NP-MRD: Showing NP-Card for (5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate (NP0234036)

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Record Information

Version

2.0

Created at

2022-09-06 15:51:29 UTC

Updated at

2022-09-06 15:51:29 UTC

NP-MRD ID

NP0234036

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate

Description

O-Demethylrenierone belongs to the class of organic compounds known as aryl ketones. These are organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R', where R = aryl group and R'=organyl group. (5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate is found in Haliclona. (5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate was first documented in 2004 (PMID: 14974621). Based on a literature review very few articles have been published on O-Demethylrenierone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    5.5760    1.7785   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5770    0.3288    0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565   -0.3570    0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4858   -1.8021    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630    0.2794    0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883    1.5221   -0.1458 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9604   -0.3947    0.2604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305    0.3284    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4317   -0.5702    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2694   -1.8902    0.5519 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3302   -2.7136    0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6088   -2.2174    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291   -0.8750    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910   -0.0796    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427    1.3297   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691    2.1182   -0.3627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263    1.7850   -0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5181    3.0158   -0.6155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4671    0.8954   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8661    1.3674   -0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1848   -0.3643    0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2580   -1.2384    0.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1559    1.9996   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6439    2.1047   -0.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1086    2.3876    0.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5027   -0.2389    0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593   -1.9242    1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293   -2.2199    0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8747   -2.4008   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7086    1.0857    0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7665    0.6886   -0.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2196   -3.7615    0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4726   -2.8532    0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4699    1.1683    0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8640    2.4634   -0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2845    0.9173   -1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4841   -1.6628    1.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 14  9  1  0
 21 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  8 31  1  0
 11 32  1  0
 12 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
 22 37  1  0
M  END


  Mrv1652309062217512D          

 22 23  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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0234036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)OCC1=NC=CC2=C1C(=O)C(=O)C(C)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C16H15NO5/c1-4-8(2)16(21)22-7-11-12-10(5-6-17-11)13(18)9(3)14(19)15(12)20/h4-6,18H,7H2,1-3H3/b8-4-

> <INCHI_KEY>
UHGGVLIEIYEISB-YWEYNIOJSA-N

> <FORMULA>
C16H15NO5

> <MOLECULAR_WEIGHT>
301.298

> <EXACT_MASS>
301.095022587

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.294488954456526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5-hydroxy-6-methyl-7,8-dioxo-7,8-dihydroisoquinolin-1-yl)methyl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
2.1576896816666675

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.014204165800123

> <JCHEM_PKA_STRONGEST_BASIC>
1.8126093104438734

> <JCHEM_POLAR_SURFACE_AREA>
93.56

> <JCHEM_REFRACTIVITY>
80.381

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         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   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   13   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₅NO₅

Average Mass

301.2980 Da

Monoisotopic Mass

301.09502 Da

IUPAC Name

(5-hydroxy-6-methyl-7,8-dioxo-7,8-dihydroisoquinolin-1-yl)methyl (2Z)-2-methylbut-2-enoate

Traditional Name

(5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)OCC1=NC=CC2=C1C(=O)C(=O)C(C)=C2O

InChI Identifier

InChI=1S/C16H15NO5/c1-4-8(2)16(21)22-7-11-12-10(5-6-17-11)13(18)9(3)14(19)15(12)20/h4-6,18H,7H2,1-3H3/b8-4-

InChI Key

UHGGVLIEIYEISB-YWEYNIOJSA-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
Haliclona	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl ketones. These are organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R', where R = aryl group and R'=organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl ketones

Alternative Parents

Substituents

Aryl ketone
Fatty acid ester
Pyridine
Fatty acyl
Heteroaromatic compound
Enoate ester
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Cyclic ketone
Carboxylic acid derivative
Enol
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.16	ChemAxon
pKa (Strongest Acidic)	5.01	ChemAxon
pKa (Strongest Basic)	1.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	93.56 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.38 m³·mol⁻¹	ChemAxon
Polarizability	30.29 Å³	ChemAxon
Number of Rings	2	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

23424592

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sandoval IT, Davis RA, Bugni TS, Concepcion GP, Harper MK, Ireland CM: Cytotoxic isoquinoline quinones from sponges of the genus Petrosia. Nat Prod Res. 2004 Feb;18(1):89-93. doi: 10.1080/1057563031000122130. [PubMed:14974621 ]
LOTUS database [Link]

Showing NP-Card for (5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate (NP0234036)

MOL for NP0234036 ((5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate)

3D MOL for NP0234036 ((5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate)

3D SDF for NP0234036 ((5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0234036 ((5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate)

PDB for NP0234036 ((5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate)

3D PDB for NP0234036 ((5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate)

SMILES for NP0234036 ((5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate)

INCHI for NP0234036 ((5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate)

Structure for NP0234036 ((5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate)

3D Structure for NP0234036 ((5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate)