NP-MRD: Showing NP-Card for (3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one (NP0261116)

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Record Information

Version

2.0

Created at

2022-09-08 03:28:42 UTC

Updated at

2022-09-08 03:28:43 UTC

NP-MRD ID

NP0261116

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one

Description

10-Epi-HSAF belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units. (3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one was first documented in 2020 (PMID: 32506015). Based on a literature review very few articles have been published on 10-epi-HSAF (PMID: 34436279).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082205282D          

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M  END


  Mrv1652309082205282D          

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    5.5858   -5.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703   -6.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9366   -5.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3274   -5.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8937   -4.4146    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8339   -3.9333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0705   -3.6205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8748   -2.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  4  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  4  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  1  0  0  0
 12 34  1  0  0  0  0
  7 34  1  0  0  0  0
 35  8  1  6  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0261116

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1C[C@H]2C[C@@H]3[C@@H]([C@H]2[C@@H]1C)[C@H](O)C[C@@H]1\C=C\C(O)=C2C(O)=N[C@@H]([C@@H](O)CCN=C(O)\C=C/C[C@@H]31)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40N2O6/c1-3-15-11-17-12-19-18-5-4-6-23(35)30-10-9-21(33)27-28(36)26(29(37)31-27)20(32)8-7-16(18)13-22(34)25(19)24(17)14(15)2/h4,6-8,14-19,21-22,24-25,27,32-34H,3,5,9-13H2,1-2H3,(H,30,35)(H,31,37)/b6-4-,8-7+,26-20?/t14-,15?,16+,17+,18-,19+,21+,22-,24+,25-,27+/m1/s1

> <INCHI_KEY>
VYCDZNHSSDXACI-KZDBETSCSA-N

> <FORMULA>
C29H40N2O6

> <MOLECULAR_WEIGHT>
512.647

> <EXACT_MASS>
512.288637016

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.81270490699044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E,5R,7R,8S,9R,10R,13S,15S,16R,18Z,24S,25S)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0^{5,16}.0^{8,15}.0^{9,13}]octacosa-1,3,18,20,26-pentaen-28-one

> <JCHEM_LOGP>
1.4392947044246613

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.834887296950687

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8201472950191198

> <JCHEM_PKA_STRONGEST_BASIC>
6.639583149275237

> <JCHEM_POLAR_SURFACE_AREA>
142.94

> <JCHEM_REFRACTIVITY>
142.67090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3E,5R,7R,8S,9R,10R,13S,15S,16R,18Z,24S,25S)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0^{5,16}.0^{8,15}.0^{9,13}]octacosa-1,3,18,20,26-pentaen-28-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.201  -6.431   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.533  -7.818   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.003  -7.933   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.812  -9.243   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.308  -8.878   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.733  -9.462   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.729  -8.287   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.919  -6.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.649  -5.621   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.839  -4.311   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.188  -5.574   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.998  -6.884   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.537  -6.838   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.267  -5.482   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.806  -5.436   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.536  -4.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.616  -6.746   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.886  -8.102   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.347  -8.148   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.696  -9.412   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      14.140  -8.717   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      14.094  -7.178   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      15.312  -6.235   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.966 -10.768   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.505 -10.722   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.776 -12.078   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.046 -13.434   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      10.507 -13.481   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       9.697 -12.171   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.427 -10.814   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.158 -12.217   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.348 -10.907   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.078  -9.551   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.268  -8.241   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.423  -7.342   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.998  -6.758   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.633  -5.262   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   34                                                  
CONECT    8    7    9   35                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   34                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   12    7                                                  
CONECT   35    8    5   36                                                  
CONECT   36   35    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀N₂O₆

Average Mass

512.6470 Da

Monoisotopic Mass

512.28864 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC1C[C@H]2C[C@@H]3[C@@H]([C@H]2[C@@H]1C)[C@H](O)C[C@@H]1\C=C\C(O)=C2C(O)=N[C@@H]([C@@H](O)CCN=C(O)\C=C/C[C@@H]31)C2=O

InChI Identifier

InChI=1S/C29H40N2O6/c1-3-15-11-17-12-19-18-5-4-6-23(35)30-10-9-21(33)27-28(36)26(29(37)31-27)20(32)8-7-16(18)13-22(34)25(19)24(17)14(15)2/h4,6-8,14-19,21-22,24-25,27,32-34H,3,5,9-13H2,1-2H3,(H,30,35)(H,31,37)/b6-4-,8-7+,26-20?/t14-,15?,16+,17+,18-,19+,21+,22-,24+,25-,27+/m1/s1

InChI Key

VYCDZNHSSDXACI-KZDBETSCSA-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 monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monoterpenoids

Alternative Parents

Substituents

Monoterpenoid
Vinylogous acid
Cyclic carboximidic acid
Pyrroline
Cyclic alcohol
Secondary alcohol
Ketone
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Enol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

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

146683098

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hou L, Liu Z, Yu D, Li H, Ju J, Li W: Targeted isolation of new polycyclic tetramate macrolactams from the deepsea-derived Streptomyces somaliensis SCSIO ZH66. Bioorg Chem. 2020 Aug;101:103954. doi: 10.1016/j.bioorg.2020.103954. Epub 2020 May 24. [PubMed:32506015 ]
Ding W, Tu J, Zhang H, Wei X, Ju J, Li Q: Genome Mining and Metabolic Profiling Uncover Polycyclic Tetramate Macrolactams from Streptomyces koyangensis SCSIO 5802. Mar Drugs. 2021 Jul 31;19(8):440. doi: 10.3390/md19080440. [PubMed:34436279 ]
LOTUS database [Link]

Showing NP-Card for (3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one (NP0261116)

MOL for NP0261116 ((3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one)

3D MOL for NP0261116 ((3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one)

3D SDF for NP0261116 ((3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one)

3D-SDF for NP0261116 ((3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one)

PDB for NP0261116 ((3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one)

3D PDB for NP0261116 ((3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one)

SMILES for NP0261116 ((3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one)

INCHI for NP0261116 ((3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one)

Structure for NP0261116 ((3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one)

3D Structure for NP0261116 ((3e,5r,7r,8s,9r,10r,13s,15s,16r,18z,24s,25s)-11-ethyl-2,7,20,24,27-pentahydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1,3,18,20,26-pentaen-28-one)