NP-MRD: Showing NP-Card for 1-alaninechlamydocin (NP0013033)

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Record Information

Version

2.0

Created at

2021-01-05 22:31:38 UTC

Updated at

2021-07-15 17:13:23 UTC

NP-MRD ID

NP0013033

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-alaninechlamydocin

Provided By

NPAtlas

Description

1-alaninechlamydocin is found in Tolypocladium sp. 1-alaninechlamydocin was first documented in 2014 (PMID: 24999749). Based on a literature review very few articles have been published on (3S,6S,9S,14aR)-9-benzyl-1,4,7-trihydroxy-6-methyl-3-{6-[(2S)-oxiran-2-yl]-6-oxohexyl}-3H,6H,9H,10H,12H,13H,14H,14aH-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119323D          

 73 76  0  0  0  0            999 V2000
    0.0033   -3.0822    2.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525   -2.6106    2.0272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4700   -2.4777    0.6022 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5201   -2.1981   -0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3942   -3.0222   -1.3572 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4320   -1.0801   -0.4914 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8245   -1.7545   -0.5152 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8952   -0.6966   -0.6487 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2636   -1.3428   -0.6544 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3495   -0.2612   -0.7985 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6606   -0.9492   -0.7829 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8587   -0.1275   -0.9410 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9254   -0.7623   -1.0793 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9699    1.3365   -0.9617 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5063    2.0912    0.2855 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.1056    1.8733    1.6256 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8274    1.7131    1.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9064    0.2479    1.2807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3494   -0.2128    1.5116 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -6.8320    0.5097   -1.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8184   -1.4751    2.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5629    3.2349   -3.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8256    4.2186   -0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5071    3.6285   -1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -0.3225    0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3071   -1.2924    1.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7829    0.3363    2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9143    2.0250    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3013    2.3793   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
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  6 17  1  0  0  0  0
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 16 14  1  0  0  0  0
 24 20  1  0  0  0  0
 34 29  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
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  3 42  1  0  0  0  0
  6 43  1  6  0  0  0
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 10 50  1  0  0  0  0
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 14 54  1  6  0  0  0
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 32 70  1  0  0  0  0
 33 71  1  0  0  0  0
 34 72  1  0  0  0  0
 35 73  1  0  0  0  0
M  END

     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
    0.0033   -3.0822    2.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525   -2.6106    2.0272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4700   -2.4777    0.6022 N   0  0  0  0  0  0  0  0  0  0  0  0
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 24 20  1  0
 34 29  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  1
  3 42  1  0
  6 43  1  6
  7 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 10 50  1  0
 10 51  1  0
 11 52  1  0
 11 53  1  0
 14 54  1  6
 15 55  1  0
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 17 57  1  0
 20 58  1  6
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 27 65  1  6
 28 66  1  0
 28 67  1  0
 30 68  1  0
 31 69  1  0
 32 70  1  0
 33 71  1  0
 34 72  1  0
 35 73  1  0
M  END


  Mrv1652306242119323D          

 73 76  0  0  0  0            999 V2000
    0.0033   -3.0822    2.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525   -2.6106    2.0272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4700   -2.4777    0.6022 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5201   -2.1981   -0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3942   -3.0222   -1.3572 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4320   -1.0801   -0.4914 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8245   -1.7545   -0.5152 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8952   -0.6966   -0.6487 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2636   -1.3428   -0.6544 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3495   -0.2612   -0.7985 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6606   -0.9492   -0.7829 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8587   -0.1275   -0.9410 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9254   -0.7623   -1.0793 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9699    1.3365   -0.9617 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5063    2.0912    0.2855 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8648    2.1456   -1.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4109   -0.0978    0.5440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0836    1.1949    0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056    1.8733    1.6256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796    1.9794   -0.4460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0448    1.4821   -1.8037 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0394    2.5528   -2.3000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4678    3.3178   -1.0446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1650    2.3169   -0.0407 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8274    1.7131    1.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3940    2.4687    1.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    0.2479    1.2807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3494   -0.2128    1.5116 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2264    0.0787    0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9427    1.2515    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7387    1.4560   -0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8320    0.5097   -1.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1143   -0.6616   -1.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3199   -0.8568   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1649   -0.1722    2.4505 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184   -1.4751    2.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9260   -1.7194    4.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4453   -3.6726    1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1526   -3.8115    3.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6502   -2.3078    2.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0526   -3.4735    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4088   -0.5892   -1.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9401   -2.2263    0.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8459   -2.4835   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4824   -1.8627    0.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4208   -2.0380   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2451    0.3837    0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2344    0.2766   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6978   -1.7239   -1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8177   -1.5558    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9957    1.7116   -1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9399    1.5837    1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0041    3.0603    0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8617   -0.4471    1.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755    2.9883   -0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345    0.5416   -1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1910    1.5307   -2.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5964   -0.3225    0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3071   -1.2924    1.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.3013    2.3793   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4651    0.6857   -2.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1980   -1.3875   -2.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7824   -1.8010   -0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690    0.6476    3.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  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  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
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 31 32  2  0  0  0  0
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 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36  2  1  0  0  0  0
 16 14  1  0  0  0  0
 24 20  1  0  0  0  0
 34 29  1  0  0  0  0
  1 38  1  0  0  0  0
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  1 40  1  0  0  0  0
  2 41  1  1  0  0  0
  3 42  1  0  0  0  0
  6 43  1  6  0  0  0
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 30 68  1  0  0  0  0
 31 69  1  0  0  0  0
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 33 71  1  0  0  0  0
 34 72  1  0  0  0  0
 35 73  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0013033

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C(=O)[C@]2([H])N(C(=O)[C@@]([H])(N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@]1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(=O)[C@@]1([H])OC1([H])[H])C([H])([H])[H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])C([H])([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H36N4O6/c1-17-24(33)30-20(15-18-9-4-2-5-10-18)27(36)31-14-8-12-21(31)26(35)29-19(25(34)28-17)11-6-3-7-13-22(32)23-16-37-23/h2,4-5,9-10,17,19-21,23H,3,6-8,11-16H2,1H3,(H,28,34)(H,29,35)(H,30,33)/t17-,19-,20-,21+,23-/m0/s1

> <INCHI_KEY>
QMNUPNOLDLHVTB-IWDBHXEASA-N

> <FORMULA>
C27H36N4O6

> <MOLECULAR_WEIGHT>
512.607

> <EXACT_MASS>
512.263484895

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.8887031928899

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6S,9S,14aR)-9-benzyl-6-methyl-3-{6-[(2S)-oxiran-2-yl]-6-oxohexyl}-tetradecahydropyrrolo[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
0.9594065706666662

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.196162202245485

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.750385356809817

> <JCHEM_PKA_STRONGEST_BASIC>
-3.367541444539142

> <JCHEM_POLAR_SURFACE_AREA>
137.21

> <JCHEM_REFRACTIVITY>
133.8719

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,9S,14aR)-9-benzyl-6-methyl-3-{6-[(2S)-oxiran-2-yl]-6-oxohexyl}-decahydropyrrolo[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
    0.0033   -3.0822    2.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525   -2.6106    2.0272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4700   -2.4777    0.6022 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5201   -2.1981   -0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3942   -3.0222   -1.3572 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4320   -1.0801   -0.4914 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8245   -1.7545   -0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8952   -0.6966   -0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2636   -1.3428   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3495   -0.2612   -0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6606   -0.9492   -0.7829 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8587   -0.1275   -0.9410 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9254   -0.7623   -1.0793 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9699    1.3365   -0.9617 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5063    2.0912    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4088   -0.5892   -1.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8630   -0.0045    0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4208   -2.0380   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2344    0.2766   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8177   -1.5558    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9957    1.7116   -1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9399    1.5837    1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0041    3.0603    0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8617   -0.4471    1.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755    2.9883   -0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345    0.5416   -1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1910    1.5307   -2.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629    3.2349   -3.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9510    2.1095   -2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8256    4.2186   -0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5071    3.6285   -1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -0.3225    0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3071   -1.2924    1.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.3013    2.3793   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4651    0.6857   -2.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1980   -1.3875   -2.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7824   -1.8010   -0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690    0.6476    3.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
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  7  8  1  0
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  9 10  1  0
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 18 20  1  0
 20 21  1  0
 21 22  1  0
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 23 24  1  0
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 33 34  2  0
 27 35  1  0
 35 36  1  0
 36 37  2  0
 36  2  1  0
 16 14  1  0
 24 20  1  0
 34 29  1  0
  1 38  1  0
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  2 41  1  1
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 31 69  1  0
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 33 71  1  0
 34 72  1  0
 35 73  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  C   UNK     0       0.003  -3.082   2.481  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.353  -2.611   2.027  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.470  -2.478   0.602  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.520  -2.198  -0.364  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.394  -3.022  -1.357  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.432  -1.080  -0.491  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.825  -1.755  -0.515  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.895  -0.697  -0.649  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.264  -1.343  -0.654  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.349  -0.261  -0.799  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.661  -0.949  -0.783  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.859  -0.128  -0.941  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.925  -0.762  -1.079  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.970   1.337  -0.962  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.506   2.091   0.286  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.865   2.146  -1.047  0.00  0.00           O+0
HETATM   17  N   UNK     0       0.411  -0.098   0.544  0.00  0.00           N+0
HETATM   18  C   UNK     0      -0.084   1.195   0.532  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.106   1.873   1.626  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.780   1.979  -0.446  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.045   1.482  -1.804  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.039   2.553  -2.300  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.468   3.318  -1.045  0.00  0.00           C+0
HETATM   24  N   UNK     0      -2.165   2.317  -0.041  0.00  0.00           N+0
HETATM   25  C   UNK     0      -2.827   1.713   1.042  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.394   2.469   1.869  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.906   0.248   1.281  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.349  -0.213   1.512  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.226   0.079   0.351  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.943   1.252   0.244  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.739   1.456  -0.879  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.832   0.510  -1.895  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.114  -0.662  -1.784  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.320  -0.857  -0.655  0.00  0.00           C+0
HETATM   35  N   UNK     0      -2.165  -0.172   2.450  0.00  0.00           N+0
HETATM   36  C   UNK     0      -1.818  -1.475   2.823  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.926  -1.719   4.084  0.00  0.00           O+0
HETATM   38  H   UNK     0       0.445  -3.673   1.655  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.153  -3.812   3.303  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.650  -2.308   2.902  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.053  -3.474   2.316  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.467  -2.640   0.247  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.409  -0.589  -1.508  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.940  -2.226   0.478  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.846  -2.483  -1.322  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.791  -0.158  -1.611  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.863  -0.005   0.214  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.482  -1.863   0.307  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.421  -2.038  -1.489  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.245   0.384   0.093  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.234   0.277  -1.752  0.00  0.00           H+0
HETATM   52  H   UNK     0       6.698  -1.724  -1.606  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.818  -1.556   0.160  0.00  0.00           H+0
HETATM   54  H   UNK     0       8.996   1.712  -1.280  0.00  0.00           H+0
HETATM   55  H   UNK     0       6.940   1.584   1.064  0.00  0.00           H+0
HETATM   56  H   UNK     0       8.004   3.060   0.515  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.862  -0.447   1.459  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.276   2.988  -0.553  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.635   0.542  -1.838  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.191   1.531  -2.480  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.563   3.235  -3.031  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.951   2.110  -2.727  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.826   4.219  -0.930  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.507   3.628  -1.074  0.00  0.00           H+0
HETATM   65  H   UNK     0      -2.596  -0.323   0.377  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.307  -1.292   1.753  0.00  0.00           H+0
HETATM   67  H   UNK     0      -4.783   0.336   2.399  0.00  0.00           H+0
HETATM   68  H   UNK     0      -5.914   2.025   1.006  0.00  0.00           H+0
HETATM   69  H   UNK     0      -7.301   2.379  -0.966  0.00  0.00           H+0
HETATM   70  H   UNK     0      -7.465   0.686  -2.775  0.00  0.00           H+0
HETATM   71  H   UNK     0      -6.198  -1.387  -2.581  0.00  0.00           H+0
HETATM   72  H   UNK     0      -4.782  -1.801  -0.633  0.00  0.00           H+0
HETATM   73  H   UNK     0      -1.869   0.648   3.080  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    1    3   36   41                                             
CONECT    3    2    4   42                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   17   43                                             
CONECT    7    6    8   44   45                                             
CONECT    8    7    9   46   47                                             
CONECT    9    8   10   48   49                                             
CONECT   10    9   11   50   51                                             
CONECT   11   10   12   52   53                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   54                                             
CONECT   15   14   16   55   56                                             
CONECT   16   15   14                                                       
CONECT   17    6   18   57                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   24   58                                             
CONECT   21   20   22   59   60                                             
CONECT   22   21   23   61   62                                             
CONECT   23   22   24   63   64                                             
CONECT   24   23   25   20                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   35   65                                             
CONECT   28   27   29   66   67                                             
CONECT   29   28   30   34                                                  
CONECT   30   29   31   68                                                  
CONECT   31   30   32   69                                                  
CONECT   32   31   33   70                                                  
CONECT   33   32   34   71                                                  
CONECT   34   33   29   72                                                  
CONECT   35   27   36   73                                                  
CONECT   36   35   37    2                                                  
CONECT   37   36                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    2                                                            
CONECT   42    3                                                            
CONECT   43    6                                                            
CONECT   44    7                                                            
CONECT   45    7                                                            
CONECT   46    8                                                            
CONECT   47    8                                                            
CONECT   48    9                                                            
CONECT   49    9                                                            
CONECT   50   10                                                            
CONECT   51   10                                                            
CONECT   52   11                                                            
CONECT   53   11                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   15                                                            
CONECT   57   17                                                            
CONECT   58   20                                                            
CONECT   59   21                                                            
CONECT   60   21                                                            
CONECT   61   22                                                            
CONECT   62   22                                                            
CONECT   63   23                                                            
CONECT   64   23                                                            
CONECT   65   27                                                            
CONECT   66   28                                                            
CONECT   67   28                                                            
CONECT   68   30                                                            
CONECT   69   31                                                            
CONECT   70   32                                                            
CONECT   71   33                                                            
CONECT   72   34                                                            
CONECT   73   35                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  152    0
END

RDKit          3D

73 76  0  0  0  0  0  0  0  0999 V2000
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    1.8245   -1.7545   -0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8952   -0.6966   -0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2636   -1.3428   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3495   -0.2612   -0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6606   -0.9492   -0.7829 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8587   -0.1275   -0.9410 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9699    1.3365   -0.9617 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5063    2.0912    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6502   -2.3078    2.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0526   -3.4735    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8617   -0.4471    1.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755    2.9883   -0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345    0.5416   -1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1910    1.5307   -2.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629    3.2349   -3.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9510    2.1095   -2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8256    4.2186   -0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5071    3.6285   -1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -0.3225    0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3071   -1.2924    1.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7829    0.3363    2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9143    2.0250    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3013    2.3793   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4651    0.6857   -2.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1980   -1.3875   -2.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7824   -1.8010   -0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690    0.6476    3.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1-Alaninechlamydocin	MeSH

Chemical Formula

C₂₇H₃₆N₄O₆

Average Mass

512.6070 Da

Monoisotopic Mass

512.26348 Da

IUPAC Name

(3S,6S,9S,14aR)-9-benzyl-6-methyl-3-{6-[(2S)-oxiran-2-yl]-6-oxohexyl}-tetradecahydropyrrolo[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

Traditional Name

(3S,6S,9S,14aR)-9-benzyl-6-methyl-3-{6-[(2S)-oxiran-2-yl]-6-oxohexyl}-decahydropyrrolo[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

CAS Registry Number

Not Available

SMILES

C[C@@H]1NC(=O)[C@H](CCCCCC(=O)[C@@H]2CO2)NC(=O)[C@H]2CCCN2C(=O)[C@H](CC2=CC=CC=C2)NC1=O

InChI Identifier

InChI=1S/C27H36N4O6/c1-17-24(33)30-20(15-18-9-4-2-5-10-18)27(36)31-14-8-12-21(31)26(35)29-19(25(34)28-17)11-6-3-7-13-22(32)23-16-37-23/h2,4-5,9-10,17,19-21,23H,3,6-8,11-16H2,1H3,(H,28,34)(H,29,35)(H,30,33)/t17-,19-,20-,21+,23-/m0/s1

InChI Key

QMNUPNOLDLHVTB-IWDBHXEASA-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
Tolypocladium sp.	NPAtlas	24999749

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	1.19	ALOGPS
logP	0.96	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	10.75	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	137.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	133.87 m³·mol⁻¹	ChemAxon
Polarizability	53.89 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

NPA008967

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58133154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

118708140

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Du L, Risinger AL, King JB, Powell DR, Cichewicz RH: A potent HDAC inhibitor, 1-alaninechlamydocin, from a Tolypocladium sp. induces G2/M cell cycle arrest and apoptosis in MIA PaCa-2 cells. J Nat Prod. 2014 Jul 25;77(7):1753-7. doi: 10.1021/np500387h. Epub 2014 Jul 7. [PubMed:24999749 ]

Showing NP-Card for 1-alaninechlamydocin (NP0013033)

MOL for NP0013033 (1-alaninechlamydocin)

3D MOL for NP0013033 (1-alaninechlamydocin)

3D SDF for NP0013033 (1-alaninechlamydocin)

3D-SDF for NP0013033 (1-alaninechlamydocin)

PDB for NP0013033 (1-alaninechlamydocin)

3D PDB for NP0013033 (1-alaninechlamydocin)

SMILES for NP0013033 (1-alaninechlamydocin)

INCHI for NP0013033 (1-alaninechlamydocin)

Structure for NP0013033 (1-alaninechlamydocin)

3D Structure for NP0013033 (1-alaninechlamydocin)