NP-MRD: Showing NP-Card for Pestalactam B (NP0009205)

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Record Information

Version

2.0

Created at

2020-12-09 06:37:41 UTC

Updated at

2021-07-15 17:02:36 UTC

NP-MRD ID

NP0009205

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pestalactam B

Provided By

NPAtlas

Description

Pestalactam B is found in Pestalotiopsis sp. Based on a literature review very few articles have been published on 5,7-dihydroxy-2-(2-hydroxy-2-methylpropyl)-4H-azepin-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106333D          

 28 28  0  0  0  0            999 V2000
   -2.0218    0.5499    1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1590    0.1019    0.2524 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7218    1.1544   -0.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2980   -0.7692    0.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242   -0.7536   -0.2910 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2537   -0.3977   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7654    0.7978   -0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0426    1.1478    0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535    2.2390    0.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338    0.4377    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038    1.1027    0.4451 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3115   -0.8770   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3494   -1.5877   -0.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8153   -2.5327   -1.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084   -1.4123   -0.9310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312    1.3323    1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0398    0.9145    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8140   -0.3205    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199    1.4693   -0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9347    0.6887   -1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1500    2.0516   -0.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4861   -1.2036   -0.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4671   -1.0795   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599   -1.7381    0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0531    1.5783   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2719    0.6254    0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2707   -1.3412   -0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4945   -2.1782   -1.4165 H   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
  2  4  1  0  0  0  0
  2  5  1  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  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15  6  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
  7 25  1  0  0  0  0
 11 26  1  0  0  0  0
 12 27  1  0  0  0  0
 15 28  1  0  0  0  0
M  END


  Mrv1652306242106333D          

 28 28  0  0  0  0            999 V2000
   -2.0218    0.5499    1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1590    0.1019    0.2524 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7218    1.1544   -0.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2980   -0.7692    0.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242   -0.7536   -0.2910 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2537   -0.3977   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7654    0.7978   -0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0426    1.1478    0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535    2.2390    0.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338    0.4377    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038    1.1027    0.4451 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3115   -0.8770   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3494   -1.5877   -0.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8153   -2.5327   -1.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084   -1.4123   -0.9310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312    1.3323    1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0398    0.9145    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8140   -0.3205    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199    1.4693   -0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9347    0.6887   -1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1500    2.0516   -0.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4861   -1.2036   -0.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4671   -1.0795   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599   -1.7381    0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0531    1.5783   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2719    0.6254    0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2707   -1.3412   -0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4945   -2.1782   -1.4165 H   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
  2  4  1  0  0  0  0
  2  5  1  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  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15  6  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
  7 25  1  0  0  0  0
 11 26  1  0  0  0  0
 12 27  1  0  0  0  0
 15 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009205

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=O)N([H])C(=C([H])C1=O)C([H])([H])C(O[H])(C([H])([H])[H])C([H])([H])[H]

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

> <INCHI_KEY>
XIZXAOCEYPTCMX-UHFFFAOYSA-N

> <FORMULA>
C10H13NO4

> <MOLECULAR_WEIGHT>
211.217

> <EXACT_MASS>
211.084457903

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.939409662520223

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-7-(2-hydroxy-2-methylpropyl)-2,5-dihydro-1H-azepine-2,5-dione

> <ALOGPS_LOGP>
-0.31

> <JCHEM_LOGP>
-0.5650137056666664

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.67913117853649

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.887076869768624

> <JCHEM_PKA_STRONGEST_BASIC>
-2.37984539944957

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
56.493700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-7-(2-hydroxy-2-methylpropyl)-1H-azepine-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.022   0.550   1.667  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.159   0.102   0.252  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.722   1.154  -0.663  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.298  -0.769   0.371  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.124  -0.754  -0.291  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.254  -0.398  -0.395  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.765   0.798  -0.011  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.043   1.148   0.371  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.154   2.239   0.971  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.234   0.438   0.172  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.404   1.103   0.445  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.312  -0.877  -0.277  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.349  -1.588  -0.933  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.815  -2.533  -1.629  0.00  0.00           O+0
HETATM   15  N   UNK     0       1.008  -1.412  -0.931  0.00  0.00           N+0
HETATM   16  H   UNK     0      -1.331   1.332   1.908  0.00  0.00           H+0
HETATM   17  H   UNK     0      -3.040   0.915   2.001  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.814  -0.321   2.321  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.720   1.469  -0.237  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.935   0.689  -1.630  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.150   2.052  -0.794  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.486  -1.204  -0.479  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.467  -1.079  -1.325  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.160  -1.738   0.277  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.053   1.578  -0.010  0.00  0.00           H+0
HETATM   26  H   UNK     0       5.272   0.625   0.314  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.271  -1.341  -0.051  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.495  -2.178  -1.417  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    1    3    4    5                                             
CONECT    3    2   19   20   21                                             
CONECT    4    2   22                                                       
CONECT    5    2    6   23   24                                             
CONECT    6    5    7   15                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10   26                                                       
CONECT   12   10   13   27                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   28                                                  
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    3                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    5                                                            
CONECT   24    5                                                            
CONECT   25    7                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   15                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₀H₁₃NO₄

Average Mass

211.2170 Da

Monoisotopic Mass

211.08446 Da

IUPAC Name

4-hydroxy-7-(2-hydroxy-2-methylpropyl)-2,5-dihydro-1H-azepine-2,5-dione

Traditional Name

4-hydroxy-7-(2-hydroxy-2-methylpropyl)-1H-azepine-2,5-dione

CAS Registry Number

Not Available

SMILES

CC(C)(O)CC1=CC(=O)C(O)=CC(=O)N1

InChI Identifier

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

InChI Key

XIZXAOCEYPTCMX-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
Pestalotiopsis sp.	NPAtlas	20449480

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azepines

Sub Class

Not Available

Direct Parent

Azepines

Alternative Parents

Substituents

Azepine
Tertiary alcohol
Vinylogous acid
Heteroaromatic compound
Vinylogous amide
Lactam
Cyclic ketone
Azacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-0.31	ALOGPS
logP	-0.57	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.89	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	56.49 m³·mol⁻¹	ChemAxon
Polarizability	20.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA004850

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74901154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54749584

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Pestalactam B (NP0009205)

MOL for NP0009205 (Pestalactam B)

3D MOL for NP0009205 (Pestalactam B)

3D SDF for NP0009205 (Pestalactam B)

3D-SDF for NP0009205 (Pestalactam B)

PDB for NP0009205 (Pestalactam B)

3D PDB for NP0009205 (Pestalactam B)

SMILES for NP0009205 (Pestalactam B)

INCHI for NP0009205 (Pestalactam B)

Structure for NP0009205 (Pestalactam B)

3D Structure for NP0009205 (Pestalactam B)