NP-MRD: Showing NP-Card for Flavoglaucin (NP0071205)

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Record Information

Version

2.0

Created at

2022-04-28 16:35:24 UTC

Updated at

2022-04-28 16:35:24 UTC

NP-MRD ID

NP0071205

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Flavoglaucin

Description

Flavoglaucin belongs to the class of organic compounds known as prenylated hydroquinones. These are quinones with a structure characterized by the hydroquinone ring substituted by an prenyl side-chain. Flavoglaucin is found in Aspergillus amstelodami, Aspergillus chevalieri, Eurotium rubrum, Microsporum sp. and Talipariti tiliaceum. Flavoglaucin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 50  0  0  0  0  0  0  0  0999 V2000
    4.5999    1.6892    2.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.8494    1.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4311   -0.5656    1.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5700   -1.5580    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9201   -1.4586   -1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4471   -1.4247   -1.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8159   -0.2361   -0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3358   -0.2018   -0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876    0.1784   -1.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5710    0.5473   -2.9919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654    0.2344   -2.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -0.1109   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8583   -0.0551   -1.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4379    1.1487   -0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4253    1.0371    0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0529   -0.2493    0.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9657    2.2920    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8966   -0.5049    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8190   -0.8152    1.1179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5371   -0.5444    0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0371   -0.9502    1.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340   -1.2857    2.5938 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3568    1.4537    3.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5415    2.7606    2.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769    1.4173    2.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8832    0.9342    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2103    1.2982    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417   -0.5952    1.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2563   -0.8429    2.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6957   -1.7853    0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2443   -2.5634    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2320   -2.4068   -1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3984   -0.6661   -1.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2202   -1.5366   -2.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0942   -2.3899   -0.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1775    0.6473   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600    0.0023    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5634    0.5783   -3.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9506    0.5402   -3.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0784   -0.0273   -2.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2842   -0.9913   -0.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0430    2.1485   -0.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1819   -0.9035   -0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1053   -0.0138    0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5071   -0.7926    1.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5219    3.1993    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0577    2.3367    0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6488    2.2705    1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811   -1.1068    2.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108   -0.9819    1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
 12 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 20  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
 10 38  1  0
 11 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  0
 21 50  1  0
M  END


  Mrv1533004181501152D          

 22 22  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0071205

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC1=C(O)C=C(CC=C(C)C)C(O)=C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O3/c1-4-5-6-7-8-9-16-17(13-20)19(22)15(12-18(16)21)11-10-14(2)3/h10,12-13,21-22H,4-9,11H2,1-3H3

> <INCHI_KEY>
RGRXZGKXEJHPQQ-UHFFFAOYSA-N

> <FORMULA>
C19H28O3

> <MOLECULAR_WEIGHT>
304.43

> <EXACT_MASS>
304.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.02166400831622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-heptyl-3,6-dihydroxy-5-(3-methylbut-2-en-1-yl)benzaldehyde

> <ALOGPS_LOGP>
4.80

> <JCHEM_LOGP>
6.638017896000001

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.013453567995299

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.737424131555889

> <JCHEM_PKA_STRONGEST_BASIC>
-5.919757483669366

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
93.4938

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-heptyl-3,6-dihydroxy-5-(3-methylbut-2-en-1-yl)benzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    8   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₈O₃

Average Mass

304.4300 Da

Monoisotopic Mass

304.20384 Da

IUPAC Name

2-heptyl-3,6-dihydroxy-5-(3-methylbut-2-en-1-yl)benzaldehyde

Traditional Name

2-heptyl-3,6-dihydroxy-5-(3-methylbut-2-en-1-yl)benzaldehyde

CAS Registry Number

Not Available

SMILES

CCCCCCCC1=C(O)C=C(CC=C(C)C)C(O)=C1C=O

InChI Identifier

InChI=1S/C19H28O3/c1-4-5-6-7-8-9-16-17(13-20)19(22)15(12-18(16)21)11-10-14(2)3/h10,12-13,21-22H,4-9,11H2,1-3H3

InChI Key

RGRXZGKXEJHPQQ-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aspergillus amstelodami	LOTUS Database	35616633
Aspergillus chevalieri	LOTUS Database	35616633
Eurotium rubrum	Fungi	KNApSAcK
Microsporum sp.	Fungi	KNApSAcK
Talipariti tiliaceum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated hydroquinones. These are quinones with a structure characterized by the hydroquinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylated hydroquinones

Alternative Parents

Substituents

Prenylbenzoquinol
Hydroxybenzaldehyde
Hydroquinone
Benzoyl
Benzaldehyde
Aryl-aldehyde
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Organic oxide
Hydrocarbon derivative
Aldehyde
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroquinones (CHEBI:68188 )

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	4.8	ALOGPS
logP	6.64	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.74	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	93.49 m³·mol⁻¹	ChemAxon
Polarizability	36.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

119037

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Flavoglaucin (NP0071205)

MOL for NP0071205 (Flavoglaucin)

3D MOL for NP0071205 (Flavoglaucin)

3D SDF for NP0071205 (Flavoglaucin)

3D-SDF for NP0071205 (Flavoglaucin)

PDB for NP0071205 (Flavoglaucin)

3D PDB for NP0071205 (Flavoglaucin)

SMILES for NP0071205 (Flavoglaucin)

INCHI for NP0071205 (Flavoglaucin)

Structure for NP0071205 (Flavoglaucin)

3D Structure for NP0071205 (Flavoglaucin)