Showing Compound Card for Zeatin (CDB005009)

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Record Information
Version1.0
Created at2020-04-17 18:59:58 UTC
Updated at2020-11-18 16:39:12 UTC
CannabisDB IDCDB005009
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameZeatin
DescriptionCis-zeatin, also known as (e)-zeatin or trans-zeatin, 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. An aminopurine factor in plant extracts that induces cell division. Cis-zeatin is a strong basic compound (based on its pKa). Outside of the human body, Cis-zeatin is found, on average, in the highest concentration within corns. Cis-zeatin has also been detected, but not quantified in, several different foods, such as green zucchinis, adzuki beans, scarlet beans, white lupines, and jicama. This could make cis-zeatin a potential biomarker for the consumption of these foods. Zeatin is a plant hormone derived from the purine adenine. Zeatin was first discovered in immature corn kernels from the genus Zea. As in the case of kinetin, zeatin has also been reported to have several in vitro anti-aging effects on human skin fibroblasts. Zeatin and derivatives were discovered to be the primary active ingredient in coconut milk, which has long been known to actively induce plant growth. It is a member of the plant growth hormone family known as cytokinins. Zeatin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight219.24
Monoisotopic Molecular Weight219.112
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

Route of exposure:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point208 to 210 °CWikipedia
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSZeatin, 3 TMS, GC-MS Spectrumsplash10-0uea-3669000000-71f80cf16f89ded4787aSpectrum
GC-MSZeatin, non-derivatized, GC-MS Spectrumsplash10-0uea-3669000000-71f80cf16f89ded4787aSpectrum
Predicted GC-MSZeatin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000f-4920000000-7210f4c3b706c05cf1afSpectrum
Predicted GC-MSZeatin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmr-9770000000-e82dbfd9ed2507037b2aSpectrum
Predicted GC-MSZeatin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSZeatin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0923000000-bb62b8c5c51101ad909a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0090000000-860e5e26a7c78621ff1b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0159-0890000000-e0d9da4d76a19fdcc38e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-73c2883cf4c5c86e52022017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-40634e98d8610da6da7e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-f685d83e661ba76c7b5f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00lr-0940000000-cb6bb2cc6e09e94bf9e92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0490000000-7a274998c68b723d3fb62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0910000000-92dd3eccb6d6c8cf56b72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-916fa5a85cf88a7955762017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udr-0980000000-3b6cbd9a900a91cda1ec2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udr-0890000000-615009ba0eecc0c276f72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-74ba65be8d88785a72a92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-17f89903bb26df54893d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0090000000-dd1e015f41cf26595e402017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0079-0980000000-71f5c1676966e90a2d172017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-597321405352604023782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-3900000000-76812b403415131902a12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-5900000000-e13e6e9ecfdac2ef5cf72017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1290000000-dc9819ee831d1fee4b162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fri-6950000000-1eb1fa1f3c0d0e305d2a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-9400000000-5bf47fcd4a35a6d1dcfa2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0490000000-be42f2c18f1d6af58fde2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-1940000000-0b1ece0d97dfba385c642016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-1900000000-9a8fa0692f031f4952182016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0012204
DrugBank IDDB11337
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available