NP-MRD: Showing NP-Card for (1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one (NP0295733)

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Record Information

Version

2.0

Created at

2022-09-10 04:53:24 UTC

Updated at

2022-09-10 04:53:25 UTC

NP-MRD ID

NP0295733

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one

Description

Pretrichodermamide A belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. (1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one was first documented in 2015 (PMID: 26439145). Based on a literature review a small amount of articles have been published on Pretrichodermamide A (PMID: 31210064) (PMID: 32427947) (PMID: 31061333) (PMID: 34163685).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102206532D          

 33 37  0  0  1  0            999 V2000
   -4.0253   -0.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6423    0.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8180    0.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4351    0.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108    0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1694    0.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3451    0.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    0.9829    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702    1.3413    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5166    0.8033    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2902    1.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470    0.8177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9882    1.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1018   -0.0055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3517   -0.4225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5514   -0.1142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9109   -0.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1771   -1.5457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0214   -0.6429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5734   -0.1065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7228    0.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1384    1.2244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8421   -0.3696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8969   -1.1928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276    0.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4728    0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7325    1.2768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6777    2.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -1.3066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3766   -0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7596   -1.3741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5839   -1.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  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  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 10 16  1  1  0  0  0
 16 17  1  0  0  0  0
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 17 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  6  0  0  0
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 21 22  1  0  0  0  0
 14 23  1  0  0  0  0
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 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
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 27 28  1  6  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -7.1207   -0.5636    2.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5406   -0.5868    0.8715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2351   -0.2477    0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3692    0.1662    1.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570    0.4907    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6877    0.3914   -0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3095    0.7334   -0.5312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7986    2.2927    0.2687 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2953    2.5150    0.0612 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0456    0.8860   -0.1741 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5198    1.0373   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2910    0.7355    0.8176 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0055    1.7498    1.7245 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8808   -0.5801    1.4033 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5868   -0.4278    1.8702 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7528    0.0701    0.9590 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3545   -0.2646    1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1282   -0.4298    2.2731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4326   -0.3983   -0.0810 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4928   -0.6662   -1.2247 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262    0.2006   -1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928    0.5342   -2.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0357   -1.7102    0.4261 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2519   -2.9532    1.0691 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1841   -1.5103   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9576   -0.4217   -0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521    0.7225    0.4712 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0703    1.9510   -0.0757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5424   -0.0186   -1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0684   -0.0811   -2.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8286   -0.3424   -0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7021   -0.7644   -1.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3936    0.1070   -2.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7324    0.3600    2.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3864   -0.5296    2.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7632   -1.4707    2.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5922    0.2681    2.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    0.8479    1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683    0.9205   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168    2.0870   -0.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7971    0.3624   -1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038    1.4246    2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5049   -0.7977    2.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0611   -1.3534   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9752    1.5010   -2.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613   -1.8271   -0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3727   -3.5903    0.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3946   -2.2780   -1.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7774   -0.3232   -1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3427    0.5803    1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9222    1.9629   -0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5296   -0.3535   -3.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3893   -0.2985   -2.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8483    0.1973   -3.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4153    1.1274   -2.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 11 12  1  0
 12 13  1  1
 12 27  1  0
 27 28  1  0
 27 26  1  0
 26 25  2  0
 25 23  1  0
 23 24  1  0
 23 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
  6 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  1  0
 31  3  1  0
 19  7  1  0
 16 10  1  0
 21 10  1  0
 14 12  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  7 39  1  6
 11 40  1  0
 11 41  1  0
 13 42  1  0
 27 50  1  1
 28 51  1  0
 26 49  1  0
 25 48  1  0
 23 46  1  6
 24 47  1  0
 14 43  1  1
 19 44  1  1
 22 45  1  0
 30 52  1  0
 33 53  1  0
 33 54  1  0
 33 55  1  0
M  END


  Mrv1652309102206532D          

 33 37  0  0  1  0            999 V2000
   -4.0253   -0.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6423    0.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8180    0.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4351    0.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108    0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1694    0.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3451    0.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    0.9829    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702    1.3413    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5166    0.8033    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2902    1.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470    0.8177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9882    1.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1018   -0.0055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3517   -0.4225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5514   -0.1142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9109   -0.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1771   -1.5457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0214   -0.6429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5734   -0.1065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7228    0.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1384    1.2244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8421   -0.3696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8969   -1.1928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276    0.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4728    0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7325    1.2768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6777    2.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -1.3066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3766   -0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7596   -1.3741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5839   -1.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  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  1  0  0  0
 12 14  1  0  0  0  0
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 10 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  6  0  0  0
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 21 22  1  0  0  0  0
 14 23  1  0  0  0  0
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 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
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  6 29  1  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0295733

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C2SS[C@@]34C[C@]5(O)[C@H](O)C=C[C@@H](O)[C@@H]5ON3C(=O)[C@@H]2N=C4O)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O9S2/c1-29-10-5-3-8(13(25)14(10)30-2)15-12-17(26)22-20(33-32-15,18(27)21-12)7-19(28)11(24)6-4-9(23)16(19)31-22/h3-6,9,11-12,15-16,23-25,28H,7H2,1-2H3,(H,21,27)/t9-,11-,12-,15?,16+,19+,20-/m1/s1

> <INCHI_KEY>
PPQRKKLHNNMQJV-GHYZKQQQSA-N

> <FORMULA>
C20H22N2O9S2

> <MOLECULAR_WEIGHT>
498.52

> <EXACT_MASS>
498.076672644

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
46.545899284671094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4R,7R,8S,12S)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0^{1,10}.0^{3,8}]heptadeca-5,16-dien-11-one

> <JCHEM_LOGP>
0.5364024800000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.71514687898878

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.254230552202976

> <JCHEM_PKA_STRONGEST_BASIC>
-0.531361746733248

> <JCHEM_POLAR_SURFACE_AREA>
161.51

> <JCHEM_REFRACTIVITY>
117.7115

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4R,7R,8S,12S)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0^{1,10}.0^{3,8}]heptadeca-5,16-dien-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.514  -1.327   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.799   0.037   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.260   0.100   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.546   1.464   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.007   1.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.183   0.226   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.644   0.289   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0      -0.082   1.835   0.000  0.00  0.00           S+0
HETATM    9  S   UNK     0       1.438   2.504   0.000  0.00  0.00           S+0
HETATM   10  C   UNK     0       2.831   1.499   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.275   2.204   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.688   1.526   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.578   3.062   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.790  -0.010   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.390  -0.789   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       2.896  -0.213   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       1.700  -1.428   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.197  -2.885   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.040  -1.200   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.070  -0.199   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.349   1.198   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.258   2.286   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.172  -0.690   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.274  -2.227   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.452   0.167   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.349   1.704   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.967   2.383   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.865   3.920   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.898  -1.138   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.074  -2.439   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.436  -1.201   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.151  -2.565   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -6.690  -2.628   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16   21                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14   27                                             
CONECT   13   12                                                            
CONECT   14   12   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    7   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   10   22                                                  
CONECT   22   21                                                            
CONECT   23   14   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   12   28                                                  
CONECT   28   27                                                            
CONECT   29    6   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    3   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂N₂O₉S₂

Average Mass

498.5200 Da

Monoisotopic Mass

498.07667 Da

IUPAC Name

(1R,3S,4R,7R,8S,12S)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0^{1,10}.0^{3,8}]heptadeca-5,16-dien-11-one

Traditional Name

(1R,3S,4R,7R,8S,12S)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0^{1,10}.0^{3,8}]heptadeca-5,16-dien-11-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C2SS[C@@]34C[C@]5(O)[C@H](O)C=C[C@@H](O)[C@@H]5ON3C(=O)[C@@H]2N=C4O)C(O)=C1OC

InChI Identifier

InChI=1S/C20H22N2O9S2/c1-29-10-5-3-8(13(25)14(10)30-2)15-12-17(26)22-20(33-32-15,18(27)21-12)7-19(28)11(24)6-4-9(23)16(19)31-22/h3-6,9,11-12,15-16,23-25,28H,7H2,1-2H3,(H,21,27)/t9-,11-,12-,15?,16+,19+,20-/m1/s1

InChI Key

PPQRKKLHNNMQJV-GHYZKQQQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

O-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Alpha-amino acid or derivatives
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Oxazinane
Monocyclic benzene moiety
1,2-oxazinane
Cyclic carboximidic acid
Tertiary alcohol
Secondary alcohol
Organic disulfide
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.54	ChemAxon
pKa (Strongest Acidic)	2.25	ChemAxon
pKa (Strongest Basic)	-0.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.51 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	117.71 m³·mol⁻¹	ChemAxon
Polarizability	46.55 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78437275

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585503

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yamazaki H, Rotinsulu H, Narita R, Takahashi R, Namikoshi M: Induced Production of Halogenated Epidithiodiketopiperazines by a Marine-Derived Trichoderma cf. brevicompactum with Sodium Halides. J Nat Prod. 2015 Oct 23;78(10):2319-21. doi: 10.1021/acs.jnatprod.5b00669. Epub 2015 Oct 6. [PubMed:26439145 ]
Harwoko H, Daletos G, Stuhldreier F, Lee J, Wesselborg S, Feldbrugge M, Muller WEG, Kalscheuer R, Ancheeva E, Proksch P: Dithiodiketopiperazine derivatives from endophytic fungi Trichoderma harzianum and Epicoccum nigrum. Nat Prod Res. 2021 Jan;35(2):257-265. doi: 10.1080/14786419.2019.1627348. Epub 2019 Jun 18. [PubMed:31210064 ]
Yamazaki H, Takahashi O, Kirikoshi R, Yagi A, Ogasawara T, Bunya Y, Rotinsulu H, Uchida R, Namikoshi M: Epipolythiodiketopiperazine and trichothecene derivatives from the NaI-containing fermentation of marine-derived Trichoderma cf. brevicompactum. J Antibiot (Tokyo). 2020 Aug;73(8):559-567. doi: 10.1038/s41429-020-0314-5. Epub 2020 May 19. [PubMed:32427947 ]
Yamazaki H: [Search for Protein Tyrosine Phosphatase 1B Inhibitors from Marine Organisms and Induced Production of New Fungal Metabolites by Modulating Culture Methods]. Yakugaku Zasshi. 2019;139(5):663-672. doi: 10.1248/yakushi.18-00221. [PubMed:31061333 ]
Liu H, Fan J, Zhang P, Hu Y, Liu X, Li SM, Yin WB: New insights into the disulfide bond formation enzymes in epidithiodiketopiperazine alkaloids. Chem Sci. 2021 Feb 8;12(11):4132-4138. doi: 10.1039/d0sc06647h. [PubMed:34163685 ]
LOTUS database [Link]

Showing NP-Card for (1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one (NP0295733)

MOL for NP0295733 ((1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one)

3D MOL for NP0295733 ((1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one)

3D SDF for NP0295733 ((1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one)

3D-SDF for NP0295733 ((1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one)

PDB for NP0295733 ((1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one)

3D PDB for NP0295733 ((1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one)

SMILES for NP0295733 ((1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one)

INCHI for NP0295733 ((1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one)

Structure for NP0295733 ((1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one)

3D Structure for NP0295733 ((1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one)