NP-MRD: Showing NP-Card for Pyridindolol (NP0003809)

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Record Information

Version

2.0

Created at

2020-12-09 00:57:21 UTC

Updated at

2021-07-15 16:47:26 UTC

NP-MRD ID

NP0003809

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyridindolol

Provided By

NPAtlas

Description

Pyridindolol is found in Streptomyces alboverticillatus and Streptomyces parvulus. Pyridindolol was first documented in 1975 (PMID: 1150547). Based on a literature review very few articles have been published on 1-[3-(hydroxymethyl)-9H-pyrido[3,4-b]indol-1-yl]ethane-1,2-diol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117503D          

 33 35  0  0  0  0            999 V2000
   -2.5221    3.5486   -0.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515    2.8394    1.0026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4505    1.6506    0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755    1.7550    0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140    0.6844    0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0363   -0.4711   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255   -1.3530   -0.5956 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2261   -0.7999   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -1.3185   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -0.4995   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4276    0.7938    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217    1.3107    0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732    0.4866    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312   -0.5391   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242   -1.7209   -0.7942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4171   -2.9271   -0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4315   -1.8229   -0.1390 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2130   -2.0899    1.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466    0.5089    0.1265 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    3.4994   -0.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987    2.5501    1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6158    3.4534    1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4793    2.6212    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7866   -2.3081   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194   -2.3129   -0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5617   -0.9430   -0.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2873    1.3704    0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    2.3238    0.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2137   -1.5945   -1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4029   -3.4987   -1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0292   -0.9358   -0.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9813   -2.7027   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -1.5587    1.5083 H   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
  7  8  1  0  0  0  0
  8  9  2  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
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  2  0  0  0  0
 19  3  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  1  0  0  0  0
  1 20  1  0  0  0  0
  2 21  1  0  0  0  0
  2 22  1  0  0  0  0
  4 23  1  0  0  0  0
  7 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 27  1  0  0  0  0
 12 28  1  0  0  0  0
 15 29  1  6  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
M  END

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -2.5221    3.5486   -0.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515    2.8394    1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505    1.6506    0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755    1.7550    0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140    0.6844    0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0363   -0.4711   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255   -1.3530   -0.5956 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2261   -0.7999   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -1.3185   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -0.4995   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4276    0.7938    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217    1.3107    0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732    0.4866    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312   -0.5391   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242   -1.7209   -0.7942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4171   -2.9271   -0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4315   -1.8229   -0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -2.0899    1.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466    0.5089    0.1265 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    3.4994   -0.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987    2.5501    1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6158    3.4534    1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4793    2.6212    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7866   -2.3081   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194   -2.3129   -0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5617   -0.9430   -0.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2873    1.3704    0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    2.3238    0.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2137   -1.5945   -1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4029   -3.4987   -1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0292   -0.9358   -0.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9813   -2.7027   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -1.5587    1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 14 19  2  0
 19  3  1  0
 13  5  1  0
 13  8  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  6
 16 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv1652306242117503D          

 33 35  0  0  0  0            999 V2000
   -2.5221    3.5486   -0.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515    2.8394    1.0026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4505    1.6506    0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755    1.7550    0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140    0.6844    0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0363   -0.4711   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255   -1.3530   -0.5956 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2261   -0.7999   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -1.3185   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -0.4995   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4276    0.7938    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217    1.3107    0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732    0.4866    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312   -0.5391   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242   -1.7209   -0.7942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4171   -2.9271   -0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4315   -1.8229   -0.1390 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2130   -2.0899    1.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466    0.5089    0.1265 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    3.4994   -0.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987    2.5501    1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6158    3.4534    1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4793    2.6212    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7866   -2.3081   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194   -2.3129   -0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5617   -0.9430   -0.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2873    1.3704    0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    2.3238    0.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2137   -1.5945   -1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4029   -3.4987   -1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0292   -0.9358   -0.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9813   -2.7027   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -1.5587    1.5083 H   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
  7  8  1  0  0  0  0
  8  9  2  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
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  2  0  0  0  0
 19  3  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  1  0  0  0  0
  1 20  1  0  0  0  0
  2 21  1  0  0  0  0
  2 22  1  0  0  0  0
  4 23  1  0  0  0  0
  7 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 27  1  0  0  0  0
 12 28  1  0  0  0  0
 15 29  1  6  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003809

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])C2=C(N([H])C3=C([H])C([H])=C([H])C([H])=C23)C(=N1)[C@@]([H])(O[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H14N2O3/c17-6-8-5-10-9-3-1-2-4-11(9)16-13(10)14(15-8)12(19)7-18/h1-5,12,16-19H,6-7H2/t12-/m0/s1

> <INCHI_KEY>
VAKXHGQDPLEUTH-UHFFFAOYSA-N

> <FORMULA>
C14H14N2O3

> <MOLECULAR_WEIGHT>
258.277

> <EXACT_MASS>
258.100442319

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.095226564467158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-1-[3-(hydroxymethyl)-9H-pyrido[3,4-b]indol-1-yl]ethane-1,2-diol

> <ALOGPS_LOGP>
0.83

> <JCHEM_LOGP>
0.023311784000000335

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.390349898849152

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.523030558136877

> <JCHEM_PKA_STRONGEST_BASIC>
4.343504793845837

> <JCHEM_POLAR_SURFACE_AREA>
89.37

> <JCHEM_REFRACTIVITY>
69.94030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1-[3-(hydroxymethyl)-9H-pyrido[3,4-b]indol-1-yl]ethane-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -2.5221    3.5486   -0.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515    2.8394    1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505    1.6506    0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755    1.7550    0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140    0.6844    0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0363   -0.4711   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255   -1.3530   -0.5956 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2261   -0.7999   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -1.3185   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -0.4995   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4276    0.7938    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217    1.3107    0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732    0.4866    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312   -0.5391   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242   -1.7209   -0.7942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4171   -2.9271   -0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4315   -1.8229   -0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -2.0899    1.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466    0.5089    0.1265 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    3.4994   -0.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987    2.5501    1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6158    3.4534    1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4793    2.6212    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7866   -2.3081   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194   -2.3129   -0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5617   -0.9430   -0.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2873    1.3704    0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    2.3238    0.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2137   -1.5945   -1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4029   -3.4987   -1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0292   -0.9358   -0.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9813   -2.7027   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -1.5587    1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 14 19  2  0
 19  3  1  0
 13  5  1  0
 13  8  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  6
 16 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.522   3.549  -0.183  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.252   2.839   1.003  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.450   1.651   0.542  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.076   1.755   0.558  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.714   0.684   0.143  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.036  -0.471  -0.281  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.026  -1.353  -0.596  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.226  -0.800  -0.382  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.507  -1.319  -0.534  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.585  -0.500  -0.205  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.428   0.794   0.261  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.122   1.311   0.413  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.073   0.487   0.082  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.331  -0.539  -0.281  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.024  -1.721  -0.794  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.417  -2.927  -0.604  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.432  -1.823  -0.139  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.213  -2.090   1.256  0.00  0.00           O+0
HETATM   19  N   UNK     0      -2.047   0.509   0.127  0.00  0.00           N+0
HETATM   20  H   UNK     0      -1.797   3.499  -0.834  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.199   2.550   1.468  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.616   3.453   1.631  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.479   2.621   0.881  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.787  -2.308  -0.948  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.619  -2.313  -0.882  0.00  0.00           H+0
HETATM   26  H   UNK     0       5.562  -0.943  -0.339  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.287   1.370   0.492  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.966   2.324   0.771  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.214  -1.595  -1.899  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.403  -3.499  -1.434  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.029  -0.936  -0.300  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.981  -2.703  -0.499  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.415  -1.559   1.508  0.00  0.00           H+0
CONECT    1    2   20                                                       
CONECT    2    1    3   21   22                                             
CONECT    3    2    4   19                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   25                                                  
CONECT   10    9   11   26                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12    5    8                                                  
CONECT   14    6   15   19                                                  
CONECT   15   14   16   17   29                                             
CONECT   16   15   30                                                       
CONECT   17   15   18   31   32                                             
CONECT   18   17   33                                                       
CONECT   19   14    3                                                       
CONECT   20    1                                                            
CONECT   21    2                                                            
CONECT   22    2                                                            
CONECT   23    4                                                            
CONECT   24    7                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   15                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

RDKit          3D

33 35  0  0  0  0  0  0  0  0999 V2000
   -2.5221    3.5486   -0.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515    2.8394    1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505    1.6506    0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755    1.7550    0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140    0.6844    0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0363   -0.4711   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255   -1.3530   -0.5956 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2261   -0.7999   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -1.3185   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -0.4995   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4276    0.7938    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217    1.3107    0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732    0.4866    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312   -0.5391   -0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242   -1.7209   -0.7942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4171   -2.9271   -0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4315   -1.8229   -0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -2.0899    1.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466    0.5089    0.1265 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    3.4994   -0.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987    2.5501    1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6158    3.4534    1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4793    2.6212    0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7866   -2.3081   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194   -2.3129   -0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5617   -0.9430   -0.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2873    1.3704    0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    2.3238    0.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2137   -1.5945   -1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4029   -3.4987   -1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0292   -0.9358   -0.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9813   -2.7027   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -1.5587    1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 14 19  2  0
 19  3  1  0
 13  5  1  0
 13  8  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  6
 16 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Pyridindolol monohydrochloride	MeSH
1-(1(R),2-Dihydroxyethyl)-3-hydroxymethyl-9H-pyrido(3,4-b)indole	MeSH
Pyridindolol monohydrobromide	MeSH

Chemical Formula

C₁₄H₁₄N₂O₃

Average Mass

258.2770 Da

Monoisotopic Mass

258.10044 Da

IUPAC Name

(1R)-1-[3-(hydroxymethyl)-9H-pyrido[3,4-b]indol-1-yl]ethane-1,2-diol

Traditional Name

(1R)-1-[3-(hydroxymethyl)-9H-pyrido[3,4-b]indol-1-yl]ethane-1,2-diol

CAS Registry Number

Not Available

SMILES

OCC(O)C1=C2NC3=CC=CC=C3C2=CC(CO)=N1

InChI Identifier

InChI=1S/C14H14N2O3/c17-6-8-5-10-9-3-1-2-4-11(9)16-13(10)14(15-8)12(19)7-18/h1-5,12,16-19H,6-7H2

InChI Key

VAKXHGQDPLEUTH-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
Streptomyces alboverticillatus	NPAtlas	1150547
Streptomyces parvulus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces alboverticilliatus MD401-C5	KNApSAcK Database	22123792
Streptoverticillium album K-251	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as harmala alkaloids. These 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
Benzenoid
Pyridine
Pyrrole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Aromatic alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
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	0.83	ALOGPS
logP	0.023	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.52	ChemAxon
pKa (Strongest Basic)	4.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.94 m³·mol⁻¹	ChemAxon
Polarizability	27.1 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

NPAtlas ID

NPA019312

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4513710

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5358591

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Aoyagi T, Kumagai M, Hazato T, Hamada M, Takeuchi T: Pyridindolol, a new beta-galactosidase inhibitor produced by actinomycetes. J Antibiot (Tokyo). 1975 Jul;28(7):555-7. doi: 10.7164/antibiotics.28.555. [PubMed:1150547 ]

Showing NP-Card for Pyridindolol (NP0003809)

MOL for NP0003809 (Pyridindolol)

3D MOL for NP0003809 (Pyridindolol)

3D SDF for NP0003809 (Pyridindolol)

3D-SDF for NP0003809 (Pyridindolol)

PDB for NP0003809 (Pyridindolol)

3D PDB for NP0003809 (Pyridindolol)

SMILES for NP0003809 (Pyridindolol)

INCHI for NP0003809 (Pyridindolol)

Structure for NP0003809 (Pyridindolol)

3D Structure for NP0003809 (Pyridindolol)