NP-MRD: Showing NP-Card for (9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone (NP0180002)

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Record Information

Version

2.0

Created at

2022-09-03 18:17:40 UTC

Updated at

2022-09-03 18:17:40 UTC

NP-MRD ID

NP0180002

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone

Description

(9R,10E,12S,13S,16S)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]Pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone is found in Streptomyces hygroscopicus. Based on a literature review very few articles have been published on (9R,10E,12S,13S,16S)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]Pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032220172D          

 37 40  0  0  1  0            999 V2000
    0.3313    1.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309032220172D          

 37 40  0  0  1  0            999 V2000
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 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 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  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 35  1  0  0  0  0
 25 36  1  0  0  0  0
 20 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0180002

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1CCC(=O)C2=C(O)C(C)=CC3=C2C(=O)C2=C(N=C(O)C=C[C@]2(C)C(=O)O[C@@H](C)[C@@H](O)\C=C\1)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H29NO8/c1-5-15-6-8-17(30)14(3)37-27(36)28(4)11-10-19(32)29-23-22(28)26(35)20-16(25(23)34)12-13(2)24(33)21(20)18(31)9-7-15/h6,8,10-12,14-15,17,30,33H,5,7,9H2,1-4H3,(H,29,32)/b8-6+/t14-,15-,17-,28-/m0/s1

> <INCHI_KEY>
YCXQGZJYZGFQSB-DTBCQNQQSA-N

> <FORMULA>
C28H29NO8

> <MOLECULAR_WEIGHT>
507.539

> <EXACT_MASS>
507.189316898

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
53.03586507985921

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,10E,12S,13S,16S)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0^{5,24}.0^{16,22}]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone

> <JCHEM_LOGP>
3.8217930756666654

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.478110575618918

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.356102018037662

> <JCHEM_PKA_STRONGEST_BASIC>
0.6019442311428682

> <JCHEM_POLAR_SURFACE_AREA>
150.56

> <JCHEM_REFRACTIVITY>
138.17539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9R,10E,12S,13S,16S)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0^{5,24}.0^{16,22}]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       0.618   3.619   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.063   3.085   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.323   1.567   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.790   2.396   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.149   1.672   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.456   2.487   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.403   4.026   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.815   1.763   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.121   2.578   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.867   0.224   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.561  -0.591   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.201   0.133   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.613  -2.130   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.802  -1.151   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.114  -2.476   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.778  -3.866   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.107  -5.251   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.064  -6.458   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       6.605  -5.590   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.403  -4.627   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.306  -2.945   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.947  -2.221   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.895  -0.682   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.641  -3.036   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.736  -4.621   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.400  -5.388   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.068  -4.614   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.267  -5.381   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.072  -3.074   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.275  -2.329   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.282  -2.312   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.151  -0.632   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.556  -0.001   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.082   0.477   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.806   1.836   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.068  -5.394   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.064  -6.934   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   21                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   36                                                  
CONECT   21   20   13   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   31                                                  
CONECT   25   24   26   36                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34    3                                                       
CONECT   36   25   20   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₉NO₈

Average Mass

507.5390 Da

Monoisotopic Mass

507.18932 Da

IUPAC Name

(9R,10E,12S,13S,16S)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0^{5,24}.0^{16,22}]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone

Traditional Name

(9R,10E,12S,13S,16S)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0^{5,24}.0^{16,22}]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone

CAS Registry Number

Not Available

SMILES

CC[C@@H]1CCC(=O)C2=C(O)C(C)=CC3=C2C(=O)C2=C(N=C(O)C=C[C@]2(C)C(=O)O[C@@H](C)[C@@H](O)\C=C\1)C3=O

InChI Identifier

InChI=1S/C28H29NO8/c1-5-15-6-8-17(30)14(3)37-27(36)28(4)11-10-19(32)29-23-22(28)26(35)20-16(25(23)34)12-13(2)24(33)21(20)18(31)9-7-15/h6,8,10-12,14-15,17,30,33H,5,7,9H2,1-4H3,(H,29,32)/b8-6+/t14-,15-,17-,28-/m0/s1

InChI Key

YCXQGZJYZGFQSB-DTBCQNQQSA-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 hygroscopicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Naphthoquinone
Naphthalene
Quinone
Aryl ketone
Aryl alkyl ketone
Azepine
Benzenoid
Vinylogous acid
Cyclic carboximidic acid
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Organoheterocyclic compound
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Oxacycle
Alcohol
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen 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	3.82	ChemAxon
pKa (Strongest Acidic)	5.36	ChemAxon
pKa (Strongest Basic)	0.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	150.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	138.18 m³·mol⁻¹	ChemAxon
Polarizability	53.04 Å³	ChemAxon
Number of Rings	4	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

163189435

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone (NP0180002)

MOL for NP0180002 ((9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone)

3D MOL for NP0180002 ((9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone)

3D SDF for NP0180002 ((9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone)

3D-SDF for NP0180002 ((9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone)

PDB for NP0180002 ((9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone)

3D PDB for NP0180002 ((9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone)

SMILES for NP0180002 ((9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone)

INCHI for NP0180002 ((9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone)

Structure for NP0180002 ((9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone)

3D Structure for NP0180002 ((9r,10e,12s,13s,16s)-9-ethyl-4,12,19-trihydroxy-3,13,16-trimethyl-14-oxa-20-azatetracyclo[19.3.1.0⁵,²⁴.0¹⁶,²²]pentacosa-1(24),2,4,10,17,19,21-heptaene-6,15,23,25-tetrone)