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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:26:24 UTC

Update Date

2023-02-21 17:30:03 UTC

HMDB ID

HMDB0060514

Secondary Accession Numbers

HMDB60514

Metabolite Identification

Common Name

trans-3-Chloro-2-propene-1-ol

Description

trans-3-Chloro-2-propene-1-ol, also known as (e)-3-chloroallyl alcohol, belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom. These are compounds comprising the primary alcohol functional group, with the general strucuture RCOH (R=alkyl, aryl). trans-3-Chloro-2-propene-1-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). trans-3-Chloro-2-propene-1-ol exists in all living organisms, ranging from bacteria to humans.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-3-Chloro-2-propen-1-ol	ChEBI
(e)-3-Chloroallyl alcohol	ChEBI
trans-3-Chloroallyl alcohol	ChEBI
3-Chloroallyl alcohol, (e)-isomer	HMDB
3-Chloroallyl alcohol, (Z)-isomer	HMDB
3-Chloro-2-propen-1-ol	HMDB
3-Chloroallyl alcohol	HMDB
trans-3-chloro-2-Propene-1-ol	ChEBI

Chemical Formula

C₃H₅ClO

Average Molecular Weight

92.524

Monoisotopic Molecular Weight

92.002892489

IUPAC Name

(2E)-3-chloroprop-2-en-1-ol

Traditional Name

trans-3-chloroallyl alcohol

CAS Registry Number

Not Available

SMILES

OC\C=C\Cl

InChI Identifier

InChI=1S/C3H5ClO/c4-2-1-3-5/h1-2,5H,3H2/b2-1+

InChI Key

HJGHXDNIPAWLLE-OWOJBTEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Vinyl halides

Sub Class

Vinyl chlorides

Direct Parent

Vinyl chlorides

Alternative Parents

Substituents

Chloroalkene
Haloalkene
Vinyl chloride
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organochloride
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-chloroprop-2-en-1-ol (CHEBI:28960 )

Ontology

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
Water Solubility	167 g/L	ALOGPS
logP	0.52	ALOGPS
logP	0.53	ChemAxon
logS	0.26	ALOGPS
pKa (Strongest Acidic)	15.58	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	22.23 m³·mol⁻¹	ChemAxon
Polarizability	8.55 Å³	ChemAxon
Number of Rings	0	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
DeepCCS	[M+H]+	120.942	30932474
DeepCCS	[M-H]-	119.047	30932474
DeepCCS	[M-2H]-	154.656	30932474
DeepCCS	[M+Na]+	129.069	30932474
AllCCS	[M+H]+	125.0	32859911
AllCCS	[M+H-H2O]+	120.6	32859911
AllCCS	[M+NH4]+	129.1	32859911
AllCCS	[M+Na]+	130.3	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	143.2	32859911
AllCCS	[M+HCOO]-	149.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.83 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7931 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.96 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	806.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	339.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	100.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	250.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	270.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	305.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	250.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	593.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	52.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	870.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	264.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	633.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	253.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	196.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-3-Chloro-2-propene-1-ol	OC\C=C\Cl	1582.1	Standard polar	33892256
trans-3-Chloro-2-propene-1-ol	OC\C=C\Cl	725.9	Standard non polar	33892256
trans-3-Chloro-2-propene-1-ol	OC\C=C\Cl	747.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-3-Chloro-2-propene-1-ol,1TMS,isomer #1	C[Si](C)(C)OC/C=C/Cl	933.1	Semi standard non polar	33892256
trans-3-Chloro-2-propene-1-ol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC/C=C/Cl	1130.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - trans-3-Chloro-2-propene-1-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-055f-9000000000-a67937e76a9ac12ca31d	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-3-Chloro-2-propene-1-ol GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9300000000-04b75f98817983db1ad5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-3-Chloro-2-propene-1-ol 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 - trans-3-Chloro-2-propene-1-ol 10V, Positive-QTOF	splash10-004l-9000000000-09855dec524cb4c221a6	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Chloro-2-propene-1-ol 20V, Positive-QTOF	splash10-004i-9000000000-69f62947f6ed4410580d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Chloro-2-propene-1-ol 40V, Positive-QTOF	splash10-004i-9000000000-7b18f7fdc291e82e043f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Chloro-2-propene-1-ol 10V, Negative-QTOF	splash10-0006-9000000000-20dfbb94b434fde66677	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Chloro-2-propene-1-ol 20V, Negative-QTOF	splash10-0006-9000000000-6cb3e8dab0d3abfc6384	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Chloro-2-propene-1-ol 40V, Negative-QTOF	splash10-0a4i-9000000000-daa2f852317e556bb45d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Chloro-2-propene-1-ol 10V, Positive-QTOF	splash10-00di-9000000000-7cc274da6d5f357c1298	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Chloro-2-propene-1-ol 20V, Positive-QTOF	splash10-022c-9000000000-8075d45c323182c3fc0a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Chloro-2-propene-1-ol 40V, Positive-QTOF	splash10-000i-9000000000-e6cae368b176706adf4b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Chloro-2-propene-1-ol 10V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Chloro-2-propene-1-ol 20V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3-Chloro-2-propene-1-ol 40V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	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, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06611

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

287955

PDB ID

Not Available

ChEBI ID

28960

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Alcohol dehydrogenase class-3

General function:: Involved in zinc ion binding
Specific function:: Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:: ADH5
Uniprot ID:: P11766
Molecular weight:: 39723.945

Reactions

trans-3-Chloro-2-propene-1-ol + NAD → trans-3-Chloroallyl aldehyde + NADH + Hydrogen Ion	details

Showing metabocard for trans-3-Chloro-2-propene-1-ol (HMDB0060514)

MOL for HMDB0060514 (trans-3-Chloro-2-propene-1-ol)

3D MOL for HMDB0060514 (trans-3-Chloro-2-propene-1-ol)

3D SDF for HMDB0060514 (trans-3-Chloro-2-propene-1-ol)

3D-SDF for HMDB0060514 (trans-3-Chloro-2-propene-1-ol)

PDB for HMDB0060514 (trans-3-Chloro-2-propene-1-ol)

3D PDB for HMDB0060514 (trans-3-Chloro-2-propene-1-ol)

SMILES for HMDB0060514 (trans-3-Chloro-2-propene-1-ol)

INCHI for HMDB0060514 (trans-3-Chloro-2-propene-1-ol)

Structure for HMDB0060514 (trans-3-Chloro-2-propene-1-ol)

3D Structure for HMDB0060514 (trans-3-Chloro-2-propene-1-ol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions