(Q1531155)

Gene Ontology release 2019-11-16

(-)-secologanin catabolic process

subject has role

reactant

1 reference

Gene Ontology release 2019-11-16

(-)-secologanin biosynthetic process

subject has role

product

1 reference

Gene Ontology release 2019-11-16

strictosidine synthase activity

1 reference

deacetylisoipecoside synthase activity

1 reference

deacetylipecoside synthase activity

1 reference

secologanin synthase activity

1 reference

imported from Wikimedia project

chemical structure

Secologanin.png
1,800 × 1,163; 20 KB

1 reference

German Wikipedia

Secologanin.svg
512 × 233; 32 KB

0 references

mass

388.137 dalton

1 reference

Secologanin (English)

methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

19 October 2016

stereoisomer of

2 references

methyl (2S,3R,4R)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

2 references

methyl (2R,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

1 reference

methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

1 reference

chemical formula

C₁₇H₂₄O₁₀

1 reference

Secologanin (English)

19 October 2016

canonical SMILES

COC(=O)C1=COC(C(C1CC=O)C=C)OC2C(C(C(C(O2)CO)O)O)O

1 reference

Secologanin (English)

19 October 2016

isomeric SMILES

COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC=O)C=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

1 reference

Accumulation of loganin and secologanin in vacuoles from suspension cultured Catharanthus roseus cells

Secologanin (English)

19 October 2016

7 references

Analysis of several iridoid and indole precursors of terpenoid indole alkaloids with a single HPLC run

Secondary metabolite biosynthesis in cultured cells of Catharanthus roseus (L.) G. Don immobilized by adhesion to glass fibres

Characterization of a second secologanin synthase isoform producing both secologanin and secoxyloganin allows enhanced de novo assembly of a Catharanthus roseus transcriptome.

2,4-D and alkaloid accumulation in periwinkle cell suspensions

The iridoid glucoside secologanin is derived from the novel triose phosphate/pyruvate pathway in a Catharanthus roseus cell culture

Mechanism for iridane skeleton formation from acyclic monoterpenes in the biosynthesis of secologanin and vindoline in Catharanthus roseus and Lonicera morrowii.

Lonicera japonica

6 references

Isolation of Secoiridoid Artifacts from Lonicera japonica

Pyridinium alkaloid-coupled secoiridoids from the flower buds of Lonicera japonica

Biosynthesis of the ipecac β-carboline alkaloid tubulosine

Secoiridoid glycosides from the flower buds of Lonicera japonica

The biosynthesis of beta-carboline and quinolizidine alkaloids of Alangium lamarckii

Secologanin synthase which catalyzes the oxidative cleavage of loganin into secologanin is a cytochrome P450

Cruckshanksia verticillata

1 reference

Iridoids of Cruckshanksia verticillata and their Chemosystematic importance

Gentiana verna

1 reference

Secologanin and Derivatives from Gentiana verna

Lonicera caerulea

2 references

Caeruleosides A and B, bis-iridoid glucosides from Lonicera caerulea

Periclymenosidic Acid, a New Biosidic Ester Iridoid Glucoside from Lonicera coerulea

Acicarpha tribuloides

1 reference

Phytochemical and pharmacological studies on medicinal herb Acicarpha tribuloides

Adina pilulifera

1 reference

Studies on monoterpene glucosides and related natural products. XLII. On the possibility of the intermediacy of 10-hydroxyloganin in the biosynthesis of secologanin.

Sinoadina racemosa

2 references

Six Secoiridoid Glucosides from Jasminum polyanthum.

Six secoiridoid glucosides from Adina racemosa

Cinchona calisaya

1 reference

Control and biological implications of alkaloid synthesis inCinchona seedlings

Cruckshanksia pumila

1 reference

Iridoids from Cruckshanksia pumila (Rubiaceae)

Curtia tenuifolia

1 reference

Iridoid glucosides from Curtia tenuifolia

Desfontainia fulgens

1 reference

Iridoids, iridoid-triterpenoid congeners and lignans from Desfontainia spinosa

Desfontainia spinosa

1 reference

Iridoids, iridoid-triterpenoid congeners and lignans from Desfontainia spinosa

Dipsacus asper

1 reference

Acylated triterpene glycoside from roots of Dipsacus asper

Guettarda speciosa

1 reference

Chemotaxonomic studies of rubiaceous plants containing iridoid Glycosides

Hydrangea macrophylla

2 references

Radioimmunoassay for the determination of loganin and the biotransformation of loganin to secologanin by plant cell cultures

Studies on monoterpene glucosides and related natural products

Lippia graveolens

1 reference

Iridoids from Lippia graveolens

Lippia origanoides

1 reference

Iridoids from Lippia graveolens

Lonicera dioica

1 reference

Radioimmunoassay for the determination of loganin and the biotransformation of loganin to secologanin by plant cell cultures

Lonicera korolkowii

1 reference

Radioimmunoassay for the determination of loganin and the biotransformation of loganin to secologanin by plant cell cultures

Lonicera morrowii

4 references

Radioimmunoassay for the determination of loganin and the biotransformation of loganin to secologanin by plant cell cultures

Studies on monoterpene glucosides and related natural products. XLII. On the possibility of the intermediacy of 10-hydroxyloganin in the biosynthesis of secologanin.

Mechanism for iridane skeleton formation from acyclic monoterpenes in the biosynthesis of secologanin and vindoline in Catharanthus roseus and Lonicera morrowii.

Studies on Monoterpene Glucosides and Related Natural Products. LII. Mechanism for Iridane Skeleton Formation from Acyclic Monoterpenes in the Biosynthesis of Secoiridoid Glucosides and Indole Alkaloids

Lonicera periclymenum

1 reference

Secoiridoid glucosides from Lonicera periclymenum

Lonicera tatarica

3 references

Mechanism for iridane skeleton formation in the biosynthesis of secologanin and indole alkaloids in Lonicera tatarica, Catharanthus roseus and suspension cultures of Rauwolfia serpentina

Radioimmunoassay for the determination of loganin and the biotransformation of loganin to secologanin by plant cell cultures

Purification of Secologanin from Lonicera tatarica Extracts Using RLCC

Strychnos nux-vomica

1 reference

Alkaloids and iridoids from Strychnos nux-vomica fruits

Symphoricarpos orbiculatus

1 reference

Radioimmunoassay for the determination of loganin and the biotransformation of loganin to secologanin by plant cell cultures

Weigela coraeensis

1 reference

Radioimmunoassay for the determination of loganin and the biotransformation of loganin to secologanin by plant cell cultures

Weigela florida

1 reference

Radioimmunoassay for the determination of loganin and the biotransformation of loganin to secologanin by plant cell cultures

Weigela japonica

1 reference

Radioimmunoassay for the determination of loganin and the biotransformation of loganin to secologanin by plant cell cultures

Weigela middendorfiana

1 reference

Radioimmunoassay for the determination of loganin and the biotransformation of loganin to secologanin by plant cell cultures

Strychnos spinosa

1 reference

Secoiridoid glucosides from Strychnos spinosa

Dipsacus inermis

1 reference

Acylated triterpene glycoside from roots of Dipsacus asper

Pterocephalus perennis

1 reference

Cantleyoside-dimethyl-acetal and other iridoid glucosides from Pterocephalus perennis--antimicrobial activities

Commons category

Secologanin

0 references

Identifiers

InChI

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

1 reference

Secologanin (English)

19 October 2016

2 references

Secologanin (English)

19 October 2016

imported from Wikimedia project

ChEBI release 2020-09-01

CAS Registry Number

19351-63-4

3 references

German Wikipedia

imported from Wikimedia project

English Wikipedia

https://commonchemistry.cas.org/detail?cas_rn=19351-63-4

10 April 2021

1 reference

LONICEROSIDE (English)

19 October 2016

1 reference

Secologanin (English)

19 October 2016

Reaxys registry number

1441446

1 reference

(-)-secologanin (English)

19 October 2016

ChEBI ID

18002

mapping relation type

3 references

(-)-secologanin (English)

19 October 2016

ChEBI release 2019-10-02

International Chemical Identifier

InChI

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

1 reference

SECOLOGANIN (English)

19 October 2016

2 references

splash10-0aor-1900000000-773184210e8bb7a9052b

1 reference

0 references

DSSTox substance ID

DTXSID30941033

1 reference

DSSTOX compound identifier

DTXCID001369483

0 references

NSC number

640525

0 references

Human Metabolome Database ID

HMDB0304482

2 references

1 reference

(-)-secologanin (English)

19 October 2016

UNII

NK7B26K93T

1 reference

0 references

0 references

0 references

0 references

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Microsoft Academic ID

0 references

1 reference

3U5Y (English)

19 October 2016

1 reference

2FPC (English)