NP-MRD: Showing NP-Card for Bismelleolide BH (NP0332869)

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Record Information

Version

2.0

Created at

2024-05-01 17:01:41 UTC

Updated at

2024-09-03 04:20:32 UTC

NP-MRD ID

NP0332869

Natural Product DOI

https://doi.org/10.57994/2148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bismelleolide BH

Description

Bismelleolide BH belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety. Bismelleolide BH was first documented in 2024 (PMID: 38390787). Based on a literature review very few articles have been published on Bismelleolide BH.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01132319382D          

 65 72  0  0  1  0            999 V2000
   -2.2333   -2.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -2.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  0  0  0  0
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  8  9  1  0  0  0  0
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  3 11  1  0  0  0  0
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  2 13  1  0  0  0  0
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 14 65  1  0  0  0  0
M  END


  Mrv2104 01132319382D          

 65 72  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0332869

> <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(OC)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/C48H60O13/c1-23-11-29(57-9)15-31(50)35(23)41(54)60-33-19-45(7)37-26(18-43(3,4)39(37)52)14-28(47(33,45)56)22-59-48-27(21-49)13-25-17-44(5,6)40(53)38(25)46(48,8)20-34(48)61-42(55)36-24(2)12-30(58-10)16-32(36)51/h11-16,21,25-26,33-34,37-40,50-53,56H,17-20,22H2,1-10H3/t25-,26-,33-,34-,37-,38-,39-,40-,45-,46-,47+,48+/m1/s1

> <INCHI_KEY>
IEYWNAVQOXBDKH-LAFADOJESA-N

> <FORMULA>
C48H60O13

> <MOLECULAR_WEIGHT>
844.995

> <EXACT_MASS>
844.403391992

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
121

> <JCHEM_AVERAGE_POLARIZABILITY>
91.26726857971215

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,2aS,4aS,7R,7aS,7bR)-2a-{[(2R,2aS,4aS,7R,7aS,7bR)-2a,7-dihydroxy-2-(2-hydroxy-4-methoxy-6-methylbenzoyloxy)-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>
7.048987938333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.063741277253362

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.461991970944768

> <JCHEM_PKA_STRONGEST_BASIC>
-3.034244879864821

> <JCHEM_POLAR_SURFACE_AREA>
198.51

> <JCHEM_REFRACTIVITY>
225.40800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2aS,4aS,7R,7aS,7bR)-2a-{[(2R,2aS,4aS,7R,7aS,7bR)-2a,7-dihydroxy-2-(2-hydroxy-4-methoxy-6-methylbenzoyloxy)-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      -0.713  -2.807   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.633  -3.556   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.259  -1.335   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      -2.808  -0.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.262  -2.021   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.763  -2.364   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      -4.891  -1.669   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.462  -1.095   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.834  -0.130   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      -7.385   3.047   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -7.499  -0.031   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -7.557  -1.570   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -8.918  -2.289   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -7.671  -4.647   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -6.192  -7.333   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       1.905  -7.587   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       1.086  -8.892   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       1.806 -10.253   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       3.444  -7.645   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       4.263  -6.341   0.000  0.00  0.00           C+0
HETATM   54  H   UNK     0       5.122  -7.619   0.000  0.00  0.00           H+0
HETATM   55  C   UNK     0       3.544  -4.979   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       4.616  -3.874   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       4.352  -2.357   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       5.998  -4.552   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       6.528  -3.106   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       7.492  -4.928   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       5.781  -6.077   0.000  0.00  0.00           C+0
HETATM   62  H   UNK     0       2.725  -6.283   0.000  0.00  0.00           H+0
HETATM   63  C   UNK     0       2.005  -4.922   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       2.458  -3.450   0.000  0.00  0.00           C+0
HETATM   65  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   65                                                  
CONECT   15   14   16   49   63                                             
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   48                                             
CONECT   31   30                                                            
CONECT   32   30   18   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35   48                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   47                                                  
CONECT   37   36   38   45                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42   44                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
CONECT   44   41   45                                                       
CONECT   45   44   37   46                                                  
CONECT   46   45                                                            
CONECT   47   36                                                            
CONECT   48   34   30                                                       
CONECT   49   15   50   52                                                  
CONECT   50   49   51                                                       
CONECT   51   50                                                            
CONECT   52   49   53                                                       
CONECT   53   52   54   55   61                                             
CONECT   54   53                                                            
CONECT   55   53   56   62   63                                             
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59   60   61                                             
CONECT   59   58                                                            
CONECT   60   58                                                            
CONECT   61   58   53                                                       
CONECT   62   55                                                            
CONECT   63   55   15   64   65                                             
CONECT   64   63                                                            
CONECT   65   63   14                                                       
MASTER        0    0    0    0    0    0    0    0   65    0  144    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₈H₆₀O₁₃

Average Mass

844.9950 Da

Monoisotopic Mass

844.40339 Da

IUPAC Name

(2R,2aS,4aS,7R,7aS,7bR)-2a-{[(2R,2aS,4aS,7R,7aS,7bR)-2a,7-dihydroxy-2-(2-hydroxy-4-methoxy-6-methylbenzoyloxy)-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)-2a,7-dihydroxy-2-(2-hydroxy-4-methoxy-6-methylbenzoyloxy)-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(OC)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/C48H60O13/c1-23-11-29(57-9)15-31(50)35(23)41(54)60-33-19-45(7)37-26(18-43(3,4)39(37)52)14-28(47(33,45)56)22-59-48-27(21-49)13-25-17-44(5,6)40(53)38(25)46(48,8)20-34(48)61-42(55)36-24(2)12-30(58-10)16-32(36)51/h11-16,21,25-26,33-34,37-40,50-53,56H,17-20,22H2,1-10H3/t25-,26-,33-,34-,37-,38-,39-,40-,45-,46-,47+,48+/m1/s1

InChI Key

IEYWNAVQOXBDKH-LAFADOJESA-N

Experimental Spectra

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

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Armillaria ostoyae		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as melleolides and analogues. These are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Melleolides and analogues

Alternative Parents

Substituents

Melleolide-skeleton
Fatty alcohol ester
O-hydroxybenzoic acid ester
P-methoxybenzoic acid or derivatives
Salicylic acid or derivatives
Methoxyphenol
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
Phenol ether
M-cresol
Benzoyl
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Cyclobutanol
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	7.05	ChemAxon
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	198.51 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	225.41 m³·mol⁻¹	ChemAxon
Polarizability	91.27 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

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 ]
DOI: 10.1002/anie.202318505

Showing NP-Card for Bismelleolide BH (NP0332869)

MOL for NP0332869 (Bismelleolide BH)

3D MOL for NP0332869 (Bismelleolide BH)

3D SDF for NP0332869 (Bismelleolide BH)

3D-SDF for NP0332869 (Bismelleolide BH)

PDB for NP0332869 (Bismelleolide BH)

3D PDB for NP0332869 (Bismelleolide BH)

SMILES for NP0332869 (Bismelleolide BH)

INCHI for NP0332869 (Bismelleolide BH)

Structure for NP0332869 (Bismelleolide BH)

3D Structure for NP0332869 (Bismelleolide BH)