NP-MRD: Showing NP-Card for Bismelleolide EH (NP0332870)

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Record Information

Version

1.0

Created at

2024-05-01 17:06:07 UTC

Updated at

2024-05-03 00:10:33 UTC

NP-MRD ID

NP0332870

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bismelleolide EH

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01132319422D          

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M  END


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M  END
> <DATABASE_ID>
NP0332870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC(C)(C)[C@H](O)[C@]1([H])[C@@]1(C)C[C@@H](OC(=O)C3=C(C)C=C(O)C=C3O)[C@@]1(O)C(CO[C@@]13[C@@H](C[C@]1(C)[C@@]1([H])[C@@H](O)C(C)(C)C[C@@]1([H])C=C3C=O)OC(=O)C1=C(C)C=C(OC)C=C1O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C47H58O13/c1-22-10-28(49)14-30(50)34(22)40(54)59-32-18-44(7)36-25(17-42(3,4)38(36)52)13-27(46(32,44)56)21-58-47-26(20-48)12-24-16-43(5,6)39(53)37(24)45(47,8)19-33(47)60-41(55)35-23(2)11-29(57-9)15-31(35)51/h10-15,20,24-25,32-33,36-39,49-53,56H,16-19,21H2,1-9H3/t24-,25-,32-,33-,36-,37-,38-,39-,44-,45-,46+,47+/m1/s1

> <INCHI_KEY>
VSUGYBNHTUHEFM-XLWUXGDWSA-N

> <FORMULA>
C47H58O13

> <MOLECULAR_WEIGHT>
830.968

> <EXACT_MASS>
830.387741928

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
118

> <JCHEM_AVERAGE_POLARIZABILITY>
89.20176955316215

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,2aS,4aS,7R,7aS,7bR)-2a-{[(2R,2aS,4aS,7R,7aS,7bR)-2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-3-yl]methoxy}-3-formyl-7-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate

> <JCHEM_LOGP>
6.903093882333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.733845530237044

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.661702049456556

> <JCHEM_PKA_STRONGEST_BASIC>
-3.034244879864821

> <JCHEM_POLAR_SURFACE_AREA>
209.51

> <JCHEM_REFRACTIVITY>
220.92570000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2aS,4aS,7R,7aS,7bR)-2a-{[(2R,2aS,4aS,7R,7aS,7bR)-2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-3-yl]methoxy}-3-formyl-7-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JAN-23         0                                  
HETATM    1  O   UNK     0      -4.169  -4.964   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.668  -4.621   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.214  -3.150   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.262  -2.021   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.763  -2.364   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.808  -0.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.307  -0.206   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.853   1.265   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.648   1.608   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.259  -1.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.713  -2.807   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.633  -3.556   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.620  -5.750   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.119  -5.407   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.186  -6.226   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.057  -7.274   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.415  -6.820   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.543  -7.868   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.200  -9.369   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.329 -10.417   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      -1.913 -11.022   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      -4.801  -9.963   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.687 -11.223   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -7.227 -11.246   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.763 -12.455   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.085 -13.245   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.115 -13.852   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.306 -11.957   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      -3.672  -8.916   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0      -5.144  -8.462   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.505  -9.182   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.015  -7.414   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.196  -6.110   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -5.063  -6.286   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -5.006  -4.747   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -6.310  -3.928   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.252  -2.389   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.557  -1.570   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -8.918  -2.289   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -7.499  -0.031   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.138   0.689   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.081   2.228   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -4.834  -0.130   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -4.891  -1.669   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -3.462  -1.095   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -7.671  -4.647   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -6.192  -7.333   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.905  -7.587   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       1.086  -8.892   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       1.806 -10.253   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       3.444  -7.645   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.263  -6.341   0.000  0.00  0.00           C+0
HETATM   53  H   UNK     0       5.122  -7.619   0.000  0.00  0.00           H+0
HETATM   54  C   UNK     0       3.544  -4.979   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.616  -3.874   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       4.352  -2.357   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       5.998  -4.552   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       6.528  -3.106   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       7.492  -4.928   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       5.781  -6.077   0.000  0.00  0.00           C+0
HETATM   61  H   UNK     0       2.725  -6.283   0.000  0.00  0.00           H+0
HETATM   62  C   UNK     0       2.005  -4.922   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       2.458  -3.450   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       0.701  -4.103   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11                                                            
CONECT   13    2   14                                                       
CONECT   14   13   15   64                                                  
CONECT   15   14   16   48   62                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22   28                                             
CONECT   21   20                                                            
CONECT   22   20   23   29   30                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   20                                                       
CONECT   29   22                                                            
CONECT   30   22   31   32   47                                             
CONECT   31   30                                                            
CONECT   32   30   18   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35   47                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   46                                                  
CONECT   37   36   38   44                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   37   45                                                  
CONECT   45   44                                                            
CONECT   46   36                                                            
CONECT   47   34   30                                                       
CONECT   48   15   49   51                                                  
CONECT   49   48   50                                                       
CONECT   50   49                                                            
CONECT   51   48   52                                                       
CONECT   52   51   53   54   60                                             
CONECT   53   52                                                            
CONECT   54   52   55   61   62                                             
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58   59   60                                             
CONECT   58   57                                                            
CONECT   59   57                                                            
CONECT   60   57   52                                                       
CONECT   61   54                                                            
CONECT   62   54   15   63   64                                             
CONECT   63   62                                                            
CONECT   64   62   14                                                       
MASTER        0    0    0    0    0    0    0    0   64    0  142    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₅₈O₁₃

Average Mass

830.9680 Da

Monoisotopic Mass

830.38774 Da

IUPAC Name

(2R,2aS,4aS,7R,7aS,7bR)-2a-{[(2R,2aS,4aS,7R,7aS,7bR)-2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-3-yl]methoxy}-3-formyl-7-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate

Traditional Name

(2R,2aS,4aS,7R,7aS,7bR)-2a-{[(2R,2aS,4aS,7R,7aS,7bR)-2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-3-yl]methoxy}-3-formyl-7-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC(C)(C)[C@H](O)[C@]1([H])[C@@]1(C)C[C@@H](OC(=O)C3=C(C)C=C(O)C=C3O)[C@@]1(O)C(CO[C@@]13[C@@H](C[C@]1(C)[C@@]1([H])[C@@H](O)C(C)(C)C[C@@]1([H])C=C3C=O)OC(=O)C1=C(C)C=C(OC)C=C1O)=C2

InChI Identifier

InChI=1S/C47H58O13/c1-22-10-28(49)14-30(50)34(22)40(54)59-32-18-44(7)36-25(17-42(3,4)38(36)52)13-27(46(32,44)56)21-58-47-26(20-48)12-24-16-43(5,6)39(53)37(24)45(47,8)19-33(47)60-41(55)35-23(2)11-29(57-9)15-31(35)51/h10-15,20,24-25,32-33,36-39,49-53,56H,16-19,21H2,1-9H3/t24-,25-,32-,33-,36-,37-,38-,39-,44-,45-,46+,47+/m1/s1

InChI Key

VSUGYBNHTUHEFM-XLWUXGDWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-05-01	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-05-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-05-01	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-05-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-05-01	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-05-01	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
ostoyae		Not Available

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	6.9	ChemAxon
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	209.51 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	220.93 m³·mol⁻¹	ChemAxon
Polarizability	89.2 Å³	ChemAxon
Number of Rings	8	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

Pfutze S, Charria-Giron E, Schulzke E, Toshe R, Khonsanit A, Franke R, Surup F, Bronstrup M, Stadler M: Depicting the Chemical Diversity of Bioactive Meroterpenoids Produced by the Largest Organism on Earth. Angew Chem Int Ed Engl. 2024 Apr 15;63(16):e202318505. doi: 10.1002/anie.202318505. Epub 2024 Mar 14. [PubMed:38390787 ]

Showing NP-Card for Bismelleolide EH (NP0332870)

MOL for NP0332870 (Bismelleolide EH)

3D MOL for NP0332870 (Bismelleolide EH)

3D SDF for NP0332870 (Bismelleolide EH)

3D-SDF for NP0332870 (Bismelleolide EH)

PDB for NP0332870 (Bismelleolide EH)

3D PDB for NP0332870 (Bismelleolide EH)

SMILES for NP0332870 (Bismelleolide EH)

INCHI for NP0332870 (Bismelleolide EH)

Structure for NP0332870 (Bismelleolide EH)

3D Structure for NP0332870 (Bismelleolide EH)