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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:58 UTC
Update Date2021-09-07 17:05:28 UTC
HMDB IDHMDB0012204
Secondary Accession Numbers
  • HMDB12204
Metabolite Identification
Common NameZeatin
DescriptionZeatin belongs to the class of organic compounds known as 6-alkylaminopurines. 6-Alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Zeatin is a cytokinin (plant growth hormone) derived from the purine adenine, which occurs in the form of a cis- and a trans-isomer and conjugates. Zeatin was first discovered in immature corn kernels from the genus Zea. Zeatin has also been detected, but not quantified in several different foods, such as figs, rowanberries, red raspberries, garlic, and tree ferns. Zeatin has also been shown to promote the resistance of tobacco against the bacterial pathogen Pseudomonas syringae, in which trans-zeatin has a more prominent effect than cis-zeatin. Zeatin has several anti-ageing effects on human skin fibroblasts. It promotes the growth of lateral buds and, when sprayed on meristems, stimulates cell division to produce bushier plants. Zeatin and its derivatives occur in many plant extracts and are the active ingredient in coconut milk, which causes plant growth.
Structure
Data?1583945901
Synonyms
ValueSource
(e)-2-Methyl-4-(1H-purin-6-ylamino)-2-buten-1-olChEBI
(e)-2-Methyl-4-(1H-purin-6-ylamino)but-2-en-1-olChEBI
(e)-2-Methyl-4-(purin-6-ylamino)-2-buten-1-olChEBI
(e)-ZeatinChEBI
N6-(4-Hydroxyisopentenyl)adenineChEBI
trans-ZeatinKegg
ZeatinChEBI, HMDB
(2E)-2-Methyl-4-(9H-purin-6-ylamino)-2-buten-1-olHMDB
6-(4-Hydroxy-3-methyl-trans-2-butenylamino)purineHMDB
N6-(4-Hydroxy-3-methyl-trans-2-butenyl)adenineHMDB
ZTHMDB
ZTAHMDB
ZeatineHMDB
trans-6-(4-Hydroxy-3-methylbut-2-enyl)amino purineHMDB
Chemical FormulaC10H13N5O
Average Molecular Weight219.2431
Monoisotopic Molecular Weight219.112010063
IUPAC Name(2E)-2-methyl-4-[(1H-purin-6-yl)amino]but-2-en-1-ol
Traditional Name(2E)-2-methyl-4-(1H-purin-6-ylamino)but-2-en-1-ol
CAS Registry Number1637-39-4
SMILES
C\C(CO)=C/CNC1=C2N=CN=C2N=CN1
InChI Identifier
InChI=1S/C10H13N5O/c1-7(4-16)2-3-11-9-8-10(13-5-12-8)15-6-14-9/h2,5-6,16H,3-4H2,1H3,(H2,11,12,13,14,15)/b7-2+
InChI KeyUZKQTCBAMSWPJD-FARCUNLSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-alkylaminopurines. 6-Alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-alkylaminopurines
Alternative Parents
Substituents
  • 6-alkylaminopurine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary amine
  • Azacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

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 Solubility0.28 g/LALOGPS
logP-0.32ALOGPS
logP-0.34ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)6.11ChemAxon
pKa (Strongest Basic)0.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.72 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.3 m³·mol⁻¹ChemAxon
Polarizability23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+154.7530932474
DeepCCS[M-H]-152.39230932474
DeepCCS[M-2H]-185.66830932474
DeepCCS[M+Na]+161.61130932474
AllCCS[M+H]+150.132859911
AllCCS[M+H-H2O]+146.232859911
AllCCS[M+NH4]+153.732859911
AllCCS[M+Na]+154.732859911
AllCCS[M-H]-151.332859911
AllCCS[M+Na-2H]-151.532859911
AllCCS[M+HCOO]-151.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ZeatinC\C(CO)=C/CNC1=C2N=CN=C2N=CN12889.6Standard polar33892256
ZeatinC\C(CO)=C/CNC1=C2N=CN=C2N=CN12122.8Standard non polar33892256
ZeatinC\C(CO)=C/CNC1=C2N=CN=C2N=CN12455.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Zeatin,1TMS,isomer #1C/C(=C\CNC1=C2N=CN=C2N=C[NH]1)CO[Si](C)(C)C2381.6Semi standard non polar33892256
Zeatin,1TMS,isomer #2C/C(=C\CN(C1=C2N=CN=C2N=C[NH]1)[Si](C)(C)C)CO2338.6Semi standard non polar33892256
Zeatin,1TMS,isomer #3C/C(=C\CNC1=C2N=CN=C2N=CN1[Si](C)(C)C)CO2467.0Semi standard non polar33892256
Zeatin,2TMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=C[NH]1)[Si](C)(C)C)CO[Si](C)(C)C2308.6Semi standard non polar33892256
Zeatin,2TMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=C[NH]1)[Si](C)(C)C)CO[Si](C)(C)C2284.7Standard non polar33892256
Zeatin,2TMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=C[NH]1)[Si](C)(C)C)CO[Si](C)(C)C3102.8Standard polar33892256
Zeatin,2TMS,isomer #2C/C(=C\CNC1=C2N=CN=C2N=CN1[Si](C)(C)C)CO[Si](C)(C)C2455.6Semi standard non polar33892256
Zeatin,2TMS,isomer #2C/C(=C\CNC1=C2N=CN=C2N=CN1[Si](C)(C)C)CO[Si](C)(C)C2387.2Standard non polar33892256
Zeatin,2TMS,isomer #2C/C(=C\CNC1=C2N=CN=C2N=CN1[Si](C)(C)C)CO[Si](C)(C)C3315.2Standard polar33892256
Zeatin,2TMS,isomer #3C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C)[Si](C)(C)C)CO2384.1Semi standard non polar33892256
Zeatin,2TMS,isomer #3C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C)[Si](C)(C)C)CO2472.1Standard non polar33892256
Zeatin,2TMS,isomer #3C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C)[Si](C)(C)C)CO3199.8Standard polar33892256
Zeatin,3TMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C)[Si](C)(C)C)CO[Si](C)(C)C2388.9Semi standard non polar33892256
Zeatin,3TMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C)[Si](C)(C)C)CO[Si](C)(C)C2435.0Standard non polar33892256
Zeatin,3TMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C)[Si](C)(C)C)CO[Si](C)(C)C2874.8Standard polar33892256
Zeatin,1TBDMS,isomer #1C/C(=C\CNC1=C2N=CN=C2N=C[NH]1)CO[Si](C)(C)C(C)(C)C2629.5Semi standard non polar33892256
Zeatin,1TBDMS,isomer #2C/C(=C\CN(C1=C2N=CN=C2N=C[NH]1)[Si](C)(C)C(C)(C)C)CO2525.2Semi standard non polar33892256
Zeatin,1TBDMS,isomer #3C/C(=C\CNC1=C2N=CN=C2N=CN1[Si](C)(C)C(C)(C)C)CO2663.8Semi standard non polar33892256
Zeatin,2TBDMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=C[NH]1)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C2662.0Semi standard non polar33892256
Zeatin,2TBDMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=C[NH]1)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C2756.2Standard non polar33892256
Zeatin,2TBDMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=C[NH]1)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C3187.5Standard polar33892256
Zeatin,2TBDMS,isomer #2C/C(=C\CNC1=C2N=CN=C2N=CN1[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C2820.9Semi standard non polar33892256
Zeatin,2TBDMS,isomer #2C/C(=C\CNC1=C2N=CN=C2N=CN1[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C2840.4Standard non polar33892256
Zeatin,2TBDMS,isomer #2C/C(=C\CNC1=C2N=CN=C2N=CN1[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C3366.0Standard polar33892256
Zeatin,2TBDMS,isomer #3C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CO2735.5Semi standard non polar33892256
Zeatin,2TBDMS,isomer #3C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CO2890.1Standard non polar33892256
Zeatin,2TBDMS,isomer #3C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CO3259.5Standard polar33892256
Zeatin,3TBDMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C2898.7Semi standard non polar33892256
Zeatin,3TBDMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C3085.9Standard non polar33892256
Zeatin,3TBDMS,isomer #1C/C(=C\CN(C1=C2N=CN=C2N=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C3071.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Zeatin GC-MS (3 TMS)splash10-0uea-3669000000-71f80cf16f89ded4787a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Zeatin GC-MS (Non-derivatized)splash10-0uea-3669000000-71f80cf16f89ded4787a2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zeatin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-4920000000-7210f4c3b706c05cf1af2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zeatin GC-MS (1 TMS) - 70eV, Positivesplash10-0fmr-9770000000-e82dbfd9ed2507037b2a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zeatin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zeatin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-qTof , Positive-QTOFsplash10-004i-0923000000-bb62b8c5c51101ad909a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QQ , negative-QTOFsplash10-014i-0090000000-860e5e26a7c78621ff1b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QQ , negative-QTOFsplash10-0159-0890000000-e0d9da4d76a19fdcc38e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QQ , negative-QTOFsplash10-001i-0900000000-73c2883cf4c5c86e52022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QQ , negative-QTOFsplash10-001i-0900000000-40634e98d8610da6da7e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QQ , negative-QTOFsplash10-001i-1900000000-f685d83e661ba76c7b5f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QTOF , negative-QTOFsplash10-00lr-0940000000-cb6bb2cc6e09e94bf9e92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QTOF , negative-QTOFsplash10-014i-0490000000-7a274998c68b723d3fb62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QTOF , negative-QTOFsplash10-001i-0910000000-92dd3eccb6d6c8cf56b72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QTOF , negative-QTOFsplash10-001i-0900000000-916fa5a85cf88a7955762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin Linear Ion Trap , negative-QTOFsplash10-0udr-0980000000-3b6cbd9a900a91cda1ec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin Linear Ion Trap , negative-QTOFsplash10-0udr-0890000000-615009ba0eecc0c276f72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin Linear Ion Trap , negative-QTOFsplash10-014i-0090000000-74ba65be8d88785a72a92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin Linear Ion Trap , negative-QTOFsplash10-014i-0090000000-17f89903bb26df54893d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QQ , positive-QTOFsplash10-00di-0090000000-dd1e015f41cf26595e402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QQ , positive-QTOFsplash10-0079-0980000000-71f5c1676966e90a2d172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QQ , positive-QTOFsplash10-000i-0900000000-597321405352604023782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QQ , positive-QTOFsplash10-000i-3900000000-76812b403415131902a12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Zeatin LC-ESI-QQ , positive-QTOFsplash10-014l-5900000000-e13e6e9ecfdac2ef5cf72017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeatin 10V, Positive-QTOFsplash10-0fk9-1290000000-dc9819ee831d1fee4b162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeatin 20V, Positive-QTOFsplash10-0fri-6950000000-1eb1fa1f3c0d0e305d2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeatin 40V, Positive-QTOFsplash10-0f79-9400000000-5bf47fcd4a35a6d1dcfa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeatin 10V, Negative-QTOFsplash10-014i-0490000000-be42f2c18f1d6af58fde2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeatin 20V, Negative-QTOFsplash10-00lr-1940000000-0b1ece0d97dfba385c642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeatin 40V, Negative-QTOFsplash10-0a59-1900000000-9a8fa0692f031f4952182016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDDB11337
Phenol Explorer Compound IDNot Available
FooDB IDFDB002239
KNApSAcK IDC00000091
Chemspider ID395716
KEGG Compound IDC00371
BioCyc IDCPD-4210
BiGG IDNot Available
Wikipedia LinkZeatin
METLIN IDNot Available
PubChem Compound449093
PDB IDZEA
ChEBI ID16522
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available