NP-MRD: Showing NP-Card for Haenamindole (NP0014760)

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Record Information

Version

2.0

Created at

2021-01-05 23:50:32 UTC

Updated at

2021-07-15 17:18:08 UTC

NP-MRD ID

NP0014760

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Haenamindole

Provided By

NPAtlas

Description

Haenamindole is found in Penicillium. Haenamindole was first documented in 2015 (PMID: 26403931). Based on a literature review a small amount of articles have been published on Haenamindole (PMID: 27328870) (PMID: 31013089) (PMID: 32189530).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120063D          

 74 79  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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 35 36  2  0
 30 37  1  0
 37 38  1  0
 38  2  1  0
 18  4  1  0
 25 20  1  0
 38 26  1  0
 15 10  1  0
 36 31  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  1
  7 45  1  0
  8 46  1  6
  9 47  1  0
  9 48  1  0
 10 49  1  1
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 19 60  1  0
 21 61  1  0
 22 62  1  0
 23 63  1  0
 24 64  1  0
 29 65  1  0
 29 66  1  0
 30 67  1  6
 32 68  1  0
 33 69  1  0
 34 70  1  0
 35 71  1  0
 36 72  1  0
 37 73  1  0
 38 74  1  6
M  END


  Mrv1652306242120063D          

 74 79  0  0  0  0            999 V2000
   -2.3121   -1.6751    1.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6921   -1.2521    0.3067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5968   -0.3028    0.4311 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5968   -0.5611    1.2483 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4989    0.6701    1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966    1.5351    2.0194 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085    0.7821   -0.0125 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6623   -0.3673   -0.7956 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0211   -0.2147   -1.4077 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1619   -0.0498   -0.4759 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4157    0.0808   -1.3471 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0839    1.4274   -1.1810 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5759    1.6337    0.2341 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4628    1.2103    1.1504 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1244    1.1479    0.4121 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4595   -1.6080   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004   -2.6768   -0.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4471   -1.6581    0.9524 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2886   -2.7971    1.7041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6660   -2.3868   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556   -3.3375   -1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802   -4.3337   -1.9593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3428   -4.4367   -2.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2809   -3.5324   -2.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9525   -2.5458   -1.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682   -1.4880   -0.6538 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1455   -1.3599   -0.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9320   -2.2585   -0.6981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6236   -0.1192    0.3235 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6620    0.9678   -0.0511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0641    2.3129    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3042    2.6181    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5973    3.9218    1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6726    4.9388    1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4343    4.6328    0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1440    3.3289    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3413    0.5996    0.4257 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8189   -0.4073   -0.4173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9195   -2.6819    1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3963   -1.8035    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1765   -0.9327    2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2431   -0.0659   -0.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0256    0.7153    0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -0.5838    2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6816    1.7193   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9454   -0.3900   -1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9790    0.7158   -2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630   -1.0296   -2.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3451   -0.9458    0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1619   -0.7152   -1.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1942   -0.0307   -2.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4544    2.2525   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9830    1.4049   -1.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8955    2.6717    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4847    0.9878    0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3709    1.9034    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6856    0.2063    1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652    1.0949    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    2.1019   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -3.2682    1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -3.3252   -0.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095   -5.0584   -2.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5815   -5.2108   -3.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -3.6185   -2.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6567   -0.3421    1.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6592    0.1129   -0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6100    0.9668   -1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0413    1.8312    1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5790    4.1167    1.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9450    5.9385    1.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    5.4204    0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1583    3.1122   -0.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4466    0.2953    1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674   -0.0054   -1.3107 H   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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38  2  1  0  0  0  0
 18  4  1  0  0  0  0
 25 20  1  0  0  0  0
 38 26  1  0  0  0  0
 15 10  1  0  0  0  0
 36 31  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  3 42  1  0  0  0  0
  3 43  1  0  0  0  0
  4 44  1  1  0  0  0
  7 45  1  0  0  0  0
  8 46  1  6  0  0  0
  9 47  1  0  0  0  0
  9 48  1  0  0  0  0
 10 49  1  1  0  0  0
 11 50  1  0  0  0  0
 11 51  1  0  0  0  0
 12 52  1  0  0  0  0
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 13 54  1  0  0  0  0
 13 55  1  0  0  0  0
 14 56  1  0  0  0  0
 14 57  1  0  0  0  0
 15 58  1  0  0  0  0
 15 59  1  0  0  0  0
 19 60  1  0  0  0  0
 21 61  1  0  0  0  0
 22 62  1  0  0  0  0
 23 63  1  0  0  0  0
 24 64  1  0  0  0  0
 29 65  1  0  0  0  0
 29 66  1  0  0  0  0
 30 67  1  6  0  0  0
 32 68  1  0  0  0  0
 33 69  1  0  0  0  0
 34 70  1  0  0  0  0
 35 71  1  0  0  0  0
 36 72  1  0  0  0  0
 37 73  1  0  0  0  0
 38 74  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0014760

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]ON1C(=O)[C@@]([H])(N([H])C(=O)[C@@]1([H])C([H])([H])[C@@]1(C2=C([H])C([H])=C([H])C([H])=C2N2C(=O)C([H])([H])[C@]([H])(N([H])[C@@]12[H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])[H])C([H])([H])C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H36N4O4/c1-30(18-25-27(36)31-23(28(37)34(25)38)16-19-10-4-2-5-11-19)21-14-8-9-15-24(21)33-26(35)17-22(32-29(30)33)20-12-6-3-7-13-20/h3,6-9,12-15,19,22-23,25,29,32,38H,2,4-5,10-11,16-18H2,1H3,(H,31,36)/t22-,23-,25+,29+,30+/m0/s1

> <INCHI_KEY>
SYRKXVJXAYRATF-OEBFQYBYSA-N

> <FORMULA>
C30H36N4O4

> <MOLECULAR_WEIGHT>
516.642

> <EXACT_MASS>
516.273655655

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
57.35162403524541

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6R)-6-{[(2S,10R,10aR)-10-methyl-4-oxo-2-phenyl-1H,2H,3H,4H,10H,10aH-pyrimido[1,2-a]indol-10-yl]methyl}-3-(cyclohexylmethyl)-1-hydroxypiperazine-2,5-dione

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
3.7594707253333333

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.803147371929379

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.666132438696835

> <JCHEM_PKA_STRONGEST_BASIC>
5.6268131827216346

> <JCHEM_POLAR_SURFACE_AREA>
101.97999999999999

> <JCHEM_REFRACTIVITY>
141.6549

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6R)-6-{[(2S,10R,10aR)-10-methyl-4-oxo-2-phenyl-1H,2H,3H,10aH-pyrimido[1,2-a]indol-10-yl]methyl}-3-(cyclohexylmethyl)-1-hydroxypiperazine-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 74 79  0  0  0  0  0  0  0  0999 V2000
   -2.3121   -1.6751    1.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6921   -1.2521    0.3067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5968   -0.3028    0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5968   -0.5611    1.2483 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4989    0.6701    1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966    1.5351    2.0194 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085    0.7821   -0.0125 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6623   -0.3673   -0.7956 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0211   -0.2147   -1.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1619   -0.0498   -0.4759 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4157    0.0808   -1.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0839    1.4274   -1.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5759    1.6337    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4628    1.2103    1.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1244    1.1479    0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4595   -1.6080   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6660   -2.3868   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0802   -4.3337   -1.9593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3428   -4.4367   -2.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2809   -3.5324   -2.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9525   -2.5458   -1.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682   -1.4880   -0.6538 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9320   -2.2585   -0.6981 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6620    0.9678   -0.0511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0641    2.3129    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5973    3.9218    1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1440    3.3289    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3413    0.5996    0.4257 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8189   -0.4073   -0.4173 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.0256    0.7153    0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6816    1.7193   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3451   -0.9458    0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1619   -0.7152   -1.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1942   -0.0307   -2.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4544    2.2525   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9830    1.4049   -1.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8955    2.6717    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4847    0.9878    0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3709    1.9034    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6856    0.2063    1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652    1.0949    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    2.1019   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -3.2682    1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -3.3252   -0.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095   -5.0584   -2.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5815   -5.2108   -3.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -3.6185   -2.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6567   -0.3421    1.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6592    0.1129   -0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6100    0.9668   -1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3674   -0.0054   -1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
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  8 16  1  0
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 18 19  1  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
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 31 32  2  0
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 37 38  1  0
 38  2  1  0
 18  4  1  0
 25 20  1  0
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 15 10  1  0
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  1 39  1  0
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  3 42  1  0
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  7 45  1  0
  8 46  1  6
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 33 69  1  0
 34 70  1  0
 35 71  1  0
 36 72  1  0
 37 73  1  0
 38 74  1  6
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  C   UNK     0      -2.312  -1.675   1.631  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.692  -1.252   0.307  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.597  -0.303   0.431  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.597  -0.561   1.248  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.499   0.670   1.124  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.497   1.535   2.019  0.00  0.00           O+0
HETATM    7  N   UNK     0       2.309   0.782  -0.013  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.662  -0.367  -0.796  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.021  -0.215  -1.408  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.162  -0.050  -0.476  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.416   0.081  -1.347  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.084   1.427  -1.181  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.576   1.634   0.234  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.463   1.210   1.150  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.124   1.148   0.412  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.459  -1.608  -0.070  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.100  -2.677  -0.251  0.00  0.00           O+0
HETATM   18  N   UNK     0       1.447  -1.658   0.952  0.00  0.00           N+0
HETATM   19  O   UNK     0       1.289  -2.797   1.704  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.666  -2.387  -0.613  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.756  -3.337  -1.057  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.080  -4.334  -1.959  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.343  -4.437  -2.472  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.281  -3.532  -2.075  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.953  -2.546  -1.180  0.00  0.00           C+0
HETATM   26  N   UNK     0      -3.768  -1.488  -0.654  0.00  0.00           N+0
HETATM   27  C   UNK     0      -5.146  -1.360  -0.373  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.932  -2.259  -0.698  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.624  -0.119   0.324  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.662   0.968  -0.051  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.064   2.313   0.410  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.304   2.618   0.930  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.597   3.922   1.343  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.673   4.939   1.248  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.434   4.633   0.728  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.144   3.329   0.317  0.00  0.00           C+0
HETATM   37  N   UNK     0      -3.341   0.600   0.426  0.00  0.00           N+0
HETATM   38  C   UNK     0      -2.819  -0.407  -0.417  0.00  0.00           C+0
HETATM   39  H   UNK     0      -1.920  -2.682   1.883  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.396  -1.804   1.449  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.176  -0.933   2.414  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.243  -0.066  -0.625  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.026   0.715   0.753  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.357  -0.584   2.362  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.682   1.719  -0.337  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.945  -0.390  -1.672  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.979   0.716  -2.046  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.263  -1.030  -2.117  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.345  -0.946   0.164  0.00  0.00           H+0
HETATM   50  H   UNK     0       7.162  -0.715  -1.117  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.194  -0.031  -2.425  0.00  0.00           H+0
HETATM   52  H   UNK     0       6.454   2.252  -1.539  0.00  0.00           H+0
HETATM   53  H   UNK     0       7.983   1.405  -1.827  0.00  0.00           H+0
HETATM   54  H   UNK     0       7.896   2.672   0.342  0.00  0.00           H+0
HETATM   55  H   UNK     0       8.485   0.988   0.352  0.00  0.00           H+0
HETATM   56  H   UNK     0       6.371   1.903   2.021  0.00  0.00           H+0
HETATM   57  H   UNK     0       6.686   0.206   1.533  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.365   1.095   1.221  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.019   2.102  -0.103  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.147  -3.268   1.730  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.254  -3.325  -0.708  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.310  -5.058  -2.272  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.582  -5.211  -3.168  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.291  -3.619  -2.486  0.00  0.00           H+0
HETATM   65  H   UNK     0      -5.657  -0.342   1.399  0.00  0.00           H+0
HETATM   66  H   UNK     0      -6.659   0.113  -0.012  0.00  0.00           H+0
HETATM   67  H   UNK     0      -4.610   0.967  -1.180  0.00  0.00           H+0
HETATM   68  H   UNK     0      -7.041   1.831   1.012  0.00  0.00           H+0
HETATM   69  H   UNK     0      -7.579   4.117   1.744  0.00  0.00           H+0
HETATM   70  H   UNK     0      -5.945   5.939   1.581  0.00  0.00           H+0
HETATM   71  H   UNK     0      -3.699   5.420   0.648  0.00  0.00           H+0
HETATM   72  H   UNK     0      -3.158   3.112  -0.091  0.00  0.00           H+0
HETATM   73  H   UNK     0      -3.447   0.295   1.408  0.00  0.00           H+0
HETATM   74  H   UNK     0      -2.367  -0.005  -1.311  0.00  0.00           H+0
CONECT    1    2   39   40   41                                             
CONECT    2    1    3   20   38                                             
CONECT    3    2    4   42   43                                             
CONECT    4    3    5   18   44                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   45                                                  
CONECT    8    7    9   16   46                                             
CONECT    9    8   10   47   48                                             
CONECT   10    9   11   15   49                                             
CONECT   11   10   12   50   51                                             
CONECT   12   11   13   52   53                                             
CONECT   13   12   14   54   55                                             
CONECT   14   13   15   56   57                                             
CONECT   15   14   10   58   59                                             
CONECT   16    8   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19    4                                                  
CONECT   19   18   60                                                       
CONECT   20    2   21   25                                                  
CONECT   21   20   22   61                                                  
CONECT   22   21   23   62                                                  
CONECT   23   22   24   63                                                  
CONECT   24   23   25   64                                                  
CONECT   25   24   26   20                                                  
CONECT   26   25   27   38                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   65   66                                             
CONECT   30   29   31   37   67                                             
CONECT   31   30   32   36                                                  
CONECT   32   31   33   68                                                  
CONECT   33   32   34   69                                                  
CONECT   34   33   35   70                                                  
CONECT   35   34   36   71                                                  
CONECT   36   35   31   72                                                  
CONECT   37   30   38   73                                                  
CONECT   38   37    2   26   74                                             
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    3                                                            
CONECT   43    3                                                            
CONECT   44    4                                                            
CONECT   45    7                                                            
CONECT   46    8                                                            
CONECT   47    9                                                            
CONECT   48    9                                                            
CONECT   49   10                                                            
CONECT   50   11                                                            
CONECT   51   11                                                            
CONECT   52   12                                                            
CONECT   53   12                                                            
CONECT   54   13                                                            
CONECT   55   13                                                            
CONECT   56   14                                                            
CONECT   57   14                                                            
CONECT   58   15                                                            
CONECT   59   15                                                            
CONECT   60   19                                                            
CONECT   61   21                                                            
CONECT   62   22                                                            
CONECT   63   23                                                            
CONECT   64   24                                                            
CONECT   65   29                                                            
CONECT   66   29                                                            
CONECT   67   30                                                            
CONECT   68   32                                                            
CONECT   69   33                                                            
CONECT   70   34                                                            
CONECT   71   35                                                            
CONECT   72   36                                                            
CONECT   73   37                                                            
CONECT   74   38                                                            
MASTER        0    0    0    0    0    0    0    0   74    0  158    0
END

RDKit          3D

74 79  0  0  0  0  0  0  0  0999 V2000
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   -1.6921   -1.2521    0.3067 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.5968   -0.5611    1.2483 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4989    0.6701    1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966    1.5351    2.0194 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085    0.7821   -0.0125 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6623   -0.3673   -0.7956 C   0  0  1  0  0  0  0  0  0  0  0  0
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    5.1619   -0.0498   -0.4759 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4157    0.0808   -1.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0839    1.4274   -1.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1440    3.3289    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8189   -0.4073   -0.4173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9195   -2.6819    1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3963   -1.8035    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1765   -0.9327    2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6816    1.7193   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1619   -0.7152   -1.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1942   -0.0307   -2.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4544    2.2525   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9830    1.4049   -1.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8955    2.6717    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4847    0.9878    0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3709    1.9034    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6856    0.2063    1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652    1.0949    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    2.1019   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -3.2682    1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -3.3252   -0.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095   -5.0584   -2.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5815   -5.2108   -3.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -3.6185   -2.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6567   -0.3421    1.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6592    0.1129   -0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6100    0.9668   -1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0413    1.8312    1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5790    4.1167    1.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9450    5.9385    1.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    5.4204    0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1583    3.1122   -0.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4466    0.2953    1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674   -0.0054   -1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 30 37  1  0
 37 38  1  0
 38  2  1  0
 18  4  1  0
 25 20  1  0
 38 26  1  0
 15 10  1  0
 36 31  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  1
  7 45  1  0
  8 46  1  6
  9 47  1  0
  9 48  1  0
 10 49  1  1
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 19 60  1  0
 21 61  1  0
 22 62  1  0
 23 63  1  0
 24 64  1  0
 29 65  1  0
 29 66  1  0
 30 67  1  6
 32 68  1  0
 33 69  1  0
 34 70  1  0
 35 71  1  0
 36 72  1  0
 37 73  1  0
 38 74  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆N₄O₄

Average Mass

516.6420 Da

Monoisotopic Mass

516.27366 Da

IUPAC Name

(3S,6R)-6-{[(2S,10R,10aR)-10-methyl-4-oxo-2-phenyl-1H,2H,3H,4H,10H,10aH-pyrimido[1,2-a]indol-10-yl]methyl}-3-(cyclohexylmethyl)-1-hydroxypiperazine-2,5-dione

Traditional Name

(3S,6R)-6-{[(2S,10R,10aR)-10-methyl-4-oxo-2-phenyl-1H,2H,3H,10aH-pyrimido[1,2-a]indol-10-yl]methyl}-3-(cyclohexylmethyl)-1-hydroxypiperazine-2,5-dione

CAS Registry Number

Not Available

SMILES

C[C@]1(C[C@H]2N(O)C(=O)[C@H](CC3CCCCC3)NC2=O)[C@@H]2N[C@@H](CC(=O)N2C2=CC=CC=C12)C1=CC=CC=C1

InChI Identifier

InChI=1S/C30H36N4O4/c1-30(18-25-27(36)31-23(28(37)34(25)38)16-19-10-4-2-5-11-19)21-14-8-9-15-24(21)33-26(35)17-22(32-29(30)33)20-12-6-3-7-13-20/h3,6-9,12-15,19,22-23,25,29,32,38H,2,4-5,10-11,16-18H2,1H3,(H,31,36)/t22-,23-,25+,29+,30+/m0/s1

InChI Key

SYRKXVJXAYRATF-OEBFQYBYSA-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
Penicillium	NPAtlas	26403931

Chemical Taxonomy

Classification

Not classified

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	3.02	ALOGPS
logP	3.76	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	5.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	101.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	141.65 m³·mol⁻¹	ChemAxon
Polarizability	57.35 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA020192

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78439865

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588722

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim JW, Ko SK, Son S, Shin KS, Ryoo IJ, Hong YS, Oh H, Hwang BY, Hirota H, Takahashi S, Kim BY, Osada H, Jang JH, Ahn JS: Haenamindole, an unusual diketopiperazine derivative from a marine-derived Penicillium sp. KCB12F005. Bioorg Med Chem Lett. 2015 Nov 15;25(22):5398-401. doi: 10.1016/j.bmcl.2015.09.026. Epub 2015 Sep 10. [PubMed:26403931 ]
Hwang IH, Che Y, Swenson DC, Gloer JB, Wicklow DT, Peterson SW, Dowd PF: Haenamindole and fumiquinazoline analogs from a fungicolous isolate of Penicillium lanosum. J Antibiot (Tokyo). 2016 Aug;69(8):631-6. doi: 10.1038/ja.2016.74. Epub 2016 Jun 22. [PubMed:27328870 ]
Li J, Hu Y, Hao X, Tan J, Li F, Qiao X, Chen S, Xiao C, Chen M, Peng Z, Gan M: Raistrickindole A, an Anti-HCV Oxazinoindole Alkaloid from Penicillium raistrickii IMB17-034. J Nat Prod. 2019 May 24;82(5):1391-1395. doi: 10.1021/acs.jnatprod.9b00259. Epub 2019 Apr 23. [PubMed:31013089 ]
Hamed A, Abdel-Razek AS, Araby M, Abu-Elghait M, El-Hosari DG, Frese M, Soliman HSM, Stammler HG, Sewald N, Shaaban M: Meleagrin from marine fungus Emericella dentata Nq45: crystal structure and diverse biological activity studies. Nat Prod Res. 2020 Mar 19:1-9. doi: 10.1080/14786419.2020.1741583. [PubMed:32189530 ]

Showing NP-Card for Haenamindole (NP0014760)

MOL for NP0014760 (Haenamindole)

3D MOL for NP0014760 (Haenamindole)

3D SDF for NP0014760 (Haenamindole)

3D-SDF for NP0014760 (Haenamindole)

PDB for NP0014760 (Haenamindole)

3D PDB for NP0014760 (Haenamindole)

SMILES for NP0014760 (Haenamindole)

INCHI for NP0014760 (Haenamindole)

Structure for NP0014760 (Haenamindole)

3D Structure for NP0014760 (Haenamindole)