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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:26 UTC
HMDB IDHMDB0001106
Secondary Accession Numbers
  • HMDB01106
Metabolite Identification
Common Name3-Aminopropionaldehyde
Description3-Aminopropionaldehyde, also known as 3-aminopropanal, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 3-Aminopropionaldehyde is a very strong basic compound (based on its pKa). 3-Aminopropionaldehyde exists in all living species, ranging from bacteria to humans. Within humans, 3-aminopropionaldehyde participates in a number of enzymatic reactions. In particular, 3-aminopropionaldehyde can be converted into β-alanine through its interaction with the enzyme aldehyde dehydrogenase, mitochondrial. In addition, 3-aminopropionaldehyde can be biosynthesized from 1,3-diaminopropane through its interaction with the enzyme membrane primary amine oxidase. In humans, 3-aminopropionaldehyde is involved in beta-alanine metabolism. Outside of the human body, 3-Aminopropionaldehyde has been detected, but not quantified in, several different foods, such as hard wheats, abalones, jackfruits, blackcurrants, and strawberries. This could make 3-aminopropionaldehyde a potential biomarker for the consumption of these foods. 3-Aminopropionaldehyde is a reactive aldehyde that mediates progressive neuronal necrosis and glial apoptosis.
Structure
Data?1676999726
Synonyms
ValueSource
beta-Aminopropion aldehydeChEBI
b-Aminopropion aldehydeGenerator
Β-aminopropion aldehydeGenerator
3-AminopropanalHMDB
Chemical FormulaC3H7NO
Average Molecular Weight73.0938
Monoisotopic Molecular Weight73.052763851
IUPAC Name3-aminopropanal
Traditional Name3-aminopropanal
CAS Registry Number352-92-1
SMILES
NCCC=O
InChI Identifier
InChI=1S/C3H7NO/c4-2-1-3-5/h3H,1-2,4H2
InChI KeyPCXDJQZLDDHMGX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility444 g/LALOGPS
logP-1.2ALOGPS
logP-1.1ChemAxon
logS0.78ALOGPS
pKa (Strongest Acidic)14.19ChemAxon
pKa (Strongest Basic)9.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.78 m³·mol⁻¹ChemAxon
Polarizability7.71 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+112.13831661259
DarkChem[M-H]-105.60731661259
AllCCS[M+H]+122.32432859911
AllCCS[M-H]-130.98132859911
DeepCCS[M+H]+120.01730932474
DeepCCS[M-H]-118.12630932474
DeepCCS[M-2H]-153.45630932474
DeepCCS[M+Na]+127.48730932474
AllCCS[M+H]+122.332859911
AllCCS[M+H-H2O]+117.932859911
AllCCS[M+NH4]+126.532859911
AllCCS[M+Na]+127.732859911
AllCCS[M-H]-131.032859911
AllCCS[M+Na-2H]-136.532859911
AllCCS[M+HCOO]-142.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-AminopropionaldehydeNCCC=O1392.5Standard polar33892256
3-AminopropionaldehydeNCCC=O676.9Standard non polar33892256
3-AminopropionaldehydeNCCC=O749.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Aminopropionaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCN988.3Semi standard non polar33892256
3-Aminopropionaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCN965.0Standard non polar33892256
3-Aminopropionaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCN1629.2Standard polar33892256
3-Aminopropionaldehyde,1TMS,isomer #2C[Si](C)(C)NCCC=O1003.8Semi standard non polar33892256
3-Aminopropionaldehyde,1TMS,isomer #2C[Si](C)(C)NCCC=O1007.4Standard non polar33892256
3-Aminopropionaldehyde,1TMS,isomer #2C[Si](C)(C)NCCC=O1332.0Standard polar33892256
3-Aminopropionaldehyde,2TMS,isomer #1C[Si](C)(C)NCC=CO[Si](C)(C)C1161.7Semi standard non polar33892256
3-Aminopropionaldehyde,2TMS,isomer #1C[Si](C)(C)NCC=CO[Si](C)(C)C1193.3Standard non polar33892256
3-Aminopropionaldehyde,2TMS,isomer #1C[Si](C)(C)NCC=CO[Si](C)(C)C1211.0Standard polar33892256
3-Aminopropionaldehyde,2TMS,isomer #2C[Si](C)(C)N(CCC=O)[Si](C)(C)C1222.9Semi standard non polar33892256
3-Aminopropionaldehyde,2TMS,isomer #2C[Si](C)(C)N(CCC=O)[Si](C)(C)C1222.8Standard non polar33892256
3-Aminopropionaldehyde,2TMS,isomer #2C[Si](C)(C)N(CCC=O)[Si](C)(C)C1276.3Standard polar33892256
3-Aminopropionaldehyde,3TMS,isomer #1C[Si](C)(C)OC=CCN([Si](C)(C)C)[Si](C)(C)C1385.5Semi standard non polar33892256
3-Aminopropionaldehyde,3TMS,isomer #1C[Si](C)(C)OC=CCN([Si](C)(C)C)[Si](C)(C)C1375.1Standard non polar33892256
3-Aminopropionaldehyde,3TMS,isomer #1C[Si](C)(C)OC=CCN([Si](C)(C)C)[Si](C)(C)C1275.7Standard polar33892256
3-Aminopropionaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCN1186.8Semi standard non polar33892256
3-Aminopropionaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCN1204.3Standard non polar33892256
3-Aminopropionaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCN1791.8Standard polar33892256
3-Aminopropionaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCC=O1242.3Semi standard non polar33892256
3-Aminopropionaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCC=O1251.2Standard non polar33892256
3-Aminopropionaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCC=O1433.4Standard polar33892256
3-Aminopropionaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC=CO[Si](C)(C)C(C)(C)C1602.0Semi standard non polar33892256
3-Aminopropionaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC=CO[Si](C)(C)C(C)(C)C1614.8Standard non polar33892256
3-Aminopropionaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC=CO[Si](C)(C)C(C)(C)C1489.8Standard polar33892256
3-Aminopropionaldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCC=O)[Si](C)(C)C(C)(C)C1608.9Semi standard non polar33892256
3-Aminopropionaldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCC=O)[Si](C)(C)C(C)(C)C1623.8Standard non polar33892256
3-Aminopropionaldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCC=O)[Si](C)(C)C(C)(C)C1472.7Standard polar33892256
3-Aminopropionaldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1977.8Semi standard non polar33892256
3-Aminopropionaldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1992.6Standard non polar33892256
3-Aminopropionaldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1630.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Aminopropionaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-13fb77ed3773ab13b10f2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Aminopropionaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 10V, Positive-QTOFsplash10-0ab9-9000000000-8e068317c3b7ab8511292015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 20V, Positive-QTOFsplash10-0a4i-9000000000-e78722b5912332b965512015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 40V, Positive-QTOFsplash10-0a4i-9000000000-63fc6b8083111d21b5612015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 10V, Negative-QTOFsplash10-00di-9000000000-bfbb5311d3b0abfbe7952015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 20V, Negative-QTOFsplash10-00di-9000000000-68e71bb6c15dff78a8c22015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 40V, Negative-QTOFsplash10-0006-9000000000-8780aca699fa02169cf42015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 10V, Positive-QTOFsplash10-0a4i-9000000000-796247bade5fd57325932021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 20V, Positive-QTOFsplash10-0a4i-9000000000-1ec800454111a0c64d462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 40V, Positive-QTOFsplash10-0a4i-9000000000-a2ff71f6703a0a4daa572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 10V, Negative-QTOFsplash10-00di-9000000000-bc974757d0839ce6b57c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 20V, Negative-QTOFsplash10-00di-9000000000-04ae037d22ea245042cf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Aminopropionaldehyde 40V, Negative-QTOFsplash10-052f-9000000000-be4ae43b8bb9483fb6242021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030407
KNApSAcK IDNot Available
Chemspider ID74
KEGG Compound IDC05665
BioCyc IDCPD-6082
BiGG ID46232
Wikipedia LinkNot Available
METLIN ID6007
PubChem Compound75
PDB IDNot Available
ChEBI ID18090
Food Biomarker OntologyNot Available
VMH IDBAMPPALD
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBott, Kaspar. Amidomethylation of trichloroethylene and acetylene: syntheses of N-protected a-chloro-b-alanines and b-aminopropanals. Journal of the Chemical Society [Section] D: Chemical Communications (1969), (22), 1304.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ivanova S, Batliwalla F, Mocco J, Kiss S, Huang J, Mack W, Coon A, Eaton JW, Al-Abed Y, Gregersen PK, Shohami E, Connolly ES Jr, Tracey KJ: Neuroprotection in cerebral ischemia by neutralization of 3-aminopropanal. Proc Natl Acad Sci U S A. 2002 Apr 16;99(8):5579-84. Epub 2002 Apr 9. [PubMed:11943872 ]
  2. Yu Z, Li W, Hillman J, Brunk UT: Human neuroblastoma (SH-SY5Y) cells are highly sensitive to the lysosomotropic aldehyde 3-aminopropanal. Brain Res. 2004 Aug 6;1016(2):163-9. [PubMed:15246852 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
Reactions
3-Aminopropionaldehyde → 3-aminopropan-1-oldetails
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
1,3-Diaminopropane + Oxygen + Water → 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxidedetails

Only showing the first 10 proteins. There are 14 proteins in total.