NP-MRD: Showing NP-Card for 4,10-dehydroxymelleolide I (NP0332880)

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Record Information

Version

1.0

Created at

2024-05-01 18:04:59 UTC

Updated at

2024-05-03 00:10:39 UTC

NP-MRD ID

NP0332880

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,10-dehydroxymelleolide I

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01132320412D          

 33 36  0  0  1  0            999 V2000
   -0.4133   -1.6429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218   -1.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788   -2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874   -1.6963    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -0.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    0.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.2498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.4336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4079    0.0052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8032    0.5665    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548    1.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    2.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.0666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5165    0.7516    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -0.6627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2455   -1.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -0.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -0.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323    0.0359    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.6934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0897   -1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480   -1.1322    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 14  1  0  0  0  0
 15 14  1  1  0  0  0
 16 15  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  1  0  0  0
 24 22  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 22 29  1  0  0  0  0
 24 30  1  1  0  0  0
 31 24  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 15 33  1  0  0  0  0
M  END


  Mrv2104 01132320412D          

 33 36  0  0  1  0            999 V2000
   -0.4133   -1.6429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218   -1.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788   -2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874   -1.6963    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -0.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    0.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.2498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.4336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4079    0.0052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8032    0.5665    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548    1.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    2.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.0666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5165    0.7516    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -0.6627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2455   -1.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -0.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -0.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323    0.0359    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.6934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0897   -1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480   -1.1322    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 14  1  0  0  0  0
 15 14  1  1  0  0  0
 16 15  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  1  0  0  0
 24 22  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 22 29  1  0  0  0  0
 24 30  1  1  0  0  0
 31 24  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 15 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332880

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@@H](C[C@]1(C)[C@@]1([H])CC(C)(C)C[C@@]1([H])C=C2CO)OC(=O)C1=C(C)C(Cl)=C(OC)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H31ClO5/c1-12-19(16(27)7-17(29-5)21(12)25)22(28)30-18-10-24(4)15-9-23(2,3)8-13(15)6-14(11-26)20(18)24/h6-7,13,15,18,20,26-27H,8-11H2,1-5H3/t13-,15+,18-,20-,24-/m1/s1

> <INCHI_KEY>
YWWRQKKITZGVTA-VJODBNTGSA-N

> <FORMULA>
C24H31ClO5

> <MOLECULAR_WEIGHT>
434.96

> <EXACT_MASS>
434.1860018

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.98089544285722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2aR,4aS,7aS,7bR)-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <JCHEM_LOGP>
5.313151559666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.147142543073015

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.32776892891295

> <JCHEM_PKA_STRONGEST_BASIC>
-2.734440139611129

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
117.17369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2aR,4aS,7aS,7bR)-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-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      -0.771  -3.067   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.225  -1.595   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.726  -1.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.774  -2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.321  -3.852   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.275  -2.038   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -6.323  -3.166   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0      -5.729  -0.566   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -7.230  -0.223   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -7.684   1.249   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.681   0.563   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.180   0.220   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.132   1.348   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.177  -0.466   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.324  -0.809   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.628   0.010   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       1.499   1.057   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       3.348   1.371   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.529   2.675   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.249   4.037   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.887   1.428   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.706   0.124   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       6.564   1.403   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       4.986  -1.237   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.058  -2.342   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.441  -1.664   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.971  -3.110   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.934  -1.288   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.223  -0.140   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       4.167   0.067   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0       3.447  -1.294   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.901  -2.766   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.143  -2.113   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11    3   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15                                                       
CONECT   15   14   16   33                                                  
CONECT   16   15   17   18   31                                             
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   24   29                                             
CONECT   23   22                                                            
CONECT   24   22   25   30   31                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   22                                                       
CONECT   30   24                                                            
CONECT   31   24   16   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   15                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₁ClO₅

Average Mass

434.9600 Da

Monoisotopic Mass

434.18600 Da

IUPAC Name

(2R,2aR,4aS,7aS,7bR)-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

Traditional Name

(2R,2aR,4aS,7aS,7bR)-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@@H](C[C@]1(C)[C@@]1([H])CC(C)(C)C[C@@]1([H])C=C2CO)OC(=O)C1=C(C)C(Cl)=C(OC)C=C1O

InChI Identifier

InChI=1S/C24H31ClO5/c1-12-19(16(27)7-17(29-5)21(12)25)22(28)30-18-10-24(4)15-9-23(2,3)8-13(15)6-14(11-26)20(18)24/h6-7,13,15,18,20,26-27H,8-11H2,1-5H3/t13-,15+,18-,20-,24-/m1/s1

InChI Key

YWWRQKKITZGVTA-VJODBNTGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] 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, C2D6OS, 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
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
COSY NMR	[¹H, ¹H] 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

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	5.31	ChemAxon
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	117.17 m³·mol⁻¹	ChemAxon
Polarizability	46.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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 4,10-dehydroxymelleolide I (NP0332880)

MOL for NP0332880 (4,10-dehydroxymelleolide I)

3D MOL for NP0332880 (4,10-dehydroxymelleolide I)

3D SDF for NP0332880 (4,10-dehydroxymelleolide I)

3D-SDF for NP0332880 (4,10-dehydroxymelleolide I)

PDB for NP0332880 (4,10-dehydroxymelleolide I)

3D PDB for NP0332880 (4,10-dehydroxymelleolide I)

SMILES for NP0332880 (4,10-dehydroxymelleolide I)

INCHI for NP0332880 (4,10-dehydroxymelleolide I)

Structure for NP0332880 (4,10-dehydroxymelleolide I)

3D Structure for NP0332880 (4,10-dehydroxymelleolide I)