NP-MRD: Showing NP-Card for bisdechlorogeodin (NP0187249)

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Record Information

Version

2.0

Created at

2022-09-04 03:21:18 UTC

Updated at

2022-09-04 03:21:18 UTC

NP-MRD ID

NP0187249

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bisdechlorogeodin

Description

Bisdechlorogeodin belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. bisdechlorogeodin is found in Oidiodendron truncatum. Bisdechlorogeodin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.2928    2.9308    3.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1198    2.5586    1.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1012    1.6973    1.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3392    1.2675    2.1767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9342    1.3202   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536    1.7923   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429    1.4571   -2.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4353    1.9137   -3.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5656    0.5551   -2.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7635    0.1009   -1.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2562   -0.7604   -2.3405 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1287   -0.3424   -3.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8360    0.4112   -0.4869 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4322    0.9489   -0.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808   -0.1159    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614   -0.2491    0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0823   -1.4156    1.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5650   -1.5553    1.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525   -2.4915    1.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9001   -2.3809    1.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0428   -3.4268    1.4516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3897   -1.1996    0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9810   -0.8148    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9908   -1.4114    0.7464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066    2.1635    3.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3883    3.1043    3.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7211    3.8638    3.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437    2.4532   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4421    0.2731   -3.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5099   -0.1531   -4.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8266   -1.1420   -3.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    0.6001   -3.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292    0.5898    0.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0046   -2.0732    0.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9532   -0.5491    1.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6834   -2.2259    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -3.4133    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4407   -4.2807    1.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  1
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 13  5  1  0
 23 13  1  0
 22 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  9 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 16 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
M  END


  Mrv1533004241512152D          

 24 26  0  0  0  0            999 V2000
    3.4387    3.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6546    2.7087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1793    2.4843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1892    0.3199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220   -1.2057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -1.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7773   -0.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3465    2.0029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3651    1.8985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0187249

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC(=O)C=C(OC)C11OC2=CC(C)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-8-4-11(19)14-12(5-8)24-17(15(14)20)10(16(21)23-3)6-9(18)7-13(17)22-2/h4-7,19H,1-3H3

> <INCHI_KEY>
JCMPRFCVZKOFIT-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.292

> <EXACT_MASS>
330.073952791

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.92976852484468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-hydroxy-2'-methoxy-6-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.3463307643333335

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.58449639010213

> <JCHEM_PKA_STRONGEST_BASIC>
-4.632515531579337

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000002

> <JCHEM_REFRACTIVITY>
84.3728

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bisdechlorogeodin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.419   6.543   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.822   5.056   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.672   3.899   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.068   4.637   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.807   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.347   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.117   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.687   0.597   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.347  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.807  -0.564   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.641  -2.251   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.256  -3.707   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.132  -0.476   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.451  -0.617   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.647   3.739   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.132   2.016   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.415   3.544   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10    5   14   23                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   13   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-6'-methoxy-6-methyl-3,4'-dioxo-spiro(benzofuran-2(3H),1'-(2,5)cyclohexadiene)-2'-carboxylic acid methyl ester	ChEBI
Bis-dechlorogeodin	ChEBI
4-Hydroxy-6'-methoxy-6-methyl-3,4'-dioxo-spiro(benzofuran-2(3H),1'-(2,5)cyclohexadiene)-2'-carboxylate methyl ester	Generator
Antibiotic C3368-a	MeSH

Chemical Formula

C₁₇H₁₄O₇

Average Mass

330.2920 Da

Monoisotopic Mass

330.07395 Da

IUPAC Name

methyl 4-hydroxy-2'-methoxy-6-methyl-3,4'-dioxo-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',5'-diene-6'-carboxylate

Traditional Name

bisdechlorogeodin

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(=O)C=C(OC)C11OC2=CC(C)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C17H14O7/c1-8-4-11(19)14-12(5-8)24-17(15(14)20)10(16(21)23-3)6-9(18)7-13(17)22-2/h4-7,19H,1-3H3

InChI Key

JCMPRFCVZKOFIT-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
Oidiodendron truncatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Coumaran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous ester
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Ether
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-benzofurans (CHEBI:22899 )
methyl ester (CHEBI:22899 )
oxaspiro compound (CHEBI:22899 )
a chalcone (CPD-1907 )

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	1.91	ALOGPS
logP	2.35	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.37 m³·mol⁻¹	ChemAxon
Polarizability	31.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

168966

PDB ID

Not Available

ChEBI ID

22899

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for bisdechlorogeodin (NP0187249)

MOL for NP0187249 (bisdechlorogeodin)

3D MOL for NP0187249 (bisdechlorogeodin)

3D SDF for NP0187249 (bisdechlorogeodin)

3D-SDF for NP0187249 (bisdechlorogeodin)

PDB for NP0187249 (bisdechlorogeodin)

3D PDB for NP0187249 (bisdechlorogeodin)

SMILES for NP0187249 (bisdechlorogeodin)

INCHI for NP0187249 (bisdechlorogeodin)

Structure for NP0187249 (bisdechlorogeodin)

3D Structure for NP0187249 (bisdechlorogeodin)