NP-MRD: Showing NP-Card for (-)-Cassipourine (NP0067729)

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Record Information

Version

2.0

Created at

2022-04-28 12:34:40 UTC

Updated at

2022-04-28 12:34:41 UTC

NP-MRD ID

NP0067729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Cassipourine

Description

(1S,4S,9S,11S,14R,15S)-2,3,12,13-tetrathia-5,19-diazapentacyclo[12.6.0.0⁴,¹¹.0⁵,⁹.0¹⁵,¹⁹]Icosane belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. (-)-Cassipourine is found in Cassipourea gerrardii , Cassipourea gummiflua, Cassipourea gummiflua Tul.var.verticillata Lewis. and Cassipourea spp.. Based on a literature review very few articles have been published on (1S,4S,9S,11S,14R,15S)-2,3,12,13-tetrathia-5,19-diazapentacyclo[12.6.0.0⁴,¹¹.0⁵,⁹.0¹⁵,¹⁹]Icosane.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 46  0  0  0  0  0  0  0  0999 V2000
    5.3789    1.0070    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0340    1.0621    0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4748   -0.2581    0.5585 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0041   -0.3840    0.5048 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1125    1.1450    0.3793 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5985    1.2444    1.5915 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9695    0.2715    1.0066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3024    1.0186    1.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070    1.1502   -0.2868 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2815    0.8682   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4152   -0.4295   -1.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0472   -1.0508   -0.9726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1833    0.0887   -1.0215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8814   -0.1493   -0.4204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6575    0.7502   -1.3704 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870   -0.4953   -2.0201 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079   -1.2941   -0.7175 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2402   -1.4929   -1.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7943   -0.2439   -0.8864 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1898   -0.0996   -0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1402    0.6502    0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6261    1.9649   -0.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4567    1.8665    0.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1798    1.2376    2.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9965   -1.0904    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6599   -0.9613    1.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562   -0.6541    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0272    0.4398    1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1053    2.0342    1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5826    2.1629   -0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7610    0.7753    0.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7881    1.6548   -1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2135   -1.0761   -0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4951   -0.1999   -2.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9813   -1.5644    0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8105   -1.7316   -1.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098   -1.2555   -0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4214   -2.2821   -0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2431   -1.7186   -2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206   -2.3250   -0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5249    0.3487   -1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7813   -0.9842   -0.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  1  1  0
 19  3  1  0
 17  4  1  0
 14  7  1  0
 13  9  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  1
  4 26  1  1
  7 27  1  1
  8 28  1  0
  8 29  1  0
  9 30  1  6
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  1
 17 38  1  1
 18 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
M  END


  Mrv1652304282214342D          

 20 24  0  0  1  0            999 V2000
    1.2142   -1.9544    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4284   -1.1577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1433   -0.7459    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9400   -0.9601    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -1.6749    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1376   -2.4716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4228   -2.8835    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6261   -2.6693    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8291   -2.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4707   -2.4029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1757   -1.6325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8173   -1.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5089   -1.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2946   -2.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7369   -0.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0953   -1.2264    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3903   -1.9969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513   -2.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428   -2.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7286   -1.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  6  9  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
  2 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
  1 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1C[C@H]2[C@H]3SS[C@H]4C[C@@H]5CCCN5[C@H]4SS[C@H]3CN2C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H22N2S4/c1-3-9-7-11-14(16(9)6-1)20-18-12-8-15-5-2-4-10(15)13(12)19-17-11/h9-14H,1-8H2/t9-,10-,11-,12-,13+,14-/m0/s1

> <INCHI_KEY>
JSMGJTNAIKSKKD-VZKILSJISA-N

> <FORMULA>
C14H22N2S4

> <MOLECULAR_WEIGHT>
346.58

> <EXACT_MASS>
346.066583412

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
36.74975564067721

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,9S,11S,14R,15S)-2,3,12,13-tetrathia-5,19-diazapentacyclo[12.6.0.0^{4,11}.0^{5,9}.0^{15,19}]icosane

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
3.211308496666666

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.065582858150735

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
94.88099999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,9S,11S,14R,15S)-2,3,12,13-tetrathia-5,19-diazapentacyclo[12.6.0.0^{4,11}.0^{5,9}.0^{15,19}]icosane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.267  -3.648   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.666  -2.161   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       4.001  -1.392   0.000  0.00  0.00           S+0
HETATM    4  S   UNK     0       5.488  -1.792   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       6.257  -3.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.857  -4.614   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       4.523  -5.383   0.000  0.00  0.00           S+0
HETATM    8  S   UNK     0       3.035  -4.983   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0       7.148  -5.454   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       8.345  -4.485   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       7.795  -3.047   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.992  -2.079   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.283  -2.919   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.883  -4.406   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.376  -1.321   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.178  -2.289   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.729  -3.728   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -0.469  -4.696   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.760  -3.856   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.360  -2.369   0.000  0.00  0.00           C+0
CONECT    1    2    8   17                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    1                                                       
CONECT    9    6   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15    2   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16    1   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₂N₂S₄

Average Mass

346.5800 Da

Monoisotopic Mass

346.06658 Da

IUPAC Name

(1S,4S,9S,11S,14R,15S)-2,3,12,13-tetrathia-5,19-diazapentacyclo[12.6.0.0^{4,11}.0^{5,9}.0^{15,19}]icosane

Traditional Name

(1S,4S,9S,11S,14R,15S)-2,3,12,13-tetrathia-5,19-diazapentacyclo[12.6.0.0^{4,11}.0^{5,9}.0^{15,19}]icosane

CAS Registry Number

Not Available

SMILES

C1C[C@H]2[C@H]3SS[C@H]4C[C@@H]5CCCN5[C@H]4SS[C@H]3CN2C1

InChI Identifier

InChI=1S/C14H22N2S4/c1-3-9-7-11-14(16(9)6-1)20-18-12-8-15-5-2-4-10(15)13(12)19-17-11/h9-14H,1-8H2/t9-,10-,11-,12-,13+,14-/m0/s1

InChI Key

JSMGJTNAIKSKKD-VZKILSJISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cassipourea gerrardii	Plant	KNApSAcK
Cassipourea gummiflua	LOTUS Database	35616633
Cassipourea gummiflua Tul.var.verticillata Lewis.	Plant	KNApSAcK
Cassipourea spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Not Available

Direct Parent

Pyrrolizidines

Alternative Parents

Substituents

Pyrrolizidine
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Organic disulfide
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.34	ALOGPS
logP	3.21	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	94.88 m³·mol⁻¹	ChemAxon
Polarizability	36.75 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	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

163104618

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Cassipourine (NP0067729)

MOL for NP0067729 ((-)-Cassipourine)

3D MOL for NP0067729 ((-)-Cassipourine)

3D SDF for NP0067729 ((-)-Cassipourine)

3D-SDF for NP0067729 ((-)-Cassipourine)

PDB for NP0067729 ((-)-Cassipourine)

3D PDB for NP0067729 ((-)-Cassipourine)

SMILES for NP0067729 ((-)-Cassipourine)

INCHI for NP0067729 ((-)-Cassipourine)

Structure for NP0067729 ((-)-Cassipourine)

3D Structure for NP0067729 ((-)-Cassipourine)