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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:44 UTC

Update Date

2023-02-21 17:21:10 UTC

HMDB ID

HMDB0031667

Secondary Accession Numbers

HMDB31667

Metabolite Identification

Common Name

Nor-psi-tropine

Description

Nor-psi-tropine, also known as nortropin or tropigenin, 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. Based on a literature review a small amount of articles have been published on Nor-psi-tropine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-alpha-H,5-alpha-H-Nortropan-3-beta-ol	HMDB
2,3-Dihydro-3-hydroxy-nortropidine	HMDB
3-beta-Nortropanol	HMDB
3-Hydroxy-nortropane	HMDB
8-Azabicyclo(3.2.1)octan-3-ol, exo- (9ci)	HMDB
8-Azabicyclo[3.2.1]octan-3-ol, 9ci	HMDB
endo-8-Azabicyclo[3.2.1]octan-3-ol	HMDB
exo-8-Azabicyclo(3.2.1)octan-3-ol	HMDB
exo-Form	HMDB
Nor-tropanol	HMDB
Nor-y-tropine	HMDB
Norpseudotropine	HMDB
Nortropin	HMDB
Nortropine	HMDB
Pseudonortropine	HMDB
Pseudotropigenine	HMDB
Tropigenin	HMDB
Tropigenine	HMDB

Chemical Formula

C₇H₁₃NO

Average Molecular Weight

127.1842

Monoisotopic Molecular Weight

127.099714043

IUPAC Name

8-azabicyclo[3.2.1]octan-3-ol

Traditional Name

8-azabicyclo[3.2.1]octan-3-ol

CAS Registry Number

501-33-7

SMILES

OC1CC2CCC(C1)N2

InChI Identifier

InChI=1S/C7H13NO/c9-7-3-5-1-2-6(4-7)8-5/h5-9H,1-4H2

InChI Key

YYMCYJLIYNNOMK-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
Secondary alcohol
Secondary aliphatic amine
Secondary amine
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Amine
Organic nitrogen 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: HMDB0031667)
Cytoplasm (HMDB: HMDB0031667)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031667)

Source

Endogenous

Endogenous (HMDB: HMDB0031667)

Plant

Plant (HMDB: HMDB0031667)

Exogenous

Food

Food (HMDB: HMDB0031667)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	134.5 - 135 °C	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	303 g/L	ALOGPS
logP	-0.06	ALOGPS
logP	-0.35	ChemAxon
logS	0.38	ALOGPS
pKa (Strongest Acidic)	15.16	ChemAxon
pKa (Strongest Basic)	10.72	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.3 m³·mol⁻¹	ChemAxon
Polarizability	14.16 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.212	31661259
DarkChem	[M-H]-	120.145	31661259
DeepCCS	[M+H]+	131.814	30932474
DeepCCS	[M-H]-	129.189	30932474
DeepCCS	[M-2H]-	165.686	30932474
DeepCCS	[M+Na]+	140.466	30932474
AllCCS	[M+H]+	130.1	32859911
AllCCS	[M+H-H2O]+	125.4	32859911
AllCCS	[M+NH4]+	134.4	32859911
AllCCS	[M+Na]+	135.7	32859911
AllCCS	[M-H]-	124.3	32859911
AllCCS	[M+Na-2H]-	126.0	32859911
AllCCS	[M+HCOO]-	127.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nor-psi-tropine	OC1CC2CCC(C1)N2	1996.0	Standard polar	33892256
Nor-psi-tropine	OC1CC2CCC(C1)N2	1210.2	Standard non polar	33892256
Nor-psi-tropine	OC1CC2CCC(C1)N2	1325.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nor-psi-tropine,1TMS,isomer #1	C[Si](C)(C)OC1CC2CCC(C1)N2	1246.7	Semi standard non polar	33892256
Nor-psi-tropine,1TMS,isomer #2	C[Si](C)(C)N1C2CCC1CC(O)C2	1374.8	Semi standard non polar	33892256
Nor-psi-tropine,2TMS,isomer #1	C[Si](C)(C)OC1CC2CCC(C1)N2[Si](C)(C)C	1410.1	Semi standard non polar	33892256
Nor-psi-tropine,2TMS,isomer #1	C[Si](C)(C)OC1CC2CCC(C1)N2[Si](C)(C)C	1460.1	Standard non polar	33892256
Nor-psi-tropine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2CCC(C1)N2	1514.1	Semi standard non polar	33892256
Nor-psi-tropine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C2CCC1CC(O)C2	1621.4	Semi standard non polar	33892256
Nor-psi-tropine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2CCC(C1)N2[Si](C)(C)C(C)(C)C	1899.6	Semi standard non polar	33892256
Nor-psi-tropine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2CCC(C1)N2[Si](C)(C)C(C)(C)C	1910.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Nor-psi-tropine GC-MS (1 TMS)	splash10-001j-9400000000-2729f49fcd134c7aa5fd	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Nor-psi-tropine GC-MS (Non-derivatized)	splash10-001j-9400000000-2729f49fcd134c7aa5fd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nor-psi-tropine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0159-9100000000-cc3c39e7429b64a21add	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nor-psi-tropine GC-MS (1 TMS) - 70eV, Positive	splash10-0089-9400000000-6e5301d34eae94b454f0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nor-psi-tropine 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 - Nor-psi-tropine 10V, Positive-QTOF	splash10-03fr-0900000000-737db543cc351b4febe7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nor-psi-tropine 20V, Positive-QTOF	splash10-03fr-1900000000-4e385b616d8cacec918b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nor-psi-tropine 40V, Positive-QTOF	splash10-03yi-9300000000-08548012b5b1a4befbef	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nor-psi-tropine 10V, Negative-QTOF	splash10-004i-0900000000-622b17d3601ede1c53d9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nor-psi-tropine 20V, Negative-QTOF	splash10-004i-0900000000-4759f5d462554080f29f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nor-psi-tropine 40V, Negative-QTOF	splash10-00mk-9300000000-34ce96bafe39648dab3d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nor-psi-tropine 10V, Positive-QTOF	splash10-004i-0900000000-2d0b886d38b6a8e41013	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nor-psi-tropine 20V, Positive-QTOF	splash10-03di-0900000000-4ece63ae52d4d6df914b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nor-psi-tropine 40V, Positive-QTOF	splash10-01qc-9300000000-d094e3e46d7efd45590e	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nor-psi-tropine 10V, Negative-QTOF	splash10-004i-0900000000-5fce2f371fcc2700e0fc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nor-psi-tropine 20V, Negative-QTOF	splash10-004i-0900000000-5fce2f371fcc2700e0fc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nor-psi-tropine 40V, Negative-QTOF	splash10-00di-0900000000-230fc672df5e0c0982a5	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

FDB008327

KNApSAcK ID

C00057413

Chemspider ID

61455

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68147

PDB ID

Not Available

ChEBI ID

165181

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

Hofner K, Oelke M, Machtens S, Grunewald V: Trospium chloride--an effective drug in the treatment of overactive bladder and detrusor hyperreflexia. World J Urol. 2001 Nov;19(5):336-43. [PubMed:11760782 ]
Xia Y, Chackalamannil S, Greenlee WJ, Jayne C, Neustadt B, Stamford A, Vaccaro H, Xu XL, Baker H, O'Neill K, Woods M, Hawes B, Kowalski T: Discovery of a nortropanol derivative as a potent and orally active GPR119 agonist for type 2 diabetes. Bioorg Med Chem Lett. 2011 Jun 1;21(11):3290-6. doi: 10.1016/j.bmcl.2011.04.035. Epub 2011 Apr 14. [PubMed:21536438 ]
Schmitz G, Braun V: Cell-bound and secreted proteases of Serratia marcescens. J Bacteriol. 1985 Mar;161(3):1002-9. [PubMed:2579058 ]
Sargent MG, Lampen JO: A mechanism for penicillinasesecretion in Bacillus licheniformis. Proc Natl Acad Sci U S A. 1970 Apr;65(4):962-9. [PubMed:5266165 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Nor-psi-tropine (HMDB0031667)

MOL for HMDB0031667 (Nor-psi-tropine)

3D MOL for HMDB0031667 (Nor-psi-tropine)

3D SDF for HMDB0031667 (Nor-psi-tropine)

3D-SDF for HMDB0031667 (Nor-psi-tropine)

PDB for HMDB0031667 (Nor-psi-tropine)

3D PDB for HMDB0031667 (Nor-psi-tropine)

SMILES for HMDB0031667 (Nor-psi-tropine)

INCHI for HMDB0031667 (Nor-psi-tropine)

Structure for HMDB0031667 (Nor-psi-tropine)

3D Structure for HMDB0031667 (Nor-psi-tropine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra