(Q2356148)

3alpha(S)-strictosidine biosynthetic process

inferred from SMILES

part of

subject has role

product

1 reference

Gene Ontology release 2019-11-16

chemical structure

Strictosidine.svg
359 × 320; 29 KB

1 reference

German Wikipedia

mass

530.226431±0 dalton

1 reference

Strictosidine (English)

(2R)-2alpha-(beta-D-Glucopyranosyloxy)-3beta-vinyl-4beta-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1alpha-yl]methyl]-3,4-dihydro-2H-pyran-5-carboxylic acid methyl ester

5 October 2016

stereoisomer of

2 references

inferred from InChIKey

methyl (2S,3R,4R)-3-ethenyl-4-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

inferred from InChI

2 references

methyl (2S,3R,4S)-3-ethenyl-4-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-2-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

inferred from InChIKey

1 reference

1 reference

inferred from InChI

chemical formula

C₂₇H₃₄N₂O₉

1 reference

Strictosidine (English)

5 October 2016

canonical SMILES

COC(=O)C1=COC(C(C1CC2C3=C(CCN2)C4=CC=CC=C4N3)C=C)OC5C(C(C(C(O5)CO)O)O)O

1 reference

Strictosidine (English)

5 October 2016

isomeric SMILES

COC(=O)C1=CO[C@H]([C@@H]([C@@H]1C[C@H]2C3=C(CCN2)C4=CC=CC=C4N3)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O

1 reference

Alkaloid Production inCatharanthus roseus Cell Cultures. VII.. Effect of parameter changes and catabolism studies on cell line PRL No. 953

Strictosidine (English)

5 October 2016

12 references

Subcellular localization of tryptophan decarboxylase, strictosidine synthase and strictosidine glucosidase in suspension cultured cells of Catharanthus roseus and Tabernaemontana divaricata

Effect of terpenoid precursor feeding and elicitation on formation of indole alkaloids in cell suspension cultures of Catharanthus roseus

Involvement of strictosidine as a defensive chemical inCatharanthus roseus

Enzymatic Synthesis of Ajmalicine and Related Indole Alkaloids

Strictosidine (isovincoside): the key intermediate in the biosynthesis of monoterpenoid indole alkaloids

Strictosidine synthase from Catharanthus roseus: purification and characterization of multiple forms

Homogeneous Strictosidine Synthase Isoenzymes from Cell Suspension Cultures of Catharanthus roseus

Influence of Precursor Availability on Alkaloid Accumulation by Transgenic Cell Line of Catharanthus roseus

Subcellular Localization of Enzymes Involved in Indole Alkaloid Biosynthesis in Catharanthus roseus.

Induction of the Secondary Metabolism in Catharanthus roseus Cell Suspension Cultures in Response to UV Irradiation and the Addition of a Benzoic Acid Derivative

The Catharanthus alkaloids: pharmacognosy and biotechnology

Alstonia angustiloba

1 reference

Angustilobine and andranginine type indole alkaloids and an uleine-secovallesamine bisindole alkaloid from Alstonia angustiloba.

Alstonia scholaris

1 reference

Indole alkaloids from the leaves of Philippine Alstonia scholaris

Chimarrhis turbinata

3 references

Indole glucoalkaloids from Chimarrhis turbinata and their evaluation as antioxidant agents and acetylcholinesterase inhibitors

Turbinatine, a potential key intermediate in the biosynthesis of corynanthean-type indole alkaloids

Indole monoterpene alkaloids from Chimarrhis turbinata DC Prodr.: a contribution to the chemotaxonomic studies of the Rubiaceae family

Tabernaemontana bovina

1 reference

Iboga-Type Alkaloids from Ervatamia officinalis

Palicourea acuminata

2 references

Chemodiversity of tryptamine-derived alkaloids in six Costa Rican Palicourea species (Rubiaceae-Palicoureeae).

Alkaloid diversification in the genus Palicourea (Rubiaceae: Palicoureeae) viewed from a (retro-)biogenetic perspective

Palicourea winkleri

1 reference

Chemodiversity of tryptamine-derived alkaloids in six Costa Rican Palicourea species (Rubiaceae-Palicoureeae).

Rauvolfia serpentina

4 references

New alkaloids of the sarpagine group from Rauvolfia serpentina hairy root culture.

Development of an efficient system for the separation of indole alkaloids by high performance liquid chromatography and its applications.

Expression of enzymatically active cloned strictosidine synthase from the higher plant Rauvolfia serpentina in Escherichia coli

Divergence of the indole alkaloid pattern in two somatic hybrid plant cell subcultures of Rauvolfia serpentina x Rhazya stricta

Amsonia orientalis

1 reference

The Isolation and Structure of Strictimine, a New Piperidine Alkaloid from the Roots of Rhazya stricta

Strychnos mellodora

2 references

Glucoindole alkaloids from stem bark of Strychnos mellodora

β-Carboline glucoalkaloids from Strychnos mellodora

Cinchona calisaya

1 reference

Control and biological implications of alkaloid synthesis inCinchona seedlings

Tabernaemontana divaricata

3 references

Subcellular localization of tryptophan decarboxylase, strictosidine synthase and strictosidine glucosidase in suspension cultured cells of Catharanthus roseus and Tabernaemontana divaricata

Terpenoid indole alkaloid biosynthesis and enzyme activities in two cell lines of Tabernaemontana divaricata

Strictosidine glucosidase from suspension cultured cells of Tabernaemontana divaricata

Stenostomum acreanum

1 reference

Phytochemical and pharmacological studies of Guettarda acreana

Cephalanthus occidentalis

1 reference

Six new triterpenoid saponins from the root and stem bark of Cephalanthus occidentalis

Strychnos spinosa

1 reference

Secoiridoid glucosides from Strychnos spinosa

Triosteum pinnatifidum

1 reference

Monoterpene indole alkaloids and monoterpene diglycosides from the roots of Triosteum pinnatifidum

Uncaria lancifolia

1 reference

Recent research progress of Uncaria spp. based on alkaloids: phytochemistry, pharmacology and structural chemistry

Uncaria rhynchophylla

1 reference

Recent research progress of Uncaria spp. based on alkaloids: phytochemistry, pharmacology and structural chemistry

Palicourea elata

1 reference

Various types of tryptamine-iridoid alkaloids from Palicourea acuminata (=Psychotria acuminata, Rubiaceae)

Palicourea croceoides

1 reference

Loganin and secologanin derived tryptamine-iridoid alkaloids from Palicourea crocea and Palicourea padifolia (Rubiaceae).

Palicourea padifolia

1 reference

Loganin and secologanin derived tryptamine-iridoid alkaloids from Palicourea crocea and Palicourea padifolia (Rubiaceae).

Nauclea latifolia

1 reference

Isolation of strictosidine (isovincoside) lactam from Nauclea latifolia

Palicourea dichroa

1 reference

Alkaloids from Cephaelis dichroa

Commons category

Strictosidine

0 references

Identifiers

InChI

InChI=1S/C27H34N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-7,12-13,16,19-20,22-24,26-33H,1,8-11H2,2H3/t13-,16+,19+,20-,22-,23+,24-,26+,27+/m1/s1

1 reference

Strictosidine (English)

XBAMJZTXGWPTRM-NTXHKPOFSA-N

5 October 2016

InChIKey

2 references

Strictosidine (English)

5 October 2016

ChEBI release 2020-09-01

CAS Registry Number

20824-29-7

4 references

German Wikipedia

Spanish Wikipedia

XBAMJZTXGWPTRM-NTXHKPOFSA-N

English Wikipedia

InChIKey

9 April 2021

https://commonchemistry.cas.org/detail?cas_rn=20824-29-7

1 reference

Strictosidine (English)

5 October 2016

1 reference

Strictosidine (English)

5 October 2016

ChEBI ID

17559

mapping relation type

1 reference

3alpha(S)-strictosidine (English)

5 October 2016

1 reference

MSBNK-Washington_State_Univ-BML82475

STRICTOSIDINE (English)

5 October 2016

1 reference

MassBank accession ID

0 references

MSBNK-Washington_State_Univ-BML82476

0 references

MSBNK-Washington_State_Univ-BML82477

0 references

DSSTox substance ID

DTXSID40943068

0 references

DSSTOX compound identifier

0 references

1 reference

3alpha(S)-strictosidine (English)

5 October 2016

0 references

0 references

Microsoft Academic ID

2778610391

0 references

Römpp online ID

RD-19-04423

1 reference