NP-MRD: Showing NP-Card for 2,8-dichlororugulovasines B (NP0333400)

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Record Information

Version

1.0

Created at

2024-06-10 02:53:36 UTC

Updated at

2024-06-12 00:05:53 UTC

NP-MRD ID

NP0333400

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,8-dichlororugulovasines B

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02222305292D          

 22 25  0  0  1  0            999 V2000
    4.6940   -0.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2287   -0.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999    0.2467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9134    1.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360    0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2700    1.5763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678   -0.5450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9374   -1.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7054   -1.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662   -0.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1719   -0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2934   -0.8482    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1057    0.6099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474    1.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6098    1.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0715    2.4020    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3534    2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0346    1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0303    0.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286    0.6486    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
  4  3  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 12 22  1  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333400

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H]1CC2=C(Cl)NC3=C(Cl)C=CC(=C23)[C@@]11OC(=O)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14Cl2N2O2/c1-7-6-16(22-15(7)21)9-3-4-10(17)13-12(9)8(14(18)20-13)5-11(16)19-2/h3-4,6,11,19-20H,5H2,1-2H3/t11-,16-/m1/s1

> <INCHI_KEY>
IENLABAWRVNXDR-BDJLRTHQSA-N

> <FORMULA>
C16H14Cl2N2O2

> <MOLECULAR_WEIGHT>
337.2

> <EXACT_MASS>
336.0432331

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
33.26336246999654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,6'R)-3',11'-dichloro-4-methyl-6'-(methylamino)-5H-2'-azaspiro[furan-2,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),3',8'(12'),9'-tetraen-5-one

> <JCHEM_LOGP>
3.3972891416666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.785747727914398

> <JCHEM_PKA_STRONGEST_BASIC>
9.066357013220852

> <JCHEM_POLAR_SURFACE_AREA>
54.12

> <JCHEM_REFRACTIVITY>
86.17829999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,6'R)-3',11'-dichloro-4-methyl-6'-(methylamino)-2'-azaspiro[furan-2,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),3',8'(12'),9'-tetraen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-FEB-23         0                                  
HETATM    1  C   UNK     0       8.762  -0.313   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.338   0.272   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.027  -0.536   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.853   0.461   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.438   1.885   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.974   1.769   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.971   2.942   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.420  -1.017   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.483  -2.131   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.050  -3.609   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.924  -1.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.860  -0.267   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.321  -0.312   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      -0.548  -1.583   0.000  0.00  0.00          Cl+0
HETATM   15  N   UNK     0      -0.197   1.138   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.022   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.138   3.615   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      -0.133   4.484   0.000  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       2.526   4.282   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.798   3.413   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.790   1.575   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.293   1.211   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8   21                                             
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    4   22                                                  
CONECT   22   21   12   16                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄Cl₂N₂O₂

Average Mass

337.2000 Da

Monoisotopic Mass

336.04323 Da

IUPAC Name

(2R,6'R)-3',11'-dichloro-4-methyl-6'-(methylamino)-5H-2'-azaspiro[furan-2,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),3',8'(12'),9'-tetraen-5-one

Traditional Name

(2R,6'R)-3',11'-dichloro-4-methyl-6'-(methylamino)-2'-azaspiro[furan-2,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),3',8'(12'),9'-tetraen-5-one

CAS Registry Number

Not Available

SMILES

CN[C@@H]1CC2=C(Cl)NC3=C(Cl)C=CC(=C23)[C@@]11OC(=O)C(C)=C1

InChI Identifier

InChI=1S/C16H14Cl2N2O2/c1-7-6-16(22-15(7)21)9-3-4-10(17)13-12(9)8(14(18)20-13)5-11(16)19-2/h3-4,6,11,19-20H,5H2,1-2H3/t11-,16-/m1/s1

InChI Key

IENLABAWRVNXDR-BDJLRTHQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	livia.soman@unifesp.br	Unifesp - Universidade Federal de São Paulo	Lívia Soman	2024-06-10	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
wortmannii		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	3.4	ChemAxon
pKa (Strongest Acidic)	11.79	ChemAxon
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.12 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.18 m³·mol⁻¹	ChemAxon
Polarizability	33.26 Å³	ChemAxon
Number of Rings	4	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

de Medeiros LS, da Silva JV, Abreu LM, Pfenning LH, Silva CL, Thomasi SS, Venancio T, van Pee KH, Nielsen KF, Rodrigues-Filho E: Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii. Molecules. 2015 Sep 23;20(9):17627-44. doi: 10.3390/molecules200917627. [PubMed:26404231 ]

Showing NP-Card for 2,8-dichlororugulovasines B (NP0333400)

MOL for NP0333400 (2,8-dichlororugulovasines B)

3D MOL for NP0333400 (2,8-dichlororugulovasines B)

3D SDF for NP0333400 (2,8-dichlororugulovasines B)

3D-SDF for NP0333400 (2,8-dichlororugulovasines B)

PDB for NP0333400 (2,8-dichlororugulovasines B)

3D PDB for NP0333400 (2,8-dichlororugulovasines B)

SMILES for NP0333400 (2,8-dichlororugulovasines B)

INCHI for NP0333400 (2,8-dichlororugulovasines B)

Structure for NP0333400 (2,8-dichlororugulovasines B)

3D Structure for NP0333400 (2,8-dichlororugulovasines B)