D-Proline
Athanor · official
C5H9NO2 · 115.13 g/mol
IUPAC name: (2R)-pyrrolidine-2-carboxylic acid
WarningCauses skin irritation · Causes serious eye irritation · May cause respiratory irritationNames and identifiers
- IUPAC name
- (2R)-pyrrolidine-2-carboxylic acid
- Synonyms
- (2R)-pyrrolidine-2-carboxylic acid, (R)-pyrrolidine-2-carboxylic acid, D-(+)-Proline
+ 34 more
D-Prolin, (R)-PROLINE, (R)-2-CARBOXYPYRROLIDINE, L01Q4LGZ5L, PROLINE, D-, EINECS 206-452-7, (+)-(R)-PROLINE, CHEBI:16313, DTXSID70883367, (2R)-pyrrolidin-1-ium-2-carboxylate, RefChem:584407, DTXCID801022904, H-D-Pro-OH, MFCD00064317, R-Proline, D-Pro, H-Pros-OH, (D)-proline, Captopril Impurity 32, D-D-Pro-OH, R)-2-Carboxypyrrolidine, SCHEMBL65555, GTPL4676, Q20035962, (2R)-pyrrolidine-2-carboxylate, d-2-pyrrolidinecarboxylic acid, H-DPro-OH, SBB006712, starbld0002768, AM20090537, UNII-L01Q4LGZ5L, NCIStruc1_001918, NCIStruc2_000132, CHEMBL80257
- Molecular formula
- C5H9NO2
- Empirical formula
- C5H9NO2
- Molecular weight
- 115.13 g/mol
- Exact mass
- 115.06333
- CAS number
- 344-25-2
- PubChem CID
- 8988
- Canonical SMILES
- C1CC(NC1)C(=O)O
- Isomeric SMILES
- C1C[C@@H](NC1)C(=O)O
- InChI
- InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1
- InChIKey
- ONIBWKKTOPOVIA-SCSAIBSYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 8
- Rings
- 1
- Aromatic rings
- 0
- Fraction sp³ carbons (Fsp3)
- 0.8
- H-bond donors
- 2
- H-bond acceptors
- 2 computed here · PubChem 3
- Rotatable bonds
- 1
- TPSA (Ų)
- 49.3
- Formal charge
- 0
- XLogP3
- -2.5 PubChem
- Complexity
- 103 PubChem
- Stereocenters
- 1 definedCIP: C4: R
- 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
- C52.16%
- H7.88%
- N12.17%
- O27.79%
Isotope pattern
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
- -0.18 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -0.38 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 2.74 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 115.13
- log P ≤ 5 (Crippen): -0.18
- H-bond donors ≤ 5: 2
- H-bond acceptors ≤ 10: 2
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: 14 company reports to ECHA. Source [1].
- Harmful or irritant
- H315Causes skin irritation (14.3% of reports)
- H319Causes serious eye irritation (14.3% of reports)
- H335May cause respiratory irritation (14.3% of reports)
Precautionary statements: P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
View all classifications (2)
- [1] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 85.7% (12 of 14) of all reports.
- [1] European Chemicals Agency (ECHA) · 14 reports · WarningH315, H319, H335
Safety data sheets on the supplier’s page: Chem-Space.com Database, Key Organics/BIONET, Xianglong Pharmaceutical Standards (XL Standards).
Always read the supplier’s safety data sheet before working with it.
Spectra
- NMRNMRShiftDB
- 1H NMRSpectraBase
- 13C NMRSpectraBase
- MS-MSHuman Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Negative)
- LC-MSMassBank of North America (MoNA) (Thermo Q Exactive HF · LC-ESI-QFT · positive) · MassBank of North America (MoNA) (Thermo Q Exactive HF · LC-ESI-QFT · negative) · MassBank of North America (MoNA) (Thermo Q Exactive HF · LC-ESI-QFT · positive)
- FTIRSpectraBase (KBr WAFER)
- ATR-IRSpectraBase (Bruker Tensor 27 FT-IR · ATR-Neat (DuraSamplIR II))
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]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [2]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
- [3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [4]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.