NP-MRD: Showing NP-Card for 3'-O-desmethyl-1-epipreussomerin C (NP0001619)

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Record Information

Version

1.0

Created at

2020-09-23 01:58:54 UTC

Updated at

2021-08-10 02:55:45 UTC

NP-MRD ID

NP0001619

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-O-desmethyl-1-epipreussomerin C

Provided By

NPAtlas

Description

(1S,2R,4R,5S,12S,13R)-5,7,13-trihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]Tetracosa-6,8,10(24),16(23),17,19-hexaen-15-one belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. 3'-O-desmethyl-1-epipreussomerin C is found in Sporormiella vexans. It was first documented in 1999 (PMID: 10217738). Based on a literature review very few articles have been published on (1S,2R,4R,5S,12S,13R)-5,7,13-trihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1¹,⁶.1¹²,¹⁶.0²,⁴.0¹⁰,²⁴.0²⁰,²³]Tetracosa-6,8,10(24),16(23),17,19-hexaen-15-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117443D          

 42 48  0  0  0  0            999 V2000
   -5.2053   -0.8550    0.9108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1163   -0.8942    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3022   -2.0860    0.0074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9221   -1.9083    0.5934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1395   -3.0531    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2067   -0.6693    0.2497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5386   -0.2257    1.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8319   -0.2517    1.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860   -0.5203    2.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802   -0.4989    2.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145   -0.2163    1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9962   -0.1932    1.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    0.0537    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5016    0.0301    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752    0.3037   -0.8069 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0826    1.5486   -0.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    1.6195   -0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2072    2.7183   -0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5962    2.6717   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2235    1.4868   -0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896    0.3890   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138    0.4483   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9111   -0.8594   -2.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5130    0.3507   -1.0572 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1888    1.5595   -0.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2298   -2.2237   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0950   -1.9202    1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593   -3.1003    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726   -0.7358    3.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5355   -0.3937    2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828    3.6326   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2004    3.5307   -1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3140    1.4049   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6041    0.8102   -2.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1029    0.7178   -3.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3128   -0.4308   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0520    1.5452   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
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M  END

     RDKit          3D

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   -4.1163   -0.8942    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3022   -2.0860    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9221   -1.9083    0.5934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1395   -3.0531    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2067   -0.6693    0.2497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5386   -0.2257    1.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8319   -0.2517    1.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860   -0.5203    2.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802   -0.4989    2.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145   -0.2163    1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9962   -0.1932    1.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    0.0537    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5016    0.0301    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752    0.3037   -0.8069 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.2298   -2.2237   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279   -3.0000    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0950   -1.9202    1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593   -3.1003    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726   -0.7358    3.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590   -0.7115    3.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5355   -0.3937    2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828    3.6326   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2004    3.5307   -1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3140    1.4049   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6041    0.8102   -2.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1029    0.7178   -3.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3128   -0.4308   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0520    1.5452   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
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M  END


  Mrv1652306242117443D          

 42 48  0  0  0  0            999 V2000
   -5.2053   -0.8550    0.9108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1163   -0.8942    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3022   -2.0860    0.0074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9221   -1.9083    0.5934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1395   -3.0531    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2067   -0.6693    0.2497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5386   -0.2257    1.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8319   -0.2517    1.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860   -0.5203    2.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802   -0.4989    2.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145   -0.2163    1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9962   -0.1932    1.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    0.0537    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5016    0.0301    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752    0.3037   -0.8069 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0826    1.5486   -0.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    1.6195   -0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2072    2.7183   -0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5962    2.6717   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2235    1.4868   -0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896    0.3890   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138    0.4483   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2298   -2.2237   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279   -3.0000    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0950   -1.9202    1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593   -3.1003    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726   -0.7358    3.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590   -0.7115    3.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5355   -0.3937    2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828    3.6326   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2004    3.5307   -1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3140    1.4049   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6041    0.8102   -2.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1029    0.7178   -3.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3128   -0.4308   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0520    1.5452   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
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  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
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 14  8  2  0  0  0  0
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  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
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  5 32  1  0  0  0  0
  9 33  1  0  0  0  0
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 18 36  1  0  0  0  0
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 26 40  1  6  0  0  0
 27 41  1  6  0  0  0
 28 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001619

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C3=C(O[C@@]45O[C@]3(OC3=C([H])C([H])=C([H])C(C(=O)C([H])([H])[C@@]4([H])O[H])=C53)[C@]3([H])O[C@]3([H])[C@@]2([H])O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H14O8/c21-8-4-5-11-15-13(8)16(24)17-18(25-17)20(15)27-10-3-1-2-7-9(22)6-12(23)19(26-11,28-20)14(7)10/h1-5,12,16-18,21,23-24H,6H2/t12-,16+,17-,18-,19-,20+/m1/s1

> <INCHI_KEY>
BCPICRNXIKGDCQ-LZVSGGPWSA-N

> <FORMULA>
C20H14O8

> <MOLECULAR_WEIGHT>
382.324

> <EXACT_MASS>
382.068867411

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
36.26114141327625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,5S,12S,13R)-5,7,13-trihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1^{1,6}.1^{12,16}.0^{2,4}.0^{10,24}.0^{20,23}]tetracosa-6,8,10(24),16(23),17,19-hexaen-15-one

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
1.6194883939999998

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.743486623070508

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.80356201118914

> <JCHEM_PKA_STRONGEST_BASIC>
-3.691758873921726

> <JCHEM_POLAR_SURFACE_AREA>
117.98000000000002

> <JCHEM_REFRACTIVITY>
90.335

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5S,12S,13R)-5,7,13-trihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1^{1,6}.1^{12,16}.0^{2,4}.0^{10,24}.0^{20,23}]tetracosa-6,8,10(24),16(23),17,19-hexaen-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 48  0  0  0  0  0  0  0  0999 V2000
   -5.2053   -0.8550    0.9108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1163   -0.8942    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3022   -2.0860    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9221   -1.9083    0.5934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1395   -3.0531    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2067   -0.6693    0.2497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5386   -0.2257    1.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8319   -0.2517    1.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860   -0.5203    2.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802   -0.4989    2.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145   -0.2163    1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9962   -0.1932    1.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    0.0537    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5016    0.0301    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752    0.3037   -0.8069 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0826    1.5486   -0.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    1.6195   -0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2072    2.7183   -0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5962    2.6717   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2235    1.4868   -0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896    0.3890   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138    0.4483   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129   -0.7721   -0.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2325    0.4011   -2.1246 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9111   -0.8594   -2.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196    0.2973   -2.2537 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5130    0.3507   -1.0572 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1888    1.5595   -0.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2298   -2.2237   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279   -3.0000    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0950   -1.9202    1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593   -3.1003    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726   -0.7358    3.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590   -0.7115    3.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5355   -0.3937    2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828    3.6326   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2004    3.5307   -1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3140    1.4049   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6041    0.8102   -2.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1029    0.7178   -3.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3128   -0.4308   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0520    1.5452   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  1
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 21  2  1  0
 26 24  1  0
 22  6  1  0
 23  6  1  0
 14  8  2  0
 22 17  1  0
 27 13  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  1
  5 32  1  0
  9 33  1  0
 10 34  1  0
 12 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 24 39  1  6
 26 40  1  6
 27 41  1  6
 28 42  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -5.205  -0.855   0.911  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.116  -0.894   0.354  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.302  -2.086   0.007  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.922  -1.908   0.593  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.139  -3.053   0.375  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.207  -0.669   0.250  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.539  -0.226   1.453  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.832  -0.252   1.533  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.586  -0.520   2.647  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.980  -0.499   2.528  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.615  -0.216   1.327  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.996  -0.193   1.201  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.846   0.054   0.207  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.502   0.030   0.334  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.575   0.304  -0.807  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.083   1.549  -0.530  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.470   1.619  -0.506  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.207   2.718  -0.836  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.596   2.672  -0.777  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.223   1.487  -0.377  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.490   0.389  -0.047  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.114   0.448  -0.108  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.313  -0.772  -0.817  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.232   0.401  -2.125  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.911  -0.859  -2.468  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.620   0.297  -2.254  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.513   0.351  -1.057  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.189   1.560  -0.959  0.00  0.00           O+0
HETATM   29  H   UNK     0      -3.230  -2.224  -1.098  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.728  -3.000   0.477  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.095  -1.920   1.717  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.459  -3.100   1.099  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.073  -0.736   3.563  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.559  -0.712   3.410  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.535  -0.394   2.033  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.683   3.633  -1.147  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.200   3.531  -1.034  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.314   1.405  -0.314  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.604   0.810  -2.930  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.103   0.718  -3.180  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.313  -0.431  -1.216  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.052   1.545  -1.430  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   29   30                                             
CONECT    4    3    5    6   31                                             
CONECT    5    4   32                                                       
CONECT    6    4    7   22   23                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   33                                                  
CONECT   10    9   11   34                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   35                                                       
CONECT   13   11   14   27                                                  
CONECT   14   13   15    8                                                  
CONECT   15   14   16   23   24                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   36                                                  
CONECT   19   18   20   37                                                  
CONECT   20   19   21   38                                                  
CONECT   21   20   22    2                                                  
CONECT   22   21    6   17                                                  
CONECT   23   15    6                                                       
CONECT   24   15   25   26   39                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   24   40                                             
CONECT   27   26   28   13   41                                             
CONECT   28   27   42                                                       
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    9                                                            
CONECT   34   10                                                            
CONECT   35   12                                                            
CONECT   36   18                                                            
CONECT   37   19                                                            
CONECT   38   20                                                            
CONECT   39   24                                                            
CONECT   40   26                                                            
CONECT   41   27                                                            
CONECT   42   28                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

RDKit          3D

42 48  0  0  0  0  0  0  0  0999 V2000
   -5.2053   -0.8550    0.9108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1163   -0.8942    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3022   -2.0860    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9221   -1.9083    0.5934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1395   -3.0531    0.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2067   -0.6693    0.2497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5386   -0.2257    1.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8319   -0.2517    1.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860   -0.5203    2.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802   -0.4989    2.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145   -0.2163    1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9962   -0.1932    1.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    0.0537    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5016    0.0301    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752    0.3037   -0.8069 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0826    1.5486   -0.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    1.6195   -0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2072    2.7183   -0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5962    2.6717   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2235    1.4868   -0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896    0.3890   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138    0.4483   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129   -0.7721   -0.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2325    0.4011   -2.1246 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9111   -0.8594   -2.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196    0.2973   -2.2537 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5130    0.3507   -1.0572 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1888    1.5595   -0.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2298   -2.2237   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279   -3.0000    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0950   -1.9202    1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593   -3.1003    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726   -0.7358    3.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590   -0.7115    3.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5355   -0.3937    2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828    3.6326   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2004    3.5307   -1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3140    1.4049   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6041    0.8102   -2.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1029    0.7178   -3.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3128   -0.4308   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0520    1.5452   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  1
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 21  2  1  0
 26 24  1  0
 22  6  1  0
 23  6  1  0
 14  8  2  0
 22 17  1  0
 27 13  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  1
  5 32  1  0
  9 33  1  0
 10 34  1  0
 12 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 24 39  1  6
 26 40  1  6
 27 41  1  6
 28 42  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3'-O-Desmethyl-1-epipreussomerin C	MeSH
3'-O-D-Epipreussomerin C	MeSH

Chemical Formula

C₂₀H₁₄O₈

Average Mass

382.3240 Da

Monoisotopic Mass

382.06887 Da

IUPAC Name

(1S,2R,4R,5S,12S,13R)-5,7,13-trihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1^{1,6}.1^{12,16}.0^{2,4}.0^{10,24}.0^{20,23}]tetracosa-6,8,10(24),16(23),17,19-hexaen-15-one

Traditional Name

(1S,2R,4R,5S,12S,13R)-5,7,13-trihydroxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.1^{1,6}.1^{12,16}.0^{2,4}.0^{10,24}.0^{20,23}]tetracosa-6,8,10(24),16(23),17,19-hexaen-15-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C3=C(O[C@@]45O[C@]3(OC3=C([H])C([H])=C([H])C(C(=O)C([H])([H])[C@@]4([H])O[H])=C53)[C@]3([H])O[C@]3([H])[C@@]2([H])O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C20H14O8/c21-8-4-5-11-15-13(8)16(24)17-18(25-17)20(15)27-10-3-1-2-7-9(22)6-12(23)19(26-11,28-20)14(7)10/h1-5,12,16-18,21,23-24H,6H2/t12-,16+,17-,18-,19-,20+/m1/s1

InChI Key

BCPICRNXIKGDCQ-LZVSGGPWSA-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
Sporormiella vexans	NPAtlas	10217738

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Ketal
Ketone
Secondary alcohol
Acetal
Dialkyl ether
Oxirane
Ether
Polyol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.18	ALOGPS
logP	1.62	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.8	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.98 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.34 m³·mol⁻¹	ChemAxon
Polarizability	36.26 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA019775

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

417692

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

475770

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Soman AG, Gloer JB, Koster B, Malloch D: Sporovexins A-C and a new preussomerin analog: antibacterial and antifungal metabolites from the coprophilous fungus Sporormiella vexans. J Nat Prod. 1999 Apr;62(4):659-61. doi: 10.1021/np980563c. [PubMed:10217738 ]

Showing NP-Card for 3'-O-desmethyl-1-epipreussomerin C (NP0001619)

MOL for NP0001619 (3'-O-desmethyl-1-epipreussomerin C)

3D MOL for NP0001619 (3'-O-desmethyl-1-epipreussomerin C)

3D SDF for NP0001619 (3'-O-desmethyl-1-epipreussomerin C)

3D-SDF for NP0001619 (3'-O-desmethyl-1-epipreussomerin C)

PDB for NP0001619 (3'-O-desmethyl-1-epipreussomerin C)

3D PDB for NP0001619 (3'-O-desmethyl-1-epipreussomerin C)

SMILES for NP0001619 (3'-O-desmethyl-1-epipreussomerin C)

INCHI for NP0001619 (3'-O-desmethyl-1-epipreussomerin C)

Structure for NP0001619 (3'-O-desmethyl-1-epipreussomerin C)

3D Structure for NP0001619 (3'-O-desmethyl-1-epipreussomerin C)