NP-MRD: Showing NP-Card for methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate (NP0225635)

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Record Information

Version

2.0

Created at

2022-09-06 04:25:10 UTC

Updated at

2022-09-06 04:25:10 UTC

NP-MRD ID

NP0225635

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate

Description

Ent-secalonic acid I, also known as ent-secalonate I, belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate is found in Orbiocrella petchii. Based on a literature review very few articles have been published on Ent-secalonic acid I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062206252D          

 46 50  0  0  1  0            999 V2000
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0573    4.3799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8053    2.1531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2295    1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 14 16  1  0  0  0  0
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 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
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 27 28  2  0  0  0  0
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 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  2  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 30 43  1  0  0  0  0
 43 44  1  6  0  0  0
 21 45  2  0  0  0  0
 16 45  1  0  0  0  0
 45 46  1  0  0  0  0
M  END

     RDKit          3D

 74 78  0  0  0  0  0  0  0  0999 V2000
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   -4.0340   -0.1218    1.6979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7467    0.4876    0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4291    1.4966    1.1402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8500    0.1632   -0.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7017    0.9983   -1.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2563    2.1202   -0.8629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9597    0.6757   -2.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8684    1.5897   -3.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4183   -0.4240   -3.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5734   -1.2740   -2.6560 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0853   -1.1511    1.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519   -0.1558    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3271    1.0900    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2454    2.3454    0.9805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5031    3.5000    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8831    3.3834    0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6770    4.5142    0.7430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4855    2.1567    0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6886    1.0219    0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6239   -0.4458    0.2141 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6077   -0.9431   -1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6499   -1.2177   -1.8502 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4036   -1.1106   -1.8513 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3594   -1.5738   -3.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    0.7780    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9020    1.9488    0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6449   -1.2285    1.5332 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5772   -0.3943    2.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2810   -1.5216    1.0199 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2848   -2.7377    0.3043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5723   -0.3947    0.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1151   -0.0171    3.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8632    2.7009   -1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0328    1.1927   -4.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8287    1.6373   -2.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6396   -0.6710   -4.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4709   -4.4479    1.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5894   -1.0230   -3.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
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 37 65  1  0
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 34 64  1  0
M  END


  Mrv1652309062206252D          

 46 50  0  0  1  0            999 V2000
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8053    2.1531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2295    1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  2  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 30 43  1  0  0  0  0
 43 44  1  6  0  0  0
 21 45  2  0  0  0  0
 16 45  1  0  0  0  0
 45 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(O)C(C)=CC(O)=C1C(=O)C1=C(O)C=CC(=C1O)C1=CC=C(O)C2=C1O[C@@]1([C@@H](O)[C@H](C)CC(=O)C1=C2O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H28O14/c1-11-9-17(35)19(22(24(11)37)30(42)44-3)26(39)20-15(33)7-5-13(25(20)38)14-6-8-16(34)21-27(40)23-18(36)10-12(2)29(41)32(23,31(43)45-4)46-28(14)21/h5-9,12,29,33-35,37-38,40-41H,10H2,1-4H3/t12-,29+,32+/m1/s1

> <INCHI_KEY>
TXVLIGZAVWOOKS-ODPCQGFPSA-N

> <FORMULA>
C32H28O14

> <MOLECULAR_WEIGHT>
636.562

> <EXACT_MASS>
636.147905582

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
61.3454971196478

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (3R,4S,4aS)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-2,3,4,4a-tetrahydro-1H-xanthene-4a-carboxylate

> <JCHEM_LOGP>
5.766932595333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.588192502550866

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.942318507020239

> <JCHEM_PKA_STRONGEST_BASIC>
-3.494165741772691

> <JCHEM_POLAR_SURFACE_AREA>
237.57999999999993

> <JCHEM_REFRACTIVITY>
159.41280000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3R,4S,4aS)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2H-xanthene-4a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.574   8.176   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.370   4.019   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       0.428   3.556   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    5   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   45                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   45                                                  
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   36                                                  
CONECT   28   27   22   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35   43                                             
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   30   36   38                                                  
CONECT   36   35   27   37                                                  
CONECT   37   36                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   30   44                                                  
CONECT   44   43                                                            
CONECT   45   21   16   46                                                  
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  100    0
END

View in JSmol

Synonyms

Value	Source
ent-Secalonate I	Generator

Chemical Formula

C₃₂H₂₈O₁₄

Average Mass

636.5620 Da

Monoisotopic Mass

636.14791 Da

IUPAC Name

methyl (3R,4S,4aS)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-2,3,4,4a-tetrahydro-1H-xanthene-4a-carboxylate

Traditional Name

methyl (3R,4S,4aS)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2H-xanthene-4a-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(O)C(C)=CC(O)=C1C(=O)C1=C(O)C=CC(=C1O)C1=CC=C(O)C2=C1O[C@@]1([C@@H](O)[C@H](C)CC(=O)C1=C2O)C(=O)OC

InChI Identifier

InChI=1S/C32H28O14/c1-11-9-17(35)19(22(24(11)37)30(42)44-3)26(39)20-15(33)7-5-13(25(20)38)14-6-8-16(34)21-27(40)23-18(36)10-12(2)29(41)32(23,31(43)45-4)46-28(14)21/h5-9,12,29,33-35,37-38,40-41H,10H2,1-4H3/t12-,29+,32+/m1/s1

InChI Key

TXVLIGZAVWOOKS-ODPCQGFPSA-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

Species Name	Source	Reference
Orbiocrella petchii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Xanthene
Biphenol
Benzophenone
Aryl-phenylketone
Diphenylmethane
M-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Salicylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Aryl ketone
Resorcinol
O-cresol
M-cresol
Hydroquinone
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Beta-hydroxy acid
Alkyl aryl ether
Benzenoid
Hydroxy acid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Vinylogous acid
Methyl ester
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Polyol
Ether
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	5.77	ChemAxon
pKa (Strongest Acidic)	4.94	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	237.58 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	159.41 m³·mol⁻¹	ChemAxon
Polarizability	61.35 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146682255

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate (NP0225635)

MOL for NP0225635 (methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate)

3D MOL for NP0225635 (methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate)

3D SDF for NP0225635 (methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate)

3D-SDF for NP0225635 (methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate)

PDB for NP0225635 (methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate)

3D PDB for NP0225635 (methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate)

SMILES for NP0225635 (methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate)

INCHI for NP0225635 (methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate)

Structure for NP0225635 (methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate)

3D Structure for NP0225635 (methyl (3r,4s,4as)-5-{3-[3,6-dihydroxy-2-(methoxycarbonyl)-4-methylbenzoyl]-2,4-dihydroxyphenyl}-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2h-xanthene-4a-carboxylate)