trans-Zeatin

Details

• Internal ID: ca0b07bc-f892-490f-ab7f-de4fd8927484
• Taxonomy: Organoheterocyclic compounds > Imidazopyrimidines > Purines and purine derivatives > 6-aminopurines > 6-alkylaminopurines
• IUPAC Name: (E)-2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol
• SMILES (Canonical): CC(=CCNC1=NC=NC2=C1NC=N2)CO
• SMILES (Isomeric): C/C(=C\CNC1=NC=NC2=C1NC=N2)/CO
• InChI: 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 Key: UZKQTCBAMSWPJD-FARCUNLSSA-N
• Popularity: 6,288 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₃N₅O
• Molecular Weight: 219.24 g/mol
• Exact Mass: 219.11201006 g/mol
• Topological Polar Surface Area (TPSA): 86.70 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.70
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• Zeatin
• 1637-39-4
• (E)-Zeatin
• Zeatine
• (E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol
• (E)-2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol
• (2E)-2-methyl-4-(9H-purin-6-ylamino)but-2-en-1-ol
• 2-Buten-1-ol, 2-methyl-4-(1H-purin-6-ylamino)-, (2E)-
• N6-(4-Hydroxyisopentenyl)adenine
• 2-Buten-1-ol, 2-methyl-4-(1H-purin-6-ylamino)-, (E)-
• 131140-27-7
• UNII-7I6OOJ9GR6
• BRN 0616241
• 7I6OOJ9GR6
• (E)-2-Methyl-4-(1H-purin-6-ylamino)but-2-en-1-ol
• CHEMBL525239
• C10H13N5O
• CHEBI:16522
• HSDB 7689
• (E)-2-methyl-4-(purin-6-ylamino)-2-buten-1-ol
• 2-Buten-1-ol, 2-methyl-4-(9H-purin-6-ylamino)-
• (2E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol
• 2-buten-1-ol, 2-methyl-4-(9H-purin-6-ylamino)-, (2E)-
• 2-BUTEN-1-OL, 2-METHYL-4-(PURIN-6-YLAMINO)-, (E)-
• (E)-2-methyl-4-(7H-purin-6-ylamino)-2-buten-1-ol
• t-zeatin
• 2flh
• MFCD00213654
• 6-(4-Hydroxy-3-methyl-cis-2-butenylamino)purine
• ZEATIN [HSDB]
• ZEATIN [INCI]
• MTH1 inhibitor, 131
• ZEATIN [MI]
• (2Z)-2-methyl-4-(9H-purin-6-ylamino)-2-buten-1-ol
• N6-(4-Hydroxy-3-methyl-2-buten-1-yl)adenine
• SCHEMBL49689
• MLS001074742
• SCHEMBL3670336
• DTXSID9040631
• SCHEMBL14876945
• CHEBI:15333
• UZKQTCBAMSWPJD-FARCUNLSSA-N
• BDBM227637
• HMS2269P18
• BCP13132
• TNP00322
• BDBM50267036
• s4884
• AKOS015840012
• AKOS015840013
• AKOS015923020
• AKOS037643348
• CCG-266716
• DB11337
• NCGC00017372-01
• NCGC00017372-02
• NCGC00142544-01
• AC-22388
• AC-30704
• AS-14879
• AS-49891
• HY-19700
• LS-47248
• SMR000471895
• CS-0016292
• C00371
• N89842
• 2-methyl-4-(9H-purin-6-ylamino)but-2-en-1-ol
• A806205
• A810507
• A900233
• 4-(9H-Purine-6-ylamino)-2-methyl-2-butene-1-ol
• J-200308
• Q2276562
• Q22807318
• Zeatin, BioReagent, plant cell culture tested, powder
• (2E)-2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol
• (2E)-2-Methyl-4-(9H-purin-6-ylamino)-2-buten-1-ol
• (E)-2-Methyl-4-(9H-purin-6-ylamino)but-2-en-1-ol
• (2E)-2-methyl-4-[(7H-purin-6-yl)amino]but-2-en-1-ol
• (2Z)-2-methyl-4-[(7H-purin-6-yl)amino]but-2-en-1-ol
• (E)-4-((9H-purin-6-yl)amino)-2-methylbut-2-en-1-ol
• 94D98F16-103C-4126-89A0-1D32FEACC220
• trans-Zeatin hydrochloride, plant cell culture tested, >=97%
• trans-Zeatin, BioReagent, plant cell culture tested, >=97%
• InChI=1/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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9721	97.21%
Caco-2	+	0.5801	58.01%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Lysosomes	0.3446	34.46%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.9292	92.92%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.9045	90.45%
P-glycoprotein inhibitior	-	0.9841	98.41%
P-glycoprotein substrate	-	0.7628	76.28%
CYP3A4 substrate	-	0.5165	51.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8573	85.73%
CYP3A4 inhibition	-	0.9711	97.11%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.5830	58.30%
CYP2C8 inhibition	-	0.7888	78.88%
CYP inhibitory promiscuity	-	0.9106	91.06%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5941	59.41%
Eye corrosion	-	0.9834	98.34%
Eye irritation	-	0.7603	76.03%
Skin irritation	-	0.7317	73.17%
Skin corrosion	-	0.9087	90.87%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4842	48.42%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5644	56.44%
skin sensitisation	-	0.8421	84.21%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.4550	45.50%
Acute Oral Toxicity (c)	III	0.6191	61.91%
Estrogen receptor binding	-	0.6969	69.69%
Androgen receptor binding	+	0.6002	60.02%
Thyroid receptor binding	-	0.6502	65.02%
Glucocorticoid receptor binding	-	0.6675	66.75%
Aromatase binding	+	0.6855	68.55%
PPAR gamma	-	0.6261	62.61%
Honey bee toxicity	-	0.8841	88.41%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.8414	84.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	2818.4 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	19952.6 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.13%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.61%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	89.58%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	88.68%	94.75%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	86.76%	89.44%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.70%	96.90%
CHEMBL2535	P11166	Glucose transporter	83.62%	98.75%
CHEMBL2581	P07339	Cathepsin D	82.21%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.91%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.90%	89.34%
CHEMBL290	Q13370	Phosphodiesterase 3B	81.33%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.18%	86.33%

Plants that contains it

• Abies balsamea
• Actinidia chinensis
• Arabidopsis thaliana
• Artemisia annua
• Brassica napus
• Cannabis sativa
• Cichorium intybus
• Codiaeum variegatum
• Croton cajucara
• Dianthus caryophyllus
• Digitalis isabelliana
• Garcinia lancilimba
• Helianthus annuus
• Helianthus tuberosus
• Ipomoea batatas
• Lablab purpureus subsp. purpureus
• Madhuca longifolia
• Mercurialis annua
• Oryza sativa
• Physcomitrella patens
• Pilocarpus goudotianus
• Pinus elliottii
• Pinus resinosa
• Rhizophora mucronata
• Samanea saman
• Sicyos edulis
• Solanum tuberosum
• Zea mays

Cross-Links

• PubChem: 449093
• NPASS: NPC57279
• ChEMBL: CHEMBL525239
• LOTUS: LTS0032706
• wikiData: Q22807318