Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:28:08 UTC

Update Date

2021-09-26 22:51:57 UTC

HMDB ID

HMDB0244302

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Fluciclovine

Description

Fluciclovine, also known as (18F)ge-148 or axumin, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Based on a literature review a significant number of articles have been published on Fluciclovine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Fluciclovine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Fluciclovine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(18F)GE-148	HMDB
(1R,3R)-1-Amino-3(18F)fluorocyclobutane-1-carboxylic acid	HMDB
1-Amino-3-fluorocyclobutane-1-carboxylic acid	HMDB
Axumin	HMDB
F(18)-FACBC	HMDB
F(18)1-Amino-3-fluorocyclobutane-1-carboxylic acid	HMDB
F-FACBC	HMDB
GE-148 (18F)	HMDB
GE-148 F-18	HMDB
NMK 36	HMDB
NMK-36	HMDB
NMK36 CPD	HMDB
Anti-(18F)facbc	HMDB
Fluciclovine (18F)	HMDB
Fluciclovine F 18	HMDB
Fluciclovine F-18	HMDB

Chemical Formula

C₅H₈FNO₂

Average Molecular Weight

133.122

Monoisotopic Molecular Weight

133.053906665

IUPAC Name

1-amino-3-fluorocyclobutane-1-carboxylic acid

Traditional Name

1-amino-3-fluorocyclobutane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

NC1(CC(F)C1)C(O)=O

InChI Identifier

InChI=1S/C5H8FNO2/c6-3-1-5(7,2-3)4(8)9/h3H,1-2,7H2,(H,8,9)

InChI Key

NTEDWGYJNHZKQW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

D-alpha-amino acid
L-alpha-amino acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Alkyl fluoride
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Amine
Alkyl halide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0244302)

Process

Not Available

Role

Not Available

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
logP	-3	ALOGPS
logP	-2.9	ChemAxon
logS	0.11	ALOGPS
pKa (Strongest Acidic)	2.07	ChemAxon
pKa (Strongest Basic)	9.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	27.75 m³·mol⁻¹	ChemAxon
Polarizability	11.66 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	123.559	30932474
DeepCCS	[M-H]-	120.391	30932474
DeepCCS	[M-2H]-	157.234	30932474
DeepCCS	[M+Na]+	132.17	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fluciclovine	NC1(CC(F)C1)C(O)=O	1872.7	Standard polar	33892256
Fluciclovine	NC1(CC(F)C1)C(O)=O	938.3	Standard non polar	33892256
Fluciclovine	NC1(CC(F)C1)C(O)=O	1408.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fluciclovine,2TMS,isomer #1	C[Si](C)(C)NC1(C(=O)O[Si](C)(C)C)CC(F)C1	1250.6	Semi standard non polar	33892256
Fluciclovine,2TMS,isomer #1	C[Si](C)(C)NC1(C(=O)O[Si](C)(C)C)CC(F)C1	1299.3	Standard non polar	33892256
Fluciclovine,2TMS,isomer #1	C[Si](C)(C)NC1(C(=O)O[Si](C)(C)C)CC(F)C1	1321.6	Standard polar	33892256
Fluciclovine,2TMS,isomer #2	C[Si](C)(C)N(C1(C(=O)O)CC(F)C1)[Si](C)(C)C	1416.9	Semi standard non polar	33892256
Fluciclovine,2TMS,isomer #2	C[Si](C)(C)N(C1(C(=O)O)CC(F)C1)[Si](C)(C)C	1365.9	Standard non polar	33892256
Fluciclovine,2TMS,isomer #2	C[Si](C)(C)N(C1(C(=O)O)CC(F)C1)[Si](C)(C)C	1608.5	Standard polar	33892256
Fluciclovine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1(N([Si](C)(C)C)[Si](C)(C)C)CC(F)C1	1435.9	Semi standard non polar	33892256
Fluciclovine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1(N([Si](C)(C)C)[Si](C)(C)C)CC(F)C1	1448.4	Standard non polar	33892256
Fluciclovine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1(N([Si](C)(C)C)[Si](C)(C)C)CC(F)C1	1395.3	Standard polar	33892256
Fluciclovine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1(C(=O)O[Si](C)(C)C(C)(C)C)CC(F)C1	1692.8	Semi standard non polar	33892256
Fluciclovine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1(C(=O)O[Si](C)(C)C(C)(C)C)CC(F)C1	1755.2	Standard non polar	33892256
Fluciclovine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1(C(=O)O[Si](C)(C)C(C)(C)C)CC(F)C1	1639.5	Standard polar	33892256
Fluciclovine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1(C(=O)O)CC(F)C1)[Si](C)(C)C(C)(C)C	1872.8	Semi standard non polar	33892256
Fluciclovine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1(C(=O)O)CC(F)C1)[Si](C)(C)C(C)(C)C	1831.6	Standard non polar	33892256
Fluciclovine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1(C(=O)O)CC(F)C1)[Si](C)(C)C(C)(C)C	1783.4	Standard polar	33892256
Fluciclovine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC(F)C1	2077.3	Semi standard non polar	33892256
Fluciclovine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC(F)C1	2101.8	Standard non polar	33892256
Fluciclovine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC(F)C1	1784.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fluciclovine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-9000000000-34665be7962d1b8b1f57	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluciclovine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluciclovine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluciclovine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluciclovine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluciclovine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - Fluciclovine 10V, Positive-QTOF	splash10-0019-9500000000-6c97fc8d1384ed6a4366	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluciclovine 20V, Positive-QTOF	splash10-00kk-9100000000-c7efde2508fee5692cc2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluciclovine 40V, Positive-QTOF	splash10-0007-9000000000-17b006c7a47dfd8b0ea3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluciclovine 10V, Negative-QTOF	splash10-001i-0900000000-81874c4509d8458ff6ad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluciclovine 20V, Negative-QTOF	splash10-00lr-6900000000-7977ca1ac3be66d4cf41	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluciclovine 40V, Negative-QTOF	splash10-030c-9000000000-7726a45f5e9d1ca4880f	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8995866

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fluciclovine (18F)

METLIN ID

Not Available

PubChem Compound

10820564

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Fluciclovine (HMDB0244302)

MOL for HMDB0244302 (Fluciclovine)

3D MOL for HMDB0244302 (Fluciclovine)

3D SDF for HMDB0244302 (Fluciclovine)

3D-SDF for HMDB0244302 (Fluciclovine)

PDB for HMDB0244302 (Fluciclovine)

3D PDB for HMDB0244302 (Fluciclovine)

SMILES for HMDB0244302 (Fluciclovine)

INCHI for HMDB0244302 (Fluciclovine)

Structure for HMDB0244302 (Fluciclovine)

3D Structure for HMDB0244302 (Fluciclovine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra