Coenzyme A
Athanor · official
C21H36N7O16P3S · 767.5 g/mol
IUPAC name: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate
Also called CoA, CoASH, vitamin B5 cofactor
WarningCauses skin irritation · Causes serious eye irritation · May cause respiratory irritationNames and identifiers
- IUPAC name
- [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate
- Synonyms
- CoA, CoASH, vitamin B5 cofactor
+ 36 more
CoA-SH, Zeel, HSCoA, COENZYME_A, SAA04E81UX, DTXSID9048302, 3'-phosphoadenosine-(5')diphospho(4')pantatheine, CHEBI:15346, [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate, 3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyl] dihydrogen diphosphate}, NSC20274, (((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl) ((3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-((3-oxo-3-(2-sulfanylethylamino)propyl)amino)butyl) hydrogen phosphate, ((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl)methyl (hydroxy-((3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-((3-oxo-3-(2-sulfanylethylamino)propyl)amino)butoxy)phosphoryl) hydrogen phosphate, [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methyl [hydroxy-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butoxy]phosphoryl] hydrogen phosphate, 3'-phosphoadenosine 5'-(3-((3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-((3-oxo-3-((2-sulfanylethyl)amino)propyl)amino)butyl) dihydrogen diphosphate), RefChem:127396, DTXCID7028277, 201-619-0, (((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(((hydroxy((hydroxy(3-hydroxy-2,2-dimethyl-3-((2-((2-sulfanylethyl)carbamoyl)ethyl)carbamoyl)propoxy)phosphoryl)oxy)phosphoryl)oxy)methyl)oxolan-3-yl)oxy)phosphonic acid, Aluzime, Depot-Zeel, Coenzyme ASH, Coenzyme A hydrate, Coenzym A, co-enzyme-A, HS-CoA, Reduced CoA, (((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-2-(((hydroxy((hydroxy((R)-3-hydroxy-2,2-dimethyl-3-((2-((2-sulfanylethyl)carbamoyl)ethyl)carbamoyl)propoxy)phosphoryl)oxy)phosphoryl)oxy)methyl)oxolan-3-yl)oxy)phosphonic acid, Co-A-SH, C21H36N7O16P3S, Coalip, Lucina, MFCD24368566, Thiol-CoA, D-Coenzyme A, [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate
- Molecular formula
- C21H36N7O16P3S
- Empirical formula
- C21H36N7O16P3S
- Molecular weight
- 767.5 g/mol
- Exact mass
- 767.11521
- CAS number
- 85-61-0
- PubChem CID
- 87642
- Canonical SMILES
- CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)C(C(=O)NCCC(=O)NCCS)O
- Isomeric SMILES
- CC(C)(COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCS)O
- InChI
- InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1
- InChIKey
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 48
- Rings
- 3
- Aromatic rings
- 2
- Fraction sp³ carbons (Fsp3)
- 0.67
- H-bond donors
- 10
- H-bond acceptors
- 17 computed here · PubChem 21
- Rotatable bonds
- 18
- TPSA (Ų)
- 346.6 computed here · PubChem 348
- Formal charge
- 0
- XLogP3
- -5.8 PubChem
- Complexity
- 1270 PubChem
- Stereocenters
- 5 defined, 2 undefinedCIP: P6: undefined · P10: undefined · C15: R · C17: R · C28: R · C30: S · C36: 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
- C32.86%
- H4.73%
- N12.77%
- O33.35%
- P12.11%
- S4.18%
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
- -1.67 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -2.5 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 5.03 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 767.54
- log P ≤ 5 (Crippen): -1.67
- H-bond donors ≤ 5: 10
- H-bond acceptors ≤ 10: 17
Breaks 3 of the 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: 32 company reports to ECHA. Source [1].
- Harmful or irritant
- H315Causes skin irritation (93.8% of reports)
- H319Causes serious eye irritation (93.8% of reports)
- H335May cause respiratory irritation (93.8% 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 6.2% (2 of 32) of reports.
- [1] European Chemicals Agency (ECHA) · 32 reports · WarningH315, H319, H335
Safety data sheets on the supplier’s page: AbMole Bioscience, Molport, Mcule.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 1H NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · Water)
- 1H-13C NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · Water)
- MS-MSHuman Metabolome Database (HMDB) (Quattro_QQQ · Positive) · Human Metabolome Database (HMDB) (Quattro_QQQ · Positive) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Quattro_QQQ · Positive)
- LC-MSMassBank Europe (impact II · LC-ESI-QTOF · POSITIVE) · MassBank Europe (impact II · LC-ESI-QTOF · POSITIVE) · MassBank Europe (impact II · LC-ESI-QTOF · POSITIVE) · MassBank Europe (impact II · LC-ESI-QTOF · POSITIVE) · MassBank Europe (impact II · LC-ESI-QTOF · POSITIVE) · MassBank Europe (impact II · LC-ESI-QTOF · POSITIVE)
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]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [3]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [4]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.