NP-MRD: Showing NP-Card for Styelsamine A (NP0070476)

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Record Information

Version

2.0

Created at

2022-04-28 15:52:35 UTC

Updated at

2022-04-28 15:52:35 UTC

NP-MRD ID

NP0070476

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Styelsamine A

Description

10-[(1R)-2-amino-1-hydroxyethyl]-8,14-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadeca-1(17),2,4,6,9,11,13,15-octaen-12-ol belongs to the class of organic compounds known as pyrido[2,3,4-kl]acridines. These are organic heterocyclic compounds with a structure based on the pyrido[2,3,4-kl]acridine skeleton. Styelsamine A is found in Eusynstyela latericius and Stelletta sp.. Based on a literature review very few articles have been published on 10-[(1R)-2-amino-1-hydroxyethyl]-8,14-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadeca-1(17),2,4,6,9,11,13,15-octaen-12-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
    4.4758   -0.2774    0.8409 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6794   -1.3761    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813   -1.0802   -0.3967 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1539   -0.4927   -1.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6140    0.0407    0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0983    1.2611    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    2.3866    0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8466    3.5162    0.9834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0805    2.2472    0.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8824    3.2996    0.7502 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2113    3.2268    0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7989    2.0038    0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9912    0.9343    0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6012    1.0521    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2144   -0.0488   -0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584   -1.2972   -0.4470 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705   -1.4322   -0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713   -2.6943   -0.8629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6198   -2.8487   -0.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4692   -1.7644   -0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9693   -0.5006   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -0.3377   -0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3808   -0.2410    0.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343   -0.3737    1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3549   -2.0342   -0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3708   -1.9994    1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0260   -1.9435   -0.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6804    0.1999   -1.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1777    1.3701    0.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3278    4.2326    1.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396    4.0874    0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8435    1.9760    0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2365   -2.1282   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887   -3.5258   -1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0830   -3.8033   -1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5254   -1.9327   -0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6585    0.2975   -0.2532 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
  3  5  1  0
  5 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  9 14  2  0
  6  5  1  0
 14 15  1  0
 22 17  1  0
 14 13  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  6
  4 28  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 12 32  1  0
 11 31  1  0
  8 30  1  0
  6 29  1  0
M  END


  Mrv1652304282217522D          

 22 25  0  0  1  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  4 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  6  0  0  0
 11 18  1  0  0  0  0
  2 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  1 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0070476

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC[C@H](O)C1=C2NC3=CC=CC=C3C3=CC=NC(C(O)=C1)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C17H15N3O2/c18-8-14(22)11-7-13(21)17-15-10(5-6-19-17)9-3-1-2-4-12(9)20-16(11)15/h1-7,14,20-22H,8,18H2/t14-/m0/s1

> <INCHI_KEY>
PZTPEBCFTKIETH-AWEZNQCLSA-N

> <FORMULA>
C17H15N3O2

> <MOLECULAR_WEIGHT>
293.326

> <EXACT_MASS>
293.116426735

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.22265289672272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-[(1R)-2-amino-1-hydroxyethyl]-8,14-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-12-ol

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
0.725209706704967

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.009543532162635

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.510446635588755

> <JCHEM_PKA_STRONGEST_BASIC>
9.24311234480388

> <JCHEM_POLAR_SURFACE_AREA>
91.4

> <JCHEM_REFRACTIVITY>
83.96050000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-[(1R)-2-amino-1-hydroxyethyl]-8,14-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-12-ol

> <JCHEM_VEBER_RULE>
0

$$$$

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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12    4   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14                                                            
CONECT   18   11                                                            
CONECT   19    2   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    1                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₅N₃O₂

Average Mass

293.3260 Da

Monoisotopic Mass

293.11643 Da

IUPAC Name

10-[(1R)-2-amino-1-hydroxyethyl]-8,14-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-12-ol

Traditional Name

10-[(1R)-2-amino-1-hydroxyethyl]-8,14-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-12-ol

CAS Registry Number

Not Available

SMILES

NC[C@H](O)C1=C2NC3=CC=CC=C3C3=CC=NC(C(O)=C1)=C23

InChI Identifier

InChI=1S/C17H15N3O2/c18-8-14(22)11-7-13(21)17-15-10(5-6-19-17)9-3-1-2-4-12(9)20-16(11)15/h1-7,14,20-22H,8,18H2/t14-/m0/s1

InChI Key

PZTPEBCFTKIETH-AWEZNQCLSA-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
Eusynstyela latericius	Animalia	KNApSAcK
Stelletta sp.	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrido[2,3,4-kl]acridines. These are organic heterocyclic compounds with a structure based on the pyrido[2,3,4-kl]acridine skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Pyrido[2,3,4-kl]acridines

Alternative Parents

Substituents

Pyrido[2,3,4-kl]acridine
Hydroxyquinoline
8-hydroxyquinoline
Diazanaphthalene
Naphthyridine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Pyridine
Benzenoid
Heteroaromatic compound
1,2-aminoalcohol
Secondary alcohol
Azacycle
Aromatic alcohol
Hydrocarbon derivative
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Amine
Alcohol
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	1.59	ALOGPS
logP	0.73	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	8.51	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	91.4 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.96 m³·mol⁻¹	ChemAxon
Polarizability	31.22 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

163094999

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Styelsamine A (NP0070476)

MOL for NP0070476 (Styelsamine A)

3D MOL for NP0070476 (Styelsamine A)

3D SDF for NP0070476 (Styelsamine A)

3D-SDF for NP0070476 (Styelsamine A)

PDB for NP0070476 (Styelsamine A)

3D PDB for NP0070476 (Styelsamine A)

SMILES for NP0070476 (Styelsamine A)

INCHI for NP0070476 (Styelsamine A)

Structure for NP0070476 (Styelsamine A)

3D Structure for NP0070476 (Styelsamine A)