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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:45:39 UTC

Update Date

2023-02-21 17:26:35 UTC

HMDB ID

HMDB0038443

Secondary Accession Numbers

HMDB38443

Metabolite Identification

Common Name

1-Isothiocyanato-4-phenylbutane

Description

1-Isothiocyanato-4-phenylbutane belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. 1-Isothiocyanato-4-phenylbutane has been detected, but not quantified in, brassicas. This could make 1-isothiocyanato-4-phenylbutane a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1-Isothiocyanato-4-phenylbutane.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   13  S   UNK     0       1.334   3.850   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    2   11                                                       
CONECT    7    3   11                                                       
CONECT    8    4   11                                                       
CONECT    9    5   12                                                       
CONECT   10   12   13                                                       
CONECT   11    6    7    8                                                  
CONECT   12    9   10                                                       
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0038443
HETATM    1  S1  UNL     1       5.357   2.681  -0.049  1.00  0.00           S  
HETATM    2  C1  UNL     1       4.101   1.805  -0.568  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.110   1.049  -0.659  1.00  0.00           N  
HETATM    4  C2  UNL     1       3.145  -0.335  -1.064  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.206  -1.084  -0.108  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.845  -0.445  -0.303  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.202  -1.082   0.583  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.488  -0.360   0.291  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.814   0.771   1.039  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.993   1.437   0.775  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.859   1.019  -0.205  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.512  -0.103  -0.930  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.338  -0.795  -0.692  1.00  0.00           C  
HETATM   14  H1  UNL     1       2.687  -0.437  -2.071  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.153  -0.780  -1.043  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.182  -2.133  -0.460  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.609  -0.961   0.899  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.913   0.639  -0.067  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.562  -0.630  -1.358  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.281  -2.159   0.399  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.024  -0.934   1.659  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.145   1.118   1.816  1.00  0.00           H  
HETATM   23  H10 UNL     1      -3.232   2.320   1.369  1.00  0.00           H  
HETATM   24  H11 UNL     1      -4.798   1.542  -0.422  1.00  0.00           H  
HETATM   25  H12 UNL     1      -4.163  -0.475  -1.717  1.00  0.00           H  
HETATM   26  H13 UNL     1      -2.070  -1.668  -1.258  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3
CONECT    3    4
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9    9   13
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   12   24
CONECT   12   13   13   25
CONECT   13   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4-Isothiocyanatobutyl)benzene, 9ci	HMDB
4-Phenylbutyl isothiocyanate	HMDB
4-PHENYLBUTYLISOLTHIOCYANATE	HMDB
4-Phenylbutylisothiocyanate	MeSH, HMDB
PBITC	MeSH, HMDB

Chemical Formula

C₁₁H₁₃NS

Average Molecular Weight

191.293

Monoisotopic Molecular Weight

191.076870111

IUPAC Name

(4-isothiocyanatobutyl)benzene

Traditional Name

4-phenylbutylisothiocyanate

CAS Registry Number

61499-10-3

SMILES

S=C=NCCCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C11H13NS/c13-10-12-9-5-4-8-11-6-2-1-3-7-11/h1-3,6-7H,4-5,8-9H2

InChI Key

CCBQOLFAKKAMLD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Isothiocyanate
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038443)
Cell membrane (HMDB: HMDB0038443)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038443)

Source

Exogenous

Exogenous (HMDB: HMDB0038443)

Food

Food (HMDB: HMDB0038443)

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Endogenous

Plant

Plant (HMDB: HMDB0038443)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038443)

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	4.00	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.01 g/L	ALOGPS
logP	4.16	ALOGPS
logP	3.97	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.9 m³·mol⁻¹	ChemAxon
Polarizability	22.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	143.166	31661259
DarkChem	[M-H]-	140.725	31661259
DeepCCS	[M+H]+	140.824	30932474
DeepCCS	[M-H]-	138.141	30932474
DeepCCS	[M-2H]-	174.785	30932474
DeepCCS	[M+Na]+	150.323	30932474
AllCCS	[M+H]+	141.1	32859911
AllCCS	[M+H-H2O]+	137.1	32859911
AllCCS	[M+NH4]+	144.9	32859911
AllCCS	[M+Na]+	146.0	32859911
AllCCS	[M-H]-	146.4	32859911
AllCCS	[M+Na-2H]-	147.3	32859911
AllCCS	[M+HCOO]-	148.5	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.	7.35 minutes	32390414
Predicted by Siyang on May 30, 2022	15.3 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.47 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1909.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	551.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	215.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	359.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	402.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	680.6 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	774.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	107.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1416.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	538.9 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	1482.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	402.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	436.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	401.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	431.6 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	27.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Isothiocyanato-4-phenylbutane	S=C=NCCCCC1=CC=CC=C1	2399.7	Standard polar	33892256
1-Isothiocyanato-4-phenylbutane	S=C=NCCCCC1=CC=CC=C1	1611.9	Standard non polar	33892256
1-Isothiocyanato-4-phenylbutane	S=C=NCCCCC1=CC=CC=C1	1684.9	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 - 1-Isothiocyanato-4-phenylbutane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-ba6579eed4c78518b72a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Isothiocyanato-4-phenylbutane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Isothiocyanato-4-phenylbutane 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 - 1-Isothiocyanato-4-phenylbutane 10V, Positive-QTOF	splash10-0006-1900000000-0bc8d3ed2812306d70ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Isothiocyanato-4-phenylbutane 20V, Positive-QTOF	splash10-001l-3900000000-ee40a0f3cc70a0a0b9b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Isothiocyanato-4-phenylbutane 40V, Positive-QTOF	splash10-0006-9300000000-c3e240ec71bddd0b2d8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Isothiocyanato-4-phenylbutane 10V, Negative-QTOF	splash10-0006-2900000000-e5a164d6b22b852da81f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Isothiocyanato-4-phenylbutane 20V, Negative-QTOF	splash10-052f-7900000000-35e43717fab8820eb22b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Isothiocyanato-4-phenylbutane 40V, Negative-QTOF	splash10-0a4i-9100000000-f25e9020aa2663bd4e29	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Isothiocyanato-4-phenylbutane 10V, Positive-QTOF	splash10-0006-1900000000-ca3523c22d8ef9265ad3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Isothiocyanato-4-phenylbutane 20V, Positive-QTOF	splash10-052f-9700000000-fd5875708e2bc0dac957	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Isothiocyanato-4-phenylbutane 40V, Positive-QTOF	splash10-0006-9300000000-4146418c9f5c20e387e5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Isothiocyanato-4-phenylbutane 10V, Negative-QTOF	splash10-0a4l-9800000000-b6aa9ce32ae624aba42d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Isothiocyanato-4-phenylbutane 20V, Negative-QTOF	splash10-0a4l-9800000000-175d399116f33427cad9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Isothiocyanato-4-phenylbutane 40V, Negative-QTOF	splash10-0a4l-9000000000-f3457b6785c6846f3cde	2021-09-25	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

Membrane

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

FDB017801

KNApSAcK ID

C00057471

Chemspider ID

111185

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124881

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 1-Isothiocyanato-4-phenylbutane (HMDB0038443)

MOL for HMDB0038443 (1-Isothiocyanato-4-phenylbutane)

3D MOL for HMDB0038443 (1-Isothiocyanato-4-phenylbutane)

3D SDF for HMDB0038443 (1-Isothiocyanato-4-phenylbutane)

3D-SDF for HMDB0038443 (1-Isothiocyanato-4-phenylbutane)

PDB for HMDB0038443 (1-Isothiocyanato-4-phenylbutane)

3D PDB for HMDB0038443 (1-Isothiocyanato-4-phenylbutane)

SMILES for HMDB0038443 (1-Isothiocyanato-4-phenylbutane)

INCHI for HMDB0038443 (1-Isothiocyanato-4-phenylbutane)

Structure for HMDB0038443 (1-Isothiocyanato-4-phenylbutane)

3D Structure for HMDB0038443 (1-Isothiocyanato-4-phenylbutane)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra