NP-MRD: Showing NP-Card for 4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid (NP0163444)

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Record Information

Version

2.0

Created at

2022-09-02 22:05:15 UTC

Updated at

2022-09-02 22:05:15 UTC

NP-MRD ID

NP0163444

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid

Description

4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid is found in Streptomyces hyaluromycini.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032200052D          

 43 47  0  0  0  0            999 V2000
    2.4900   -0.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 41 43  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309032200052D          

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    1.1146   -3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5350   -3.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -2.8190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -2.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9810   -1.8652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596   -1.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -2.6923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393   -1.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6169   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4383   -0.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730    0.0759    0.0000 O   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
  2  4  1  0  0  0  0
  4  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 14 21  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CCC1O)C1=CC=C2C(=O)C3=C4C(OC(C)=O)C(OC(=O)CCC(O)=O)C(C)(O)C(=O)C4=CC3=C(O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O13/c1-11-17(32)6-7-18(41-11)13-4-5-14-23(24(13)36)26(38)15-10-16-22(21(15)25(14)37)27(42-12(2)31)29(30(3,40)28(16)39)43-20(35)9-8-19(33)34/h4-5,10-11,17-18,27,29,32,36,38,40H,6-9H2,1-3H3,(H,33,34)

> <INCHI_KEY>
SSXGBMNAJWFAPL-UHFFFAOYSA-N

> <FORMULA>
C30H30O13

> <MOLECULAR_WEIGHT>
598.557

> <EXACT_MASS>
598.168641026

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
60.719785267358226

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-1H,2H,3H,4H,5H-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
-0.15220710866666776

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.257848790460806

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.709970823746744

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1472866082492814

> <JCHEM_POLAR_SURFACE_AREA>
214.18999999999997

> <JCHEM_REFRACTIVITY>
146.75170000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3H,4H-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       4.648  -0.538   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.006  -1.938   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.473  -2.082   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.898  -3.193   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.256  -4.593   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.147  -5.849   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.677  -6.027   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.833  -5.009   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.529  -3.499   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.292  -5.501   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.448  -4.483   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.907  -4.975   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.210  -6.485   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.670  -6.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.825  -5.959   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.285  -6.451   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.588  -7.961   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      18.048  -8.453   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      15.433  -8.979   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.736 -10.489   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.973  -8.487   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.055  -7.503   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.358  -9.013   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.595  -7.011   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.440  -8.029   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.743  -9.539   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.980  -7.537   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.638  -8.292   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.505  -7.249   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.972  -7.393   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.330  -8.793   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.081  -6.137   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.999  -7.233   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.814  -5.262   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.723  -4.737   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.831  -3.482   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.298  -3.626   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.344  -5.026   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.594  -2.370   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.127  -2.514   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -3.018  -1.258   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -4.551  -1.402   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -2.376   0.142   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7   29                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14                                                       
CONECT   22   13   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   10   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    7   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28    6   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32    5   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₀O₁₃

Average Mass

598.5570 Da

Monoisotopic Mass

598.16864 Da

IUPAC Name

4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-1H,2H,3H,4H,5H-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid

Traditional Name

4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3H,4H-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

CC1OC(CCC1O)C1=CC=C2C(=O)C3=C4C(OC(C)=O)C(OC(=O)CCC(O)=O)C(C)(O)C(=O)C4=CC3=C(O)C2=C1O

InChI Identifier

InChI=1S/C30H30O13/c1-11-17(32)6-7-18(41-11)13-4-5-14-23(24(13)36)26(38)15-10-16-22(21(15)25(14)37)27(42-12(2)31)29(30(3,40)28(16)39)43-20(35)9-8-19(33)34/h4-5,10-11,17-18,27,29,32,36,38,40H,6-9H2,1-3H3,(H,33,34)

InChI Key

SSXGBMNAJWFAPL-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Streptomyces hyaluromycini	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	1.29	ALOGPS
logP	-0.15	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	214.19 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	146.75 m³·mol⁻¹	ChemAxon
Polarizability	60.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid (NP0163444)

MOL for NP0163444 (4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid)

3D MOL for NP0163444 (4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid)

3D SDF for NP0163444 (4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid)

3D-SDF for NP0163444 (4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid)

PDB for NP0163444 (4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid)

3D PDB for NP0163444 (4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid)

SMILES for NP0163444 (4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid)

INCHI for NP0163444 (4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid)

Structure for NP0163444 (4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid)

3D Structure for NP0163444 (4-{[4-(acetyloxy)-2,9,10-trihydroxy-8-(5-hydroxy-6-methyloxan-2-yl)-2-methyl-1,5-dioxo-3h,4h-benzo[b]fluoren-3-yl]oxy}-4-oxobutanoic acid)