Molecule

Tabersonine

AlkaPlorer ID: AK003683

Synonym: None

IUPAC Name: None

Structure

SMILES: CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)[NH2+]C1=CC=CC=C14)[C@@H]32

InChI: InChI=1S/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/p+1/t19-,20-,21-/m0/s1

InChIKey: FNGGIPWAZSFKCN-ACRUOGEOSA-O

Reference

Altered Alkaloid Pattern in Dark Grown Seedlings of Catharanthus roseus. The Isolation and Characterization of 4-Desacetoxyvindoline: A Novel Indole Alkaloid and Proposed Precursor of Vindoline

PubChem CID: 25201472

LOTUS: LTS0064596

SuperNatural Ⅲ: SN0090285-01

NPASS: NPC210955

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Holacantha emoryi	Holacantha	Simaroubaceae	Sapindales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Dorstenia zenkeri	Dorstenia	Moraceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Melodinus suaveolens	Melodinus	Apocynaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Catharanthus roseus	Catharanthus	Apocynaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Gelsemium elegans	Gelsemium	Gelsemiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 337.44300000000004

TPSA？: 46.150000000000006

MolLogP？: 2.0041999999999995

Number of H-Donors: 1

Number of H-Acceptors: 3

RingCount: 5

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	A549	IC50	14700.0	nM	10.1021/np2009169
Homo sapiens	HL-60	IC50	4500.0	nM	10.1021/np2009169
Homo sapiens	MCF7	IC50	9900.0	nM	10.1021/np2009169
Homo sapiens	MDA-MB-231	Activity	nan	None	10.1039/d3md00049d
Homo sapiens	MDA-MB-231	IC50	5590.0	nM	10.1039/d3md00049d
Homo sapiens	SMMC-7721	IC50	5600.0	nM	10.1021/np2009169
Homo sapiens	SW480	IC50	12100.0	nM	10.1021/np2009169
Rattus norvegicus	Aortic artery	EC50	10000.0	nM	10.1021/acs.jnatprod.9b00925

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT001528	C/C=C1/CN2CCc3c([nH]c4ccccc34)[C@@](CO)(C(=O)OC)[C@H]1CC2>>CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32	R05853
AKRT001601	C=C(C(=O)OC)c1[nH]c2ccccc2c1CCN1C=C(CC)C=CC1>>CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32	RXN-19974
AKRT001885	C=C[C@@H]1[C@H](C[C@@H]2NCCc3c2[nH]c2ccccc32)C(C(=O)OC)=CO[C@H]1O>>CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32	MNXR186997
AKRT007325	CCC1C=[N+]2CCc3c([nH]c4ccccc34)[C@@](COC(C)=O)(C(=O)OC)[C@H]1CC2>>CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32	58584
AKRT010318	CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32>>CC[C@@]12CC(C(=O)OC)=C3Nc4ccccc4[C@@]34CCN(CC3OC31)[C@@H]24	R05866
AKRT010319	CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32>>CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1cc(O)ccc14)[C@@H]32	1.14.13.73-RXN
AKRT010320	CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32>>CC[C@]12C=CCN3CC[C@]4(C(=Nc5ccccc54)[C@@](O)(C(=O)OC)C1)[C@@H]32	RXN-18615
AKRT010321	CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32>>COC(=O)C1=C2Nc3ccccc3[C@@]23CCN2CC4OC4[C@@](C(C)O)(C1)[C@H]23	R05868
AKRT010322	CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32>>COC(=O)C1=C2Nc3ccccc3[C@@]23CCN2CC=C[C@@](C(C)O)(C1)[C@H]23	R05872
AKRT010323	CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32>>COC(=O)C1=C2Nc3ccccc3[C@@]23CCN2CCC[C@@](C(C)O)(C1)[C@H]23	R05869
AKRT010324	CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32>>COC(=O)C1=C2Nc3ccccc3[C@@]23CCN2CCC[C@@]([C@@H](C)O)(C1)[C@H]23	MNXR149391