NP-MRD: Showing NP-Card for (3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol (NP0323606)

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Record Information

Version

2.0

Created at

2022-09-12 03:08:29 UTC

Updated at

2022-09-12 03:08:29 UTC

NP-MRD ID

NP0323606

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol

Description

Macrotermycin C belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol was first documented in 2019 (PMID: 31651919). Based on a literature review very few articles have been published on Macrotermycin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122205082D          

 36 37  0  0  1  0            999 V2000
    5.0013    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    7.1447    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1652309122205082D          

 36 37  0  0  1  0            999 V2000
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 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 14 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0323606

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CN=C(O)\C=C\C=C\[C@](C)(O)[C@H](O[C@H]2OC[C@H](O)[C@@H](O)[C@@H]2N)\C=C/C=C/C=C\C=C\[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H38N2O8/c1-17-15-28-21(31)13-9-10-14-26(2,34)20(36-25-22(27)24(33)19(30)16-35-25)12-8-6-4-3-5-7-11-18(29)23(17)32/h3-14,17-20,22-25,29-30,32-34H,15-16,27H2,1-2H3,(H,28,31)/b5-3-,6-4+,11-7+,12-8-,13-9+,14-10+/t17-,18-,19+,20-,22+,23+,24-,25-,26+/m1/s1

> <INCHI_KEY>
ZHZBXNGMWSNGPS-OCDFGKNASA-N

> <FORMULA>
C26H38N2O8

> <MOLECULAR_WEIGHT>
506.596

> <EXACT_MASS>
506.262816192

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.37601070787566

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E,5E,7S,8R,9Z,11E,13Z,15E,17R,18S,19R)-8-{[(2R,3S,4S,5S)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol

> <JCHEM_LOGP>
-1.8603224468345478

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.864766262392838

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.740873169272875

> <JCHEM_PKA_STRONGEST_BASIC>
8.143288763657827

> <JCHEM_POLAR_SURFACE_AREA>
178.21999999999997

> <JCHEM_REFRACTIVITY>
141.19020000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3E,5E,7S,8R,9Z,11E,13Z,15E,17R,18S,19R)-8-{[(2R,3S,4S,5S)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  17.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  16.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  15.400   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      12.003  16.170   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      13.337  15.400   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.670  16.170   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      13.337  13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003  13.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.186   9.507   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.196   7.793   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669   7.700   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336   5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337   3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.003   5.390   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      13.337   6.160   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.336  13.090   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002  15.400   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.668  16.170   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16   24                                                  
CONECT   24   23                                                            
CONECT   25   14   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    2   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈N₂O₈

Average Mass

506.5960 Da

Monoisotopic Mass

506.26282 Da

IUPAC Name

(3E,5E,7S,8R,9Z,11E,13Z,15E,17R,18S,19R)-8-{[(2R,3S,4S,5S)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol

Traditional Name

(3E,5E,7S,8R,9Z,11E,13Z,15E,17R,18S,19R)-8-{[(2R,3S,4S,5S)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol

CAS Registry Number

Not Available

SMILES

C[C@@H]1CN=C(O)\C=C\C=C\[C@](C)(O)[C@H](O[C@H]2OC[C@H](O)[C@@H](O)[C@@H]2N)\C=C/C=C/C=C\C=C\[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H38N2O8/c1-17-15-28-21(31)13-9-10-14-26(2,34)20(36-25-22(27)24(33)19(30)16-35-25)12-8-6-4-3-5-7-11-18(29)23(17)32/h3-14,17-20,22-25,29-30,32-34H,15-16,27H2,1-2H3,(H,28,31)/b5-3-,6-4+,11-7+,12-8-,13-9+,14-10+/t17-,18-,19+,20-,22+,23+,24-,25-,26+/m1/s1

InChI Key

ZHZBXNGMWSNGPS-OCDFGKNASA-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 o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Sugar acid
Oxane
Monosaccharide
Cyclic carboximidic acid
Tertiary alcohol
Secondary alcohol
1,2-aminoalcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Acetal
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-1.9	ChemAxon
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	8.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	141.19 m³·mol⁻¹	ChemAxon
Polarizability	52.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

78439309

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132821224

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guchhait S, Goswami RK: Studies toward the synthesis of macrotermycin C: stereoselective construction of the acyclic skeleton of the aglycon. Org Biomol Chem. 2019 Nov 6;17(43):9502-9509. doi: 10.1039/c9ob01999e. [PubMed:31651919 ]
LOTUS database [Link]

Showing NP-Card for (3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol (NP0323606)

MOL for NP0323606 ((3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol)

3D MOL for NP0323606 ((3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol)

3D SDF for NP0323606 ((3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol)

3D-SDF for NP0323606 ((3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol)

PDB for NP0323606 ((3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol)

3D PDB for NP0323606 ((3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol)

SMILES for NP0323606 ((3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol)

INCHI for NP0323606 ((3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol)

Structure for NP0323606 ((3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol)

3D Structure for NP0323606 ((3e,5e,7s,8r,9z,11e,13z,15e,17r,18s,19r)-8-{[(2r,3s,4s,5s)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-7,19-dimethyl-1-azacycloicosa-1,3,5,9,11,13,15-heptaene-2,7,17,18-tetrol)