ContaminantDB: Taxine B

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:30:05 UTC

Update Date

2026-05-21 01:48:08 UTC

Accession Number

CHEM003094

Identification

Common Name

Taxine B

Class

Small Molecule

Description

Taxine B is a cardiotoxic alkaloid found in Yew trees. It is significantly more toxic than its counterpart, taxine A, and has both negative inotropic and atrioventricular conduction delay effects. Taxine B induced AV conduction delay produces the classic increase in the electro-cardiographic QRS complex duration that is observed in people, pigs, and guinea pigs with yew toxicosis. The p wave may also be depressed or absent. Taxine B also acts as a class I antiarrhythmic drug and, thus, reduces cardiac contractility and the maximum rate of depolarization. (1).

Contaminant Sources

T3DB toxins

Contaminant Type

Amine
Ester
Ether
Natural Compound
Organic Compound
PFAS
Phytotoxin
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
10-(Acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoic acid	Generator

Chemical Formula

C₃₃H₄₅NO₈

Average Molecular Mass

583.712 g/mol

Monoisotopic Mass

583.315 g/mol

CAS Registry Number

1361-51-9

IUPAC Name

Not Available

Traditional Name

10-(acetyloxy)-1,2,9-trihydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxotricyclo[9.3.1.0³,⁸]pentadec-11-en-5-yl 3-(dimethylamino)-3-phenylpropanoate

SMILES

CN(C)C(CC(=O)OC1CCC2(C)C(C(O)C3(O)CC(=O)C(C)=C(C(OC(C)=O)C2O)C3(C)C)C1=C)C1=CC=CC=C1

InChI Identifier

InChI=1S/C33H45NO8/c1-18-23(36)17-33(40)29(38)27-19(2)24(42-25(37)16-22(34(7)8)21-12-10-9-11-13-21)14-15-32(27,6)30(39)28(41-20(3)35)26(18)31(33,4)5/h9-13,22,24,27-30,38-40H,2,14-17H2,1,3-8H3

InChI Key

XMZFIBDTPOUHMW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] propellane ring system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Taxanes and derivatives

Alternative Parents

Substituents

Taxane diterpenoid
Fatty acid ester
Cyclohexenone
Aralkylamine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Ketone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Cyclic ketone
Polyol
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic oxygen compound
Amine
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.039 g/L	ALOGPS
logP	2.71	ALOGPS
logP	2.52	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.92	ChemAxon
pKa (Strongest Basic)	8.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	133.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	156.46 m³·mol⁻¹	ChemAxon
Polarizability	61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00o3-0202090000-10f0c0ac7dbfa8a339ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05ec-0908160000-77b147e3b784f828d8ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ov-2409010000-05c4929e7e37b09c179b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053u-2101190000-6ac5211c6d24475a1d3b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-4504490000-bf8e8a6f1b5903cc5137	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pi0-8924000000-fca615e1a32149d5e400	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Taxine B is a cardiotoxic alkaloid found in Yew trees.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0258750

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Taxine alkaloids

Chemspider ID

108387

ChEBI ID

Not Available

PubChem Compound ID

121443

Kegg Compound ID

C19989

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Taxine B (CHEM003094)

Structure for CHEM003094: Taxine B