NP-MRD: Showing NP-Card for 6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde (NP0221167)

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Record Information

Version

1.0

Created at

2022-09-05 22:40:18 UTC

Updated at

2022-09-05 22:40:18 UTC

NP-MRD ID

NP0221167

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde

Description

Frequentin belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group. It was first documented in 2005 (PMID: 16124252). Based on a literature review a significant number of articles have been published on Frequentin (PMID: 36075691) (PMID: 36075690) (PMID: 36075689) (PMID: 21255913).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 38  0  0  0  0  0  0  0  0999 V2000
    6.6195    0.8712    0.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2868    0.1983    1.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    0.0856   -0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021   -0.5785   -0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0668    0.0393   -0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -0.6100    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3439    0.0169   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6892   -0.5638   -0.0237 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4384    0.1477    1.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739    0.3718    0.7993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0808    1.6791    0.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5738   -0.6177   -0.0537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2319   -1.6083    0.6797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7283   -1.2337   -1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453   -2.1963   -1.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3950   -0.6100   -1.3570 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6159    0.7586   -1.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    0.9225   -2.6594 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4867    1.9734    0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2870    0.6673    1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955    0.5033   -0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7033    0.7463    1.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4738   -0.8203    1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1212   -0.5389   -0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3923    1.0757   -0.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -1.5757    0.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0794    1.0361   -0.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -1.6264    0.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2952    1.0151   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5076   -1.6276    0.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9468    1.1549    1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2513   -0.3752    2.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3956    0.3795    1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0363    1.7405    0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951   -0.0681   -0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6160   -1.1248    1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7763   -1.2282   -2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0307    1.6203   -1.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 16  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  1
  9 31  1  0
  9 32  1  0
 10 33  1  1
 11 34  1  0
 12 35  1  6
 13 36  1  0
 16 37  1  6
 17 38  1  0
M  END


  Mrv1652309062200402D          

 18 18  0  0  0  0            999 V2000
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0221167

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C\C=C\C1CC(O)C(O)C(=O)C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O4/c1-2-3-4-5-6-7-10-8-12(16)14(18)13(17)11(10)9-15/h4-7,9-12,14,16,18H,2-3,8H2,1H3/b5-4+,7-6+

> <INCHI_KEY>
MHZVWXOKIRZLCJ-YTXTXJHMSA-N

> <FORMULA>
C14H20O4

> <MOLECULAR_WEIGHT>
252.31

> <EXACT_MASS>
252.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.964830444274003

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1E,3E)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde

> <JCHEM_LOGP>
1.3488751350000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.0423799799933

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.899243055502021

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2316858143735914

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
70.8552

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1E,3E)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀O₄

Average Mass

252.3100 Da

Monoisotopic Mass

252.13616 Da

IUPAC Name

6-[(1E,3E)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde

Traditional Name

6-[(1E,3E)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde

CAS Registry Number

Not Available

SMILES

CCC\C=C\C=C\C1CC(O)C(O)C(=O)C1C=O

InChI Identifier

InChI=1S/C14H20O4/c1-2-3-4-5-6-7-10-8-12(16)14(18)13(17)11(10)9-15/h4-7,9-12,14,16,18H,2-3,8H2,1H3/b5-4+,7-6+

InChI Key

MHZVWXOKIRZLCJ-YTXTXJHMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

1,3-dicarbonyl compounds

Alternative Parents

Substituents

1,3-dicarbonyl compound
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
1,2-diol
Organic oxide
Hydrocarbon derivative
Aldehyde
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	1.35	ChemAxon
pKa (Strongest Acidic)	9.9	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	70.86 m³·mol⁻¹	ChemAxon
Polarizability	27.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4786797

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6036812

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abioye AI, Sudfeld CR, Hughes MD, Aboud S, Muhihi A, Ulenga N, Nagu TJ, Wang M, Mugusi F, Fawzi WW: Iron status among HIV-infected adults during the first year of antiretroviral therapy in Tanzania. HIV Med. 2022 Sep 8. doi: 10.1111/hiv.13396. [PubMed:36075691 ]
Authors unspecified: Resources Round-up. Altern Lab Anim. 2022 Sep 8:2611929221121256. doi: 10.1177/02611929221121256. [PubMed:36075690 ]
Kim JU, Khan W, Arowoshola L, Ahmad M: Correspondence. Eur Heart J Qual Care Clin Outcomes. 2022 Aug 26. pii: 6677390. doi: 10.1093/ehjqcco/qcac051. [PubMed:36075689 ]
Zhang Y, Wang R, Song H, Huang G, Yi J, Zheng Y, Wang J, Chen L: Methylation of multiple genes as a candidate biomarker in non-small cell lung cancer. Cancer Lett. 2011 Apr 1;303(1):21-8. doi: 10.1016/j.canlet.2010.12.011. Epub 2011 Jan 20. [PubMed:21255913 ]
Yamaji K, Hashidoko Y, Fukushi Y, Tahara S: Chemical response of Picea glehnii seed-epiphytic Penicillium species to Pythium vexans under in vitro competitive conditions for mycelial growth. J Chem Ecol. 2005 Apr;31(4):805-17. doi: 10.1007/s10886-005-3545-9. [PubMed:16124252 ]
LOTUS database [Link]

Showing NP-Card for 6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde (NP0221167)

MOL for NP0221167 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde)

3D MOL for NP0221167 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde)

3D SDF for NP0221167 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde)

3D-SDF for NP0221167 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde)

PDB for NP0221167 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde)

3D PDB for NP0221167 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde)

SMILES for NP0221167 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde)

INCHI for NP0221167 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde)

Structure for NP0221167 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde)

3D Structure for NP0221167 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-3,4-dihydroxy-2-oxocyclohexane-1-carbaldehyde)