NP-MRD: Showing NP-Card for (10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione (NP0312425)

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Record Information

Version

2.0

Created at

2022-09-11 09:12:12 UTC

Updated at

2022-09-11 09:12:12 UTC

NP-MRD ID

NP0312425

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione

Description

Ostreogrycin a, also known as staphylomycin m or pristinamycin iia, belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group. (10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione was first documented in 2004 (PMID: 15480455). Based on a literature review very few articles have been published on Ostreogrycin a.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112211122D          

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M  END

     RDKit          3D

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  Mrv1652309112211122D          

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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  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  2  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  4  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312425

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1OC(=O)C2=CCCN2C(=O)C2=COC(CC(=O)C[C@@H](O)\C=C(/C)\C=C\CN=C(O)\C=C\[C@@H]1C)=N2

> <INCHI_IDENTIFIER>
InChI=1S/C28H35N3O7/c1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b7-5+,10-9+,18-13+/t19-,20-,26-/m0/s1

> <INCHI_KEY>
DAIKHDNSXMZDCU-YKOULBBISA-N

> <FORMULA>
C28H35N3O7

> <MOLECULAR_WEIGHT>
525.602

> <EXACT_MASS>
525.247500479

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.80460078665312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10S,11S,12E,17E,19E,21R)-14,21-dihydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^{3,7}]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione

> <JCHEM_LOGP>
3.1960252089999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.375984661830495

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.56924522899309

> <JCHEM_PKA_STRONGEST_BASIC>
4.488989260425858

> <JCHEM_POLAR_SURFACE_AREA>
142.53000000000003

> <JCHEM_REFRACTIVITY>
144.69349999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(10S,11S,12E,17E,19E,21R)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^{3,7}]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      10.789  10.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.695   8.663   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.979   7.812   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.357   8.499   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.451  10.036   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      14.641   7.649   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.611   5.964   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.152   5.469   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.569   4.758   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.718   3.474   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      13.235   3.886   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      11.695   3.201   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.843   1.834   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.376   1.973   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.411   4.051   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.506   5.588   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       9.033   3.365   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       8.621   1.881   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.082   1.814   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.688   3.094   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.749   4.215   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.370   3.528   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.276   1.991   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.086   4.379   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.708   3.692   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.614   2.155   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.897   1.305   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.235   1.468   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.424   4.542   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.046   3.856   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.519   6.079   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.897   6.766   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.992   8.303   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.708   9.154   0.000  0.00  0.00           O+0
HETATM   35  N   UNK     0       5.370   8.990   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       6.654   8.140   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.032   8.826   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.316   7.976   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37    2                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
Ostreogrycin g	MeSH
Pristinamycin iia	MeSH
Pristinamycin iib	MeSH
Staphylomycin m	MeSH
Staphylomycin m1	MeSH
Streptogramin a	MeSH
Virginiamycin factor m1	MeSH
Virginiamycin iib	MeSH
Virginiamycin m1	MeSH

Chemical Formula

C₂₈H₃₅N₃O₇

Average Mass

525.6020 Da

Monoisotopic Mass

525.24750 Da

IUPAC Name

(10S,11S,12E,17E,19E,21R)-14,21-dihydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^{3,7}]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione

Traditional Name

(10S,11S,12E,17E,19E,21R)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^{3,7}]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1OC(=O)C2=CCCN2C(=O)C2=COC(CC(=O)C[C@@H](O)\C=C(/C)\C=C\CN=C(O)\C=C\[C@@H]1C)=N2

InChI Identifier

InChI=1S/C28H35N3O7/c1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b7-5+,10-9+,18-13+/t19-,20-,26-/m0/s1

InChI Key

DAIKHDNSXMZDCU-YKOULBBISA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolide lactams

Sub Class

Not Available

Direct Parent

Macrolide lactams

Alternative Parents

Substituents

Macrolide lactam
Macrolactam
Alpha-amino acid or derivatives
2-heteroaryl carboxamide
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary carboxylic acid amide
Pyrroline
Oxazole
Azole
Cyclic ketone
Secondary carboxylic acid amide
Secondary alcohol
Lactone
Lactam
Ketone
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	3.2	ChemAxon
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	4.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	142.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	144.69 m³·mol⁻¹	ChemAxon
Polarizability	54.8 Å³	ChemAxon
Number of Rings	3	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

34526462

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6474110

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dang J, Bergdahl M, Separovic F, Brownlee RT, Metzger RP: Solvent affects the conformation of virginiamycin M1 (pristinamycin IIA, streptogramin A). Org Biomol Chem. 2004 Oct 21;2(20):2919-24. doi: 10.1039/B407724E. Epub 2004 Sep 16. [PubMed:15480455 ]
LOTUS database [Link]

Showing NP-Card for (10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione (NP0312425)

MOL for NP0312425 ((10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione)

3D MOL for NP0312425 ((10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione)

3D SDF for NP0312425 ((10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione)

3D-SDF for NP0312425 ((10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione)

PDB for NP0312425 ((10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione)

3D PDB for NP0312425 ((10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione)

SMILES for NP0312425 ((10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione)

INCHI for NP0312425 ((10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione)

Structure for NP0312425 ((10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione)

3D Structure for NP0312425 ((10s,11s,12e,17e,19e,21r)-14,21-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione)