NP-MRD: Showing NP-Card for Ophiuroidine (NP0083589)

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Record Information

Version

2.0

Created at

2022-04-29 04:35:04 UTC

Updated at

2022-04-29 04:35:04 UTC

NP-MRD ID

NP0083589

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ophiuroidine

Description

2,3,10-Trihydroxy-6H,12H-indolo[2,1-b]quinazoline-6,12-dione belongs to the class of organic compounds known as indoloquinazolines. These are polycyclic aromatic compounds containing an indole fused to a quinazoline. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Quinazoline is a heterocyclic compound consisting of two fused six-membered simple aromatic rings, a benzene ring and a pyrimidine ring. Ophiuroidine is found in Ophiocoma riisei and Ophiomastix wendtii. 2,3,10-Trihydroxy-6H,12H-indolo[2,1-b]quinazoline-6,12-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 33  0  0  0  0  0  0  0  0999 V2000
    0.9746    3.3008    0.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9021    2.0601    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460    1.1644    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206    1.3294    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2880    0.2662    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6716    0.4161    0.2303 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7754   -1.0031   -0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5835   -2.1134   -0.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146   -1.1612   -0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5369   -0.1008    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133   -0.0229    0.0211 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3022    1.2437    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332    1.5493    0.2018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5338    0.5566    0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569    0.8882    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2712    2.2062    0.2272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8128   -0.0950   -0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4435   -1.4006   -0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1164   -1.7361   -0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1572   -0.7584   -0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028   -1.0183   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -2.2021   -0.3067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8283    2.3059    0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0193    1.3543    0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1786   -3.0256   -0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058   -2.1691   -0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480    2.8985    0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8787    0.1965   -0.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1803   -2.1650   -0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8089   -2.7645   -0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  2  0
  9 10  1  0
 10  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  3  2  1  0
  2  1  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 11  1  0
  5  7  1  0
 11 12  1  0
 11 10  1  0
 20 14  1  0
  8 25  1  0
  9 26  1  0
  4 23  1  0
  6 24  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
M  END


  Mrv1533004161519112D          

 22 25  0  0  0  0            999 V2000
    0.9810   -1.8652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -2.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7574   -3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769   -3.2287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5969   -2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787   -2.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -3.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9222   -4.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0848   -4.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -4.3011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -4.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -4.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253   -5.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -3.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146   -3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933   -3.3650    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  4 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1O)C(=O)C1=NC3=C(O)C=CC=C3C(=O)N21

> <INCHI_IDENTIFIER>
InChI=1S/C15H8N2O5/c18-9-3-1-2-6-12(9)16-14-13(21)7-4-10(19)11(20)5-8(7)17(14)15(6)22/h1-5,18-20H

> <INCHI_KEY>
ZZKGGGBICHNKBI-UHFFFAOYSA-N

> <FORMULA>
C15H8N2O5

> <MOLECULAR_WEIGHT>
296.238

> <EXACT_MASS>
296.043321366

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
28.294697033591564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3,10-trihydroxy-6H,12H-indolo[2,1-b]quinazoline-6,12-dione

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.4849664286666666

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.564999227222041

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.905266010493261

> <JCHEM_PKA_STRONGEST_BASIC>
-4.77760735249534

> <JCHEM_POLAR_SURFACE_AREA>
110.42999999999999

> <JCHEM_REFRACTIVITY>
77.5609

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3,10-trihydroxyindolo[2,1-b]quinazoline-6,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       1.831  -3.482   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.723  -4.737   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.256  -4.593   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.147  -5.849   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       6.677  -6.027   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.833  -5.009   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.529  -3.499   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.292  -5.501   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.448  -4.483   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.907  -4.975   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.210  -6.485   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.055  -7.503   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.358  -9.013   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.595  -7.011   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       8.440  -8.029   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       6.980  -7.537   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.638  -8.292   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.460  -9.822   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.505  -7.249   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.972  -7.393   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.081  -6.137   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.547  -6.281   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    5   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    4   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    2   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₈N₂O₅

Average Mass

296.2380 Da

Monoisotopic Mass

296.04332 Da

IUPAC Name

2,3,10-trihydroxy-6H,12H-indolo[2,1-b]quinazoline-6,12-dione

Traditional Name

2,3,10-trihydroxyindolo[2,1-b]quinazoline-6,12-dione

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C=C1O)C(=O)C1=NC3=C(O)C=CC=C3C(=O)N21

InChI Identifier

InChI=1S/C15H8N2O5/c18-9-3-1-2-6-12(9)16-14-13(21)7-4-10(19)11(20)5-8(7)17(14)15(6)22/h1-5,18-20H

InChI Key

ZZKGGGBICHNKBI-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
Ophiocoma riisei	-	KNApSAcK
Ophiomastix wendtii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoloquinazolines. These are polycyclic aromatic compounds containing an indole fused to a quinazoline. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Quinazoline is a heterocyclic compound consisting of two fused six-membered simple aromatic rings, a benzene ring and a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Indoloquinazolines

Alternative Parents

Substituents

Indoloquinazoline
Indole
Indole or derivatives
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyrimidone
Pyrimidine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Lactam
Ketone
Polyol
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
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	1.8	ALOGPS
logP	1.48	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	6.91	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.43 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	77.56 m³·mol⁻¹	ChemAxon
Polarizability	28.29 Å³	ChemAxon
Number of Rings	4	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

135798128

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ophiuroidine (NP0083589)

MOL for NP0083589 (Ophiuroidine)

3D MOL for NP0083589 (Ophiuroidine)

3D SDF for NP0083589 (Ophiuroidine)

3D-SDF for NP0083589 (Ophiuroidine)

PDB for NP0083589 (Ophiuroidine)

3D PDB for NP0083589 (Ophiuroidine)

SMILES for NP0083589 (Ophiuroidine)

INCHI for NP0083589 (Ophiuroidine)

Structure for NP0083589 (Ophiuroidine)

3D Structure for NP0083589 (Ophiuroidine)