Identification

PhytoHub ID
PHUB000855
Name
Tomatidine
Systematic Name
Not Available
Synonyms
  • 5alpha-tomatidan-3beta-ol
CAS Number
Not Available
Average Mass
415.662
Monoisotopic Mass
415.345029693
Chemical Formula
C27H45NO2
IUPAC Name
(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-16-ol
InChI Key
XYNPYHXGMWJBLV-VXPJTDKGSA-N
InChI Identifier
InChI=1S/C27H45NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28-29H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-/m0/s1
SMILES
C[[email protected]]1[[email protected]]2[[email protected]](C[[email protected]]3[[email protected]@H]4CC[[email protected]]5C[[email protected]@H](O)CC[[email protected]]5(C)[[email protected]]4CC[[email protected]]23C)O[[email protected]@]11CC[[email protected]](C)CN1
Structure

Calculated Properties

Solubility (ALOGPS)
1.89e-04 g/l
LogS (ALOGPS)
-6.34
LogP (ALOGPS)
4.72
Hydrogen Acceptors
3
Hydrogen Donors
2
Rotatable Bond Count
0
Polar Surface Area
41.49
Refractivity
121.09679999999999
Polarizability
51.867651146678305
Formal Charge
0
Physiological Charge
1
pKa (strongest basic)
9.541647886074307
pKa (strongest acidic)
18.2963963211217
Number of Rings
6
Rule of Five
No
Bioavailability
Yes
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
No

Taxonomy

Family
N-containing compounds
Class
Alkaloids
Sub-class
Steroid alkaloids

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Steroids and steroid derivatives
Super-class
Lipids and lipid-like molecules
Sub-class
Steroidal alkaloids
Direct Parent Name
Spirosolanes and derivatives
Alternative Parent Names
["3-beta-hydroxysteroids", "Alkaloids and derivatives", "Azacyclic compounds", "Azaspirodecane derivatives", "Azasteroids and derivatives", "Cyclic alcohols and derivatives", "Dialkylamines", "Hemiaminals", "Hydrocarbon derivatives", "Organopnictogen compounds", "Oxacyclic compounds", "Piperidines", "Secondary alcohols", "Tetrahydrofurans"]
External Descriptor Annotations
["3beta-hydroxy steroid", "Solanidines and alkaloid derivatives", "Steroidal alkaloids", "azaspiro compound", "oxaspiro compound"]
Substituent Names
["3-beta-hydroxysteroid", "3-hydroxysteroid", "Alcohol", "Aliphatic heteropolycyclic compound", "Alkaloid or derivatives", "Amine", "Azacycle", "Azaspirodecane", "Azasteroid", "Cyclic alcohol", "Hemiaminal", "Hydrocarbon derivative", "Hydroxysteroid", "Organic nitrogen compound", "Organic oxygen compound", "Organoheterocyclic compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Oxacycle", "Piperidine", "Secondary alcohol", "Secondary aliphatic amine", "Secondary amine", "Spirosolane skeleton", "Tetrahydrofuran"]

Spectra

No spectra information available

Food Sources

PrecursorFood SourceFood Source Group
TomatineCherry tomatoVegetables, Fruit vegetables PublicationsShow
TomatineGreen tomatoVegetables, Fruit vegetables PublicationsShow
TomatineKetchupCondiments and seasonings PublicationsShow
TomatineTomatoVegetables, Fruit vegetables PublicationsShow
TomatineTomato juiceBeverages, Non-alcoholic PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginFormulaMonoisotopic mass
Tomatidine Tomatidine O-glucuronidehumanplasmahost metabolismC33H53NO8591.377117671
Tomatine TomatidinemouseplasmaunknownC27H45NO2415.345029693 Publications
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