NP-MRD: Showing NP-Card for Pityriacitrin (NP0004187)

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Record Information

Version

2.0

Created at

2020-12-09 01:40:44 UTC

Updated at

2021-07-15 16:48:29 UTC

NP-MRD ID

NP0004187

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pityriacitrin

Provided By

NPAtlas

Description

3-{9H-pyrido[3,4-b]indole-1-carbonyl}-1H-indole 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. Pityriacitrin is found in Exophiala dermatitidis and Malassezia furfur. Pityriacitrin was first documented in 2002 (PMID: 12029500). Based on a literature review very few articles have been published on 3-{9H-pyrido[3,4-b]indole-1-carbonyl}-1H-indole.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118043D          

 37 41  0  0  0  0            999 V2000
    0.6478   -1.2469   -2.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840   -0.6145   -1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0025   -1.0304   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -2.3026   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2632   -2.3402    0.6326 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9121   -1.1512    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1020   -0.7191    1.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315    0.5582    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7476    1.3638    0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5523    0.9544   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057   -0.3381   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0445    0.4537   -1.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.7253   -1.3241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    2.7470   -1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137    2.4654   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    1.1594   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101    0.1390   -0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9607   -1.0061   -0.4693 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2185   -0.7651   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240   -1.6300    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4329   -1.1257    0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6370    0.2369    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133    1.0827    0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4066    0.6204    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056   -3.0657   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6611   -3.1505    1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6780   -1.3862    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4761    0.9484    1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0593    2.3844   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631    1.5908   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    3.7644   -1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5342    3.2675   -0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4899   -1.9407   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1066   -2.7032    0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2489   -1.7651    1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5876    0.6647    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526    2.1552    0.4779 H   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  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
 10 11  2  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 11  3  1  0  0  0  0
 17 12  1  0  0  0  0
 24 19  1  0  0  0  0
 11  6  1  0  0  0  0
 24 16  1  0  0  0  0
  4 25  1  0  0  0  0
  5 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  0  0  0  0
 14 31  1  0  0  0  0
 15 32  1  0  0  0  0
 18 33  1  0  0  0  0
 20 34  1  0  0  0  0
 21 35  1  0  0  0  0
 22 36  1  0  0  0  0
 23 37  1  0  0  0  0
M  END

     RDKit          3D

 37 41  0  0  0  0  0  0  0  0999 V2000
    0.6478   -1.2469   -2.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840   -0.6145   -1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0025   -1.0304   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -2.3026   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2632   -2.3402    0.6326 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9121   -1.1512    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1020   -0.7191    1.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315    0.5582    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7476    1.3638    0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5523    0.9544   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057   -0.3381   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0445    0.4537   -1.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.7253   -1.3241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    2.7470   -1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137    2.4654   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    1.1594   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101    0.1390   -0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9607   -1.0061   -0.4693 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2185   -0.7651   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240   -1.6300    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4329   -1.1257    0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6370    0.2369    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133    1.0827    0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4066    0.6204    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056   -3.0657   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6611   -3.1505    1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6780   -1.3862    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4761    0.9484    1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0593    2.3844   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631    1.5908   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    3.7644   -1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5342    3.2675   -0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4899   -1.9407   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1066   -2.7032    0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2489   -1.7651    1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5876    0.6647    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526    2.1552    0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 11  3  1  0
 17 12  1  0
 24 19  1  0
 11  6  1  0
 24 16  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 18 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  1  0
M  END


  Mrv1652306242118043D          

 37 41  0  0  0  0            999 V2000
    0.6478   -1.2469   -2.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840   -0.6145   -1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0025   -1.0304   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -2.3026   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2632   -2.3402    0.6326 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9121   -1.1512    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1020   -0.7191    1.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315    0.5582    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7476    1.3638    0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5523    0.9544   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057   -0.3381   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0445    0.4537   -1.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.7253   -1.3241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    2.7470   -1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137    2.4654   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    1.1594   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101    0.1390   -0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9607   -1.0061   -0.4693 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2185   -0.7651   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240   -1.6300    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4329   -1.1257    0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6370    0.2369    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133    1.0827    0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4066    0.6204    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056   -3.0657   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6611   -3.1505    1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6780   -1.3862    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4761    0.9484    1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0593    2.3844   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631    1.5908   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    3.7644   -1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5342    3.2675   -0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4899   -1.9407   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1066   -2.7032    0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2489   -1.7651    1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5876    0.6647    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526    2.1552    0.4779 H   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  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
 10 11  2  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 11  3  1  0  0  0  0
 17 12  1  0  0  0  0
 24 19  1  0  0  0  0
 11  6  1  0  0  0  0
 24 16  1  0  0  0  0
  4 25  1  0  0  0  0
  5 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  0  0  0  0
 14 31  1  0  0  0  0
 15 32  1  0  0  0  0
 18 33  1  0  0  0  0
 20 34  1  0  0  0  0
 21 35  1  0  0  0  0
 22 36  1  0  0  0  0
 23 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004187

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C([H])=C(C(=O)C2=NC([H])=C([H])C3=C2N([H])C2=C([H])C([H])=C([H])C([H])=C32)C2=C([H])C([H])=C([H])C([H])=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H13N3O/c24-20(15-11-22-16-7-3-1-6-13(15)16)19-18-14(9-10-21-19)12-5-2-4-8-17(12)23-18/h1-11,22-23H

> <INCHI_KEY>
BQTUGQOWZZUYIA-UHFFFAOYSA-N

> <FORMULA>
C20H13N3O

> <MOLECULAR_WEIGHT>
311.344

> <EXACT_MASS>
311.105862051

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
33.77544911284238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{9H-pyrido[3,4-b]indole-1-carbonyl}-1H-indole

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
3.817178618333333

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.056941110362963

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.909841168729757

> <JCHEM_PKA_STRONGEST_BASIC>
2.6634443497609737

> <JCHEM_POLAR_SURFACE_AREA>
61.54

> <JCHEM_REFRACTIVITY>
92.60530000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{9H-pyrido[3,4-b]indole-1-carbonyl}-1H-indole

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 41  0  0  0  0  0  0  0  0999 V2000
    0.6478   -1.2469   -2.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840   -0.6145   -1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0025   -1.0304   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -2.3026   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2632   -2.3402    0.6326 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9121   -1.1512    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1020   -0.7191    1.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315    0.5582    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7476    1.3638    0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5523    0.9544   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057   -0.3381   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0445    0.4537   -1.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.7253   -1.3241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    2.7470   -1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137    2.4654   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    1.1594   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101    0.1390   -0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9607   -1.0061   -0.4693 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2185   -0.7651   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240   -1.6300    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4329   -1.1257    0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6370    0.2369    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133    1.0827    0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4066    0.6204    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056   -3.0657   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6611   -3.1505    1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6780   -1.3862    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4761    0.9484    1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0593    2.3844   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631    1.5908   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    3.7644   -1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5342    3.2675   -0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4899   -1.9407   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1066   -2.7032    0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2489   -1.7651    1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5876    0.6647    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526    2.1552    0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 11  3  1  0
 17 12  1  0
 24 19  1  0
 11  6  1  0
 24 16  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 18 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  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       0.648  -1.247  -2.571  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.884  -0.615  -1.465  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.002  -1.030  -0.654  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.130  -2.303  -0.069  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.263  -2.340   0.633  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.912  -1.151   0.551  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.102  -0.719   1.097  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.532   0.558   0.842  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.748   1.364   0.044  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.552   0.954  -0.514  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.106  -0.338  -0.263  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.045   0.454  -1.183  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.286   1.725  -1.324  0.00  0.00           N+0
HETATM   14  C   UNK     0      -0.551   2.747  -1.045  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.814   2.465  -0.590  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.222   1.159  -0.421  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.310   0.139  -0.727  0.00  0.00           C+0
HETATM   18  N   UNK     0      -1.961  -1.006  -0.469  0.00  0.00           N+0
HETATM   19  C   UNK     0      -3.219  -0.765  -0.021  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.224  -1.630   0.366  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.433  -1.126   0.799  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.637   0.237   0.844  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.613   1.083   0.450  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.407   0.620   0.019  0.00  0.00           C+0
HETATM   25  H   UNK     0       1.406  -3.066  -0.201  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.661  -3.151   1.198  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.678  -1.386   1.714  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.476   0.948   1.256  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.059   2.384  -0.177  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.963   1.591  -1.139  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.253   3.764  -1.173  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.534   3.268  -0.351  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.490  -1.941  -0.618  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.107  -2.703   0.346  0.00  0.00           H+0
HETATM   35  H   UNK     0      -6.249  -1.765   1.115  0.00  0.00           H+0
HETATM   36  H   UNK     0      -6.588   0.665   1.185  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.753   2.155   0.478  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6   26                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   28                                                  
CONECT    9    8   10   29                                                  
CONECT   10    9   11   30                                                  
CONECT   11   10    3    6                                                  
CONECT   12    2   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   31                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   12                                                  
CONECT   18   17   19   33                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21   34                                                  
CONECT   21   20   22   35                                                  
CONECT   22   21   23   36                                                  
CONECT   23   22   24   37                                                  
CONECT   24   23   19   16                                                  
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   18                                                            
CONECT   34   20                                                            
CONECT   35   21                                                            
CONECT   36   22                                                            
CONECT   37   23                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

RDKit          3D

37 41  0  0  0  0  0  0  0  0999 V2000
    0.6478   -1.2469   -2.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840   -0.6145   -1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0025   -1.0304   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -2.3026   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2632   -2.3402    0.6326 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9121   -1.1512    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1020   -0.7191    1.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315    0.5582    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7476    1.3638    0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5523    0.9544   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057   -0.3381   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0445    0.4537   -1.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.7253   -1.3241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    2.7470   -1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137    2.4654   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    1.1594   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101    0.1390   -0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9607   -1.0061   -0.4693 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2185   -0.7651   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240   -1.6300    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4329   -1.1257    0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6370    0.2369    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133    1.0827    0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4066    0.6204    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056   -3.0657   -0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6611   -3.1505    1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6780   -1.3862    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4761    0.9484    1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0593    2.3844   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631    1.5908   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    3.7644   -1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5342    3.2675   -0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4899   -1.9407   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1066   -2.7032    0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2489   -1.7651    1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5876    0.6647    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526    2.1552    0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 11  3  1  0
 17 12  1  0
 24 19  1  0
 11  6  1  0
 24 16  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 18 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Pityriacitrin	MeSH

Chemical Formula

C₂₀H₁₃N₃O

Average Mass

311.3440 Da

Monoisotopic Mass

311.10586 Da

IUPAC Name

3-{9H-pyrido[3,4-b]indole-1-carbonyl}-1H-indole

Traditional Name

3-{9H-pyrido[3,4-b]indole-1-carbonyl}-1H-indole

CAS Registry Number

Not Available

SMILES

O=C(C1=CNC2=CC=CC=C12)C1=NC=CC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C20H13N3O/c24-20(15-11-22-16-7-3-1-6-13(15)16)19-18-14(9-10-21-19)12-5-2-4-8-17(12)23-18/h1-11,22-23H

InChI Key

BQTUGQOWZZUYIA-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
Exophiala dermatitidis	LOTUS Database	35616633
Malassezia furfur	NPAtlas	12029500

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
Indolecarboxylic acid derivative
Indole
Indole or derivatives
Pyridine carboxylic acid or derivatives
Aryl ketone
Benzenoid
Substituted pyrrole
Pyridine
Heteroaromatic compound
Vinylogous amide
Pyrrole
Ketone
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
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	4	ALOGPS
logP	3.82	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	2.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.61 m³·mol⁻¹	ChemAxon
Polarizability	33.78 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

NPAtlas ID

NPA017837

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28486003

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56649540

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mayser P, Schafer U, Kramer HJ, Irlinger B, Steglich W: Pityriacitrin -- an ultraviolet-absorbing indole alkaloid from the yeast Malassezia furfur. Arch Dermatol Res. 2002 May;294(3):131-4. doi: 10.1007/s00403-002-0294-2. Epub 2002 Apr 5. [PubMed:12029500 ]

Showing NP-Card for Pityriacitrin (NP0004187)

MOL for NP0004187 (Pityriacitrin)

3D MOL for NP0004187 (Pityriacitrin)

3D SDF for NP0004187 (Pityriacitrin)

3D-SDF for NP0004187 (Pityriacitrin)

PDB for NP0004187 (Pityriacitrin)

3D PDB for NP0004187 (Pityriacitrin)

SMILES for NP0004187 (Pityriacitrin)

INCHI for NP0004187 (Pityriacitrin)

Structure for NP0004187 (Pityriacitrin)

3D Structure for NP0004187 (Pityriacitrin)