NP-MRD: Showing NP-Card for Angustine (NP0050834)

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Record Information

Version

2.0

Created at

2022-04-27 22:12:29 UTC

Updated at

2022-04-27 22:12:29 UTC

NP-MRD ID

NP0050834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Angustine

Description

Angustine belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Angustine is found in Cephalanthus natalensis, Crinum angustum, Nauclea orientalis, Neisosperma kilneri, Psychotria bahiensis, Sarcocephalus latifolius, Strychnos angustiflora and Strychnos johnsonii. Angustine is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 43  0  0  0  0  0  0  0  0999 V2000
    3.1379    2.9134   -0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7936    1.9623   -0.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8746    0.5686   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1323   -0.0402   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1861   -1.3247    0.2544 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1021   -2.0605    0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358   -1.5250    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103   -2.2848    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8915   -3.4984    0.8983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779   -1.7683    0.4297 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3791   -0.4819    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4920    0.3238   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7559   -0.1749   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9341    0.1255   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233    1.3668   -0.4248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6757    1.3881   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5961    2.4011   -0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9483    2.1377   -0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4501    0.9010   -0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5354   -0.0956   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784    0.1508   -0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0481   -0.6509    0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9786   -2.0624    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6269   -2.6395    0.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1450    3.9113   -0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5992    2.7045    0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488    2.2677   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9811    0.5980   -0.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1553   -3.1219    0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3437    1.3379   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7472    2.2042   -0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2036    3.3720   -0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6175    2.9510   -0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5160    0.6935   -0.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8367   -1.0962    0.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5531   -2.6395   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6067   -2.1962    1.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948   -3.5228   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4716   -3.0954    1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10 24  1  0
 24 23  1  0
 23 22  1  0
 22 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 10  8  1  0
  8  9  2  0
 13  3  1  0
 14 11  1  0
 21 16  1  0
  8  7  1  0
 21 22  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  6 29  1  0
 12 30  1  0
 24 38  1  0
 24 39  1  0
 23 36  1  0
 23 37  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END


  Mrv1533004261503492D          

 24 28  0  0  0  0            999 V2000
    2.8316   -1.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978   -3.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6304   -6.0907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131   -5.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -5.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342   -4.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957   -4.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239   -3.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0269   -3.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7048   -3.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4509   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8411   -4.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -4.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852   -4.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6362   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  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
 16 17  2  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  2  0  0  0  0
 13 21  1  0  0  0  0
 16 21  1  0  0  0  0
 14 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  3 24  1  0  0  0  0
  7 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C=CC1=CN=CC2=C1C=C1N(CCC3=C1NC1=CC=CC=C31)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H15N3O/c1-2-12-10-21-11-16-15(12)9-18-19-14(7-8-23(18)20(16)24)13-5-3-4-6-17(13)22-19/h2-6,9-11,22H,1,7-8H2

> <INCHI_KEY>
FACXQEOSOVJIPD-UHFFFAOYSA-N

> <FORMULA>
C20H15N3O

> <MOLECULAR_WEIGHT>
313.36

> <EXACT_MASS>
313.121512115

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
34.81319476422931

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
19-ethenyl-3,13,17-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(10),4,6,8,15(20),16,18-octaen-14-one

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
2.4234915963333337

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.765575618294655

> <JCHEM_PKA_STRONGEST_BASIC>
3.722320421906624

> <JCHEM_POLAR_SURFACE_AREA>
48.99

> <JCHEM_REFRACTIVITY>
95.81859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-ethenyl-3,13,17-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(10),4,6,8,15(20),16,18-octaen-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       5.286  -3.507   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.291  -4.674   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.783  -6.128   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.270  -6.415   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.762  -7.869   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.767  -9.036   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.280  -8.749   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.285  -9.916   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.777 -11.369   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       8.798  -9.629   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       9.803 -10.795   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.316 -10.508   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.824  -9.055   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.819  -7.888   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      11.618  -6.571   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      13.117  -6.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.382  -6.047   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.775  -6.704   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.902  -8.239   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.637  -9.117   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.244  -8.459   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.306  -8.175   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.301  -7.008   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.788  -7.295   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   24                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   13   16                                                  
CONECT   22   14   10   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₅N₃O

Average Mass

313.3600 Da

Monoisotopic Mass

313.12151 Da

IUPAC Name

19-ethenyl-3,13,17-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(10),4,6,8,15(20),16,18-octaen-14-one

Traditional Name

19-ethenyl-3,13,17-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(10),4,6,8,15(20),16,18-octaen-14-one

CAS Registry Number

Not Available

SMILES

C=CC1=CN=CC2=C1C=C1N(CCC3=C1NC1=CC=CC=C31)C2=O

InChI Identifier

InChI=1S/C20H15N3O/c1-2-12-10-21-11-16-15(12)9-18-19-14(7-8-23(18)20(16)24)13-5-3-4-6-17(13)22-19/h2-6,9-11,22H,1,7-8H2

InChI Key

FACXQEOSOVJIPD-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, 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
Cephalanthus natalensis	LOTUS Database	35616633
Crinum angustum	Plant	KNApSAcK
Nauclea orientalis	LOTUS Database	35616633
Neisosperma kilneri	-	KNApSAcK
Psychotria bahiensis	Plant	KNApSAcK
Sarcocephalus latifolius	LOTUS Database	35616633
Strychnos angustiflora	Plant	KNApSAcK
Strychnos johnsonii	LOTUS Database	35616633

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
Diazanaphthalene
Naphthyridine
3-alkylindole
Indole
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Pyrrole
Lactam
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-carbolines (CHEBI:2725 )
Quinoline alkaloids (C09032 )

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	3.13	ALOGPS
logP	2.42	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.77	ChemAxon
pKa (Strongest Basic)	3.72	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	48.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.82 m³·mol⁻¹	ChemAxon
Polarizability	34.81 Å³	ChemAxon
Number of Rings	5	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

C00001685

Chemspider ID

Not Available

KEGG Compound ID

C09032

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441983

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Angustine (NP0050834)

MOL for NP0050834 (Angustine)

3D MOL for NP0050834 (Angustine)

3D SDF for NP0050834 (Angustine)

3D-SDF for NP0050834 (Angustine)

PDB for NP0050834 (Angustine)

3D PDB for NP0050834 (Angustine)

SMILES for NP0050834 (Angustine)

INCHI for NP0050834 (Angustine)

Structure for NP0050834 (Angustine)

3D Structure for NP0050834 (Angustine)