NP-MRD: Showing NP-Card for 9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate (NP0254914)

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Record Information

Version

2.0

Created at

2022-09-07 19:13:43 UTC

Updated at

2022-09-07 19:13:43 UTC

NP-MRD ID

NP0254914

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate

Description

NSC635471 belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds. 9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate is found in Shiraia bambusicola. Based on a literature review very few articles have been published on NSC635471.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072221132D          

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M  END

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M  END


  Mrv1652309072221132D          

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 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  3 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 27 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 29 39  2  0  0  0  0
  6 39  1  0  0  0  0
 13 39  1  0  0  0  0
 28 40  2  0  0  0  0
 21 40  1  0  0  0  0
 14 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254914

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C2=C(O)C(OC)=C3CC(C)=C(OC(C)=O)C4=C(OC)C(O)=C5C(=O)C=C(OC)C6=C1C2=C3C4=C56

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O10/c1-10-7-12-17-22-18(26(34)29(12)38-5)13(32)8-15(36-3)20(22)21-16(37-4)9-14(33)19-24(21)23(17)25(28(10)40-11(2)31)30(39-6)27(19)35/h8-9,34-35H,7H2,1-6H3

> <INCHI_KEY>
QPQNBGHSICMGOP-UHFFFAOYSA-N

> <FORMULA>
C30H24O10

> <MOLECULAR_WEIGHT>
544.512

> <EXACT_MASS>
544.136946973

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
54.79635191157758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{4,22}.0^{18,23}]tricosa-1(23),2,4(22),5,8,10,12,15,17,20-decaen-12-yl acetate

> <JCHEM_LOGP>
3.065059042333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.656554013041941

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.027417452290126

> <JCHEM_PKA_STRONGEST_BASIC>
3.648561065205031

> <JCHEM_POLAR_SURFACE_AREA>
137.82000000000002

> <JCHEM_REFRACTIVITY>
147.9792

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{4,22}.0^{18,23}]tricosa-1(23),2,4(22),5,8,10,12,15,17,20-decaen-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.576   9.188   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.941   8.474   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.004   6.936   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.333   6.157   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.672   6.918   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.323   4.617   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.652   3.839   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.990   4.600   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.642   2.299   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.303   1.537   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.293  -0.003   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.622  -0.781   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.975   2.316   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.636   1.554   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.626   0.014   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.955  -0.764   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.945  -2.304   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.287  -0.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.041   0.032   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.380  -0.730   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.031   1.572   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.360   2.350   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.699   1.589   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.350   3.890   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.640   4.731   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.013   4.035   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.113   4.445   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.317   3.873   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.656   4.634   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.895   6.156   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.855   7.291   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.319   7.186   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.443   8.525   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.557   5.919   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.078   6.159   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.632   7.596   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.153   7.835   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.664   8.794   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.985   3.856   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.307   2.333   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   39                                                  
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   14   39                                                  
CONECT   14   13   15   40                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   40                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   34                                                  
CONECT   28   27   29   40                                                  
CONECT   29   28   30   39                                                  
CONECT   30   29    3   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   29    6   13                                                  
CONECT   40   28   21   14                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₄O₁₀

Average Mass

544.5120 Da

Monoisotopic Mass

544.13695 Da

IUPAC Name

9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{4,22}.0^{18,23}]tricosa-1(23),2,4(22),5,8,10,12,15,17,20-decaen-12-yl acetate

Traditional Name

9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{4,22}.0^{18,23}]tricosa-1(23),2,4(22),5,8,10,12,15,17,20-decaen-12-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=C(O)C(OC)=C3CC(C)=C(OC(C)=O)C4=C(OC)C(O)=C5C(=O)C=C(OC)C6=C1C2=C3C4=C56

InChI Identifier

InChI=1S/C30H24O10/c1-10-7-12-17-22-18(26(34)29(12)38-5)13(32)8-15(36-3)20(22)21-16(37-4)9-14(33)19-24(21)23(17)25(28(10)40-11(2)31)30(39-6)27(19)35/h8-9,34-35H,7H2,1-6H3

InChI Key

QPQNBGHSICMGOP-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
Shiraia bambusicola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Perylenequinones

Sub Class

Not Available

Direct Parent

Perylenequinones

Alternative Parents

Substituents

Perylenequinone
Phenanthrol
Anthracene
Phenanthrene
2-naphthol
1-naphthol
Anisole
Alkyl aryl ether
Enol ester
Vinylogous ester
Vinylogous acid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.07	ChemAxon
pKa (Strongest Acidic)	7.03	ChemAxon
pKa (Strongest Basic)	3.65	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	137.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	147.98 m³·mol⁻¹	ChemAxon
Polarizability	54.8 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

325559

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

366744

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate (NP0254914)

MOL for NP0254914 (9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate)

3D MOL for NP0254914 (9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate)

3D SDF for NP0254914 (9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate)

3D-SDF for NP0254914 (9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate)

PDB for NP0254914 (9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate)

3D PDB for NP0254914 (9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate)

SMILES for NP0254914 (9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate)

INCHI for NP0254914 (9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate)

Structure for NP0254914 (9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate)

3D Structure for NP0254914 (9,17-dihydroxy-5,10,16,21-tetramethoxy-13-methyl-7,19-dioxohexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,12,16,18(23),20-decaen-12-yl acetate)