NP-MRD: Showing NP-Card for (+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E (NP0331906)

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Record Information

Version

1.0

Created at

2023-10-04 16:29:23 UTC

Updated at

2024-05-05 00:33:42 UTC

NP-MRD ID

NP0331906

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 10042316292D          

 28 32  0  0  1  0            999 V2000
    4.9292    2.5839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333    1.8601    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8095    2.2560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571    1.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374    1.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    0.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705   -0.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5994   -0.9970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457   -0.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9498   -1.0351    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9168    0.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    1.1172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7085    1.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2796    2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548    2.5267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    1.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4879    1.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -0.5761    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.8132   -1.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025   -1.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7295   -0.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317    0.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355    0.8699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383    1.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2672    0.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    1.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8053    2.4886    0.0000 O   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
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 11  1  6  0  0  0
 12  5  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 22 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  CHG  1  19   1
M  END


  Mrv2104 10042316292D          

 28 32  0  0  1  0            999 V2000
    4.9292    2.5839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333    1.8601    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8095    2.2560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571    1.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374    1.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    0.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705   -0.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5994   -0.9970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457   -0.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9498   -1.0351    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9168    0.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    1.1172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7085    1.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2796    2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548    2.5267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    1.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4879    1.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920    0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -0.5761    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.8132   -1.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025   -1.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7295   -0.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317    0.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355    0.8699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383    1.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2672    0.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    1.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8053    2.4886    0.0000 O   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
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 11  1  6  0  0  0
 12  5  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 22 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  CHG  1  19   1
M  END
> <DATABASE_ID>
NP0331906

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OS(=O)(=O)C1=CC(=O)C(Br)=C[C@]11C=CNC2=C1C1=[NH+]CCC3=CNC(=C13)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H12BrN3O5S/c19-9-6-18(11(5-10(9)23)28(25,26)27)2-4-21-16-13(18)14-12-8(1-3-20-14)7-22-15(12)17(16)24/h2,4-7,21-22H,1,3H2,(H,25,26,27)/p+1/t18-/m1/s1

> <INCHI_KEY>
MXNFEJLNYOVSOW-GOSISDBHSA-O

> <FORMULA>
C18H13BrN3O5S

> <MOLECULAR_WEIGHT>
463.28

> <EXACT_MASS>
461.975381

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
39.38183084862647

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-3-bromo-4,8'-dioxo-6-sulfo-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadecane]-1'(15'),2,2'(7'),4',5,9'(16'),11'-heptaen-15'-ium

> <JCHEM_LOGP>
-1.3253974305415845

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.26743148686237

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3125354178006456

> <JCHEM_PKA_STRONGEST_BASIC>
7.378757984635128

> <JCHEM_POLAR_SURFACE_AREA>
130.29999999999998

> <JCHEM_REFRACTIVITY>
120.01259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-3-bromo-4,8'-dioxo-6-sulfo-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadecane]-1'(15'),2,2'(7'),4',5,9'(16'),11'-heptaen-15'-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-OCT-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-OCT-23         0                                  
HETATM    1  O   UNK     0       9.201   4.823   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0       8.462   3.472   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       7.111   4.211   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.813   2.733   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.723   2.121   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.524   0.806   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.785  -0.546   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.585  -1.861   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.245  -0.581   0.000  0.00  0.00           C+0
HETATM   10 Br   UNK     0       5.506  -1.932   0.000  0.00  0.00          Br+0
HETATM   11  C   UNK     0       5.445   0.734   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.184   2.086   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.923   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.122   4.752   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.582   4.717   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.843   3.365   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.644   2.050   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.905   0.699   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.388  -1.075   0.000  0.00  0.00           N+1
HETATM   20  C   UNK     0       3.385  -2.243   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.871  -1.958   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.362  -0.505   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.059   0.089   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       0.066   1.624   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       1.565   1.979   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.365   0.663   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.304   3.330   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.503   4.645   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    5   13   17                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   18   22                                                  
CONECT   27   25   16   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₃BrN₃O₅S

Average Mass

463.2800 Da

Monoisotopic Mass

461.97538 Da

IUPAC Name

(1S)-3-bromo-4,8'-dioxo-6-sulfo-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadecane]-1'(15'),2,2'(7'),4',5,9'(16'),11'-heptaen-15'-ium

Traditional Name

(1S)-3-bromo-4,8'-dioxo-6-sulfo-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadecane]-1'(15'),2,2'(7'),4',5,9'(16'),11'-heptaen-15'-ium

CAS Registry Number

Not Available

SMILES

OS(=O)(=O)C1=CC(=O)C(Br)=C[C@]11C=CNC2=C1C1=[NH+]CCC3=CNC(=C13)C2=O

InChI Identifier

InChI=1S/C18H12BrN3O5S/c19-9-6-18(11(5-10(9)23)28(25,26)27)2-4-21-16-13(18)14-12-8(1-3-20-14)7-22-15(12)17(16)24/h2,4-7,21-22H,1,3H2,(H,25,26,27)/p+1/t18-/m1/s1

InChI Key

MXNFEJLNYOVSOW-GOSISDBHSA-O

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	maria.orfanoudaki@nih.gov	National Cancer Institute, MD, USA	Maria Orfanoudaki	2024-05-03	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	maria.orfanoudaki@nih.gov	National Cancer Institute, MD, USA	Maria Orfanoudaki	2024-05-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	maria.orfanoudaki@nih.gov	National Cancer Institute, MD, USA	Maria Orfanoudaki	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	maria.orfanoudaki@nih.gov	National Cancer Institute, MD, USA	Maria Orfanoudaki	2024-05-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	maria.orfanoudaki@nih.gov	National Cancer Institute, MD, USA	Maria Orfanoudaki	2024-05-03	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, 600.314502325, C2D6OS, simulated)	maria.orfanoudaki@nih.gov	National Cancer Institute, MD, USA	Maria Orfanoudaki	2024-05-03	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, DMSO, simulated)	maria.orfanoudaki@nih.gov	National Cancer Institute, MD, USA	Maria Orfanoudaki	2023-10-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO, simulated)	maria.orfanoudaki@nih.gov	National Cancer Institute, MD, USA	Maria Orfanoudaki	2023-10-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, simulated)	maria.orfanoudaki@nih.gov	National Cancer Institute, MD, USA	Maria Orfanoudaki	2023-10-04	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
brevis		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	-1.3	ChemAxon
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	7.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	130.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	120.01 m³·mol⁻¹	ChemAxon
Polarizability	39.38 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Orfanoudaki M, Smith EA, Hill NT, Garman KA, Brownell I, Copp BR, Grkovic T, Henrich CJ: An Investigation of Structure-Activity Relationships and Cell Death Mechanisms of the Marine Alkaloids Discorhabdins in Merkel Cell Carcinoma Cells. Mar Drugs. 2023 Aug 29;21(9):474. doi: 10.3390/md21090474. [PubMed:37755087 ]

Showing NP-Card for (+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E (NP0331906)

MOL for NP0331906 ((+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E )

3D MOL for NP0331906 ((+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E )

3D SDF for NP0331906 ((+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E )

3D-SDF for NP0331906 ((+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E )

PDB for NP0331906 ((+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E )

3D PDB for NP0331906 ((+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E )

SMILES for NP0331906 ((+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E )

INCHI for NP0331906 ((+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E )

Structure for NP0331906 ((+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E )

3D Structure for NP0331906 ((+)-(6S) sulphonyl-7,8-dehydrodiscorhabdin E )