NP-MRD: Showing NP-Card for Dodecanamide (NP0075300)

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Record Information

Version

2.0

Created at

2022-04-28 20:35:47 UTC

Updated at

2022-04-28 20:35:47 UTC

NP-MRD ID

NP0075300

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dodecanamide

Description

Dodecanamide, also known as lauramide, belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine. Thus, dodecanamide is considered to be a fatty amide. Dodecanamide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Dodecanamide is found in Apis cerana, Rhizoclonium hieroglyphicum and Vitis vinifera. Dodecanamide was first documented in 2017 (PMID: 29179468). Based on a literature review a significant number of articles have been published on Dodecanamide (PMID: 35369588) (PMID: 34515383) (PMID: 33389242) (PMID: 33168861) (PMID: 32605744) (PMID: 31048120).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 38  0  0  0  0  0  0  0  0999 V2000
   -4.8891    1.8698   -1.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0075    0.6980   -0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7897    0.6215   -1.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229   -0.5358   -1.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072   -0.4751    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530   -1.7139    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0193   -1.7537    1.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8890   -0.5626    2.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666   -0.4686    1.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8632    0.7389    1.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0679    0.9290    0.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7374    1.1378   -0.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7565    1.1600   -1.8118 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571    1.2990   -1.1783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4009    2.8068   -0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8595    1.7165   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0076    1.8043   -2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005   -0.2164   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6715    0.8132    0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1735    0.4995   -2.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329    1.5843   -1.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428   -1.4878   -1.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0447   -0.5571   -1.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2164   -0.4700    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8075    0.4417    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539   -1.7202   -0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459   -2.6372    0.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7898   -1.7650    2.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6185   -2.6660    1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886    0.3486    2.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3203   -0.7214    3.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7721   -0.4283    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6706   -1.3960    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1379    0.7373    2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588    1.6871    1.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7094    1.7741    0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7102    0.0209    0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5388    0.8730   -2.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7266    1.4506   -1.6061 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
M  END

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  N   UNK     0      10.216   7.438   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.550   5.128   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.220   7.438   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    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                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
Lauramide	ChEBI

Chemical Formula

C₁₂H₂₅NO

Average Mass

199.3380 Da

Monoisotopic Mass

199.19361 Da

IUPAC Name

dodecanamide

Traditional Name

dodecanamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC(N)=O

InChI Identifier

InChI=1S/C12H25NO/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H2,13,14)

InChI Key

ILRSCQWREDREME-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Rhizoclonium hieroglyphicum	Viridiplantae	KNApSAcK
Vitis vinifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

Fatty amides

Alternative Parents

Substituents

Fatty amide
Primary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

fatty amide (CHEBI:34726 )
Primary amides (C13831 )
N-acyl amides (C13831 )
Primary amides (LMFA08010001 )

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	4.95	ALOGPS
logP	3.67	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	16.88	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	60.5 m³·mol⁻¹	ChemAxon
Polarizability	26.23 Å³	ChemAxon
Number of Rings	0	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

HMDB0251566

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037063

Chemspider ID

13618

KEGG Compound ID

C13831

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14256

PDB ID

Not Available

ChEBI ID

34726

Good Scents ID

rw1301001

References

General References

Swantara MD, Rita WS, Dira MA, Karang Agustina K: Cervical anticancer activities of Annona squamosa Linn. leaf isolate. Vet World. 2022 Jan;15(1):124-131. doi: 10.14202/vetworld.2022.124-131. Epub 2022 Jan 24. [PubMed:35369588 ]
Andre R, Guedes R, Lopez J, Serralheiro ML: Untargeted metabolomic study of HepG2 cells under the effect of Fucus vesiculosus aqueous extract. Rapid Commun Mass Spectrom. 2021 Dec 15;35(23):e9197. doi: 10.1002/rcm.9197. [PubMed:34515383 ]
Kumar A, Patel S, Bhatkar D, Sarode SC, Sharma NK: A novel method to detect intracellular metabolite alterations in MCF-7 cells by doxorubicin induced cell death. Metabolomics. 2021 Jan 3;17(1):3. doi: 10.1007/s11306-020-01755-2. [PubMed:33389242 ]
Crivelli SM, van Kruining D, Luo Q, Stevens JAA, Giovagnoni C, Paulus A, Bauwens M, Berkes D, de Vries HE, Mulder MT, Walter J, Waelkens E, Derua R, Swinnen JV, Dehairs J, Mottaghy FM, Losen M, Bieberich E, Martinez-Martinez P: Ceramide analog [(18)F]F-HPA-12 detects sphingolipid disbalance in the brain of Alzheimer's disease transgenic mice by functioning as a metabolic probe. Sci Rep. 2020 Nov 9;10(1):19354. doi: 10.1038/s41598-020-76335-4. [PubMed:33168861 ]
Zhang L, Wang T, Song M, Jin M, Liu S, Guo K, Zhang Y: Rab1b-GBF1-ARFs mediated intracellular trafficking is required for classical swine fever virus replication in swine umbilical vein endothelial cells. Vet Microbiol. 2020 Jul;246:108743. doi: 10.1016/j.vetmic.2020.108743. Epub 2020 Jun 1. [PubMed:32605744 ]
Al-Malki AL, Razvi SS, Mohammed FA, Zamzami MA, Choudhry H, Kumosani TA, Balamash KS, Alshubaily FA, ALGhamdi SA, Abualnaja KO, Abdulaal WH, Zeyadi MA, Al-Zahrani MH, Alhosin M, Asami T, Moselhy SS: Synthesis and in vitro antitumor activity of novel acylspermidine derivative N-(4-aminobutyl)-N-(3-aminopropyl)-8-hydroxy-dodecanamide (AAHD) against HepG2 cells. Bioorg Chem. 2019 Jul;88:102937. doi: 10.1016/j.bioorg.2019.102937. Epub 2019 Apr 16. [PubMed:31048120 ]
Abd El-Mawgoud HK, Mohamed Hemdan M: Utility of Lauroyl Isothiocyanate as a Scaffold in the Synthesis of Some Novel Pyrimidine Derivatives and Their Antimicrobial Assessment. Chem Pharm Bull (Tokyo). 2018;66(11):1072-1077. doi: 10.1248/cpb.c18-00595. [PubMed:30381659 ]
Janus MM, Volgenant CMC, Krom BP: [Innovative application of small molecules to influence -pathogenicity of dental plaque]. Ned Tijdschr Tandheelkd. 2018 May;125(5):269-275. doi: 10.5177/ntvt.2018.05.17169. [PubMed:29754156 ]
Tan G, Zhao B, Li Y, Liu X, Zou Z, Wan J, Yao Y, Xiong H, Wang Y: Pharmacometabolomics identifies dodecanamide and leukotriene B4 dimethylamide as a predictor of chemosensitivity for patients with acute myeloid leukemia treated with cytarabine and anthracycline. Oncotarget. 2017 Sep 8;8(51):88697-88707. doi: 10.18632/oncotarget.20733. eCollection 2017 Oct 24. [PubMed:29179468 ]
Crivelli SM, Paulus A, Markus J, Bauwens M, Berkes D, De Vries HE, Mulder MT, Walter J, Mottaghy FM, Losen M, Martinez-Martinez P: Synthesis, Radiosynthesis, and Preliminary in vitro and in vivo Evaluation of the Fluorinated Ceramide Trafficking Inhibitor (HPA-12) for Brain Applications. J Alzheimers Dis. 2017;60(3):783-794. doi: 10.3233/JAD-161231. [PubMed:28922150 ]

Showing NP-Card for Dodecanamide (NP0075300)

MOL for NP0075300 (Dodecanamide)

3D MOL for NP0075300 (Dodecanamide)

3D SDF for NP0075300 (Dodecanamide)

3D-SDF for NP0075300 (Dodecanamide)

PDB for NP0075300 (Dodecanamide)

3D PDB for NP0075300 (Dodecanamide)

SMILES for NP0075300 (Dodecanamide)

INCHI for NP0075300 (Dodecanamide)

Structure for NP0075300 (Dodecanamide)

3D Structure for NP0075300 (Dodecanamide)