Deoxyadenosine monophosphate

Deoxyadenosine monophosphate (dAMP), also known as deoxyadenylic acid or deoxyadenylate in its conjugate acid and conjugate base forms, respectively, is a derivative of the common nucleotide AMP, or adenosine monophosphate, in which the -OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been reduced to just a hydrogen atom (hence the "deoxy-" part of the name). Deoxyadenosine monophosphate is abbreviated dAMP. It is a monomer used in DNA.

Deoxyadenosine monophosphate

Names
IUPAC name 2′-Deoxyadenylic acid
Systematic IUPAC name [(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
Identifiers
CAS Number	653-63-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17713 Y
ChemSpider	12079 Y
ECHA InfoCard	100.010.459
IUPHAR/BPS	5120
MeSH	Deoxyadenosine+monophosphate
PubChem CID	621
UNII	VFR8I97ORM Y
CompTox Dashboard (EPA)	DTXSID901034859
InChI InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1 Y Key: KHWCHTKSEGGWEX-RRKCRQDMSA-N Y InChI=1/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1 Key: KHWCHTKSEGGWEX-RRKCRQDMBS
SMILES c1nc(c2c(n1)n(cn2)[C@H]3C[C@@H]([C@H](O3)COP(=O)(O)O)O)N
Properties
Chemical formula	C10H14N5O6P
Molar mass	331.222 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

See also

• Nucleic acid
• DNA metabolism
• Cofactor
• Guanosine
• Cyclic AMP (cAMP)
• ATP

Sources

• Wishart, David S.; Guo, An Chi; Oler, Eponine; Wang, Fel; Anjum, Afia; Peters, Harrison; Dizon, Raynard; Sayeeda, Zinat; Tian, Siyang; Lee, Brian L.; Berjanskii, Mark; Mah, Robert; Yamamoto, Mai; Jovel Castillo, Juan; Torres Calzada, Claudia; Hiebert Giesbrecht, Mickel; Lui, Vicki W.; Varshavi, Dorna; Varshavi, Dorsa; Allen, Dana; Arndt, David; Khetarpal, Nitya; Sivakumaran, Aadhavya; Harford, Karxena; Sanford, Selena; Yee, Kristen; Cao, Xuan; Budinsky, Zachary; Liigand, Jaanus; Zhang, Lun; Zheng, Jiamin; Mandal, Rupasri; Karu, Naama; Dambrova, Maija; Schiöth, Helgi B.; Gautam, Vasuk. "Showing metabocard for Deoxyadenosine monophosphate (HMDB0000905)". Human Metabolome Database, HMDB. 5.0.