NP-MRD: Showing NP-Card for Bengazole Z (NP0082778)

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Record Information

Version

2.0

Created at

2022-04-29 03:52:07 UTC

Updated at

2022-04-29 03:52:07 UTC

NP-MRD ID

NP0082778

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bengazole Z

Description

Bengazole Z belongs to the class of organic compounds known as 2,4-disubstituted oxazoles. 2,4-Disubstituted oxazoles are compounds containing an oxazole ring substituted at positions 2 and 4 only. Oxazole is a five-membered aromatic heterocycle with one oxygen, one nitrogen, and three carbon atoms. Isomers include 1,2-oxazole and 1,3-oxazole. Bengazole Z is found in Jaspis sp. Based on a literature review very few articles have been published on Bengazole Z.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    4.0090   -1.8618   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1699   -0.4229   -0.5823 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5109   -0.2697   -0.9411 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864    0.5551    0.5223 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1293    1.8278    0.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221    0.4189    1.1158 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4278    1.3208    2.1774 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996    0.7093    0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1242    0.5147    0.9663 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1385    1.4030    2.0387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813    0.6143    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2282    0.6440   -1.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5304    0.7429   -1.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1981    0.7764   -0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6843    0.8823   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2943   -0.4801   -0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4456   -1.2082    1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0237   -2.3794    0.7544 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2249   -2.3708   -0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7753   -1.2178   -1.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277    0.6987    0.6371 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3871   -2.5014   -0.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6341   -2.0572    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9449   -2.1384    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5731   -0.2116   -1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0594   -0.1636   -0.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6216    0.3572    1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5678    2.5204    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3772   -0.5830    1.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5506    0.8900    3.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4466    0.0459   -0.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3905    1.7594   -0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1685   -0.5312    1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0246    2.3208    1.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4166    0.5941   -1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9293    1.4989    0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0758    1.3861   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1479   -0.8905    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6803   -3.1933   -1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 14 21  2  0
 21 11  1  0
 20 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  6
  3 26  1  0
  4 27  1  1
  5 28  1  0
  6 29  1  1
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  1
 10 34  1  0
 12 35  1  0
 15 36  1  0
 15 37  1  0
 17 38  1  0
 19 39  1  0
M  END


  Mrv1652304292205522D          

 21 22  0  0  1  0            999 V2000
   -0.8561   -3.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6098   -3.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1618   -3.0026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7493   -2.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9424   -2.4596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0849   -1.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054   -1.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574   -2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111   -1.7257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1248   -0.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3179   -0.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1417   -3.6926    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5728   -3.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2873   -3.6926    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2873   -4.5176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018   -3.2801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0018   -2.4551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7162   -3.6926    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4307   -3.2801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7162   -4.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1417   -4.5176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 12 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0082778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@@H](O)[C@@H](O)C[C@@H](O)C1=COC(CC2=CN=CO2)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O6/c1-7(16)13(19)11(18)3-10(17)9-5-20-12(15-9)2-8-4-14-6-21-8/h4-7,10-11,13,16-19H,2-3H2,1H3/t7-,10+,11-,13+/m0/s1

> <INCHI_KEY>
YRTRIOYYQNZBGH-LXOIKGMDSA-N

> <FORMULA>
C13H18N2O6

> <MOLECULAR_WEIGHT>
298.295

> <EXACT_MASS>
298.116486308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.622965132246325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4R,5S)-1-{2-[(1,3-oxazol-5-yl)methyl]-1,3-oxazol-4-yl}hexane-1,3,4,5-tetrol

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-2.2137244623333325

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.548650367969643

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.930160323345774

> <JCHEM_PKA_STRONGEST_BASIC>
0.7592701934361972

> <JCHEM_POLAR_SURFACE_AREA>
132.98000000000002

> <JCHEM_REFRACTIVITY>
70.05739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4R,5S)-1-[2-(1,3-oxazol-5-ylmethyl)-1,3-oxazol-4-yl]hexane-1,3,4,5-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.598  -6.123   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.005  -6.749   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.035  -5.605   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.265  -4.271   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.759  -4.591   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -3.892  -2.864   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.423  -2.703   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.454  -3.848   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -7.861  -3.221   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -7.700  -1.690   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.193  -1.370   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.264  -6.893   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.069  -6.123   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.403  -6.893   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.403  -8.433   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.737  -6.123   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.737  -4.583   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.070  -6.893   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.404  -6.123   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.070  -8.433   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.264  -8.433   0.000  0.00  0.00           O+0
CONECT    1    2    5   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7                                                       
CONECT   12    1   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   12                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈N₂O₆

Average Mass

298.2950 Da

Monoisotopic Mass

298.11649 Da

IUPAC Name

(1R,3S,4R,5S)-1-{2-[(1,3-oxazol-5-yl)methyl]-1,3-oxazol-4-yl}hexane-1,3,4,5-tetrol

Traditional Name

(1R,3S,4R,5S)-1-[2-(1,3-oxazol-5-ylmethyl)-1,3-oxazol-4-yl]hexane-1,3,4,5-tetrol

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@@H](O)[C@@H](O)C[C@@H](O)C1=COC(CC2=CN=CO2)=N1

InChI Identifier

InChI=1S/C13H18N2O6/c1-7(16)13(19)11(18)3-10(17)9-5-20-12(15-9)2-8-4-14-6-21-8/h4-7,10-11,13,16-19H,2-3H2,1H3/t7-,10+,11-,13+/m0/s1

InChI Key

YRTRIOYYQNZBGH-LXOIKGMDSA-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
Jaspis sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,4-disubstituted oxazoles. 2,4-Disubstituted oxazoles are compounds containing an oxazole ring substituted at positions 2 and 4 only. Oxazole is a five-membered aromatic heterocycle with one oxygen, one nitrogen, and three carbon atoms. Isomers include 1,2-oxazole and 1,3-oxazole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Oxazoles

Direct Parent

2,4-disubstituted oxazoles

Alternative Parents

Substituents

2,4-disubstituted 1,3-oxazole
Heteroaromatic compound
Secondary alcohol
Oxacycle
Azacycle
Polyol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
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	-0.74	ALOGPS
logP	-2.2	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.93	ChemAxon
pKa (Strongest Basic)	0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	70.06 m³·mol⁻¹	ChemAxon
Polarizability	29.62 Å³	ChemAxon
Number of Rings	2	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00049710

Chemspider ID

427070

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

487134

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Bengazole Z (NP0082778)

MOL for NP0082778 (Bengazole Z)

3D MOL for NP0082778 (Bengazole Z)

3D SDF for NP0082778 (Bengazole Z)

3D-SDF for NP0082778 (Bengazole Z)

PDB for NP0082778 (Bengazole Z)

3D PDB for NP0082778 (Bengazole Z)

SMILES for NP0082778 (Bengazole Z)

INCHI for NP0082778 (Bengazole Z)

Structure for NP0082778 (Bengazole Z)

3D Structure for NP0082778 (Bengazole Z)