NP-MRD: Showing NP-Card for goondansamycin H (NP0332859)

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Record Information

Version

2.0

Created at

2024-04-29 22:12:43 UTC

Updated at

2026-02-28 01:56:33 UTC

NP-MRD ID

NP0332859

Natural Product DOI

https://doi.org/10.57994/2137

Secondary Accession Numbers

None

Natural Product Identification

Common Name

goondansamycin H

Description

goondansamycin H was first documented in 2024 (PMID: 38747559). Based on a literature review very few articles have been published on goondansamycin H.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01122300492D          

 26 28  0  0  0  0            999 V2000
    1.5642   -1.2409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2373   -0.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448   -1.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3259   -2.4703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7725   -1.1207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6085   -0.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3897   -0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7858   -1.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6752   -1.9696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3932   -1.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8157   -2.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9925   -1.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6106   -0.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4178    0.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5645    0.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7189    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230    0.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652    0.6916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5649    0.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0116    1.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339    2.0761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2014    1.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409    0.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    0.0052    0.0000 N   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
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
M  END


  Mrv2104 01122300492D          

 26 28  0  0  0  0            999 V2000
    1.5642   -1.2409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2373   -0.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448   -1.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3259   -2.4703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7725   -1.1207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6085   -0.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3897   -0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7858   -1.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6752   -1.9696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3932   -1.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8157   -2.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9925   -1.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6106   -0.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4178    0.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5645    0.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7189    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230    0.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652    0.6916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5649    0.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0116    1.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339    2.0761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2014    1.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409    0.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250    0.0052    0.0000 N   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
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332859

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C\C(C)=C\C(C)C(O)C2=C3OC(CO)(C(=O)NC3=CC(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1/C19H23NO6/c1-9-4-10(2)15(23)13-6-12(22)7-14-16(13)26-19(8-21,18(25)20-14)17(24)11(3)5-9/h4,6-7,10-11,15,21-23H,5,8H2,1-3H3,(H,20,25)/b9-4+

> <INCHI_KEY>
QXWKFYUPJFURMH-RUDMXATFNA-N

> <FORMULA>
C19H23NO6

> <MOLECULAR_WEIGHT>
361.394

> <EXACT_MASS>
361.152537465

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.48079432466713

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E)-2,14-dihydroxy-9-(hydroxymethyl)-3,5,7-trimethyl-17-oxa-11-azatricyclo[7.6.2.0^{12,16}]heptadeca-1(16),4,12,14-tetraene-8,10-dione

> <JCHEM_LOGP>
1.8033730733333326

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.235099009825849

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.420771918814781

> <JCHEM_PKA_STRONGEST_BASIC>
-3.244149704927802

> <JCHEM_POLAR_SURFACE_AREA>
116.09000000000002

> <JCHEM_REFRACTIVITY>
96.22329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4E)-2,14-dihydroxy-9-(hydroxymethyl)-3,5,7-trimethyl-17-oxa-11-azatricyclo[7.6.2.0^{12,16}]heptadeca-1(16),4,12,14-tetraene-8,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-JAN-23         0                                  
HETATM    1  O   UNK     0       2.920  -2.316   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.334  -1.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.043  -1.511   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.310  -3.199   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.342  -4.611   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       7.042  -2.092   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.736  -0.521   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.194  -0.589   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.933  -1.976   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.727  -3.677   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.067  -3.009   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.856  -4.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.186  -1.936   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.473  -0.549   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.238  -0.987   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.113   1.002   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.520   1.720   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.809   3.437   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.136   0.372   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.095   1.291   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.521   0.788   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.488   2.250   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.717   3.875   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.976   2.072   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.490   0.693   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       4.153   0.010   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4    6   19                                             
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    3   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24    7   26                                                  
CONECT   26   25    2                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₃NO₆

Average Mass

361.3940 Da

Monoisotopic Mass

361.15254 Da

IUPAC Name

(4E)-2,14-dihydroxy-9-(hydroxymethyl)-3,5,7-trimethyl-17-oxa-11-azatricyclo[7.6.2.0^{12,16}]heptadeca-1(16),4,12,14-tetraene-8,10-dione

Traditional Name

(4E)-2,14-dihydroxy-9-(hydroxymethyl)-3,5,7-trimethyl-17-oxa-11-azatricyclo[7.6.2.0^{12,16}]heptadeca-1(16),4,12,14-tetraene-8,10-dione

CAS Registry Number

Not Available

SMILES

CC1C\C(C)=C\C(C)C(O)C2=C3OC(CO)(C(=O)NC3=CC(O)=C2)C1=O

InChI Identifier

InChI=1/C19H23NO6/c1-9-4-10(2)15(23)13-6-12(22)7-14-16(13)26-19(8-21,18(25)20-14)17(24)11(3)5-9/h4,6-7,10-11,15,21-23H,5,8H2,1-3H3,(H,20,25)/b9-4+

InChI Key

QXWKFYUPJFURMH-RUDMXATFNA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-04-29	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-04-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-04-29	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-04-29	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-04-29	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-04-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-04-29	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-04-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-04-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-04-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-04-29	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actinomadura sp.		Not Available
Actinomadura sp.		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	1.8	ChemAxon
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.09 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.22 m³·mol⁻¹	ChemAxon
Polarizability	36.48 Å³	ChemAxon
Number of Rings	3	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

Han J, Bernhardt PV, Capon RJ: Goondansamycins A-H: Benzenoid Ansamycins from an Australian Volcanic Crater Soil-Derived Actinomadura sp. S4S-00069B08. J Nat Prod. 2024 May 24;87(5):1471-1478. doi: 10.1021/acs.jnatprod.4c00336. Epub 2024 May 15. [PubMed:38747559 ]
DOI: 10.1021/acs.jnatprod.4c00336
PMID: 38747559

Showing NP-Card for goondansamycin H (NP0332859)

MOL for NP0332859 (goondansamycin H)

3D MOL for NP0332859 (goondansamycin H)

3D SDF for NP0332859 (goondansamycin H)

3D-SDF for NP0332859 (goondansamycin H)

PDB for NP0332859 (goondansamycin H)

3D PDB for NP0332859 (goondansamycin H)

SMILES for NP0332859 (goondansamycin H)

INCHI for NP0332859 (goondansamycin H)

Structure for NP0332859 (goondansamycin H)

3D Structure for NP0332859 (goondansamycin H)