CHEMBL	CHEMBL373496
CTD	Gramicidin S
Wikipedia	Gramicidin S
KEGG Compound/Drug	Gramicidin S
CHEBI	CHEBI:5530
EPA DSSTox	DTXSID6046008
FDA Global Substance Registration System (GSRS)	WHM29QA23F
DTP/NCI	Gramicidin S
Chemspider	IUAYMJGZBVDSGL-AXYZPTJPNA-N
VARIDT	DR01276

Reference

Pubmed_ID	Title	DOI	Journal
15615410	[Studies on chemical constituents of the mycelia from fermented culture of Flammulina velutipes]	None	Zhongguo Zhong Yao Za Zhi
[Studies on chemical constituents of the mycelia from fermented culture of Flammulina velutipes] Abstract To study the chemical constituents from the mycelia of Flammulina velutipes. The compounds were isolated with silica gel column chromatography and their structures were elucidated on the basis of spectral analysis (IR, EL-MS, FAB-MS, 1H-NMR, 13NMR). Seven compounds were identified as cyclo-(R-pro-R-leu) (1), cyclo-(R-isoleu-R-leu) (2), phenylalanine (3), alanine (4), leucine (5), guanosine (6), adenosine (7), The compounds 1-6 were isolated from the mycelia of Flammulina velutipes for the first time.
16724845	Antineoplastic Agents. 554. The manitoba bacterium Streptomyces sp	10.1021/np058087v.	J Nat Prod
Antineoplastic Agents. 554. The manitoba bacterium Streptomyces sp Abstract A Streptomyces sp. isolated from riverbank soil in Manitoba, Canada, was found to contain two cancer cell growth inhibitories: diazaanthraqui 1 and 3-(hydroxyacetyl)indole (8). The structures were determined by interpretation of data from HRMS, UV, and high-field (400 MHz) NMR experiments. The red-colored diazaanthraqui 1 and 3-(hydroxyacetyl)indole (8) were found to inhibit (0.1-3 microg/mL) growth of a minipanel of human cancer cell lines and P388 lymphocytic leukemia cells. Diazaanthraqui 1 was also found to inhibit growth of the bacteria Streptococcus pneumoniae and Neisseria gonorrheae. However, three companion constituents, cyclo-Pro-Leu (5), cyclo-Pro-Phe (6), and cyclo-Pro-Val (7), did not inhibit cancer cell growth.
21985013	A bisamide and four diketopiperazines from a marine-derived Streptomyces sp	10.1080/10286020.2011.617744.	J Asian Nat Prod Res
A bisamide and four diketopiperazines from a marine-derived Streptomyces sp Abstract A new bisamide N₁-acetyl-N₇-phenylacetyl cadaverine (1) and a series of diketopiperazines including a new diketopiperazine cyclo(2-hydroxy-Pro-R-Leu) (2), together with a new natural product cyclo(4-hydroxy-S-Pro-S-Trp) (3) and two known leucine-based diketopiperazines cyclo(4-hydroxy-R-Pro-S-Leu) (4) and cyclo (S-Pro-R-Leu) (5), were isolated from ethyl acetate extract of a fermentation broth of a marine-derived Streptomyces sp. Their structures were elucidated by the interpretation of spectroscopic analysis. The antitumor activities of compounds 1-3 against HL-60 cell lines were tested by MTT assay.