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Ap4A

CAT: 0804-HY-113337Size: 1 EachDry Ice: NoHazardous: No
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Description
Ap4A (P1, P4-Di- (adenosine-5') -tetraphosphate) is a conserved second messenger in organisms ranging from bacteria to humans. Ap4A binds to the histidine triad nucleotide-binding protein 1 (HINT1) activates the transcription of genes downstream of MITF. Ap4A induces apoptosis[1][2].
CAS Number
5542-28-9
Product Name Alternative
P1, P4-Di- (adenosine-5') -tetraphosphate
UNSPSC
12352005
Target
Apoptosis
Type
Reference compound
Related Pathways
Apoptosis
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/ap4a.html
Smiles
O[C@H]1[C@@H](O)[C@H](N2C=NC3=C2N=CN=C3N)O[C@@H]1COP(OP(OP(OP(OC[C@H]4O[C@@H](N5C=NC6=C5N=CN=C6N)[C@H](O)[C@@H]4O)(O)=O)(O)=O)(O)=O)(O)=O
Molecular Formula
C20H28N10O19P4
Molecular Weight
836.39
References & Citations
[1]Yu J, et al. Second messenger Ap4A polymerizes target protein HINT1 to transduce signals in FcεRI-activated mast cells. Nat Commun. 2019 Oct 11;10 (1) :4664.|[2]Vartanian A, et al. Ap4A induces apoptosis in human cultured cells. FEBS Lett. 1999 Jul 30;456 (1) :175-80.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
Phase 2

Chemical Information

Ap4A

P(1),P(4)-bis(5'-adenosyl) tetraphosphate is a diadenosyl tetraphosphate compound having the two 5'-adenosyl residues attached at the P1- and P4-positions. It has a role as a mouse metabolite and an Escherichia coli metabolite. It is a conjugate acid of a P(1),P(4)-bis(5'-adenosyl) tetraphosphate(4-).

CAS Number5542-28-9
PubChem CID21706
IUPAC Name[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate
Molecular FormulaC20H28N10O19P4
Molecular Weight836.4
XLogP-8.3
Topological Polar Surface Area434
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count27
Rotatable Bond Count14
Heavy Atom Count53
Formal Charge0
Complexity1410
SMILES
C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=NC6=C(N=CN=C65)N)O)O)O)O)N
InChI
InChI=1S/C20H28N10O19P4/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(45-19)1-43-50(35,36)47-52(39,40)49-53(41,42)48-51(37,38)44-2-8-12(32)14(34)20(46-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
InChIKey
YOAHKNVSNCMZGQ-XPWFQUROSA-N
Chemical Structure
2D Structure
2D structure of Ap4A
CAS: 5542-28-9
CID: 21706
Formula: C20H28N10O19P4
MW: 836.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight836.4
XLogP3-8.3
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count27
Rotatable Bond Count14
Exact Mass836.04826669
Monoisotopic Mass836.04826669
Topological Polar Surface Area434 Ų
Heavy Atom Count53
Formal Charge0
Complexity1410
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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