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Showing NP-Card for Makomotine D (NP0044094)

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Record Information
Version1.0
Created at2021-11-12 23:49:40 UTC
Updated at2021-11-26 17:45:22 UTC
NP-MRD IDNP0044094
Secondary Accession NumbersNone
Natural Product Identification
Common NameMakomotine D
DescriptionMakomotine D belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Makomotine D is found in Ustilago esculenta. It was first documented in 2014 (PMID: 25419997). Based on a literature review a significant number of articles have been published on Makomotine D (PMID: 34758536) (PMID: 34758546) (PMID: 34758513) (PMID: 34758458).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044094 (Makomotine D)


  Mrv1652311132100492D          

 15 15  0  0  0  0            999 V2000
    2.7112    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  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
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
Download

3D MOL for NP0044094 (Makomotine D)

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
    3.3051   -1.0886   -1.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544   -0.3170   -0.5444 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5334   -0.5987    0.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8345   -1.6547    1.2321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311    0.2761    1.0635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1761   -0.3327    2.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5418    0.6007    0.0694 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0365    1.8583   -0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6583    3.0464    0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1820    4.1542    0.3586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544    1.8188   -1.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0251    0.5270   -1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1364   -0.2118   -0.8225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227   -1.6616   -0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7773   -2.4139   -0.1543 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1791   -2.1648   -0.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -0.8162   -2.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526   -0.7561   -0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    1.2116    1.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8353    0.4129    2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6772   -1.2827    2.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6889   -0.4889    3.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0626    3.0378    1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5319    2.6499   -1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6584    0.1801   -2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2249   -1.9764   -2.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057   -1.9999   -0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737   -2.0097   -0.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 13 12  2  0
 12 11  1  0
 11  8  2  0
  8  9  1  0
  9 10  2  0
  8  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  1
  6 20  1  0
  6 21  1  0
  6 22  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 12 25  1  0
 11 24  1  0
  9 23  1  0
M  END
Download

3D SDF for NP0044094 (Makomotine D)


  Mrv1652311132100492D          

 15 15  0  0  0  0            999 V2000
    2.7112    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  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
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0044094

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(C)N1C(CO)=CC=C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H13NO4/c1-7(10(14)15-2)11-8(5-12)3-4-9(11)6-13/h3-5,7,13H,6H2,1-2H3

> <INCHI_KEY>
GDPVGSOBUOFHQM-UHFFFAOYSA-N

> <FORMULA>
C10H13NO4

> <MOLECULAR_WEIGHT>
211.217

> <EXACT_MASS>
211.084457903

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.998086272411744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]propanoate

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
0.254602425666667

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.616191750707031

> <JCHEM_PKA_STRONGEST_BASIC>
-2.966677728240744

> <JCHEM_POLAR_SURFACE_AREA>
68.53

> <JCHEM_REFRACTIVITY>
54.216

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[2-formyl-5-(hydroxymethyl)pyrrol-1-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0044094 (Makomotine D)

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PDB for NP0044094 (Makomotine D)
HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       5.061   4.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.727   3.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.060   2.080   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.915   0.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.971   3.157   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0044094 (Makomotine D)
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SMILES for NP0044094 (Makomotine D)
COC(=O)C(C)N1C(CO)=CC=C1C=O
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INCHI for NP0044094 (Makomotine D)
InChI=1S/C10H13NO4/c1-7(10(14)15-2)11-8(5-12)3-4-9(11)6-13/h3-5,7,13H,6H2,1-2H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H13NO4
Average Mass211.2170 Da
Monoisotopic Mass211.08446 Da
IUPAC Namemethyl 2-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]propanoate
Traditional Namemethyl 2-[2-formyl-5-(hydroxymethyl)pyrrol-1-yl]propanoate
CAS Registry NumberNot Available
SMILES
COC(=O)C(C)N1C(CO)=CC=C1C=O
InChI Identifier
InChI=1S/C10H13NO4/c1-7(10(14)15-2)11-8(5-12)3-4-9(11)6-13/h3-5,7,13H,6H2,1-2H3
InChI KeyGDPVGSOBUOFHQM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ustilago esculentaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acid esters  
Alternative Parents
Substituents
  • Alpha-amino acid ester
    • 

  • Aryl-aldehyde
    • 

  • Substituted pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Methyl ester
    • 

  • Pyrrole
    • 

  • Carboxylic acid ester
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic alcohol
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Aldehyde
    • 

  • Alcohol
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.62ALOGPS
logP0.25ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)14.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity54.22 m³·mol⁻¹ChemAxon
Polarizability21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78434862  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102367926  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hu ZX, Xue YB, Bi XB, Zhang JW, Luo ZW, Li XN, Yao GM, Wang JP, Zhang YH: Five new secondary metabolites produced by a marine-associated fungus, Daldinia eschscholzii. Mar Drugs. 2014 Nov 20;12(11):5563-75. doi: 10.3390/md12115563. [PubMed:25419997  ] 
  2. Ren SQ, Wei Y, Wang YQ, Ou Y, Wang Q, Feng HL, Luo C, Nie Y, Lyu Q, Fan SD, Zhou F, Chen ZJ, Zhong S, Tian JZ, Wang D: [Comparison of single incision robot-assisted laparoscopic radical prostatectomy with and without extraperitoneal special channel device]. Zhonghua Yi Xue Za Zhi. 2021 Nov 2;101(40):3345-3350. doi: 10.3760/cma.j.cn112137-20210303-00545. [PubMed:34758536  ] 
  3. Dong HH, Cai YS, Liang XN, Miao JB, Chen QS, Gao YD, Li H: [Analysis of incidence and risk factors for postoperative venous thromboembolism in patients with stage a non-small-cell lung cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3417-3421. doi: 10.3760/cma.j.cn112137-20210418-00929. [PubMed:34758546  ] 
  4. Reisel D, Burnell M, Side L, Loggenberg K, Gessler S, Desai R, Sanderson S, Brady AF, Dorkins H, Wallis Y, Jacobs C, Legood R, Beller U, Tomlinson I, Wardle J, Menon U, Jacobs I, Manchanda R: Jewish cultural and religious factors and uptake of population-based BRCA testing across denominations: a cohort study. BJOG. 2021 Nov 10. doi: 10.1111/1471-0528.16994. [PubMed:34758513  ] 
  5. Bauermann A, de Sa KSG, Santos ZA, Costa E Silva AA: Supplementation and Performance for Wheelchair Athletes: A Systematic Review. Adapt Phys Activ Q. 2021 Nov 10:1-15. doi: 10.1123/apaq.2020-0241. [PubMed:34758458  ]