NP-MRD: Showing NP-Card for (5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid (NP0291318)

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Record Information

Version

1.0

Created at

2022-09-09 22:21:50 UTC

Updated at

2022-09-09 22:21:50 UTC

NP-MRD ID

NP0291318

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid

Description

Amphimic acid a, also known as amphimate a, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. It was first documented in 2022 (PMID: 36111068). Based on a literature review a significant number of articles have been published on Amphimic acid a (PMID: 36110537) (PMID: 36109723) (PMID: 36109198) (PMID: 36107364) (PMID: 36093881) (PMID: 36106296).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200212D          

 30 30  0  0  1  0            999 V2000
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   10.2020   -4.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309102200212D          

 30 30  0  0  1  0            999 V2000
    9.4875   -4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0291318

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC[C@H]1C\C1=C/CC\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H50O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-19-22-26-25-27(26)23-20-17-14-15-18-21-24-28(29)30/h14-15,23,26H,2-13,16-22,24-25H2,1H3,(H,29,30)/b15-14-,27-23+/t26-/m0/s1

> <INCHI_KEY>
GNTJEDVVFIJAMK-TXVUYSAVSA-N

> <FORMULA>
C28H50O2

> <MOLECULAR_WEIGHT>
418.706

> <EXACT_MASS>
418.38108085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.600171820333756

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z)-9-[(1E,2S)-2-hexadecylcyclopropylidene]non-5-enoic acid

> <JCHEM_LOGP>
10.045080579666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.922347462675991

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
132.35520000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5Z)-9-[(1E,2S)-2-hexadecylcyclopropylidene]non-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      17.710  -7.796   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.044  -8.566   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.377  -7.796   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.711  -8.566   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.045  -7.796   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.378  -8.566   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.712  -7.796   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.046  -8.566   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.379  -7.796   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.713  -8.566   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.047  -7.796   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.380  -8.566   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.714  -7.796   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.048  -8.566   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.382  -7.796   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.715  -8.566   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      39.049  -7.796   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      39.819  -6.462   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      40.589  -7.796   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      41.923  -8.566   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      43.256  -7.796   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      44.590  -8.566   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      44.590 -10.106   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      45.924 -10.876   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      47.257 -10.106   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      48.591 -10.876   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      49.925 -10.106   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      51.258 -10.876   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      52.592 -10.106   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      51.258 -12.416   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                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   19                                                       
CONECT   19   18   17   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

View in JSmol

Synonyms

Value	Source
Amphimate a	Generator

Chemical Formula

C₂₈H₅₀O₂

Average Mass

418.7060 Da

Monoisotopic Mass

418.38108 Da

IUPAC Name

(5Z)-9-[(1E,2S)-2-hexadecylcyclopropylidene]non-5-enoic acid

Traditional Name

(5Z)-9-[(1E,2S)-2-hexadecylcyclopropylidene]non-5-enoic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC[C@H]1C\C1=C/CC\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C28H50O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-19-22-26-25-27(26)23-20-17-14-15-18-21-24-28(29)30/h14-15,23,26H,2-13,16-22,24-25H2,1H3,(H,29,30)/b15-14-,27-23+/t26-/m0/s1

InChI Key

GNTJEDVVFIJAMK-TXVUYSAVSA-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 medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	10.05	ChemAxon
pKa (Strongest Acidic)	4.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	132.36 m³·mol⁻¹	ChemAxon
Polarizability	56.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00038445

Chemspider ID

8821088

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10645729

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Goodrich JA, Walker D, Lin X, Wang H, Lim T, McConnell R, Conti DV, Chatzi L, Setiawan VW: Exposure to perfluoroalkyl substances and risk of hepatocellular carcinoma in a multiethnic cohort. JHEP Rep. 2022 Aug 8;4(10):100550. doi: 10.1016/j.jhepr.2022.100550. eCollection 2022 Oct. [PubMed:36111068 ]
Guoyun X, Dawei D, Ning L, Yinan H, Fangfang Y, Siyuan T, Hao S, Jiaqi Y, Ang X, Guanya G, Xi C, Yulong S, Ying H: Efficacy and safety of fenofibrate add-on therapy in patients with primary biliary cholangitis refractory to ursodeoxycholic acid: A retrospective study and updated meta-analysis. Front Pharmacol. 2022 Aug 30;13:948362. doi: 10.3389/fphar.2022.948362. eCollection 2022. [PubMed:36110537 ]
Ma S, Xu Q, Hu Q, Huang L, Wu D, Lin G, Chen X, Luo W: Post-operative uric acid: a predictor for 30-days mortality of acute type A aortic dissection repair. BMC Cardiovasc Disord. 2022 Sep 15;22(1):411. doi: 10.1186/s12872-022-02749-9. [PubMed:36109723 ]
Hu Z, Zhu Y, Chen J, Chen J, Li C, Gao Z, Li J, Liu L: Sesquiterpenoids with Phytotoxic and Antifungal Activities from a Pathogenic Fungus Aspergillus alabamensis. J Agric Food Chem. 2022 Sep 28;70(38):12065-12073. doi: 10.1021/acs.jafc.2c05703. Epub 2022 Sep 15. [PubMed:36109198 ]
Liu S, Lin H, Chen Y, Wang Y, Zhang X, Xiang Z, Cai X: Metabolic Profiling of Glabridin in Rat Plasma, Urine, Bile, and Feces After Intragastric and Intravenous Administration. Eur J Drug Metab Pharmacokinet. 2022 Nov;47(6):879-887. doi: 10.1007/s13318-022-00797-2. Epub 2022 Sep 15. [PubMed:36107364 ]
Liu J, Chen G, Yang J, Sheng L, Tang X, Zhang X, Hua H: Deciphering the chemical composition of Ganoderma lucidum from different geographical origins by mass spectrometry molecular networking coupled with multivariate analysis. Biomed Chromatogr. 2023 Jan;37(1):e5506. doi: 10.1002/bmc.5506. Epub 2022 Sep 30. [PubMed:36093881 ]
Kamarudin NA, Abdul Rahim N, Azman M, Mat Baki M: Subchordal Cyst Containing Non-degraded Hyaluronic Acid: A Rare Complication of Injection Laryngoplasty. Cureus. 2022 Aug 8;14(8):e27801. doi: 10.7759/cureus.27801. eCollection 2022 Aug. [PubMed:36106296 ]
Yang X, Deng B, Wang S, Wang X, Cao L, Chen X, Zhao X: Anti-gamma-aminobutyric acid-A receptor encephalitis with refractory seizures and cognitive impairment in a young woman: A case report. Front Neurol. 2022 Aug 29;13:954494. doi: 10.3389/fneur.2022.954494. eCollection 2022. [PubMed:36105778 ]
Zheng Y, Fan W, Jiang L, Lu Y: Sonophoresis enhances the skin penetration of 5-aminolevulinic acid: A promising pretreatment for photodynamic therapy. Exp Dermatol. 2022 Dec;31(12):1939-1943. doi: 10.1111/exd.14670. Epub 2022 Sep 22. [PubMed:36089333 ]
Dahchour A: Anxiolytic and antidepressive potentials of rosmarinic acid: A review with a focus on antioxidant and anti-inflammatory effects. Pharmacol Res. 2022 Oct;184:106421. doi: 10.1016/j.phrs.2022.106421. Epub 2022 Sep 9. [PubMed:36096427 ]
LOTUS database [Link]

Showing NP-Card for (5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid (NP0291318)

MOL for NP0291318 ((5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid)

3D MOL for NP0291318 ((5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid)

3D SDF for NP0291318 ((5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid)

3D-SDF for NP0291318 ((5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid)

PDB for NP0291318 ((5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid)

3D PDB for NP0291318 ((5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid)

SMILES for NP0291318 ((5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid)

INCHI for NP0291318 ((5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid)

Structure for NP0291318 ((5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid)

3D Structure for NP0291318 ((5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid)