NP-MRD: Showing NP-Card for (+)-Brasiliquinone D (NP0082779)

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Record Information

Version

2.0

Created at

2022-04-29 03:52:10 UTC

Updated at

2022-04-29 03:52:10 UTC

NP-MRD ID

NP0082779

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Brasiliquinone D

Description

N-[(2R,3R,4R,6R)-6-{[(3S)-3-ethyl-6-hydroxy-1,7,12-trioxo-1,2,3,4,7,12-hexahydrotetraphen-8-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]ethanimidic acid belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone. (+)-Brasiliquinone D is found in Nocardia brasiliensis IFM0667. Based on a literature review very few articles have been published on N-[(2R,3R,4R,6R)-6-{[(3S)-3-ethyl-6-hydroxy-1,7,12-trioxo-1,2,3,4,7,12-hexahydrotetraphen-8-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]ethanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205522D          

 37 41  0  0  1  0            999 V2000
    3.6850    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850   -1.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347   -2.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4459    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1955   -0.8348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4656   -1.6143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.2757   -1.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7356   -0.2111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5458   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8158   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  9 17  1  0  0  0  0
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  2 21  1  0  0  0  0
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  1 24  1  0  0  0  0
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 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292205522D          

 37 41  0  0  1  0            999 V2000
    3.6850    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 30 32  1  1  0  0  0
 29 33  1  1  0  0  0
 28 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0082779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1CC(=O)C2=C(C1)C=C(O)C1=C2C(=O)C2=C(C1=O)C(O[C@@H]1C[C@@H](NC(C)=O)[C@@H](O)[C@@H](C)O1)=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C28H29NO8/c1-4-14-8-15-10-19(32)24-25(22(15)18(31)9-14)27(34)16-6-5-7-20(23(16)28(24)35)37-21-11-17(29-13(3)30)26(33)12(2)36-21/h5-7,10,12,14,17,21,26,32-33H,4,8-9,11H2,1-3H3,(H,29,30)/t12-,14+,17-,21-,26+/m1/s1

> <INCHI_KEY>
IVLQWYIHDNEUEU-RVGQDBFCSA-N

> <FORMULA>
C28H29NO8

> <MOLECULAR_WEIGHT>
507.539

> <EXACT_MASS>
507.189316898

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
52.501999983567984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3R,4R,6R)-6-{[(3S)-3-ethyl-6-hydroxy-1,7,12-trioxo-1,2,3,4,7,12-hexahydrotetraphen-8-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]acetamide

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
3.3924867876666656

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.543939131867202

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.555056966713007

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2822088624338424

> <JCHEM_POLAR_SURFACE_AREA>
139.23000000000002

> <JCHEM_REFRACTIVITY>
132.7224

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2R,3R,4R,6R)-6-{[(3S)-3-ethyl-6-hydroxy-1,7,12-trioxo-3,4-dihydro-2H-tetraphen-8-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]acetamide

> <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       6.879   1.061   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.375  -1.558   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.879  -3.013   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.862   2.807   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.342  -2.140   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.854  -2.431   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.358  -3.887   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.350   3.098   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.691   1.352   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.699   0.188   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.399  -2.140   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.911  -2.431   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.919  -1.267   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.432  -1.558   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.936  -3.013   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.928  -4.178   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.415  -3.887   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.432  -5.633   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.448  -3.304   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0      14.440  -0.394   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      15.952  -0.685   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      16.960   0.479   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      16.456  -2.140   0.000  0.00  0.00           C+0
CONECT    1    2    7   24                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   17                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16    9   18                                                  
CONECT   18   17                                                            
CONECT   19   15   20                                                       
CONECT   20   19                                                            
CONECT   21    2   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    1                                                       
CONECT   25   21   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30                                                            
CONECT   33   29                                                            
CONECT   34   28   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
N-[(2R,3R,4R,6R)-6-{[(3S)-3-ethyl-6-hydroxy-1,7,12-trioxo-1,2,3,4,7,12-hexahydrotetraphen-8-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]ethanimidate	Generator

Chemical Formula

C₂₈H₂₉NO₈

Average Mass

507.5390 Da

Monoisotopic Mass

507.18932 Da

IUPAC Name

N-[(2R,3R,4R,6R)-6-{[(3S)-3-ethyl-6-hydroxy-1,7,12-trioxo-1,2,3,4,7,12-hexahydrotetraphen-8-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]acetamide

Traditional Name

N-[(2R,3R,4R,6R)-6-{[(3S)-3-ethyl-6-hydroxy-1,7,12-trioxo-3,4-dihydro-2H-tetraphen-8-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]acetamide

CAS Registry Number

Not Available

SMILES

CC[C@@H]1CC(=O)C2=C(C1)C=C(O)C1=C2C(=O)C2=C(C1=O)C(O[C@@H]1C[C@@H](NC(C)=O)[C@@H](O)[C@@H](C)O1)=CC=C2

InChI Identifier

InChI=1S/C28H29NO8/c1-4-14-8-15-10-19(32)24-25(22(15)18(31)9-14)27(34)16-6-5-7-20(23(16)28(24)35)37-21-11-17(29-13(3)30)26(33)12(2)36-21/h5-7,10,12,14,17,21,26,32-33H,4,8-9,11H2,1-3H3,(H,29,30)/t12-,14+,17-,21-,26+/m1/s1

InChI Key

IVLQWYIHDNEUEU-RVGQDBFCSA-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
Nocardia brasiliensis IFM0667	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Angucyclines

Sub Class

Not Available

Direct Parent

Angucyclines

Alternative Parents

Substituents

Angucycline core
Anthraquinone
9,10-anthraquinone
Phenanthrol
Phenanthrene
Anthracene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Carboximidic acid
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.71	ALOGPS
logP	3.39	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	6.56	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.72 m³·mol⁻¹	ChemAxon
Polarizability	52.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

162936523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Brasiliquinone D (NP0082779)

MOL for NP0082779 ((+)-Brasiliquinone D)

3D MOL for NP0082779 ((+)-Brasiliquinone D)

3D SDF for NP0082779 ((+)-Brasiliquinone D)

3D-SDF for NP0082779 ((+)-Brasiliquinone D)

PDB for NP0082779 ((+)-Brasiliquinone D)

3D PDB for NP0082779 ((+)-Brasiliquinone D)

SMILES for NP0082779 ((+)-Brasiliquinone D)

INCHI for NP0082779 ((+)-Brasiliquinone D)

Structure for NP0082779 ((+)-Brasiliquinone D)

3D Structure for NP0082779 ((+)-Brasiliquinone D)