NP-MRD: Showing NP-Card for 24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone (NP0257548)

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Record Information

Version

2.0

Created at

2022-09-07 22:41:58 UTC

Updated at

2022-09-07 22:41:58 UTC

NP-MRD ID

NP0257548

Secondary Accession Numbers

None

Natural Product Identification

Common Name

24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone

Description

24-Hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]Nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. 24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone is found in Streptomyces griseus. Based on a literature review very few articles have been published on 24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]Nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082200412D          

 38 44  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1652309082200412D          

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 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 23 36  1  0  0  0  0
 18 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0257548

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(=O)C3=C(OC2=C1)C(=O)C1=CC=C2C=C4CC5(OC)OCCN5C(=O)C4=CC2=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H19NO9/c1-35-20-10-19-17(9-18(20)30)23(31)22-25(33)21-14(24(32)26(22)38-19)4-3-12-7-13-11-28(36-2)29(5-6-37-28)27(34)16(13)8-15(12)21/h3-4,7-10,30H,5-6,11H2,1-2H3

> <INCHI_KEY>
JQHVKHVBFDXYKS-UHFFFAOYSA-N

> <FORMULA>
C28H19NO9

> <MOLECULAR_WEIGHT>
513.458

> <EXACT_MASS>
513.105981196

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
52.68713260906342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0^{2,14}.0^{4,12}.0^{6,10}.0^{19,28}.0^{21,26}]nonacosa-1,3,12,14,16,19(28),21,23,25-nonaene-5,18,27,29-tetrone

> <JCHEM_LOGP>
2.6360931040000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.106453081223652

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7084511758951164

> <JCHEM_POLAR_SURFACE_AREA>
128.67000000000002

> <JCHEM_REFRACTIVITY>
133.92949999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0^{2,14}.0^{4,12}.0^{6,10}.0^{19,28}.0^{21,26}]nonacosa-1,3,12,14,16,19(28),21,23,25-nonaene-5,18,27,29-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      20.017   1.548   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      19.234   2.874   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      17.694   2.858   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.910   4.184   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.371   4.169   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.587   5.495   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      13.047   5.479   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.291   4.138   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.074   2.812   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.318   1.471   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.614   2.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.397   1.501   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.937   1.517   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.721   0.191   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.751   4.122   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.994   2.781   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.967   5.448   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.724   6.789   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.941   8.115   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.401   8.100   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.644   6.759   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.104   6.743   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.348   5.402   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.131   4.076   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.671   4.091   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.428   5.433   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.374   2.734   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.158   1.409   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0       3.835   2.719   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       2.816   1.564   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.403   2.176   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.548   3.710   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.051   4.045   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.134   5.282   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.604   5.105   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.808   5.386   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.264   6.805   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      13.020   8.146   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13                                                            
CONECT   15    8   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   26                                                  
CONECT   18   17   19   37                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   36                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   17   21                                                  
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   29   34   36                                             
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   23                                                       
CONECT   37   18    7   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₁₉NO₉

Average Mass

513.4580 Da

Monoisotopic Mass

513.10598 Da

IUPAC Name

24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0^{2,14}.0^{4,12}.0^{6,10}.0^{19,28}.0^{21,26}]nonacosa-1,3,12,14,16,19(28),21,23,25-nonaene-5,18,27,29-tetrone

Traditional Name

24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0^{2,14}.0^{4,12}.0^{6,10}.0^{19,28}.0^{21,26}]nonacosa-1,3,12,14,16,19(28),21,23,25-nonaene-5,18,27,29-tetrone

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(=O)C3=C(OC2=C1)C(=O)C1=CC=C2C=C4CC5(OC)OCCN5C(=O)C4=CC2=C1C3=O

InChI Identifier

InChI=1S/C28H19NO9/c1-35-20-10-19-17(9-18(20)30)23(31)22-25(33)21-14(24(32)26(22)38-19)4-3-12-7-13-11-28(36-2)29(5-6-37-28)27(34)16(13)8-15(12)21/h3-4,7-10,30H,5-6,11H2,1-2H3

InChI Key

JQHVKHVBFDXYKS-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
Streptomyces griseus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Naphthopyranone
Phenanthrene
Naphthopyran
Isoquinolone
Chromone
Tetrahydroisoquinoline
Naphthalene
Aryl ketone
Anisole
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Amide acetal
Heteroaromatic compound
Tertiary carboxylic acid amide
Oxazolidine
Orthocarboxylic acid derivative
Lactam
Ketone
Carboxamide group
Oxacycle
Azacycle
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	2.64	ChemAxon
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	128.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.93 m³·mol⁻¹	ChemAxon
Polarizability	52.69 Å³	ChemAxon
Number of Rings	7	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

162816384

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone (NP0257548)

MOL for NP0257548 (24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone)

3D MOL for NP0257548 (24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone)

3D SDF for NP0257548 (24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone)

3D-SDF for NP0257548 (24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone)

PDB for NP0257548 (24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone)

3D PDB for NP0257548 (24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone)

SMILES for NP0257548 (24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone)

INCHI for NP0257548 (24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone)

Structure for NP0257548 (24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone)

3D Structure for NP0257548 (24-hydroxy-10,23-dimethoxy-9,20-dioxa-6-azaheptacyclo[15.12.0.0²,¹⁴.0⁴,¹².0⁶,¹⁰.0¹⁹,²⁸.0²¹,²⁶]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone)