NP-MRD: Showing NP-Card for rubellin c (NP0283654)

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Record Information

Version

2.0

Created at

2022-09-09 11:00:16 UTC

Updated at

2022-09-09 11:00:16 UTC

NP-MRD ID

NP0283654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

rubellin c

Description

UNII-M73UPM72AK belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. rubellin c is found in Mycosphaerella rubella and Ramularia collo-cygni. Based on a literature review very few articles have been published on UNII-M73UPM72AK.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092213002D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309092213002D          

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M  END
> <DATABASE_ID>
NP0283654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)O[C@@H](C2=C1)[C@]12CC3=CC(O)=C4C(=O)C5=C(O)C=CC=C5C(=O)C4=C3[C@H]1C=C[C@@H](O)[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O9/c1-11-7-14-22(18(33)8-11)29(38)39-28(14)30-10-12-9-19(34)23-24(20(12)15(30)5-6-17(32)27(30)37)25(35)13-3-2-4-16(31)21(13)26(23)36/h2-9,15,17,27-28,31-34,37H,10H2,1H3/t15-,17-,27-,28+,30-/m1/s1

> <INCHI_KEY>
FWHRHQWEGRLEBF-QKXMQONGSA-N

> <FORMULA>
C30H22O9

> <MOLECULAR_WEIGHT>
526.497

> <EXACT_MASS>
526.126382288

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
51.80381104115031

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,6R,7S,8R)-6,7,12,16-tetrahydroxy-8-[(1S)-4-hydroxy-6-methyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl]pentacyclo[11.8.0.0^{2,10}.0^{3,8}.0^{15,20}]henicosa-1,4,10,12,15,17,19-heptaene-14,21-dione

> <JCHEM_LOGP>
5.092407972666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.466339096781189

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.827344238427251

> <JCHEM_PKA_STRONGEST_BASIC>
-3.317102632720421

> <JCHEM_POLAR_SURFACE_AREA>
161.59

> <JCHEM_REFRACTIVITY>
139.64929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,6R,7S,8R)-6,7,12,16-tetrahydroxy-8-[(1S)-4-hydroxy-6-methyl-3-oxo-1H-2-benzofuran-1-yl]pentacyclo[11.8.0.0^{2,10}.0^{3,8}.0^{15,20}]henicosa-1,4,10,12,15,17,19-heptaene-14,21-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       8.398   8.330   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.531   7.287   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.001   7.746   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.133   6.702   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.603   7.161   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.795   5.199   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.325   4.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.193   5.784   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.308   3.201   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.051   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.749   3.820   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.219   3.999   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.328   5.255   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.795   5.112   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.904   6.368   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.152   3.712   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.043   2.456   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.576   2.599   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.709   1.555   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.691   0.016   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.016  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.358  -0.015   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.683  -0.801   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.376   1.524   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.886   1.827   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.400   1.056   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.291  -0.200   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.867   0.913   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.224  -0.486   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.691  -0.629   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.200   0.627   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.443   2.026   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.448   3.283   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.976   2.169   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.619   3.569   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.728   4.825   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      11.767   2.708   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.686   3.943   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      14.226   3.925   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   38                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   37                                                  
CONECT   10    9   11   19   24                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   35                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18   10   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   10   25                                                  
CONECT   25   24                                                            
CONECT   26   17   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   28   35                                                  
CONECT   35   34   16   36                                                  
CONECT   36   35                                                            
CONECT   37    9   38                                                       
CONECT   38   37    6   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₉

Average Mass

526.4970 Da

Monoisotopic Mass

526.12638 Da

IUPAC Name

(3R,6R,7S,8R)-6,7,12,16-tetrahydroxy-8-[(1S)-4-hydroxy-6-methyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl]pentacyclo[11.8.0.0^{2,10}.0^{3,8}.0^{15,20}]henicosa-1,4,10,12,15,17,19-heptaene-14,21-dione

Traditional Name

(3R,6R,7S,8R)-6,7,12,16-tetrahydroxy-8-[(1S)-4-hydroxy-6-methyl-3-oxo-1H-2-benzofuran-1-yl]pentacyclo[11.8.0.0^{2,10}.0^{3,8}.0^{15,20}]henicosa-1,4,10,12,15,17,19-heptaene-14,21-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)O[C@@H](C2=C1)[C@]12CC3=CC(O)=C4C(=O)C5=C(O)C=CC=C5C(=O)C4=C3[C@H]1C=C[C@@H](O)[C@H]2O

InChI Identifier

InChI=1S/C30H22O9/c1-11-7-14-22(18(33)8-11)29(38)39-28(14)30-10-12-9-19(34)23-24(20(12)15(30)5-6-17(32)27(30)37)25(35)13-3-2-4-16(31)21(13)26(23)36/h2-9,15,17,27-28,31-34,37H,10H2,1H3/t15-,17-,27-,28+,30-/m1/s1

InChI Key

FWHRHQWEGRLEBF-QKXMQONGSA-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
Mycosphaerella rubella	LOTUS Database	35616633
Ramularia collo-cygni	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Fluorene
Isobenzofuranone
Benzofuranone
Phthalide
Isocoumaran
Indane
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
1,2-diol
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen 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	5.09	ChemAxon
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	139.65 m³·mol⁻¹	ChemAxon
Polarizability	51.8 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

52085318

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119026103

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for rubellin c (NP0283654)

MOL for NP0283654 (rubellin c)

3D MOL for NP0283654 (rubellin c)

3D SDF for NP0283654 (rubellin c)

3D-SDF for NP0283654 (rubellin c)

PDB for NP0283654 (rubellin c)

3D PDB for NP0283654 (rubellin c)

SMILES for NP0283654 (rubellin c)

INCHI for NP0283654 (rubellin c)

Structure for NP0283654 (rubellin c)

3D Structure for NP0283654 (rubellin c)