NP-MRD: Showing NP-Card for Luxocinnamycin D (NP0351477)

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Record Information

Version

2.0

Created at

2025-08-22 06:49:53 UTC

Updated at

2025-10-08 03:35:29 UTC

NP-MRD ID

NP0351477

Natural Product DOI

https://doi.org/10.57994/4524

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luxocinnamycin D

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02262300012D          

 18 18  0  0  1  0            999 V2000
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   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
   -1.4289    0.8250    0.0000 O   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
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 14  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0351477

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(\C=C\C(=O)N[C@@H](CO)C(O)=O)C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H15NO4/c1-9-4-2-3-5-10(9)6-7-12(16)14-11(8-15)13(17)18/h2-7,11,15H,8H2,1H3,(H,14,16)(H,17,18)/b7-6+/t11-/m0/s1

> <INCHI_KEY>
DSYYLXPMXPYVIH-MLRMMBSGSA-N

> <FORMULA>
C13H15NO4

> <MOLECULAR_WEIGHT>
249.266

> <EXACT_MASS>
249.100107967

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.906015900933244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-3-hydroxy-2-[(2E)-3-(2-methylphenyl)prop-2-enamido]propanoic acid

> <JCHEM_LOGP>
1.0660786853333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.108021856891002

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.857667708759309

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7330377437204849

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
66.94220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-hydroxy-2-[(2E)-3-(2-methylphenyl)prop-2-enamido]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-FEB-23         0                                  
HETATM    1  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668   3.850   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      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -5.335   0.000   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6                                                            
CONECT   15    3   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₅NO₄

Average Mass

249.2660 Da

Monoisotopic Mass

249.10011 Da

IUPAC Name

(2S)-3-hydroxy-2-[(2E)-3-(2-methylphenyl)prop-2-enamido]propanoic acid

Traditional Name

(2S)-3-hydroxy-2-[(2E)-3-(2-methylphenyl)prop-2-enamido]propanoic acid

CAS Registry Number

Not Available

SMILES

CC1=C(\C=C\C(=O)N[C@@H](CO)C(O)=O)C=CC=C1

InChI Identifier

InChI=1S/C13H15NO4/c1-9-4-2-3-5-10(9)6-7-12(16)14-11(8-15)13(17)18/h2-7,11,15H,8H2,1H3,(H,14,16)(H,17,18)/b7-6+/t11-/m0/s1

InChI Key

DSYYLXPMXPYVIH-MLRMMBSGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹⁵N] NMR Spectrum (2D, 800 MHz, C2D6OS, experimental)	Not Available	Natural Products Research Institute, College of Pharmacy, Seoul National University	Sangwook Kang	2025-08-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, C2D6OS, experimental)	Not Available	Natural Products Research Institute, College of Pharmacy, Seoul National University	Sangwook Kang	2025-08-22	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, C2D6OS, experimental)	Not Available	Natural Products Research Institute, College of Pharmacy, Seoul National University	Sangwook Kang	2025-08-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, C2D6OS, experimental)	Not Available	Natural Products Research Institute, College of Pharmacy, Seoul National University	Sangwook Kang	2025-08-22	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, C2D6OS, experimental)	Not Available	Natural Products Research Institute, College of Pharmacy, Seoul National University	Sangwook Kang	2025-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C2D6OS, experimental)	Not Available	Natural Products Research Institute, College of Pharmacy, Seoul National University	Sangwook Kang	2025-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, C2D6OS, experimental)	Not Available	Natural Products Research Institute, College of Pharmacy, Seoul National University	Sangwook Kang	2025-08-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, C2D6OS, experimental)	Not Available	Natural Products Research Institute, College of Pharmacy, Seoul National University	Sangwook Kang	2025-08-22	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces spp NPDC021753, OID7 and TW1S1		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Cinnamic acid amide
Serine or derivatives
Cinnamic acid or derivatives
Styrene
Beta-hydroxy acid
Toluene
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic 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	1.07	ChemAxon
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	-0.73	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	66.94 m³·mol⁻¹	ChemAxon
Polarizability	25.91 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

112496691

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Luxocinnamycin D (NP0351477)

MOL for NP0351477 (Luxocinnamycin D)

3D MOL for NP0351477 (Luxocinnamycin D)

3D SDF for NP0351477 (Luxocinnamycin D)

3D-SDF for NP0351477 (Luxocinnamycin D)

PDB for NP0351477 (Luxocinnamycin D)

3D PDB for NP0351477 (Luxocinnamycin D)

SMILES for NP0351477 (Luxocinnamycin D)

INCHI for NP0351477 (Luxocinnamycin D)

Structure for NP0351477 (Luxocinnamycin D)

3D Structure for NP0351477 (Luxocinnamycin D)