NP-MRD: Showing NP-Card for (1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one (NP0251876)

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Record Information

Version

2.0

Created at

2022-09-07 15:12:33 UTC

Updated at

2022-09-07 15:12:33 UTC

NP-MRD ID

NP0251876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one

Description

(1S,4E,6R,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]Docosa-4,12,21-trien-3-one 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. (1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one is found in Boeremia exigua and Sonchus mauritanicus. Based on a literature review very few articles have been published on (1S,4E,6R,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]Docosa-4,12,21-trien-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217122D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072217122D          

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 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 29  1  1  0  0  0
 15 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0251876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)N=C(O)[C@]22OC(=O)\C=C\[C@H](O)CCCCC\C=C\[C@H]2[C@@H]2O[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H35NO5/c1-18-24-22(17-19-11-7-6-8-12-19)29-26(32)28(24)21(25-27(18,2)34-25)14-10-5-3-4-9-13-20(30)15-16-23(31)33-28/h6-8,10-12,14-16,18,20-22,24-25,30H,3-5,9,13,17H2,1-2H3,(H,29,32)/b14-10+,16-15+/t18-,20+,21-,22-,24-,25-,27+,28+/m0/s1

> <INCHI_KEY>
WHFRGAGFFDXGCA-IZYCEXTPSA-N

> <FORMULA>
C28H35NO5

> <MOLECULAR_WEIGHT>
465.59

> <EXACT_MASS>
465.251523231

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.88629928300109

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4E,6R,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0^{1,19}.0^{15,17}]docosa-4,12,21-trien-3-one

> <JCHEM_LOGP>
3.5916844736239937

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.833654503480513

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8938544260560213

> <JCHEM_PKA_STRONGEST_BASIC>
4.780394718989687

> <JCHEM_POLAR_SURFACE_AREA>
91.65

> <JCHEM_REFRACTIVITY>
130.63060000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4E,6R,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0^{1,19}.0^{15,17}]docosa-4,12,21-trien-3-one

> <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       9.766  -3.932   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.902  -2.657   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.366  -2.768   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.421  -3.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.849  -5.463   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.781  -6.574   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.209  -8.053   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.142  -9.163   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.647  -8.794   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.219  -7.314   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.286  -6.204   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.973  -3.460   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       4.982  -2.135   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.807  -0.976   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.502  -1.494   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.966  -1.604   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.294  -2.990   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.158  -4.265   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.758  -3.101   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.894  -1.826   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.358  -1.937   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.314  -3.323   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.506  -0.662   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.166   0.724   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.702   0.834   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.374   2.220   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.910   2.331   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.774   1.056   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.310   1.167   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.174  -0.108   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.710   0.003   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.246   0.114   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.574  -1.272   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.960  -1.944   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    4   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    3   16   30                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   15   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   33                                                       
CONECT   33   32    2   31   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅NO₅

Average Mass

465.5900 Da

Monoisotopic Mass

465.25152 Da

IUPAC Name

(1S,4E,6R,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0^{1,19}.0^{15,17}]docosa-4,12,21-trien-3-one

Traditional Name

(1S,4E,6R,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0^{1,19}.0^{15,17}]docosa-4,12,21-trien-3-one

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)N=C(O)[C@]22OC(=O)\C=C\[C@H](O)CCCCC\C=C\[C@H]2[C@@H]2O[C@]12C

InChI Identifier

InChI=1S/C28H35NO5/c1-18-24-22(17-19-11-7-6-8-12-19)29-26(32)28(24)21(25-27(18,2)34-25)14-10-5-3-4-9-13-20(30)15-16-23(31)33-28/h6-8,10-12,14-16,18,20-22,24-25,30H,3-5,9,13,17H2,1-2H3,(H,29,32)/b14-10+,16-15+/t18-,20+,21-,22-,24-,25-,27+,28+/m0/s1

InChI Key

WHFRGAGFFDXGCA-IZYCEXTPSA-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
Phoma exigua	LOTUS Database	35616633
Sonchus mauritanicus	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
Isoindole or derivatives
Oxepane
Monocyclic benzene moiety
Benzenoid
Pyrroline
Cyclic carboximidic acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen 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	3.59	ChemAxon
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	4.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.65 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	130.63 m³·mol⁻¹	ChemAxon
Polarizability	50.89 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162955063

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one (NP0251876)

MOL for NP0251876 ((1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one)

3D MOL for NP0251876 ((1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one)

3D SDF for NP0251876 ((1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one)

3D-SDF for NP0251876 ((1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one)

PDB for NP0251876 ((1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one)

3D PDB for NP0251876 ((1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one)

SMILES for NP0251876 ((1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one)

INCHI for NP0251876 ((1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one)

Structure for NP0251876 ((1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one)

3D Structure for NP0251876 ((1s,4e,6r,12e,14s,15s,17r,18s,19s,20s)-20-benzyl-6,22-dihydroxy-17,18-dimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.0¹,¹⁹.0¹⁵,¹⁷]docosa-4,12,21-trien-3-one)