NP-MRD: Showing NP-Card for 9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol (NP0223782)

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Record Information

Version

2.0

Created at

2022-09-06 01:58:24 UTC

Updated at

2022-09-06 01:58:24 UTC

NP-MRD ID

NP0223782

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol

Description

Batzelline B belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. 9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol was first documented in 2020 (PMID: 32623895). Based on a literature review very few articles have been published on Batzelline B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062203582D          

 17 19  0  0  0  0            999 V2000
    2.6431   -0.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226   -0.6406    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127    0.0269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578    0.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4959    1.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1634    0.6621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358    2.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    2.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0009    3.2729    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8390    2.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9252    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926    0.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463    1.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    2.4525    0.0000 N   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  2  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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0223782

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC1=NC2=C(O)C(O)=C(Cl)C3=NCCC1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C11H9ClN2O2S/c1-17-11-4-2-3-13-7-5(4)8(14-11)10(16)9(15)6(7)12/h15-16H,2-3H2,1H3

> <INCHI_KEY>
WDBVYQDGWBCZDK-UHFFFAOYSA-N

> <FORMULA>
C11H9ClN2O2S

> <MOLECULAR_WEIGHT>
268.72

> <EXACT_MASS>
268.0073264

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
26.265898653073485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol

> <JCHEM_LOGP>
0.8947813576666674

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.642903095519687

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.148403413211027

> <JCHEM_PKA_STRONGEST_BASIC>
3.525577487001094

> <JCHEM_POLAR_SURFACE_AREA>
65.18

> <JCHEM_REFRACTIVITY>
71.9556

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.934  -1.035   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       3.402  -1.196   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       2.497   0.050   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.957   0.050   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.481   1.515   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.926   2.141   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.172   1.236   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.087   3.673   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.494   4.299   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.159   4.578   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0      -0.002   6.109   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       1.566   3.952   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.727   2.420   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.973   1.515   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.380   2.141   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.541   3.673   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.295   4.578   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₉ClN₂O₂S

Average Mass

268.7200 Da

Monoisotopic Mass

268.00733 Da

IUPAC Name

9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol

Traditional Name

9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol

CAS Registry Number

Not Available

SMILES

CSC1=NC2=C(O)C(O)=C(Cl)C3=NCCC1=C23

InChI Identifier

InChI=1S/C11H9ClN2O2S/c1-17-11-4-2-3-13-7-5(4)8(14-11)10(16)9(15)6(7)12/h15-16H,2-3H2,1H3

InChI Key

WDBVYQDGWBCZDK-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Imidothiolactone
Benzenoid
Aryl halide
Aryl chloride
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.89	ChemAxon
pKa (Strongest Acidic)	6.15	ChemAxon
pKa (Strongest Basic)	3.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.18 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.96 m³·mol⁻¹	ChemAxon
Polarizability	26.27 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026887

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

135438178

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yamashita Y, Poignant L, Sakata J, Tokuyama H: Divergent Total Syntheses of Isobatzellines A/B and Batzelline A. Org Lett. 2020 Aug 21;22(16):6239-6243. doi: 10.1021/acs.orglett.0c01894. Epub 2020 Jul 5. [PubMed:32623895 ]
LOTUS database [Link]

Showing NP-Card for 9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol (NP0223782)

MOL for NP0223782 (9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol)

3D MOL for NP0223782 (9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol)

3D SDF for NP0223782 (9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol)

3D-SDF for NP0223782 (9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol)

PDB for NP0223782 (9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol)

3D PDB for NP0223782 (9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol)

SMILES for NP0223782 (9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol)

INCHI for NP0223782 (9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol)

Structure for NP0223782 (9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol)

3D Structure for NP0223782 (9-chloro-3-(methylsulfanyl)-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),2,4(12),7,9-pentaene-10,11-diol)