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Citrulline

Athanor · official

C6H13N3O3 · 175.19 g/mol

IUPAC name: (2S)-2-amino-5-(carbamoylamino)pentanoic acid

Also called L-citrulline, urea cycle

Amino acids
Open in Athanor
The structure of Citrulline
Drawn from its SMILES with RDKit
Harmful or irritantWarningCauses skin irritation · Causes serious eye irritation

Names and identifiers

IUPAC name
(2S)-2-amino-5-(carbamoylamino)pentanoic acid
Synonyms
L-citrulline, urea cycle, delta-Ureidonorvaline
+ 36 more

Sitrulline, N5-Carbamoyl-L-ornithine, (S)-2-Amino-5-ureidopentanoic acid, L-Cytrulline, N5-(Aminocarbonyl)-L-ornithine, Citrulline, L-, N(delta)-Carbamylornithine, N5-(Aminocarbonyl)ornithine, L-2-Amino-5-ureidovaleric acid, N5-carbamoylornithine, alpha-Amino-delta-ureidovaleric acid, (2S)-2-amino-5-(carbamoylamino)pentanoic acid, L-Ornithine, N5-(aminocarbonyl)-, 2-Amino-5-ureidovaleric acid, 29VT07BGDA, 2-Amino-5-uredovaleric acid, DTXSID80883373, Ngamma-carbamylornithine, N(5)-(aminocarbonyl)-L-ornithine, NSC-27425, CHEBI:16349, CHEBI:18211, alpha-amino-gamma-ureidovaleric acid, RefChem:5693, DTXCID301022909, 206-759-6, (2S)-2-azaniumyl-5-(carbamoylamino)pentanoate, NSC27425, H-cit-oh, L(+)-citrulline, Ornithine, N5-(aminocarbonyl)-, MFCD00064397, N~5~-carbamoyl-L-ornithine, d-ureidonorvaline, M03230, (2S)-2-amino-5-(aminocarbonylamino)pentanoic acid

Molecular formula
C6H13N3O3
Empirical formula
C6H13N3O3
Molecular weight
175.19 g/mol
Exact mass
175.09569
CAS number
372-75-8
PubChem CID
9750
Canonical SMILES
C(CC(C(=O)O)N)CNC(=O)N
Isomeric SMILES
C(C[C@@H](C(=O)O)N)CNC(=O)N
InChI
InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
InChIKey
RHGKLRLOHDJJDR-BYPYZUCNSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
12
Rings
0
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0.67
H-bond donors
4
H-bond acceptors
3 computed here · PubChem 4
Rotatable bonds
5
TPSA (Ų)
118.4 computed here · PubChem 118
Formal charge
0
XLogP3
-4.3 PubChem
Complexity
171 PubChem
Stereocenters
1 definedCIP: C8: S
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C41.14%
  • H7.48%
  • N23.99%
  • O27.40%

Isotope pattern

100%175.0967.9%176.098177.100

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
-1.15 Crippen (Wildman and Crippen 1999)
log S (water solubility)
0.13 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
2.56 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 175.19
  • log P ≤ 5 (Crippen): -1.15
  • H-bond donors ≤ 5: 4
  • H-bond acceptors ≤ 10: 3

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 69 company reports to ECHA. Source [1].

  • Harmful or irritant
  • H315Causes skin irritation (85.5% of reports)
  • H319Causes serious eye irritation (85.5% of reports)

Precautionary statements: P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364

View all classifications (2)
  • [1] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 14.5% (10 of 69) of reports.
  • [1] European Chemicals Agency (ECHA) · 69 reports · WarningH315, H319

Safety data sheets on the supplier’s page: Enamine, Alfa Chemistry, AiFChem, an XtalPi Company.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  2. [2]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  3. [3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  5. [5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  6. [6]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  7. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  8. ·Literature on PubChem

Data last updated 2026-10-14.