Thiamine pyrophosphate
Athanor · official
C12H19N4O7P2S+ · 425.32 g/mol
IUPAC name: 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate
Also called TPP, ThDP, cocarboxylase, thiamine diphosphate, vitamin B1
Names and identifiers
- IUPAC name
- 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate
- Synonyms
- TPP, ThDP, cocarboxylase
+ 39 more
thiamine diphosphate, vitamin B1, ThPP, thiamin diphosphate, thiamin pyrophosphate, Coenzymate, thiamine-pyrophosphate, Pyrophosphoric ester of thiamine, thiamine(1+) diphosphate, 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate, CHEBI:9532, thiamine-PPi, thiamin-PPi, 3-((4-Amino-2-methylpyrimidin-5-yl)methyl)-5-(2-((hydroxy(phosphonooxy)phosphoryl)oxy)ethyl)-4-methylthiazol-3-ium, NCGC00160617-01, 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate, 1ols, 1olu, 1olx, Thaimine pyrophosphate, 1v1m, starbld0000845, Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)-, inner salt, SCHEMBL80028, COCARBOXYLASE [MART.], COCARBOXYLASE [WHO-DD], CHEMBL1236376, DTXSID2048404, SCHEMBL27279703, SCHEMBL30192281, BDBM92962, 1v11, 1v16, AYEKOFBPNLCAJY-UHFFFAOYSA-O, AKOS015961391, NCGC00160617-02, NCGC00160617-03, 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[4,6,6-trihydroxy-4,6-dioxo-3,5-dioxa-4,6-diph, AC-13726
- Molecular formula
- C12H19N4O7P2S+
- Empirical formula
- C12H19N4O7P2S
- Molecular weight
- 425.32 g/mol
- Exact mass
- 425.04497
- CAS number
- 154-87-0
- PubChem CID
- 1132
- Canonical SMILES
- CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCOP(=O)(O)OP(=O)(O)O
- Isomeric SMILES
- CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCOP(=O)(O)OP(=O)(O)O
- InChI
- InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1
- InChIKey
- AYEKOFBPNLCAJY-UHFFFAOYSA-O
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 26
- Rings
- 2
- Aromatic rings
- 2
- Fraction sp³ carbons (Fsp3)
- 0.42
- H-bond donors
- 4
- H-bond acceptors
- 8 computed here · PubChem 11
- Rotatable bonds
- 8
- TPSA (Ų)
- 169 computed here · PubChem 197
- Formal charge
- 1
- XLogP3
- -1.2 PubChem
- Complexity
- 568 PubChem
- Stereocenters
- 0 defined, 1 undefinedCIP: P14: undefined
- 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
- C33.89%
- H4.50%
- N13.17%
- O26.33%
- P14.57%
- S7.54%
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
- 0.84 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -2.79 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 3.92 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 425.32
- log P ≤ 5 (Crippen): 0.84
- H-bond donors ≤ 5: 4
- H-bond acceptors ≤ 10: 8
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
No GHS hazard classification was found in the sources.
Safety data sheets on the supplier’s page: EvitaChem, AKos Consulting & Solutions, Smolecule.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 1H NMRHuman Metabolome Database (HMDB) (600 MHz · H2O) · Human Metabolome Database (HMDB) (600 MHz · H2O) · Human Metabolome Database (HMDB) (Bruker · 600 MHz · Water)
- 1H-13C NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · Water)
- MS-MSHuman Metabolome Database (HMDB) (LC-ESI-QQ · negative) · Human Metabolome Database (HMDB) (LC-ESI-QQ · negative) · Human Metabolome Database (HMDB) (LC-ESI-QQ · negative) · Human Metabolome Database (HMDB) (Quattro_QQQ · Positive) · Human Metabolome Database (HMDB) (Quattro_QQQ · Positive) · Human Metabolome Database (HMDB) (Quattro_QQQ · Positive)
- LC-MSMassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · POSITIVE)
- Other MSMassBank of North America (MoNA) (TQD, Waters · Flow-injection QqQ/MS · ESI) · MassBank of North America (MoNA) (TQD, Waters · Flow-injection QqQ/MS · ESI) · MassBank of North America (MoNA) (TQD, Waters · Flow-injection QqQ/MS · ESI)
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]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [2]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [3]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.