NP-MRD: Showing NP-Card for Glenthenamine B (NP0333207)

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Record Information

Version

2.0

Created at

2024-05-12 15:38:15 UTC

Updated at

2026-02-17 14:04:38 UTC

NP-MRD ID

NP0333207

Natural Product DOI

https://doi.org/10.57994/2535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glenthenamine B

Description

Glenthenamine B was first documented in 2022 (PMID: 35073486).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311162200062D          

 30 34  0  0  1  0            999 V2000
    1.8040    1.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2281    1.0796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0530    1.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8273    0.3585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3668    1.0429    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.3896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766   -0.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987   -1.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790   -0.7969    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7010   -1.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373    0.0128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153    0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7736    1.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5540    1.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7123    2.4418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    1.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    0.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403   -1.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -2.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3600   -2.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379   -1.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190   -1.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958   -2.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915   -3.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105   -3.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3825   -3.6952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5712   -0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500   -0.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084    0.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  6  0  0  0
  4  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
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  2  0  0  0  0
  8 18  1  0  0  0  0
  9 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  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
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 23 28  2  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  0  0  0  0
M  END


  Mrv1652311162200062D          

 30 34  0  0  1  0            999 V2000
    1.8040    1.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2281    1.0796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0530    1.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8273    0.3585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3668    1.0429    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.3896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766   -0.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987   -1.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790   -0.7969    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7010   -1.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373    0.0128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153    0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7736    1.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5540    1.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7123    2.4418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    1.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    0.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403   -1.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -2.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3600   -2.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379   -1.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190   -1.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958   -2.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915   -3.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105   -3.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3825   -3.6952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5712   -0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500   -0.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084    0.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  6  0  0  0
  4  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
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  2  0  0  0  0
  8 18  1  0  0  0  0
  9 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  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
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 23 28  2  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333207

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CCC2=C3C=CC(=O)C4=C3C(N12)=C1C=C(CC(O)=O)O[C@@H](C)C1=C4O)[C@@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C22H21NO6/c1-9(24)14-4-5-15-12-3-6-16(25)20-19(12)21(23(14)15)13-7-11(8-17(26)27)29-10(2)18(13)22(20)28/h3,6-7,9-10,14,24,28H,4-5,8H2,1-2H3,(H,26,27)/t9-,10+,14+/m1/s1

> <INCHI_KEY>
OCIPLYCMVXSIDW-BFVZDQMLSA-N

> <FORMULA>
C22H21NO6

> <MOLECULAR_WEIGHT>
395.411

> <EXACT_MASS>
395.1368874

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
40.83514515689885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3S,14S)-12-hydroxy-3-[(1R)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-1(18),6,8,11(19),12,16-hexaen-16-yl]acetic acid

> <JCHEM_LOGP>
2.4781899266666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.012550407547456

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7770194089343763

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8744009053809076

> <JCHEM_POLAR_SURFACE_AREA>
108.99000000000001

> <JCHEM_REFRACTIVITY>
108.34959999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,14S)-12-hydroxy-3-[(1R)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-1(18),6,8,11(19),12,16-hexaen-16-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-NOV-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-NOV-22         0                                  
HETATM    1  O   UNK     0       3.367   3.336   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.159   2.015   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.699   2.040   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.411   0.669   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       2.551   1.947   0.000  0.00  0.00           H+0
HETATM    6  N   UNK     0       4.060  -0.727   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.406  -1.475   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.863  -0.976   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.024  -1.987   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.481  -1.488   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.642  -2.499   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.776   0.024   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.615   1.035   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.911   2.547   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.367   3.047   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.663   4.558   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      11.529   2.035   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.159   0.536   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.729  -3.499   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.890  -4.510   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.272  -3.998   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.111  -2.987   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.582  -3.173   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.979  -4.590   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.904  -5.821   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.433  -5.635   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.314  -6.898   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.933  -1.776   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.587  -1.028   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.882   0.483   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   30                                             
CONECT    5    4                                                            
CONECT    6    4    7   28                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13    8                                                       
CONECT   19    9   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21    7   23                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28   23    6   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29    4                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₁NO₆

Average Mass

395.4110 Da

Monoisotopic Mass

395.13689 Da

IUPAC Name

2-[(3S,14S)-12-hydroxy-3-[(1R)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-1(18),6,8,11(19),12,16-hexaen-16-yl]acetic acid

Traditional Name

[(3S,14S)-12-hydroxy-3-[(1R)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-1(18),6,8,11(19),12,16-hexaen-16-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(CCC2=C3C=CC(=O)C4=C3C(N12)=C1C=C(CC(O)=O)O[C@@H](C)C1=C4O)[C@@H](C)O

InChI Identifier

InChI=1S/C22H21NO6/c1-9(24)14-4-5-15-12-3-6-16(25)20-19(12)21(23(14)15)13-7-11(8-17(26)27)29-10(2)18(13)22(20)28/h3,6-7,9-10,14,24,28H,4-5,8H2,1-2H3,(H,26,27)/t9-,10+,14+/m1/s1

InChI Key

OCIPLYCMVXSIDW-BFVZDQMLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	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, 600.08, Dimethylsulfoxide-d6, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.91, Dimethylsulfoxide-d6, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-17	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Streptomyces sp. CMB-PB042		Not Available
Streptomyces sp. CMB-PB042		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	2.48	ChemAxon
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.35 m³·mol⁻¹	ChemAxon
Polarizability	40.84 Å³	ChemAxon
Number of Rings	5	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

Not Available

References

General References

DOI: 10.1021/acs.jnatprod.1c00821

Showing NP-Card for Glenthenamine B (NP0333207)

MOL for NP0333207 (Glenthenamine B)

3D MOL for NP0333207 (Glenthenamine B)

3D SDF for NP0333207 (Glenthenamine B)

3D-SDF for NP0333207 (Glenthenamine B)

PDB for NP0333207 (Glenthenamine B)

3D PDB for NP0333207 (Glenthenamine B)

SMILES for NP0333207 (Glenthenamine B)

INCHI for NP0333207 (Glenthenamine B)

Structure for NP0333207 (Glenthenamine B)

3D Structure for NP0333207 (Glenthenamine B)