NP-MRD: Showing NP-Card for [1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate (NP0238986)

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Record Information

Version

2.0

Created at

2022-09-06 22:28:57 UTC

Updated at

2022-09-06 22:28:57 UTC

NP-MRD ID

NP0238986

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate

Description

[1-(1,2-Dihydroxyethyl)-9H-pyrido[3,4-b]indol-3-yl]methyl acetate belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. [1-(1,2-Dihydroxyethyl)-9H-pyrido[3,4-b]indol-3-yl]methyl acetate is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    5.1299    0.7118    0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9223   -0.1522    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1570   -0.0768    1.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903   -1.0276   -0.2937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4816   -1.8592   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1743   -1.2003   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058    0.1477   -0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2650    0.6735   -0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3674   -0.1406   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624    0.6303   -0.2041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1417    1.9341   -0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8739    3.1051   -0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2638    4.3268   -0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8887    4.3490   -0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1556    3.1806   -0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7636    1.9561   -0.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1612   -1.5110   -0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2863   -2.4226    0.0870 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0250   -2.1880    1.2391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7809   -3.8452    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9754   -4.0156    1.3075 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871   -1.9934   -0.1416 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9613    1.7143    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6211    0.7191   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8682    0.2178    1.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330   -2.4232   -1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4788   -2.6514    0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8741    0.7713   -0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4293    0.3018   -0.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9475    3.0902   -0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8369    5.2651   -0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4189    5.3202   -0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9039    3.2182   -0.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9278   -2.3797   -0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9531   -1.9966    0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1993   -4.0515   -0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6688   -4.4968    0.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958   -3.2014    1.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
  9 17  1  0
 17 22  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 22  6  1  0
 16  8  1  0
 12 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
 10 29  1  0
 15 33  1  0
 14 32  1  0
 13 31  1  0
 12 30  1  0
 18 34  1  6
 19 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
M  END


  Mrv1533004261517222D          

 22 24  0  0  0  0            999 V2000
   -2.0485   -0.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415   -0.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9866    0.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895   -0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6695   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9154   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4410   -3.0712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146   -2.1447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117   -3.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953   -3.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637   -4.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0088   -4.9401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  6 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238986

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=CC2=C(NC3=C2C=CC=C3)C(=N1)C(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C16H16N2O4/c1-9(20)22-8-10-6-12-11-4-2-3-5-13(11)18-15(12)16(17-10)14(21)7-19/h2-6,14,18-19,21H,7-8H2,1H3

> <INCHI_KEY>
SETMAEUYTGAAQD-UHFFFAOYSA-N

> <FORMULA>
C16H16N2O4

> <MOLECULAR_WEIGHT>
300.314

> <EXACT_MASS>
300.111007003

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.826779383143567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[1-(1,2-dihydroxyethyl)-9H-pyrido[3,4-b]indol-3-yl]methyl acetate

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
0.46443719433333325

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.4268653350663

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.529066266172485

> <JCHEM_PKA_STRONGEST_BASIC>
3.4179174981281553

> <JCHEM_POLAR_SURFACE_AREA>
95.44000000000001

> <JCHEM_REFRACTIVITY>
79.0918

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[1-(1,2-dihydroxyethyl)-9H-pyrido[3,4-b]indol-3-yl]methyl acetate

> <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      -3.824  -0.890   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.317  -0.570   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.842   0.895   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.287  -1.715   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.219  -1.394   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.250  -2.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.756  -2.219   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.787  -3.363   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.327  -3.363   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.357  -2.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.863  -2.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.339  -4.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.309  -5.148   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.802  -4.828   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.557  -5.733   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.311  -4.828   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.804  -5.148   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.774  -4.003   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       1.328  -6.612   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.178  -6.933   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.359  -7.757   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.883  -9.222   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17    6                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
[1-(1,2-Dihydroxyethyl)-9H-pyrido[3,4-b]indol-3-yl]methyl acetic acid	Generator

Chemical Formula

C₁₆H₁₆N₂O₄

Average Mass

300.3140 Da

Monoisotopic Mass

300.11101 Da

IUPAC Name

[1-(1,2-dihydroxyethyl)-9H-pyrido[3,4-b]indol-3-yl]methyl acetate

Traditional Name

[1-(1,2-dihydroxyethyl)-9H-pyrido[3,4-b]indol-3-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=CC2=C(NC3=C2C=CC=C3)C(=N1)C(O)CO

InChI Identifier

InChI=1S/C16H16N2O4/c1-9(20)22-8-10-6-12-11-4-2-3-5-13(11)18-15(12)16(17-10)14(21)7-19/h2-6,14,18-19,21H,7-8H2,1H3

InChI Key

SETMAEUYTGAAQD-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 harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Indole
Indole or derivatives
Pyridine
Benzenoid
Heteroaromatic compound
Pyrrole
Carboxylic acid ester
1,2-diol
Secondary alcohol
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Aromatic alcohol
Hydrocarbon derivative
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	1.15	ALOGPS
logP	0.46	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.53	ChemAxon
pKa (Strongest Basic)	3.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.09 m³·mol⁻¹	ChemAxon
Polarizability	31.83 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

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

72824827

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate (NP0238986)

MOL for NP0238986 ([1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate)

3D MOL for NP0238986 ([1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate)

3D SDF for NP0238986 ([1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate)

3D-SDF for NP0238986 ([1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate)

PDB for NP0238986 ([1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate)

3D PDB for NP0238986 ([1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate)

SMILES for NP0238986 ([1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate)

INCHI for NP0238986 ([1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate)

Structure for NP0238986 ([1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate)

3D Structure for NP0238986 ([1-(1,2-dihydroxyethyl)-9h-pyrido[3,4-b]indol-3-yl]methyl acetate)