Structure Database (LMSD)
Common Name
Secologanin
Systematic Name
Synonyms
3D model of Secologanin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
Secologanin is a monoterpene that has been found in V. rosea and is an intermediate in the synthesis of monoterpene indole alkaloids from geraniol.1,2 It is a metabolite of loganin formed by the cytochrome P450 (CYP) isoform CYP72A1, also known as secologanin synthase.3
This information has been provided by Cayman Chemical
References
1. Irmler, S., Schröder, G., St-Pierre, B., et al. Indole alkaloid biosynthesis in Catharanthus roseus: New enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase. Plant J. 24(6), 797-804 (2000).
2. Battersby, A.R., Burnett, A.R., and Parsons, P.G. Alkaloid biosynthesis. XIV. Secologanin: Its conversion into ipecoside and its role as biological precursor of the indole alkaloids. J. Chem. Soc. C Organic 8, 1187-1192 (1969).
3. Miettinen, K., Dong, L., Navrot, N., et al. The seco-iridoid pathway from Catharanthus roseus. Nat. Commun. 5:3606, (2014).
String Representations
InChiKey (Click to copy)
CSKKDSFETGLMSB-NRZPKYKESA-N
InChi (Click to copy)
InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1
SMILES (Click to copy)
[C@@]1([H])(C=C)[C@@H](OC=C(C(=O)OC)[C@@]1([H])CC=O)O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
2
Aromatic Rings
0
Rotatable Bonds
8
Van der Waals Molecular Volume
355.28
Topological Polar Surface Area
156.12
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
10
logP
0.23
Molar Refractivity
91.24
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Updated at
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