NP-MRD: Showing NP-Card for 6-hydroxymetatacarboline D (NP0011430)

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Record Information

Version

2.0

Created at

2021-01-05 21:07:31 UTC

Updated at

2026-02-05 04:01:47 UTC

NP-MRD ID

NP0011430

Natural Product DOI

https://doi.org/10.57994/5356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxymetatacarboline D

Provided By

NPAtlas

Description

(2S)-1-[3-(3-{[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl}-6-hydroxy-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylic acid 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. 6-hydroxymetatacarboline D is found in Mycena metata. 6-hydroxymetatacarboline D was first documented in 2013 (PMID: 23330951). Based on a literature review very few articles have been published on (2S)-1-[3-(3-{[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl}-6-hydroxy-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

6-hydroxymetatacarboline D
  Mrv1652301052122072D          

 36 39  0  0  0  0            999 V2000
   -5.1033   -2.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3496   -2.3564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6822   -2.8413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7684   -3.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010   -4.1467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5221   -3.9974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9285   -2.5058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611   -2.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3472   -3.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5073   -2.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8399   -3.1401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862   -2.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -1.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -1.4991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5812   -3.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4949   -4.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -4.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161   -4.2593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0762   -5.4153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6893   -5.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3537   -6.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5332   -6.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3617   -5.8278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3920   -5.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4782   -4.6718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0594   -5.9772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2633   -1.5359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  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
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 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
 21 23  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  2 36  1  0  0  0  0
 15 10  1  0  0  0  0
 18 13  1  0  0  0  0
 22 16  1  0  0  0  0
 32 28  1  0  0  0  0
M  END

NP0011430
     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
   -6.8361   -0.0875    2.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0865   -1.1977    2.8357 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9497   -2.1641    3.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1283   -1.9045    1.8865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1926   -0.9716    1.3010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8235   -1.0688    1.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3931   -2.0006    2.3179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8180   -0.1685    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465    0.8749    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1767    1.7227   -0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1592    1.5446   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8858    2.5003   -0.6479 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871    3.3155   -1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191    4.4169   -2.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7508    5.0369   -2.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391    4.5740   -2.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    5.1841   -3.2075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459    3.4584   -1.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1931    2.8220   -1.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    0.4936    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8638    0.2333    1.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376   -0.4382    0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4138   -0.2658    1.6096 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9569   -1.3463   -0.3538 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7183   -1.8927   -1.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0350   -2.4904   -2.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6582   -2.8652   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3539   -1.5925    0.0292 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1641   -0.4595   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175    0.4892   -1.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5338   -0.3626   -0.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5003   -0.3104    1.2913 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8623   -2.6816    0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6195   -2.4874   -0.3425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8005   -3.6062    1.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6650   -0.0719    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9311   -0.2699    2.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6615    0.9188    2.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5028   -0.7911    3.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1132   -1.9868    4.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5461   -2.6312    2.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5642   -0.2164    0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1842    1.0380   -0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275    2.6220   -0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    4.8172   -2.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6248    5.9140   -3.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4001    4.8285   -4.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637    3.0916   -1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8926   -0.4153    2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1262   -1.3637   -0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280    0.2509   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4529   -1.1102   -2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9564   -2.7016   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9126   -3.3762   -2.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6279   -1.6859   -2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0880   -3.6879   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7434   -3.0523   -0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4508   -1.7778    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1166   -1.0297    0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3251   -4.1409    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 20 33  2  0
  4 34  1  0
 34 35  2  0
 34 36  1  0
 33  8  1  0
 19 10  1  0
 29 25  1  0
 19 13  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  1
  3 41  1  0
  4 42  1  1
  5 43  1  0
  9 44  1  0
 12 45  1  0
 14 46  1  0
 15 47  1  0
 17 48  1  0
 18 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 29 60  1  1
 32 61  1  0
 36 62  1  0
M  END

6-hydroxymetatacarboline D
  Mrv1652301052122072D          

 36 39  0  0  0  0            999 V2000
   -5.1033   -2.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3496   -2.3564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6822   -2.8413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7684   -3.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010   -4.1467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5221   -3.9974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9285   -2.5058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611   -2.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3472   -3.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5073   -2.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8399   -3.1401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862   -2.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -1.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5332   -6.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3617   -5.8278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3920   -5.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4782   -4.6718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0594   -5.9772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2633   -1.5359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  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
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 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
 21 23  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  2 36  1  0  0  0  0
 15 10  1  0  0  0  0
 18 13  1  0  0  0  0
 22 16  1  0  0  0  0
 32 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@H](NC(=O)C1=NC(CCC(=O)N2CCC[C@H]2C(O)=O)=C2NC3=C(C=C(O)C=C3)C2=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26N4O8/c1-11(29)20(24(35)36)27-22(32)17-10-14-13-9-12(30)4-5-15(13)26-21(14)16(25-17)6-7-19(31)28-8-2-3-18(28)23(33)34/h4-5,9-11,18,20,26,29-30H,2-3,6-8H2,1H3,(H,27,32)(H,33,34)(H,35,36)/t11-,18+,20+/m1/s1

> <INCHI_KEY>
HYBYPROKTWYUIQ-PEECDGGASA-N

> <FORMULA>
C24H26N4O8

> <MOLECULAR_WEIGHT>
498.492

> <EXACT_MASS>
498.175063813

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.014697822710374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[3-(3-{[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl}-6-hydroxy-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
0.13860673133333423

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.9960799543794305

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3750464607568627

> <JCHEM_PKA_STRONGEST_BASIC>
0.867578722176597

> <JCHEM_POLAR_SURFACE_AREA>
193.15

> <JCHEM_REFRACTIVITY>
123.91159999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[3-(3-{[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl}-6-hydroxy-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

NP0011430
     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
   -6.8361   -0.0875    2.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0865   -1.1977    2.8357 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9497   -2.1641    3.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1283   -1.9045    1.8865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1926   -0.9716    1.3010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8235   -1.0688    1.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3931   -2.0006    2.3179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8180   -0.1685    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465    0.8749    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1767    1.7227   -0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1592    1.5446   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8858    2.5003   -0.6479 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871    3.3155   -1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191    4.4169   -2.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7508    5.0369   -2.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391    4.5740   -2.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    5.1841   -3.2075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459    3.4584   -1.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1931    2.8220   -1.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    0.4936    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8638    0.2333    1.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376   -0.4382    0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0408   -0.6718    0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4138   -0.2658    1.6096 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9569   -1.3463   -0.3538 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7183   -1.8927   -1.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0350   -2.4904   -2.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6582   -2.8652   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3539   -1.5925    0.0292 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1641   -0.4595   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175    0.4892   -1.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5338   -0.3626   -0.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5003   -0.3104    1.2913 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8623   -2.6816    0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6195   -2.4874   -0.3425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8005   -3.6062    1.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6650   -0.0719    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9311   -0.2699    2.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6615    0.9188    2.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5028   -0.7911    3.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1132   -1.9868    4.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5461   -2.6312    2.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5642   -0.2164    0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1842    1.0380   -0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275    2.6220   -0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    4.8172   -2.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6248    5.9140   -3.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4001    4.8285   -4.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637    3.0916   -1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8926   -0.4153    2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658    1.1953    1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1262   -1.3637   -0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280    0.2509   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4529   -1.1102   -2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9564   -2.7016   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9126   -3.3762   -2.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6279   -1.6859   -2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0880   -3.6879   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7434   -3.0523   -0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4508   -1.7778    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1166   -1.0297    0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3251   -4.1409    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 20 33  2  0
  4 34  1  0
 34 35  2  0
 34 36  1  0
 33  8  1  0
 19 10  1  0
 29 25  1  0
 19 13  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  1
  3 41  1  0
  4 42  1  1
  5 43  1  0
  9 44  1  0
 12 45  1  0
 14 46  1  0
 15 47  1  0
 17 48  1  0
 18 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 29 60  1  1
 32 61  1  0
 36 62  1  0
M  END

HEADER    PROTEIN                                 05-JAN-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6-hydroxymetatacarboline D                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JAN-21         0                                  
HETATM    1  C   UNK     0      -9.526  -5.025   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.119  -4.399   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.873  -5.304   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.034  -6.835   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.788  -7.741   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -8.441  -7.462   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      -5.467  -4.677   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -4.221  -5.583   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.382  -7.114   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.814  -4.956   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.568  -5.861   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -0.161  -5.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -3.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.246  -2.798   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.653  -3.425   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.246  -2.798   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.540   2.667   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.085  -6.140   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.924  -7.672   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.170  -8.577   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.577  -7.951   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0       2.009 -10.109   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       3.153 -11.139   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.527 -12.546   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.995 -12.385   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.675 -10.879   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.732 -10.252   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.893  -8.721   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.978 -11.157   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -7.958  -2.867   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   16                                                       
CONECT   23   21                                                            
CONECT   24   12   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   28                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36    2                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    NP0011430
HETATM    1  C1  UNL     1      -6.836  -0.087   2.143  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.087  -1.198   2.836  1.00  0.00           C  
HETATM    3  O1  UNL     1      -6.950  -2.164   3.350  1.00  0.00           O  
HETATM    4  C3  UNL     1      -5.128  -1.905   1.887  1.00  0.00           C  
HETATM    5  N1  UNL     1      -4.193  -0.972   1.301  1.00  0.00           N  
HETATM    6  C4  UNL     1      -2.823  -1.069   1.555  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.393  -2.001   2.318  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.818  -0.169   1.005  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.147   0.875   0.167  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.177   1.723  -0.344  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.159   1.545  -0.028  1.00  0.00           C  
HETATM   12  N2  UNL     1       0.886   2.500  -0.648  1.00  0.00           N  
HETATM   13  C9  UNL     1       0.087   3.316  -1.371  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.319   4.417  -2.165  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.751   5.037  -2.774  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.039   4.574  -2.601  1.00  0.00           C  
HETATM   17  O3  UNL     1      -3.143   5.184  -3.208  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.246   3.458  -1.793  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.193   2.822  -1.174  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.456   0.494   0.811  1.00  0.00           C  
HETATM   21  C16 UNL     1       1.864   0.233   1.194  1.00  0.00           C  
HETATM   22  C17 UNL     1       2.638  -0.438   0.082  1.00  0.00           C  
HETATM   23  C18 UNL     1       4.041  -0.672   0.496  1.00  0.00           C  
HETATM   24  O4  UNL     1       4.414  -0.266   1.610  1.00  0.00           O  
HETATM   25  N3  UNL     1       4.957  -1.346  -0.354  1.00  0.00           N  
HETATM   26  C19 UNL     1       4.718  -1.893  -1.673  1.00  0.00           C  
HETATM   27  C20 UNL     1       6.035  -2.490  -2.082  1.00  0.00           C  
HETATM   28  C21 UNL     1       6.658  -2.865  -0.758  1.00  0.00           C  
HETATM   29  C22 UNL     1       6.354  -1.592   0.029  1.00  0.00           C  
HETATM   30  C23 UNL     1       7.164  -0.459  -0.429  1.00  0.00           C  
HETATM   31  O5  UNL     1       6.618   0.489  -1.034  1.00  0.00           O  
HETATM   32  O6  UNL     1       8.534  -0.363  -0.234  1.00  0.00           O  
HETATM   33  N4  UNL     1      -0.500  -0.310   1.291  1.00  0.00           N  
HETATM   34  C24 UNL     1      -5.862  -2.682   0.864  1.00  0.00           C  
HETATM   35  O7  UNL     1      -5.619  -2.487  -0.343  1.00  0.00           O  
HETATM   36  O8  UNL     1      -6.800  -3.606   1.241  1.00  0.00           O  
HETATM   37  H1  UNL     1      -6.665  -0.072   1.040  1.00  0.00           H  
HETATM   38  H2  UNL     1      -7.931  -0.270   2.271  1.00  0.00           H  
HETATM   39  H3  UNL     1      -6.662   0.919   2.608  1.00  0.00           H  
HETATM   40  H4  UNL     1      -5.503  -0.791   3.695  1.00  0.00           H  
HETATM   41  H5  UNL     1      -7.113  -1.987   4.315  1.00  0.00           H  
HETATM   42  H6  UNL     1      -4.546  -2.631   2.490  1.00  0.00           H  
HETATM   43  H7  UNL     1      -4.564  -0.216   0.679  1.00  0.00           H  
HETATM   44  H8  UNL     1      -3.184   1.038  -0.098  1.00  0.00           H  
HETATM   45  H9  UNL     1       1.928   2.622  -0.596  1.00  0.00           H  
HETATM   46  H10 UNL     1       1.298   4.817  -2.332  1.00  0.00           H  
HETATM   47  H11 UNL     1      -0.625   5.914  -3.414  1.00  0.00           H  
HETATM   48  H12 UNL     1      -3.400   4.828  -4.140  1.00  0.00           H  
HETATM   49  H13 UNL     1      -3.264   3.092  -1.656  1.00  0.00           H  
HETATM   50  H14 UNL     1       1.893  -0.415   2.094  1.00  0.00           H  
HETATM   51  H15 UNL     1       2.366   1.195   1.506  1.00  0.00           H  
HETATM   52  H16 UNL     1       2.126  -1.364  -0.189  1.00  0.00           H  
HETATM   53  H17 UNL     1       2.628   0.251  -0.803  1.00  0.00           H  
HETATM   54  H18 UNL     1       4.453  -1.110  -2.416  1.00  0.00           H  
HETATM   55  H19 UNL     1       3.956  -2.702  -1.630  1.00  0.00           H  
HETATM   56  H20 UNL     1       5.913  -3.376  -2.746  1.00  0.00           H  
HETATM   57  H21 UNL     1       6.628  -1.686  -2.579  1.00  0.00           H  
HETATM   58  H22 UNL     1       6.088  -3.688  -0.323  1.00  0.00           H  
HETATM   59  H23 UNL     1       7.743  -3.052  -0.832  1.00  0.00           H  
HETATM   60  H24 UNL     1       6.451  -1.778   1.111  1.00  0.00           H  
HETATM   61  H25 UNL     1       9.117  -1.030   0.209  1.00  0.00           H  
HETATM   62  H26 UNL     1      -7.325  -4.141   0.570  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3    4   40
CONECT    3   41
CONECT    4    5   34   42
CONECT    5    6   43
CONECT    6    7    7    8
CONECT    8    9    9   33
CONECT    9   10   44
CONECT   10   11   11   19
CONECT   11   12   20
CONECT   12   13   45
CONECT   13   14   14   19
CONECT   14   15   46
CONECT   15   16   16   47
CONECT   16   17   18
CONECT   17   48
CONECT   18   19   19   49
CONECT   20   21   33   33
CONECT   21   22   50   51
CONECT   22   23   52   53
CONECT   23   24   24   25
CONECT   25   26   29
CONECT   26   27   54   55
CONECT   27   28   56   57
CONECT   28   29   58   59
CONECT   29   30   60
CONECT   30   31   31   32
CONECT   32   61
CONECT   34   35   35   36
CONECT   36   62
END

NP0011430
     RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
   -6.8361   -0.0875    2.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0865   -1.1977    2.8357 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9497   -2.1641    3.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1283   -1.9045    1.8865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1926   -0.9716    1.3010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8235   -1.0688    1.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3931   -2.0006    2.3179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8180   -0.1685    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465    0.8749    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1767    1.7227   -0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1592    1.5446   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8858    2.5003   -0.6479 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871    3.3155   -1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191    4.4169   -2.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7508    5.0369   -2.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391    4.5740   -2.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    5.1841   -3.2075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459    3.4584   -1.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1931    2.8220   -1.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    0.4936    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8638    0.2333    1.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376   -0.4382    0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0408   -0.6718    0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4138   -0.2658    1.6096 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9569   -1.3463   -0.3538 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7183   -1.8927   -1.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0350   -2.4904   -2.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6582   -2.8652   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3539   -1.5925    0.0292 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1641   -0.4595   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175    0.4892   -1.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5338   -0.3626   -0.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5003   -0.3104    1.2913 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8623   -2.6816    0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6195   -2.4874   -0.3425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8005   -3.6062    1.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6650   -0.0719    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9311   -0.2699    2.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6615    0.9188    2.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5028   -0.7911    3.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1132   -1.9868    4.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5461   -2.6312    2.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5642   -0.2164    0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1842    1.0380   -0.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275    2.6220   -0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    4.8172   -2.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6248    5.9140   -3.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4001    4.8285   -4.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637    3.0916   -1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8926   -0.4153    2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658    1.1953    1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1262   -1.3637   -0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280    0.2509   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4529   -1.1102   -2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9564   -2.7016   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9126   -3.3762   -2.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6279   -1.6859   -2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0880   -3.6879   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7434   -3.0523   -0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4508   -1.7778    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1166   -1.0297    0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3251   -4.1409    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 20 33  2  0
  4 34  1  0
 34 35  2  0
 34 36  1  0
 33  8  1  0
 19 10  1  0
 29 25  1  0
 19 13  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  1
  3 41  1  0
  4 42  1  1
  5 43  1  0
  9 44  1  0
 12 45  1  0
 14 46  1  0
 15 47  1  0
 17 48  1  0
 18 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 29 60  1  1
 32 61  1  0
 36 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S)-1-[3-(3-{[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl}-6-hydroxy-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylate	Generator

Chemical Formula

C₂₄H₂₆N₄O₈

Average Mass

498.4920 Da

Monoisotopic Mass

498.17506 Da

IUPAC Name

(2S)-1-[3-(3-{[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl}-6-hydroxy-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[3-(3-{[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl}-6-hydroxy-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@H](NC(=O)C1=NC(CCC(=O)N2CCC[C@H]2C(O)=O)=C2NC3=C(C=C(O)C=C3)C2=C1)C(O)=O

InChI Identifier

InChI=1S/C24H26N4O8/c1-11(29)20(24(35)36)27-22(32)17-10-14-13-9-12(30)4-5-15(13)26-21(14)16(25-17)6-7-19(31)28-8-2-3-18(28)23(33)34/h4-5,9-11,18,20,26,29-30H,2-3,6-8H2,1H3,(H,27,32)(H,33,34)(H,35,36)/t11-,18+,20+/m1/s1

InChI Key

HYBYPROKTWYUIQ-PEECDGGASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.0, Dimethylsulfoxide-d6, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.0, Dimethylsulfoxide-d6, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-05	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Mycena metata		Not Available
Mycena metata	NPAtlas	23330951

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
Pyridoindole
N-acyl-alpha amino acid or derivatives
Beta-carboline
N-acyl-alpha-amino acid
Proline or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid or derivatives
Hydroxyindole
Pyridine carboxylic acid or derivatives
Indole or derivatives
Indole
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
2-heteroaryl carboxamide
1-hydroxy-2-unsubstituted benzenoid
Phenol
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Benzenoid
Pyridine
Pyrrole
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Organonitrogen 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	1	ALOGPS
logP	0.14	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.38	ChemAxon
pKa (Strongest Basic)	0.87	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	193.15 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	123.91 m³·mol⁻¹	ChemAxon
Polarizability	51.01 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA002890

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28637704

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71578715

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jaeger RJ, Lamshoft M, Gottfried S, Spiteller M, Spiteller P: HR-MALDI-MS imaging assisted screening of beta-carboline alkaloids discovered from Mycena metata. J Nat Prod. 2013 Feb 22;76(2):127-34. doi: 10.1021/np300455a. Epub 2013 Jan 18. [PubMed:23330951 ]
DOI: 10.1021/np300455a
PMID: 23330951

Showing NP-Card for 6-hydroxymetatacarboline D (NP0011430)

MOL for NP0011430 (6-hydroxymetatacarboline D)

3D MOL for NP0011430 (6-hydroxymetatacarboline D)

3D SDF for NP0011430 (6-hydroxymetatacarboline D)

3D-SDF for NP0011430 (6-hydroxymetatacarboline D)

PDB for NP0011430 (6-hydroxymetatacarboline D)

3D PDB for NP0011430 (6-hydroxymetatacarboline D)

SMILES for NP0011430 (6-hydroxymetatacarboline D)

INCHI for NP0011430 (6-hydroxymetatacarboline D)

Structure for NP0011430 (6-hydroxymetatacarboline D)

3D Structure for NP0011430 (6-hydroxymetatacarboline D)