NP-MRD: Showing NP-Card for 15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine (NP0217297)

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Record Information

Version

2.0

Created at

2022-09-05 17:36:19 UTC

Updated at

2022-09-05 17:36:19 UTC

NP-MRD ID

NP0217297

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine

Description

15-Bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]Octadeca-1(11),12(17),13,15-tetraen-3-amine belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. 15-Bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]Octadeca-1(11),12(17),13,15-tetraen-3-amine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -1.2362    2.7788   -0.1953 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8722    1.4951   -0.5132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3085    1.6068   -0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1181    0.0096    0.1045 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5252   -1.1683   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1340   -1.0492   -1.1633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7672   -0.8084    0.1002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2221   -1.9046    0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993   -1.7790    1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9473   -0.7217    0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725    0.3909    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1821    1.1660   -0.5620 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3996    0.5789   -0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6574    0.9261   -0.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681    0.1248   -0.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4616    0.6634   -1.4630 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.6173   -1.0739   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3817   -1.4572    0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2879   -0.6359    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1835    0.4603    0.3360 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2332    3.4194   -1.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7180    3.1953    0.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7520    1.2888   -1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    2.1409    0.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183    2.1940   -0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7493   -2.2031   -0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9696   -0.9618   -2.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8516   -2.0880    1.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3577   -2.8262    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2710   -1.6193    2.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254   -2.7586    1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855    2.0849   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7584    1.8617   -1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4916   -1.6930    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2283   -2.3833    0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3532    0.7458    1.3951 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 11 20  1  0
 20  2  1  0
 20  7  1  0
 19 10  1  0
 19 13  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 14 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  1
M  END


  Mrv1533004241505362D          

 20 23  0  0  0  0            999 V2000
    1.9646   -0.9751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498   -0.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6456   -0.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -0.0005    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444    1.3392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489    1.1562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132    1.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359    1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0943    1.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6300    0.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1351   -0.3004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9116   -0.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6383   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3398    0.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666   -0.3685    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.3146    0.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5879    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864    0.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073    0.4131    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
  4  5  1  0  0  0  0
  5  6  1  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  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  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
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 10 19  1  0  0  0  0
 13 19  1  0  0  0  0
 11 20  1  0  0  0  0
  2 20  1  0  0  0  0
  7 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217297

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1CSCON2CCC3=C(NC4=CC(Br)=CC=C34)C12

> <INCHI_IDENTIFIER>
InChI=1S/C14H16BrN3OS/c15-8-1-2-9-10-3-4-18-14(11(16)6-20-7-19-18)13(10)17-12(9)5-8/h1-2,5,11,14,17H,3-4,6-7,16H2

> <INCHI_KEY>
DBJUZIDWYRVTSZ-UHFFFAOYSA-N

> <FORMULA>
C14H16BrN3OS

> <MOLECULAR_WEIGHT>
354.27

> <EXACT_MASS>
353.019746

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
33.73435306138865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
1.9438635039999994

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.989441405854706

> <JCHEM_PKA_STRONGEST_BASIC>
8.784829181807915

> <JCHEM_POLAR_SURFACE_AREA>
54.28

> <JCHEM_REFRACTIVITY>
85.0403

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  N   UNK     0       3.667  -1.820   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.706  -0.617   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.205  -0.960   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       0.000  -0.001   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0      -0.000   1.539   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.203   2.500   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       2.705   2.158   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.571   3.431   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.107   3.317   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.776   1.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.909   0.657   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       5.852  -0.561   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       7.302  -0.040   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.658  -0.769   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.968   0.041   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0      11.324  -0.688   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       9.921   1.580   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.564   2.309   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.255   1.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.374   0.771   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   10   13                                                  
CONECT   20   11    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆BrN₃OS

Average Mass

354.2700 Da

Monoisotopic Mass

353.01975 Da

IUPAC Name

15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine

Traditional Name

15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine

CAS Registry Number

Not Available

SMILES

NC1CSCON2CCC3=C(NC4=CC(Br)=CC=C34)C12

InChI Identifier

InChI=1S/C14H16BrN3OS/c15-8-1-2-9-10-3-4-18-14(11(16)6-20-7-19-18)13(10)17-12(9)5-8/h1-2,5,11,14,17H,3-4,6-7,16H2

InChI Key

DBJUZIDWYRVTSZ-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 beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
3-alkylindole
Indole
Aralkylamine
Aryl bromide
Aryl halide
Benzenoid
Heteroaromatic compound
Pyrrole
Oxacycle
Azacycle
N-organohydroxylamine
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Primary aliphatic amine
Amine
Hydrocarbon derivative
Organic oxygen compound
Primary amine
Organic nitrogen 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	1.66	ALOGPS
logP	1.94	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	15.99	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.28 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.04 m³·mol⁻¹	ChemAxon
Polarizability	33.73 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

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

14056866

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine (NP0217297)

MOL for NP0217297 (15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine)

3D MOL for NP0217297 (15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine)

3D SDF for NP0217297 (15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine)

3D-SDF for NP0217297 (15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine)

PDB for NP0217297 (15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine)

3D PDB for NP0217297 (15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine)

SMILES for NP0217297 (15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine)

INCHI for NP0217297 (15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine)

Structure for NP0217297 (15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine)

3D Structure for NP0217297 (15-bromo-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.0²,⁸.0¹²,¹⁷]octadeca-1(11),12,14,16-tetraen-3-amine)