7-Deoxyloganic acid

7-Deoxyloganic acid
Names
	IUPAC name (1S,4aS,7S,7aR)-1-(β-D-Glucopyranosyloxy)-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
	Systematic IUPAC name (1S,4aS,7S,7aR)-7-Methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
Identifiers
CAS Number	22487-36-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	391558;
PubChem CID	443322;
UNII	SZ67QWR9D3 ;
CompTox Dashboard (EPA)	DTXSID40945163 ;
	InChI InChI=1S/C16H24O9/c1-6-2-3-7-8(14(21)22)5-23-15(10(6)7)25-16-13(20)12(19)11(18)9(4-17)24-16/h5-7,9-13,15-20H,2-4H2,1H3,(H,21,22)/t6-,7+,9+,10+,11+,12-,13+,15-,16-/m0/s1 Key: DSXFHNSGLYXPNG-YDYVGBNJSA-N; InChI=1/C16H24O9/c1-6-2-3-7-8(14(21)22)5-23-15(10(6)7)25-16-13(20)12(19)11(18)9(4-17)24-16/h5-7,9-13,15-20H,2-4H2,1H3,(H,21,22)/t6-,7+,9+,10+,11+,12-,13+,15-,16-/m0/s1 Key: DSXFHNSGLYXPNG-YDYVGBNJBM;
	SMILES C[C@H]1CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O;
Properties
Chemical formula	C16H24O9
Molar mass	360.359 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

7-Deoxyloganic acid is an iridoid monoterpene. 7-Deoxyloganic acid is produced from 7-deoxyloganetic acid by the enzyme 7-deoxyloganetic acid glucosyltransferase (7-DLGT).^[1]^[2] The metabolite is a substrate for the enzyme 7-deoxyloganic acid hydroxylase (7-DLH) which synthesizes loganic acid.

References

^ Miettinen, Dong, Navrot, Schneider, Burlat, et al. (2014) The seco-iridoid pathway from Catharanthus roseus. Nat Commun. 5
^ Salim, Yu, Altarejos and De Luca (2013) Virus-induced gene silencing identifies Catharanthus roseus 7-deoxyloganic acid-7-hydroxylase, a step in iridoid and monoterpene indole alkaloid biosynthesis. The Plant Journal. 76(5). 754-765

[1] Miettinen, Dong, Navrot, Schneider, Burlat, et al. (2014) The seco-iridoid pathway from Catharanthus roseus. Nat Commun. 5

[2] Salim, Yu, Altarejos and De Luca (2013) Virus-induced gene silencing identifies Catharanthus roseus 7-deoxyloganic acid-7-hydroxylase, a step in iridoid and monoterpene indole alkaloid biosynthesis. The Plant Journal. 76(5). 754-765

[1]

[2]