NP-MRD: Showing NP-Card for Microthecaline B (NP0333042)

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Record Information

Version

1.0

Created at

2024-05-04 02:24:11 UTC

Updated at

2024-05-06 00:10:46 UTC

NP-MRD ID

NP0333042

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Microthecaline B

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01162305002D          

 23 25  0  0  1  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
  4 15  2  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19  5  1  0  0  0  0
 19 20  1  6  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333042

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H](O)C2=C(CCC=C(C)C)C=NC3=C(C)C=C(O)C1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C20H25NO2/c1-11(2)6-5-7-14-10-21-20-13(4)9-15(22)17-12(3)8-16(23)18(14)19(17)20/h6,9-10,12,16,22-23H,5,7-8H2,1-4H3/t12-,16-/m1/s1

> <INCHI_KEY>
PZIZECGJFPHPHO-MLGOLLRUSA-N

> <FORMULA>
C20H25NO2

> <MOLECULAR_WEIGHT>
311.425

> <EXACT_MASS>
311.188529049

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.462427440662495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R,8R)-8,12-dimethyl-4-(4-methylpent-3-en-1-yl)-2-azatricyclo[7.3.1.0^{5,13}]trideca-1(12),2,4,9(13),10-pentaene-6,10-diol

> <JCHEM_LOGP>
4.577785773666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.578213273413581

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.030345567209258

> <JCHEM_PKA_STRONGEST_BASIC>
5.342688526042612

> <JCHEM_POLAR_SURFACE_AREA>
53.35000000000001

> <JCHEM_REFRACTIVITY>
94.7905

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6R,8R)-8,12-dimethyl-4-(4-methylpent-3-en-1-yl)-2-azatricyclo[7.3.1.0^{5,13}]trideca-1(12),2,4,9(13),10-pentaene-6,10-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-JAN-23         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    6   14                                                       
CONECT   14   13    3                                                       
CONECT   15    4   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    5   20                                                  
CONECT   20   19                                                            
CONECT   21   15   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₅NO₂

Average Mass

311.4250 Da

Monoisotopic Mass

311.18853 Da

IUPAC Name

(6R,8R)-8,12-dimethyl-4-(4-methylpent-3-en-1-yl)-2-azatricyclo[7.3.1.0^{5,13}]trideca-1(12),2,4,9(13),10-pentaene-6,10-diol

Traditional Name

(6R,8R)-8,12-dimethyl-4-(4-methylpent-3-en-1-yl)-2-azatricyclo[7.3.1.0^{5,13}]trideca-1(12),2,4,9(13),10-pentaene-6,10-diol

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](O)C2=C(CCC=C(C)C)C=NC3=C(C)C=C(O)C1=C23

InChI Identifier

InChI=1S/C20H25NO2/c1-11(2)6-5-7-14-10-21-20-13(4)9-15(22)17-12(3)8-16(23)18(14)19(17)20/h6,9-10,12,16,22-23H,5,7-8H2,1-4H3/t12-,16-/m1/s1

InChI Key

PZIZECGJFPHPHO-MLGOLLRUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	chen.zhang7@griffithuni.edu.au	Griffith Institute for Drug Discovery	Chen Zhang	2024-05-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	chen.zhang7@griffithuni.edu.au	Griffith Institute for Drug Discovery	Chen Zhang	2024-05-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	chen.zhang7@griffithuni.edu.au	Griffith Institute for Drug Discovery	Chen Zhang	2024-05-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	chen.zhang7@griffithuni.edu.au	Griffith Institute for Drug Discovery	Chen Zhang	2024-05-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)	chen.zhang7@griffithuni.edu.au	Griffith Institute for Drug Discovery	Chen Zhang	2024-05-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	chen.zhang7@griffithuni.edu.au	Griffith Institute for Drug Discovery	Chen Zhang	2024-05-04	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 800.23494142, CD₃OD, simulated)	chen.zhang7@griffithuni.edu.au	Griffith Institute for Drug Discovery	Chen Zhang	2024-05-04	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
microtheca		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	4.58	ChemAxon
pKa (Strongest Acidic)	10.03	ChemAxon
pKa (Strongest Basic)	5.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.35 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.79 m³·mol⁻¹	ChemAxon
Polarizability	36.46 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

Not Available

References

General References

Zhang C, Lum KY, White JM, Duffy S, Lock AM, Avery VM, Davis RA: Chemical and Antiplasmodial Investigations on Eremophila-Derived Alkaloids and Semisynthetic Ether Analogues. J Nat Prod. 2024 Apr 26;87(4):849-854. doi: 10.1021/acs.jnatprod.3c01072. Epub 2024 Feb 28. [PubMed:38416027 ]

Showing NP-Card for Microthecaline B (NP0333042)

MOL for NP0333042 (Microthecaline B)

3D MOL for NP0333042 (Microthecaline B)

3D SDF for NP0333042 (Microthecaline B)

3D-SDF for NP0333042 (Microthecaline B)

PDB for NP0333042 (Microthecaline B)

3D PDB for NP0333042 (Microthecaline B)

SMILES for NP0333042 (Microthecaline B)

INCHI for NP0333042 (Microthecaline B)

Structure for NP0333042 (Microthecaline B)

3D Structure for NP0333042 (Microthecaline B)