gramicidin S

antibioticmech:aro-0734abf918 ·ANTIBACTERIAL ·MINTED SEEDED

Gramicidin S is a cyclical decapeptide with two pentapeptides (Val-Orn-Leu-D-Phe-Pro) joined head to tail. Like other gramicidins, Gramicidin S disrupts membrane permeability of cations while also destabilizing the membrane at higher concentrations. — PMID:10590309

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

nonribosomal peptide antibioticsARO:3009657

Strictly broader compounds or drug classes this molecule belongs to.

nonribosomal peptide antibiotics ARO:3009657

Chemical structure

Computed structure properties
Molecular formula	C60H92N12O10
Charge	0
Average mass	1141.4 Da
Monoisotopic mass	1140.70593718 Da
Source	PubChem · retrieved 2026-08-29
InChIKey	IUAYMJGZBVDSGL-XNNAEKOYSA-N

SMILES

CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N3CCC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCN)C(C)C)CC4=CC=CC=C4)CC(C)C)CCCN)C(C)C)CC5=CC=CC=C5

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

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

gramicidin SARO:3000200
pubchem.compound:73357

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3000200`	gramicidin S	`antibioticmech:aro-0734abf918`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

cell membrane component targeted by antibiotic MEMBRANE ATTACKED_COMPONENT

ARO:3000710

CARD/ARO database assertion; target organism, strain, and assay are not specified. ARO describes interaction with membrane phospholipids and loss of membrane integrity. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000710 (CARD/ARO asserts targeted_by_antibiotic ARO:3000200 (gramicidin S); database assertion, not a primary citation.)

Discussions

Open questions, knowledge gaps and curation todos attached to this compound.

CURATION_TODO OPEN

gramicidin S shares InChIKey IUAYMJGZBVDSGL-XNNAEKOYSA-N with gramicidin C, but the sources name them as different compounds. Which record does this structure belong to?

Both structures come from PubChem CIDs cross-referenced by CARD. Identical structures under different names mean at least one cross-reference is wrong upstream; the seeder cannot tell which, so it flags rather than merges.

Attached to: chemical_structure

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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