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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:55:03 UTC

Update Date

2022-03-07 02:55:50 UTC

HMDB ID

HMDB0038593

Secondary Accession Numbers

HMDB38593

Metabolite Identification

Common Name

Calystegin A3

Description

Calystegin A3 belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. Calystegin A3 has been detected, but not quantified in, several different foods, such as alcoholic beverages, eggplants (Solanum melongena), potatos (Solanum tuberosum), and sweet potatos (Ipomoea batatas). This could make calystegin A3 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Calystegin A3.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₇H₁₃NO₃

Average Molecular Weight

159.183

Monoisotopic Molecular Weight

159.089543287

IUPAC Name

8-azabicyclo[3.2.1]octane-1,2,3-triol

Traditional Name

8-azabicyclo[3.2.1]octane-1,2,3-triol

CAS Registry Number

131580-36-4

SMILES

OC1CC2CCC(O)(N2)C1O

InChI Identifier

InChI=1S/C7H13NO3/c9-5-3-4-1-2-7(11,8-4)6(5)10/h4-6,8-11H,1-3H2

InChI Key

XOCBOVUINUHZJA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Tropane alkaloid
Piperidine
Cyclic alcohol
Pyrrolidine
1,2-diol
Hemiaminal
Secondary alcohol
Alkanolamine
Secondary aliphatic amine
Polyol
Azacycle
Organoheterocyclic compound
Secondary amine
Organonitrogen compound
Organopnictogen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038593)
Cytoplasm (HMDB: HMDB0038593)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038593)

Source

Exogenous

Exogenous (HMDB: HMDB0038593)

Food

Food (HMDB: HMDB0038593)

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)

Tuber

Potato (FooDB: FOOD00175)
Sweet potato (FooDB: FOOD00092)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0038593)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038593)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	660 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.5	ChemAxon
logS	0.62	ALOGPS
pKa (Strongest Acidic)	12.23	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	37.97 m³·mol⁻¹	ChemAxon
Polarizability	15.79 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.952	31661259
DarkChem	[M-H]-	126.658	31661259
DeepCCS	[M+H]+	136.768	30932474
DeepCCS	[M-H]-	133.77	30932474
DeepCCS	[M-2H]-	170.851	30932474
DeepCCS	[M+Na]+	146.014	30932474
AllCCS	[M+H]+	136.8	32859911
AllCCS	[M+H-H2O]+	132.4	32859911
AllCCS	[M+NH4]+	140.9	32859911
AllCCS	[M+Na]+	142.0	32859911
AllCCS	[M-H]-	128.5	32859911
AllCCS	[M+Na-2H]-	129.4	32859911
AllCCS	[M+HCOO]-	130.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Calystegin A3	OC1CC2CCC(O)(N2)C1O	2950.5	Standard polar	33892256
Calystegin A3	OC1CC2CCC(O)(N2)C1O	1518.9	Standard non polar	33892256
Calystegin A3	OC1CC2CCC(O)(N2)C1O	1620.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Calystegin A3,1TMS,isomer #1	C[Si](C)(C)OC1CC2CCC(O)(N2)C1O	1607.1	Semi standard non polar	33892256
Calystegin A3,1TMS,isomer #2	C[Si](C)(C)OC12CCC(CC(O)C1O)N2	1655.0	Semi standard non polar	33892256
Calystegin A3,1TMS,isomer #3	C[Si](C)(C)OC1C(O)CC2CCC1(O)N2	1626.1	Semi standard non polar	33892256
Calystegin A3,1TMS,isomer #4	C[Si](C)(C)N1C2CCC1(O)C(O)C(O)C2	1730.7	Semi standard non polar	33892256
Calystegin A3,2TMS,isomer #1	C[Si](C)(C)OC1CC2CCC(O[Si](C)(C)C)(N2)C1O	1648.2	Semi standard non polar	33892256
Calystegin A3,2TMS,isomer #2	C[Si](C)(C)OC1CC2CCC(O)(N2)C1O[Si](C)(C)C	1623.7	Semi standard non polar	33892256
Calystegin A3,2TMS,isomer #3	C[Si](C)(C)OC1CC2CCC(O)(C1O)N2[Si](C)(C)C	1697.2	Semi standard non polar	33892256
Calystegin A3,2TMS,isomer #4	C[Si](C)(C)OC1C(O)CC2CCC1(O[Si](C)(C)C)N2	1639.6	Semi standard non polar	33892256
Calystegin A3,2TMS,isomer #5	C[Si](C)(C)OC12CCC(CC(O)C1O)N2[Si](C)(C)C	1739.9	Semi standard non polar	33892256
Calystegin A3,2TMS,isomer #6	C[Si](C)(C)OC1C(O)CC2CCC1(O)N2[Si](C)(C)C	1723.6	Semi standard non polar	33892256
Calystegin A3,3TMS,isomer #1	C[Si](C)(C)OC1CC2CCC(O[Si](C)(C)C)(N2)C1O[Si](C)(C)C	1680.0	Semi standard non polar	33892256
Calystegin A3,3TMS,isomer #2	C[Si](C)(C)OC1CC2CCC(O[Si](C)(C)C)(C1O)N2[Si](C)(C)C	1755.4	Semi standard non polar	33892256
Calystegin A3,3TMS,isomer #3	C[Si](C)(C)OC1CC2CCC(O)(C1O[Si](C)(C)C)N2[Si](C)(C)C	1740.8	Semi standard non polar	33892256
Calystegin A3,3TMS,isomer #4	C[Si](C)(C)OC1C(O)CC2CCC1(O[Si](C)(C)C)N2[Si](C)(C)C	1759.3	Semi standard non polar	33892256
Calystegin A3,4TMS,isomer #1	C[Si](C)(C)OC1CC2CCC(O[Si](C)(C)C)(C1O[Si](C)(C)C)N2[Si](C)(C)C	1832.8	Semi standard non polar	33892256
Calystegin A3,4TMS,isomer #1	C[Si](C)(C)OC1CC2CCC(O[Si](C)(C)C)(C1O[Si](C)(C)C)N2[Si](C)(C)C	1834.8	Standard non polar	33892256
Calystegin A3,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2CCC(O)(N2)C1O	1841.3	Semi standard non polar	33892256
Calystegin A3,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC12CCC(CC(O)C1O)N2	1885.0	Semi standard non polar	33892256
Calystegin A3,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C(O)CC2CCC1(O)N2	1852.3	Semi standard non polar	33892256
Calystegin A3,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C2CCC1(O)C(O)C(O)C2	1943.1	Semi standard non polar	33892256
Calystegin A3,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2CCC(O[Si](C)(C)C(C)(C)C)(N2)C1O	2083.1	Semi standard non polar	33892256
Calystegin A3,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1CC2CCC(O)(N2)C1O[Si](C)(C)C(C)(C)C	2055.1	Semi standard non polar	33892256
Calystegin A3,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1CC2CCC(O)(C1O)N2[Si](C)(C)C(C)(C)C	2144.4	Semi standard non polar	33892256
Calystegin A3,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C(O)CC2CCC1(O[Si](C)(C)C(C)(C)C)N2	2063.5	Semi standard non polar	33892256
Calystegin A3,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC12CCC(CC(O)C1O)N2[Si](C)(C)C(C)(C)C	2200.1	Semi standard non polar	33892256
Calystegin A3,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1C(O)CC2CCC1(O)N2[Si](C)(C)C(C)(C)C	2150.5	Semi standard non polar	33892256
Calystegin A3,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2CCC(O[Si](C)(C)C(C)(C)C)(N2)C1O[Si](C)(C)C(C)(C)C	2318.2	Semi standard non polar	33892256
Calystegin A3,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1CC2CCC(O[Si](C)(C)C(C)(C)C)(C1O)N2[Si](C)(C)C(C)(C)C	2405.2	Semi standard non polar	33892256
Calystegin A3,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1CC2CCC(O)(C1O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2396.0	Semi standard non polar	33892256
Calystegin A3,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C(O)CC2CCC1(O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2409.3	Semi standard non polar	33892256
Calystegin A3,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2CCC(O[Si](C)(C)C(C)(C)C)(C1O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2662.7	Semi standard non polar	33892256
Calystegin A3,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2CCC(O[Si](C)(C)C(C)(C)C)(C1O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2617.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Calystegin A3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9600000000-8716a965d8778f3af4e2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calystegin A3 GC-MS (3 TMS) - 70eV, Positive	splash10-05g0-8796000000-2c3e642d65a5e13ad791	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calystegin A3 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 10V, Positive-QTOF	splash10-03di-0900000000-66ce9f462f996bfa29a9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 20V, Positive-QTOF	splash10-03dl-0900000000-39c60ef6243300c271a2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 40V, Positive-QTOF	splash10-008c-9700000000-441e6ecf2707e07c317b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 10V, Negative-QTOF	splash10-0a4i-2900000000-99221f4a87e4f7a880e7	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 20V, Negative-QTOF	splash10-0a4i-1900000000-739daad75bcbde6f860c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 40V, Negative-QTOF	splash10-003s-9600000000-f8acc278afb6c2427cca	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 10V, Negative-QTOF	splash10-0a4i-0900000000-bae995f985c28e19f14c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 20V, Negative-QTOF	splash10-0a4i-0900000000-58de0a69f664f93ddec7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 40V, Negative-QTOF	splash10-052f-7900000000-2bbf3dd68e681c25d694	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 10V, Positive-QTOF	splash10-03di-0900000000-dfe272abd2e78480a741	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 20V, Positive-QTOF	splash10-03di-2900000000-2dab5f2997098526f874	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calystegin A3 40V, Positive-QTOF	splash10-03dv-8900000000-59405bec2f8d2a69c799	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017984

KNApSAcK ID

C00002282

Chemspider ID

3684607

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4486820

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Calystegin A3 (HMDB0038593)

MOL for HMDB0038593 (Calystegin A3)

3D MOL for HMDB0038593 (Calystegin A3)

3D SDF for HMDB0038593 (Calystegin A3)

3D-SDF for HMDB0038593 (Calystegin A3)

PDB for HMDB0038593 (Calystegin A3)

3D PDB for HMDB0038593 (Calystegin A3)

SMILES for HMDB0038593 (Calystegin A3)

INCHI for HMDB0038593 (Calystegin A3)

Structure for HMDB0038593 (Calystegin A3)

3D Structure for HMDB0038593 (Calystegin A3)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra