NP-MRD: Showing NP-Card for brefeldindole H (NP0351056)

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Record Information

Version

2.0

Created at

2025-05-26 12:27:37 UTC

Updated at

2025-07-31 01:09:35 UTC

NP-MRD ID

NP0351056

Natural Product DOI

https://doi.org/10.57994/4045

Secondary Accession Numbers

None

Natural Product Identification

Common Name

brefeldindole H

Description

Based on a literature review very few articles have been published on brefeldindole H.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03082314522D          

 31 36  0  0  1  0            999 V2000
    1.5487   -1.5032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8139   -0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230   -0.5609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881    0.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578   -0.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841   -1.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085    0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    0.6795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698   -0.1017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9635   -0.1205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3836   -0.8305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9789   -1.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549    1.7759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5694    1.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921    0.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4189    1.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5014    0.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4442    0.0046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886    1.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3407    0.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1657    0.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -0.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5231    0.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7809    0.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885    1.1159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8463    1.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2311    1.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235    1.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7578    1.8812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6092    1.6218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10  2  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 14  9  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 10 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 20 30  1  0  0  0  0
  8 31  2  0  0  0  0
M  END


  Mrv2104 03082314522D          

 31 36  0  0  1  0            999 V2000
    1.5487   -1.5032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8139   -0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230   -0.5609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881    0.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578   -0.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841   -1.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085    0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    0.6795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698   -0.1017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9635   -0.1205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3836   -0.8305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9789   -1.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549    1.7759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5694    1.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921    0.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4189    1.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5014    0.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4442    0.0046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886    1.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3407    0.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1657    0.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -0.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5231    0.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7809    0.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885    1.1159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8463    1.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2311    1.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235    1.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7578    1.8812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6092    1.6218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10  2  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 14  9  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 10 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 20 30  1  0  0  0  0
  8 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0351056

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C2=C(NC3=CC(OC)=CC=C23)[C@@H]2CC(C)(C)O[C@@]11N2C(=O)C2CCCN2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H27N3O5/c1-22(2)11-16-18-17(13-8-7-12(29-3)10-14(13)24-18)19(30-4)23(31-22)21(28)25-9-5-6-15(25)20(27)26(16)23/h7-8,10,15-16,19,24H,5-6,9,11H2,1-4H3/t15?,16-,19-,23-/m0/s1

> <INCHI_KEY>
JRGFJJBTYRDLDB-XVTSQKCNSA-N

> <FORMULA>
C23H27N3O5

> <MOLECULAR_WEIGHT>
425.485

> <EXACT_MASS>
425.195070981

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.17702833748121

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,12S)-2,7-dimethoxy-22,22-dimethyl-21-oxa-10,13,19-triazahexacyclo[10.8.3.0^{1,13}.0^{3,11}.0^{4,9}.0^{15,19}]tricosa-3(11),4,6,8-tetraene-14,20-dione

> <JCHEM_LOGP>
1.6670647636666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.512301084495043

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.761315844202363

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8841945590972062

> <JCHEM_POLAR_SURFACE_AREA>
84.1

> <JCHEM_REFRACTIVITY>
111.6573

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,12S)-2,7-dimethoxy-22,22-dimethyl-21-oxa-10,13,19-triazahexacyclo[10.8.3.0^{1,13}.0^{3,11}.0^{4,9}.0^{15,19}]tricosa-3(11),4,6,8-tetraene-14,20-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-23         0                                  
HETATM    1  O   UNK     0       2.891  -2.806   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.386  -1.348   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.896  -1.047   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.391   0.411   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.864   0.599   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.388  -1.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.130  -1.968   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.309   1.776   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.865   1.268   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.370  -0.190   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.665  -0.225   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.449  -1.550   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.694  -2.892   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.529   3.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.063   2.845   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.359   1.475   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.782   2.510   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.936   0.641   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.829   0.009   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.899   2.611   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.369   1.145   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.909   1.139   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.936  -0.009   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.443   0.305   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.924   1.768   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.432   2.083   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.913   3.546   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.898   2.917   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.390   2.602   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       5.148   3.512   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0       4.871   3.027   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    3                                                       
CONECT    8    4    9   31                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9    2   11   19                                             
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    9   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   10                                                       
CONECT   20   14   21   30                                                  
CONECT   21   20   11   22                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   22   30                                                  
CONECT   30   29   20                                                       
CONECT   31    8                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₇N₃O₅

Average Mass

425.4850 Da

Monoisotopic Mass

425.19507 Da

IUPAC Name

(1S,2S,12S)-2,7-dimethoxy-22,22-dimethyl-21-oxa-10,13,19-triazahexacyclo[10.8.3.0^{1,13}.0^{3,11}.0^{4,9}.0^{15,19}]tricosa-3(11),4,6,8-tetraene-14,20-dione

Traditional Name

(1S,2S,12S)-2,7-dimethoxy-22,22-dimethyl-21-oxa-10,13,19-triazahexacyclo[10.8.3.0^{1,13}.0^{3,11}.0^{4,9}.0^{15,19}]tricosa-3(11),4,6,8-tetraene-14,20-dione

CAS Registry Number

Not Available

SMILES

CO[C@H]1C2=C(NC3=CC(OC)=CC=C23)[C@@H]2CC(C)(C)O[C@@]11N2C(=O)C2CCCN2C1=O

InChI Identifier

InChI=1S/C23H27N3O5/c1-22(2)11-16-18-17(13-8-7-12(29-3)10-14(13)24-18)19(30-4)23(31-22)21(28)25-9-5-6-15(25)20(27)26(16)23/h7-8,10,15-16,19,24H,5-6,9,11H2,1-4H3/t15?,16-,19-,23-/m0/s1

InChI Key

JRGFJJBTYRDLDB-XVTSQKCNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, CD3OD, experimental)	2275322055@qq.com	Jinan University	Jiamin Wang	2025-05-26	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 176 MHz, CD3OD, experimental)	2275322055@qq.com	Jinan University	Jiamin Wang	2025-05-26	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 700 MHz, CD3OD, experimental)	2275322055@qq.com	Jinan University	Jiamin Wang	2025-05-26	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, CD3OD, experimental)	2275322055@qq.com	Jinan University	Jiamin Wang	2025-05-26	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 700 MHz, CD3OD, experimental)	2275322055@qq.com	Jinan University	Jiamin Wang	2025-05-26	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, CD3OD, experimental)	2275322055@qq.com	Jinan University	Jiamin Wang	2025-05-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD3OD, experimental)	2275322055@qq.com	Jinan University	Jiamin Wang	2025-05-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700, CD₃OD, simulated)	2275322055@qq.com	Jinan University	Jiamin Wang	2025-05-26	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Penicillium brefeldianum		Not Available

Chemical Taxonomy

Classification

Not classified

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	1.67	ChemAxon
pKa (Strongest Acidic)	14.76	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.1 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	111.66 m³·mol⁻¹	ChemAxon
Polarizability	45.18 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for brefeldindole H (NP0351056)

MOL for NP0351056 (brefeldindole H)

3D MOL for NP0351056 (brefeldindole H)

3D SDF for NP0351056 (brefeldindole H)

3D-SDF for NP0351056 (brefeldindole H)

PDB for NP0351056 (brefeldindole H)

3D PDB for NP0351056 (brefeldindole H)

SMILES for NP0351056 (brefeldindole H)

INCHI for NP0351056 (brefeldindole H)

Structure for NP0351056 (brefeldindole H)

3D Structure for NP0351056 (brefeldindole H)