NP-MRD: Showing NP-Card for asterresin A (NP0332300)

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Record Information

Version

2.0

Created at

2024-01-04 04:04:20 UTC

Updated at

2024-09-03 04:18:45 UTC

NP-MRD ID

NP0332300

Natural Product DOI

https://doi.org/10.57994/1502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

asterresin A

Description

(1R,9S)-5-(1H-indol-3-yl)-3,6-dimethoxy-8-oxa-10-azatetracyclo[7.7.0.0²,⁷.0¹¹,¹⁶]Hexadeca-2,4,6,11,13,15-hexaene-1,4-diol belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Based on a literature review very few articles have been published on (1R,9S)-5-(1H-indol-3-yl)-3,6-dimethoxy-8-oxa-10-azatetracyclo[7.7.0.0²,⁷.0¹¹,¹⁶]Hexadeca-2,4,6,11,13,15-hexaene-1,4-diol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01042404042D          

 32 37  0  0  1  0            999 V2000
    2.9760   -2.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -1.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1321   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6170   -2.2281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -2.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773    0.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8568    0.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -0.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062   -1.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -0.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005   -0.7881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5937   -1.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486   -2.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2966   -3.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4896   -3.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2347   -2.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676    0.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522    0.2730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2522    1.0980    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369    0.5279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5218   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6778   -0.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1929   -1.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522   -0.5520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2522   -1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
  2 11  1  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  7 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 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
 25 30  1  0  0  0  0
 31 30  1  0  0  0  0
 22 31  1  0  0  0  0
 31  6  1  0  0  0  0
 31 32  1  1  0  0  0
M  END


  Mrv2104 01042404042D          

 32 37  0  0  1  0            999 V2000
    2.9760   -2.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -1.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1321   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6170   -2.2281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -2.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773    0.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8568    0.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -0.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062   -1.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -0.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005   -0.7881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5937   -1.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486   -2.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2966   -3.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4896   -3.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2347   -2.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676    0.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522    0.2730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2522    1.0980    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369    0.5279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5218   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6778   -0.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1929   -1.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724   -1.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522   -0.5520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2522   -1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
  2 11  1  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  7 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 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
 25 30  1  0  0  0  0
 31 30  1  0  0  0  0
 22 31  1  0  0  0  0
 31  6  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0332300

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12NC3=CC=CC=C3[C@]1(O)C1=C(O2)C(OC)=C(C2=CNC3=C2C=CC=C3)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H20N2O5/c1-29-20-17(13-11-25-15-9-5-3-7-12(13)15)19(27)21(30-2)18-22(20)31-23-24(18,28)14-8-4-6-10-16(14)26-23/h3-11,23,25-28H,1-2H3/t23-,24-/m0/s1

> <INCHI_KEY>
BNNQNJBXFAFMOE-ZEQRLZLVSA-N

> <FORMULA>
C24H20N2O5

> <MOLECULAR_WEIGHT>
416.433

> <EXACT_MASS>
416.137221752

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.13978827706997

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S)-5-(1H-indol-3-yl)-3,6-dimethoxy-8-oxa-10-azatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,11,13,15-hexaene-1,4-diol

> <JCHEM_LOGP>
3.2001998916666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.074394190880504

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.843133581813213

> <JCHEM_PKA_STRONGEST_BASIC>
-1.483512790804065

> <JCHEM_POLAR_SURFACE_AREA>
95.97

> <JCHEM_REFRACTIVITY>
115.83390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S)-5-(1H-indol-3-yl)-3,6-dimethoxy-8-oxa-10-azatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,11,13,15-hexaene-1,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JAN-24         0                                  
HETATM    1  O   UNK     0       5.555  -4.481   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.182  -3.074   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.713  -2.913   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.618  -4.159   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.150  -3.998   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.340  -1.506   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.434  -0.260   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.903  -0.421   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.998   0.824   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.466   0.663   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.276  -1.828   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.745  -1.989   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.714  -0.845   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.308  -1.471   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.469  -3.003   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.975  -3.323   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.451  -4.788   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.420  -5.932   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.914  -5.612   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.438  -4.147   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.340   0.985   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.804   0.510   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       9.804   2.050   0.000  0.00  0.00           H+0
HETATM   24  N   UNK     0      11.269   0.985   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      12.174  -0.260   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.706  -0.421   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.332  -1.828   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.427  -3.074   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.895  -2.913   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.269  -1.506   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.804  -1.030   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.804  -2.570   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7   31                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8    2   12                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    7   22                                                       
CONECT   22   21   23   24   31                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30   22    6   32                                             
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₀N₂O₅

Average Mass

416.4330 Da

Monoisotopic Mass

416.13722 Da

IUPAC Name

(1S,9S)-5-(1H-indol-3-yl)-3,6-dimethoxy-8-oxa-10-azatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,11,13,15-hexaene-1,4-diol

Traditional Name

(1S,9S)-5-(1H-indol-3-yl)-3,6-dimethoxy-8-oxa-10-azatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,11,13,15-hexaene-1,4-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]12NC3=CC=CC=C3[C@]1(O)C1=C(O2)C(OC)=C(C2=CNC3=C2C=CC=C3)C(O)=C1OC

InChI Identifier

InChI=1S/C24H20N2O5/c1-29-20-17(13-11-25-15-9-5-3-7-12(13)15)19(27)21(30-2)18-22(20)31-23-24(18,28)14-8-4-6-10-16(14)26-23/h3-11,23,25-28H,1-2H3/t23-,24-/m0/s1

InChI Key

BNNQNJBXFAFMOE-ZEQRLZLVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	t.sritharan@uq.edu.au	Not Available	Not Available	2024-01-04	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Coumaran
Dihydroindole
Indole
Anisole
Secondary aliphatic/aromatic amine
Alkyl aryl ether
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Oxacycle
Azacycle
Secondary amine
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
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)	9.84	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	95.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	115.83 m³·mol⁻¹	ChemAxon
Polarizability	43.14 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

100738720

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1021/acs.jnatprod.3c00869

Showing NP-Card for asterresin A (NP0332300)

MOL for NP0332300 (asterresin A)

3D MOL for NP0332300 (asterresin A)

3D SDF for NP0332300 (asterresin A)

3D-SDF for NP0332300 (asterresin A)

PDB for NP0332300 (asterresin A)

3D PDB for NP0332300 (asterresin A)

SMILES for NP0332300 (asterresin A)

INCHI for NP0332300 (asterresin A)

Structure for NP0332300 (asterresin A)

3D Structure for NP0332300 (asterresin A)