NP-MRD: Showing NP-Card for 19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione (NP0216148)

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Record Information

Version

2.0

Created at

2022-09-05 15:59:45 UTC

Updated at

2022-09-05 15:59:46 UTC

NP-MRD ID

NP0216148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione

Description

19-[(4,5-Dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]Henicosa-1(13),7(12),8,10,15(20),16,18-heptaene-4,14,21-trione belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond. 19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione is found in Streptomyces venezuelae. 19-[(4,5-Dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]Henicosa-1(13),7(12),8,10,15(20),16,18-heptaene-4,14,21-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241509062D          

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M  END

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M  END


  Mrv1533004241509062D          

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 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  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
 18 34  1  0  0  0  0
 27 34  1  0  0  0  0
 19 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 11 37  1  0  0  0  0
 15 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0216148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1N2C(OC1=O)C1=CC(C)=CC(O)=C1C1=C2C(=O)C2=C(C=CC=C2OC2CC(O)C(O)C(C)O2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H25NO9/c1-10-7-14-19(15(29)8-10)21-22(28-11(2)27(34)37-26(14)28)25(33)20-13(24(21)32)5-4-6-17(20)36-18-9-16(30)23(31)12(3)35-18/h4-8,11-12,16,18,23,26,29-31H,9H2,1-3H3

> <INCHI_KEY>
RZOHWPFQSWBZBM-UHFFFAOYSA-N

> <FORMULA>
C27H25NO9

> <MOLECULAR_WEIGHT>
507.495

> <EXACT_MASS>
507.152931389

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.94504640649766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15(20),16,18-heptaene-4,14,21-trione

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.5061882019999997

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.877180766185681

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.183477005999986

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2528866875223716

> <JCHEM_POLAR_SURFACE_AREA>
142.83

> <JCHEM_REFRACTIVITY>
129.09329999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15(20),16,18-heptaene-4,14,21-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.961   4.863   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.465   3.408   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.978   3.117   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.482   1.661   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.473   0.497   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.961   0.788   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.953  -0.376   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.457   2.243   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.945   2.534   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.994   1.370   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.498  -0.085   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.490  -1.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.994  -2.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.506  -2.995   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.514  -1.831   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.027  -2.122   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.531  -3.577   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.035  -0.958   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.531   0.497   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      12.539   1.661   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      12.348   3.190   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.000   3.934   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.743   3.843   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.034   5.355   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      14.795   2.719   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.051   1.370   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.555  -0.085   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.067  -0.376   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.571  -1.831   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.084  -2.122   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.563  -2.995   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.051  -2.704   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.043  -3.868   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      13.547  -1.249   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.018   0.788   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.514   2.243   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.010  -0.376   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12   37                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   37                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   34                                                  
CONECT   19   18   20   35                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20   27                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   18   27                                                  
CONECT   35   19   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   11   15                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₅NO₉

Average Mass

507.4950 Da

Monoisotopic Mass

507.15293 Da

IUPAC Name

19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15(20),16,18-heptaene-4,14,21-trione

Traditional Name

19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15(20),16,18-heptaene-4,14,21-trione

CAS Registry Number

Not Available

SMILES

CC1N2C(OC1=O)C1=CC(C)=CC(O)=C1C1=C2C(=O)C2=C(C=CC=C2OC2CC(O)C(O)C(C)O2)C1=O

InChI Identifier

InChI=1S/C27H25NO9/c1-10-7-14-19(15(29)8-10)21-22(28-11(2)27(34)37-26(14)28)25(33)20-13(24(21)32)5-4-6-17(20)36-18-9-16(30)23(31)12(3)35-18/h4-8,11-12,16,18,23,26,29-31H,9H2,1-3H3

InChI Key

RZOHWPFQSWBZBM-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 venezuelae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Phenylpyridines

Direct Parent

Phenylpyridines

Alternative Parents

Substituents

3-phenylpyridine
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Hydroxypyridine
Phenol
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Secondary alcohol
Ketone
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.91	ALOGPS
logP	2.51	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	142.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	129.09 m³·mol⁻¹	ChemAxon
Polarizability	50.95 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	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione (NP0216148)

MOL for NP0216148 (19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

3D MOL for NP0216148 (19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

3D SDF for NP0216148 (19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

3D-SDF for NP0216148 (19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

PDB for NP0216148 (19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

3D PDB for NP0216148 (19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

SMILES for NP0216148 (19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

INCHI for NP0216148 (19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

Structure for NP0216148 (19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

3D Structure for NP0216148 (19-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-11-hydroxy-3,9-dimethyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)