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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:43:16 UTC

Update Date

2023-02-21 17:24:52 UTC

HMDB ID

HMDB0035706

Secondary Accession Numbers

HMDB35706

Metabolite Identification

Common Name

alpha-Cyclocitral

Description

alpha-Cyclocitral, also known as α-cyclocitral, belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group. Based on a literature review very few articles have been published on alpha-Cyclocitral.

Structure

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

COMPND    HMDB0035706
HETATM    1  C1  UNL     1       2.683  -0.018  -0.193  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.348   0.538   0.090  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.947   1.757  -0.282  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.436   2.193   0.072  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.338   1.094  -0.503  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.927  -0.259  -0.037  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.086  -0.927   0.636  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.552  -1.089  -1.271  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.304  -0.252   0.843  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.799  -1.615   1.116  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.487  -2.196   2.139  1.00  0.00           O  
HETATM   12  H1  UNL     1       2.979  -0.749   0.606  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.777  -0.457  -1.210  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.443   0.789  -0.141  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.659   2.363  -0.825  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.617   3.139  -0.460  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.587   2.271   1.165  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.331   1.198  -1.610  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.367   1.313  -0.162  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.988  -0.781   0.010  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.922  -2.042   0.719  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.246  -0.576   1.673  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.357  -0.910  -2.012  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.575  -2.149  -0.926  1.00  0.00           H  
HETATM   25  H14 UNL     1       0.439  -0.791  -1.636  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.024   0.272   1.780  1.00  0.00           H  
HETATM   27  H16 UNL     1       1.439  -2.115   0.418  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    9
CONECT    3    4   15
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    6    7    8    9
CONECT    7   20   21   22
CONECT    8   23   24   25
CONECT    9   10   26
CONECT   10   11   11   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Cyclocitral	Generator
Α-cyclocitral	Generator
1-Formyl-2,6,6-trimethyl-2-cyclohexene	HMDB
2,6,6-Trimethyl-2-cyclohexen-1-carboxaldehyde	HMDB
2,6,6-Trimethyl-2-cyclohexene-1-carbaldehyde	HMDB
2,6,6-Trimethyl-2-cyclohexene-1-carboxaldehyde	HMDB
2,6,6-Trimethylcyclohex-2-en-1-carboxaldehyde	HMDB
2,6,6-Trimethylcyclohex-2-ene-1-carbaldehyde	HMDB
alpha -Cyclocitral	HMDB
Filipendulal	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

2,6,6-trimethylcyclohex-2-ene-1-carbaldehyde

Traditional Name

2,6,6-trimethylcyclohex-2-ene-1-carbaldehyde

CAS Registry Number

432-24-6

SMILES

CC1=CCCC(C)(C)C1C=O

InChI Identifier

InChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h5,7,9H,4,6H2,1-3H3

InChI Key

ZVZRJSHOOULAGB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organic oxides

Sub Class

Not Available

Direct Parent

Organic oxides

Alternative Parents

Substituents

Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0035706)

Exogenous

Food

Food (HMDB: HMDB0035706)

Exogenous (HMDB: HMDB0035706)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0035706)

Role

Biological role

Energy source (HMDB: HMDB0035706)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035706)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0035706)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	196.00 to 197.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	111.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.855 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.17 g/L	ALOGPS
logP	2.84	ALOGPS
logP	2.2	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	18.45	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.34 m³·mol⁻¹	ChemAxon
Polarizability	17.92 Å³	ChemAxon
Number of Rings	1	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]+	134.33	31661259
DarkChem	[M-H]-	129.446	31661259
DeepCCS	[M+H]+	139.32	30932474
DeepCCS	[M-H]-	136.478	30932474
DeepCCS	[M-2H]-	173.262	30932474
DeepCCS	[M+Na]+	148.44	30932474
AllCCS	[M+H]+	131.7	32859911
AllCCS	[M+H-H2O]+	127.3	32859911
AllCCS	[M+NH4]+	135.8	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	135.2	32859911
AllCCS	[M+Na-2H]-	136.8	32859911
AllCCS	[M+HCOO]-	138.7	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.	5.5 minutes	32390414
Predicted by Siyang on May 30, 2022	15.4439 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.62 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2055.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	516.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	196.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	322.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	154.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	555.5 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	710.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1227.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	447.6 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	1172.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	453.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	350.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	441.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	516.8 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	10.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Cyclocitral	CC1=CCCC(C)(C)C1C=O	1428.2	Standard polar	33892256
alpha-Cyclocitral	CC1=CCCC(C)(C)C1C=O	1106.4	Standard non polar	33892256
alpha-Cyclocitral	CC1=CCCC(C)(C)C1C=O	1119.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-Cyclocitral,1TMS,isomer #1	CC1=CCCC(C)(C)C1=CO[Si](C)(C)C	1351.6	Semi standard non polar	33892256
alpha-Cyclocitral,1TMS,isomer #1	CC1=CCCC(C)(C)C1=CO[Si](C)(C)C	1329.1	Standard non polar	33892256
alpha-Cyclocitral,1TBDMS,isomer #1	CC1=CCCC(C)(C)C1=CO[Si](C)(C)C(C)(C)C	1594.2	Semi standard non polar	33892256
alpha-Cyclocitral,1TBDMS,isomer #1	CC1=CCCC(C)(C)C1=CO[Si](C)(C)C(C)(C)C	1558.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Cyclocitral GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abi-8900000000-4a3fe80b12af809e19dc	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Cyclocitral 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 - alpha-Cyclocitral 10V, Positive-QTOF	splash10-0udi-0900000000-97324505311710a03a80	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cyclocitral 20V, Positive-QTOF	splash10-0uxr-9700000000-cff3340902f149b29fa9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cyclocitral 40V, Positive-QTOF	splash10-0gb9-9100000000-10092caceeb1617add98	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cyclocitral 10V, Negative-QTOF	splash10-0udi-0900000000-eeccc4d08fce73b9f581	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cyclocitral 20V, Negative-QTOF	splash10-0udi-0900000000-8a7016290964e8ba85b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cyclocitral 40V, Negative-QTOF	splash10-0f7x-8900000000-8491df02dfd5899e80e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cyclocitral 10V, Negative-QTOF	splash10-0fk9-0900000000-5faf1aa3a1d7573ce3ee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cyclocitral 20V, Negative-QTOF	splash10-00di-0900000000-bf330a997a00d4f4dc59	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cyclocitral 40V, Negative-QTOF	splash10-00di-0900000000-51e0630e0612f83e376a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cyclocitral 10V, Positive-QTOF	splash10-00di-2900000000-15e145baa52b9ae5445b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cyclocitral 20V, Positive-QTOF	splash10-0aor-9800000000-07ed783e385985dabfc0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cyclocitral 40V, Positive-QTOF	splash10-00kf-9200000000-27759a147a9af43fd36b	2021-09-24	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

Extracellular
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

FDB014428

KNApSAcK ID

Not Available

Chemspider ID

84960

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94143

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1103311

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 alpha-Cyclocitral (HMDB0035706)

MOL for HMDB0035706 (alpha-Cyclocitral)

3D MOL for HMDB0035706 (alpha-Cyclocitral)

3D SDF for HMDB0035706 (alpha-Cyclocitral)

3D-SDF for HMDB0035706 (alpha-Cyclocitral)

PDB for HMDB0035706 (alpha-Cyclocitral)

3D PDB for HMDB0035706 (alpha-Cyclocitral)

SMILES for HMDB0035706 (alpha-Cyclocitral)

INCHI for HMDB0035706 (alpha-Cyclocitral)

Structure for HMDB0035706 (alpha-Cyclocitral)

3D Structure for HMDB0035706 (alpha-Cyclocitral)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra