Molecule

Strictosidine

AlkaPlorer ID: AK003917

Synonym: None

IUPAC Name: methyl (2S,3R,4S)-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

Structure

SMILES: C=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1C[C@@H]1NCCC2=C1NC1=CC=CC=C21

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

InChIKey: XBAMJZTXGWPTRM-NTXHKPOFSA-N

Reference

Iboga-Type Alkaloids from <i>Ervatamia officinalis</i>

PubChem CID: 161336

CAS: 20824-29-7

LOTUS: LTS0210201

NPASS: NPC82070

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Uncaria macrophylla	Uncaria	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Chimarrhis turbinata	Chimarrhis	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Uncaria rhynchophylla	Uncaria	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Uncaria sinensis	Uncaria	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 530.5740000000003

TPSA？: 162.73

MolLogP？: 0.3929000000000009

Number of H-Donors: 6

Number of H-Acceptors: 10

RingCount: 5

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Catharanthus roseus	Strictosidine beta-glucosidase	Km	220000.0	nM	10.1016/j.bmcl.2007.11.063
Catharanthus roseus	Strictosidine beta-glucosidase	Ratio	1.0	/min	10.1016/j.bmcl.2007.11.063
Catharanthus roseus	Strictosidine beta-glucosidase	Vmax	0.078	mM/min	10.1016/j.bmcl.2007.11.063
Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	100.0	ug ml-1	10.1021/np020547m
Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	250.0	ug ml-1	10.1021/np020547m
None	Radical scavenging activity	IC50	56000.0	nM	10.1021/np049863m

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT001882	C=C[C@@H]1[C@H](CC=O)C(C(=O)OC)=CO[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.NCCc1c[nH]c2ccccc12>>C=C[C@@H]1[C@H](C[C@@H]2NCCc3c2[nH]c2ccccc32)C(C(=O)OC)=CO[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O	None
AKRT001887	C=C[C@@H]1[C@H](C[C@@H]2NCCc3c2[nH]c2ccccc32)C(C(=O)OC)=CO[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O>>C=C[C@@H]1[C@H](CC=O)C(C(=O)OC)=CO[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.NCCc1c[nH]c2ccccc12	None
AKRT001888	C=C[C@@H]1[C@H](C[C@@H]2NCCc3c2[nH]c2ccccc32)C(C(=O)OC)=CO[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O>>C=C[C@H]1[C@H](O)OC=C(C(=O)OC)[C@H]1C[C@@H]1NCCc2c1[nH]c1ccccc21.OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O	None
AKRT001904	C=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC=O.NCCc1c[nH]c2ccccc12>>C=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1C[C@@H]1NCCc2c1[nH]c1ccccc21	R03738
AKRT001908	C=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1C[C@@H]1NCCc2c1[nH]c1ccccc21>>C=C[C@@H]1[C@H](C[C@@H]2NCCc3c2[nH]c2ccccc32)C(C(=O)OC)=CO[C@H]1O	R03820
AKRT001909	C=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1C[C@@H]1NCCc2c1[nH]c1ccccc21>>C=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC=O	enzymemap_85918
AKRT001910	C=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1C[C@@H]1NCCc2c1[nH]c1ccccc21>>NCCc1c[nH]c2ccccc12	enzymemap_85918
AKRT001911	C=C[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1C[C@@H]1NCCc2c1[nH]c1ccccc21>>OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O	R03820