NP-MRD: Showing NP-Card for Glechomanin (NP0350903)

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Record Information

Version

2.0

Created at

2025-04-05 21:45:31 UTC

Updated at

2025-04-09 01:01:51 UTC

NP-MRD ID

NP0350903

Natural Product DOI

https://doi.org/10.57994/3888

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glechomanin

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01172300112D          

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M  END


  Mrv2104 01172300112D          

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M  END
> <DATABASE_ID>
NP0350903

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1[C@H](NC(=O)[C@@H]2CCC(=O)N2)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H]2C(=O)N[C@@H](CC3=CNC4=C3C=CC1=C4)C(=O)NCC(=O)N[C@@H](CC1=CNC3=C1C=CC(=C3)C2(C)C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C49H55N9O9/c1-24(2)40-26-10-12-30-27(21-50-33(30)17-26)18-36-43(61)52-23-39(60)54-37(48(66)67)19-28-22-51-34-20-29(11-13-31(28)34)49(3,4)42(47(65)56-36)58-45(63)35(16-25-8-6-5-7-9-25)55-46(64)41(40)57-44(62)32-14-15-38(59)53-32/h5-13,17,20-22,24,32,35-37,40-42,50-51H,14-16,18-19,23H2,1-4H3,(H,52,61)(H,53,59)(H,54,60)(H,55,64)(H,56,65)(H,57,62)(H,58,63)(H,66,67)/t32-,35-,36-,37-,40+,41-,42+/m0/s1

> <INCHI_KEY>
WKRKRFULAGCQHE-MGDWOXQRSA-N

> <FORMULA>
C49H55N9O9

> <MOLECULAR_WEIGHT>
914.033

> <EXACT_MASS>
913.412274387

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
122

> <JCHEM_AVERAGE_POLARIZABILITY>
95.2328432731934

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,12S,18S,28R,29S,32S)-32-benzyl-2,2-dimethyl-14,17,30,33,35-pentaoxo-29-[(2S)-5-oxopyrrolidine-2-amido]-28-(propan-2-yl)-8,13,16,22,31,34,36-heptaazahexacyclo[16.16.2.1^{3,7}.1^{23,27}.0^{6,10}.0^{20,24}]octatriaconta-3(38),4,6,9,20,23,25,27(37)-octaene-12-carboxylic acid

> <JCHEM_LOGP>
1.6946505276666661

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.558389717766046

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6841111226391874

> <JCHEM_POLAR_SURFACE_AREA>
272.5799999999999

> <JCHEM_REFRACTIVITY>
243.0212000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,18S,28R,29S,32S)-32-benzyl-28-isopropyl-2,2-dimethyl-14,17,30,33,35-pentaoxo-29-[(2S)-5-oxopyrrolidine-2-amido]-8,13,16,22,31,34,36-heptaazahexacyclo[16.16.2.1^{3,7}.1^{23,27}.0^{6,10}.0^{20,24}]octatriaconta-3(38),4,6,9,20,23,25,27(37)-octaene-12-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JAN-23         0                                  
HETATM    1  O   UNK     0      -3.855   1.345   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.326   1.164   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.280   2.295   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.118   1.650   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.063   0.121   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.068  -0.924   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.729  -2.427   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.859  -3.472   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.095  -2.552   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.579  -2.141   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.111  -2.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.543  -0.815   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.478   0.298   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.982  -0.068   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.918   1.045   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.350   2.523   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.846   2.889   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.910   1.776   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.485  -2.989   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       8.515  -4.135   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       9.061  -5.574   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.444  -4.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.921  -3.433   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.979  -4.766   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.459  -4.343   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.566  -5.413   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.605  -6.260   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.712  -7.330   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.193  -6.907   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.053  -8.185   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.104  -9.397   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      12.657  -8.870   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       9.282  -3.887   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.051  -7.114   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       8.484  -8.546   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       7.439  -9.677   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.986 -11.117   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0       9.015 -12.262   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      10.389 -12.958   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.921 -13.111   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0      13.406 -12.700   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0      14.641 -11.780   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      15.461 -10.476   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      15.772 -12.825   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      17.242 -12.369   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      15.432 -14.327   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      12.053 -14.645   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       6.671 -11.919   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       6.056 -10.354   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.522 -10.486   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       3.572 -11.699   0.000  0.00  0.00           C+0
HETATM   52  N   UNK     0       2.126 -11.171   0.000  0.00  0.00           N+0
HETATM   53  C   UNK     0       2.181  -9.632   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       3.661  -9.209   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.035  -7.715   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       2.928  -6.644   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       1.448  -7.067   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       1.074  -8.561   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      10.562  -7.408   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       8.422  -1.767   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       2.418  -1.169   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0       1.040  -4.776   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -0.472  -4.481   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -1.483  -5.642   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -0.972  -3.024   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0       2.539  -0.468   0.000  0.00  0.00           O+0
HETATM   67  N   UNK     0      -1.573  -0.180   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   67                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   67                                                  
CONECT    6    5    7   66                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   62                                                  
CONECT    9    8   10   61                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   11   20   60                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   34                                                  
CONECT   22   21   23   24   33                                             
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   29                                                       
CONECT   27   24   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   26   30                                                  
CONECT   30   29   31   43                                                  
CONECT   31   30   32                                                       
CONECT   32   31   28                                                       
CONECT   33   22                                                            
CONECT   34   21   35   59                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   49                                                  
CONECT   37   36   38   48                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   47                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42   30                                                       
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   40                                                            
CONECT   48   37                                                            
CONECT   49   36   50                                                       
CONECT   50   49   51   54                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   58                                                  
CONECT   54   53   50   55                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58   62                                                  
CONECT   58   57   53                                                       
CONECT   59   34                                                            
CONECT   60   19                                                            
CONECT   61    9                                                            
CONECT   62    8   57   63                                                  
CONECT   63   62   64   65                                                  
CONECT   64   63                                                            
CONECT   65   63                                                            
CONECT   66    6                                                            
CONECT   67    5    2                                                       
MASTER        0    0    0    0    0    0    0    0   67    0  148    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₉H₅₅N₉O₉

Average Mass

914.0330 Da

Monoisotopic Mass

913.41227 Da

IUPAC Name

(1S,12S,18S,28R,29S,32S)-32-benzyl-2,2-dimethyl-14,17,30,33,35-pentaoxo-29-[(2S)-5-oxopyrrolidine-2-amido]-28-(propan-2-yl)-8,13,16,22,31,34,36-heptaazahexacyclo[16.16.2.1^{3,7}.1^{23,27}.0^{6,10}.0^{20,24}]octatriaconta-3(38),4,6,9,20,23,25,27(37)-octaene-12-carboxylic acid

Traditional Name

(1S,12S,18S,28R,29S,32S)-32-benzyl-28-isopropyl-2,2-dimethyl-14,17,30,33,35-pentaoxo-29-[(2S)-5-oxopyrrolidine-2-amido]-8,13,16,22,31,34,36-heptaazahexacyclo[16.16.2.1^{3,7}.1^{23,27}.0^{6,10}.0^{20,24}]octatriaconta-3(38),4,6,9,20,23,25,27(37)-octaene-12-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1[C@H](NC(=O)[C@@H]2CCC(=O)N2)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H]2C(=O)N[C@@H](CC3=CNC4=C3C=CC1=C4)C(=O)NCC(=O)N[C@@H](CC1=CNC3=C1C=CC(=C3)C2(C)C)C(O)=O

InChI Identifier

InChI=1S/C49H55N9O9/c1-24(2)40-26-10-12-30-27(21-50-33(30)17-26)18-36-43(61)52-23-39(60)54-37(48(66)67)19-28-22-51-34-20-29(11-13-31(28)34)49(3,4)42(47(65)56-36)58-45(63)35(16-25-8-6-5-7-9-25)55-46(64)41(40)57-44(62)32-14-15-38(59)53-32/h5-13,17,20-22,24,32,35-37,40-42,50-51H,14-16,18-19,23H2,1-4H3,(H,52,61)(H,53,59)(H,54,60)(H,55,64)(H,56,65)(H,57,62)(H,58,63)(H,66,67)/t32-,35-,36-,37-,40+,41-,42+/m0/s1

InChI Key

WKRKRFULAGCQHE-MGDWOXQRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C2D6OS, experimental)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, C2D6OS, experimental)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, C2D6OS, experimental)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, C2D6OS, experimental)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, C2D6OS, experimental)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, C2D6OS, experimental)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, C2D6OS, experimental)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C2D6OS, experimental)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C2D6OS, experimental)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C2D6OS, experimental)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C2D6OS, experimental)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800.255201625 MHz, C2D6OS, 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, 800.255201625, C2D6OS, simulated)	rkersten@umich.edu	Not Available	Not Available	2025-04-05	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Glechoma hederacea		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	1.69	ChemAxon
pKa (Strongest Acidic)	3.68	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	272.58 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	243.02 m³·mol⁻¹	ChemAxon
Polarizability	95.23 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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 Glechomanin (NP0350903)

MOL for NP0350903 (Glechomanin)

3D MOL for NP0350903 (Glechomanin)

3D SDF for NP0350903 (Glechomanin)

3D-SDF for NP0350903 (Glechomanin)

PDB for NP0350903 (Glechomanin)

3D PDB for NP0350903 (Glechomanin)

SMILES for NP0350903 (Glechomanin)

INCHI for NP0350903 (Glechomanin)

Structure for NP0350903 (Glechomanin)

3D Structure for NP0350903 (Glechomanin)