NP-MRD: Showing NP-Card for (4R,4aS,9aR)-1,9a-dihydronidulalin A (NP0029529)

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Record Information

Version

2.0

Created at

2021-06-19 21:07:48 UTC

Updated at

2021-06-29 23:56:56 UTC

NP-MRD ID

NP0029529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4R,4aS,9aR)-1,9a-dihydronidulalin A

Provided By

JEOL Database JEOL Logo

Description

(4R,4aS,9aR)-1,9a-dihydronidulalin A is found in Neurospora micropertusa and Gelasinospora santi-florii. (4R,4aS,9aR)-1,9a-dihydronidulalin A was first documented in 2006 (Fujimoto, H., et al.). Based on a literature review very few articles have been published on Dihydronidulalin A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123073D          

 38 40  0  0  0  0            999 V2000
    0.9376   -3.2772   -2.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1858   -3.3504   -0.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8622   -2.2764   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -1.3227   -1.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361   -2.4069    1.1366 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7478   -2.6653    1.7462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954   -1.5835    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4579   -1.8687    1.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016   -0.8322    1.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687   -1.1396    1.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    0.4933    1.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6016    0.7781    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2546    2.0988    1.5715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356   -0.2582    1.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    0.0121    1.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859    1.1710    1.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6904   -1.1838    1.7967 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1112   -0.9124    1.2868 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9181   -2.1699    1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3879   -3.3999    1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -3.6560    1.4010 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7820   -4.1030    2.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807   -3.2404   -2.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3144   -2.4083   -2.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3971   -4.1806   -2.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -2.9042    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4141   -0.3307    2.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0490   -2.0540    2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2714   -1.2707    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6777    1.3133    1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7268    2.1543    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439   -1.3522    2.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -0.2553    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053   -0.3718    0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9891   -2.0548    0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0349   -4.2708    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192   -4.4967    0.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -4.1397    2.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
  7  8  2  0  0  0  0
 18 19  1  0  0  0  0
  6  7  1  0  0  0  0
 19 20  2  0  0  0  0
  8  9  1  0  0  0  0
 20 21  1  0  0  0  0
 21  5  1  0  0  0  0
 14 15  1  0  0  0  0
 12 13  1  0  0  0  0
  9 11  2  0  0  0  0
 15 16  2  0  0  0  0
 21 22  1  0  0  0  0
  5  3  1  6  0  0  0
 11 12  1  0  0  0  0
 12 14  2  0  0  0  0
  3  2  1  0  0  0  0
 17 15  1  0  0  0  0
  2  1  1  0  0  0  0
 14  7  1  0  0  0  0
  3  4  2  0  0  0  0
  5 17  1  0  0  0  0
  9 10  1  0  0  0  0
  5  6  1  0  0  0  0
 17 32  1  1  0  0  0
  8 26  1  0  0  0  0
 11 30  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  0  0  0  0
 20 36  1  0  0  0  0
 21 37  1  6  0  0  0
 13 31  1  0  0  0  0
 22 38  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 10 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
M  END

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    0.9376   -3.2772   -2.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1858   -3.3504   -0.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8622   -2.2764   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -1.3227   -1.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361   -2.4069    1.1366 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7478   -2.6653    1.7462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954   -1.5835    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4579   -1.8687    1.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016   -0.8322    1.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687   -1.1396    1.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    0.4933    1.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6016    0.7781    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2546    2.0988    1.5715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356   -0.2582    1.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    0.0121    1.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859    1.1710    1.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6904   -1.1838    1.7967 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1112   -0.9124    1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9181   -2.1699    1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3879   -3.3999    1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -3.6560    1.4010 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7820   -4.1030    2.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807   -3.2404   -2.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3144   -2.4083   -2.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3971   -4.1806   -2.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -2.9042    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4141   -0.3307    2.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0490   -2.0540    2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2714   -1.2707    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6777    1.3133    1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7268    2.1543    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439   -1.3522    2.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -0.2553    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053   -0.3718    0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9891   -2.0548    0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0349   -4.2708    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192   -4.4967    0.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -4.1397    2.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
  7  8  2  0
 18 19  1  0
  6  7  1  0
 19 20  2  0
  8  9  1  0
 20 21  1  0
 21  5  1  0
 14 15  1  0
 12 13  1  0
  9 11  2  0
 15 16  2  0
 21 22  1  0
  5  3  1  6
 11 12  1  0
 12 14  2  0
  3  2  1  0
 17 15  1  0
  2  1  1  0
 14  7  1  0
  3  4  2  0
  5 17  1  0
  9 10  1  0
  5  6  1  0
 17 32  1  1
  8 26  1  0
 11 30  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  6
 13 31  1  0
 22 38  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
M  END


  Mrv1652306192123073D          

 38 40  0  0  0  0            999 V2000
    0.9376   -3.2772   -2.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1858   -3.3504   -0.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8622   -2.2764   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -1.3227   -1.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361   -2.4069    1.1366 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7478   -2.6653    1.7462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954   -1.5835    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4579   -1.8687    1.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016   -0.8322    1.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687   -1.1396    1.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    0.4933    1.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6016    0.7781    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2546    2.0988    1.5715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356   -0.2582    1.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    0.0121    1.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859    1.1710    1.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6904   -1.1838    1.7967 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1112   -0.9124    1.2868 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9181   -2.1699    1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3879   -3.3999    1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -3.6560    1.4010 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7820   -4.1030    2.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807   -3.2404   -2.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3144   -2.4083   -2.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3971   -4.1806   -2.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -2.9042    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4141   -0.3307    2.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0490   -2.0540    2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2714   -1.2707    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6777    1.3133    1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7268    2.1543    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439   -1.3522    2.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -0.2553    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053   -0.3718    0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9891   -2.0548    0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0349   -4.2708    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192   -4.4967    0.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -4.1397    2.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
  7  8  2  0  0  0  0
 18 19  1  0  0  0  0
  6  7  1  0  0  0  0
 19 20  2  0  0  0  0
  8  9  1  0  0  0  0
 20 21  1  0  0  0  0
 21  5  1  0  0  0  0
 14 15  1  0  0  0  0
 12 13  1  0  0  0  0
  9 11  2  0  0  0  0
 15 16  2  0  0  0  0
 21 22  1  0  0  0  0
  5  3  1  6  0  0  0
 11 12  1  0  0  0  0
 12 14  2  0  0  0  0
  3  2  1  0  0  0  0
 17 15  1  0  0  0  0
  2  1  1  0  0  0  0
 14  7  1  0  0  0  0
  3  4  2  0  0  0  0
  5 17  1  0  0  0  0
  9 10  1  0  0  0  0
  5  6  1  0  0  0  0
 17 32  1  1  0  0  0
  8 26  1  0  0  0  0
 11 30  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  0  0  0  0
 20 36  1  0  0  0  0
 21 37  1  6  0  0  0
 13 31  1  0  0  0  0
 22 38  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 10 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(O[C@]3(C(=O)OC([H])([H])[H])[C@]([H])(O[H])C([H])=C([H])C([H])([H])[C@@]3([H])C2=O)=C([H])C(=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-8-6-10(17)13-11(7-8)22-16(15(20)21-2)9(14(13)19)4-3-5-12(16)18/h3,5-7,9,12,17-18H,4H2,1-2H3/t9-,12+,16-/m0/s1

> <INCHI_KEY>
SQQVLPAZXRNECF-DUZHOBMZSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.154022655379123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4R,4aS,9aR)-4,8-dihydroxy-6-methyl-9-oxo-4,4a,9,9a-tetrahydro-1H-xanthene-4a-carboxylate

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
2.205453065666666

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.686593143721518

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.804354149506375

> <JCHEM_PKA_STRONGEST_BASIC>
-3.531417365996159

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
77.62010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4R,4aS,9aR)-4,8-dihydroxy-6-methyl-9-oxo-4,9a-dihydro-1H-xanthene-4a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    0.9376   -3.2772   -2.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1858   -3.3504   -0.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8622   -2.2764   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -1.3227   -1.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361   -2.4069    1.1366 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7478   -2.6653    1.7462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954   -1.5835    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4579   -1.8687    1.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016   -0.8322    1.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687   -1.1396    1.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    0.4933    1.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6016    0.7781    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2546    2.0988    1.5715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356   -0.2582    1.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    0.0121    1.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859    1.1710    1.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6904   -1.1838    1.7967 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1112   -0.9124    1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9181   -2.1699    1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3879   -3.3999    1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -3.6560    1.4010 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7820   -4.1030    2.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807   -3.2404   -2.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3144   -2.4083   -2.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3971   -4.1806   -2.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -2.9042    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4141   -0.3307    2.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0490   -2.0540    2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2714   -1.2707    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6777    1.3133    1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7268    2.1543    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439   -1.3522    2.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -0.2553    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053   -0.3718    0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9891   -2.0548    0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0349   -4.2708    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192   -4.4967    0.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -4.1397    2.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
  7  8  2  0
 18 19  1  0
  6  7  1  0
 19 20  2  0
  8  9  1  0
 20 21  1  0
 21  5  1  0
 14 15  1  0
 12 13  1  0
  9 11  2  0
 15 16  2  0
 21 22  1  0
  5  3  1  6
 11 12  1  0
 12 14  2  0
  3  2  1  0
 17 15  1  0
  2  1  1  0
 14  7  1  0
  3  4  2  0
  5 17  1  0
  9 10  1  0
  5  6  1  0
 17 32  1  1
  8 26  1  0
 11 30  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  6
 13 31  1  0
 22 38  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.938  -3.277  -2.306  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.186  -3.350  -0.900  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.862  -2.276  -0.394  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.232  -1.323  -1.066  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.036  -2.407   1.137  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.748  -2.665   1.746  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.095  -1.583   1.753  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.458  -1.869   1.859  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.402  -0.832   1.865  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.869  -1.140   1.935  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.963   0.493   1.747  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.602   0.778   1.660  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.255   2.099   1.571  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.336  -0.258   1.672  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.785   0.012   1.636  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.186   1.171   1.561  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.690  -1.184   1.797  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.111  -0.912   1.287  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.918  -2.170   1.129  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.388  -3.400   1.208  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.922  -3.656   1.401  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.782  -4.103   2.755  0.00  0.00           O+0
HETATM   23  H   UNK     0       1.881  -3.240  -2.860  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.314  -2.408  -2.539  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.397  -4.181  -2.601  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.786  -2.904   1.926  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.414  -0.331   2.432  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.049  -2.054   2.510  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.271  -1.271   0.925  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.678   1.313   1.730  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.727   2.154   1.518  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.744  -1.352   2.884  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.623  -0.255   2.002  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.105  -0.372   0.334  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.989  -2.055   0.975  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.035  -4.271   1.136  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.619  -4.497   0.767  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.824  -4.140   2.934  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5   21    3   17    6                                             
CONECT    6    7    5                                                       
CONECT    7    8    6   14                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9   27   28   29                                             
CONECT   11    9   12   30                                                  
CONECT   12   13   11   14                                                  
CONECT   13   12   31                                                       
CONECT   14   15   12    7                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   18   15    5   32                                             
CONECT   18   17   19   33   34                                             
CONECT   19   18   20   35                                                  
CONECT   20   19   21   36                                                  
CONECT   21   20    5   22   37                                             
CONECT   22   21   38                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    8                                                            
CONECT   27   10                                                            
CONECT   28   10                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   13                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   21                                                            
CONECT   38   22                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

RDKit          3D

38 40  0  0  0  0  0  0  0  0999 V2000
    0.9376   -3.2772   -2.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1858   -3.3504   -0.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8622   -2.2764   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -1.3227   -1.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361   -2.4069    1.1366 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7478   -2.6653    1.7462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954   -1.5835    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4579   -1.8687    1.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016   -0.8322    1.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8687   -1.1396    1.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    0.4933    1.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6016    0.7781    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2546    2.0988    1.5715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356   -0.2582    1.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    0.0121    1.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859    1.1710    1.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6904   -1.1838    1.7967 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1112   -0.9124    1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9181   -2.1699    1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3879   -3.3999    1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -3.6560    1.4010 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7820   -4.1030    2.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807   -3.2404   -2.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3144   -2.4083   -2.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3971   -4.1806   -2.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -2.9042    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4141   -0.3307    2.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0490   -2.0540    2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2714   -1.2707    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6777    1.3133    1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7268    2.1543    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439   -1.3522    2.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -0.2553    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053   -0.3718    0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9891   -2.0548    0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0349   -4.2708    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192   -4.4967    0.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -4.1397    2.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
  7  8  2  0
 18 19  1  0
  6  7  1  0
 19 20  2  0
  8  9  1  0
 20 21  1  0
 21  5  1  0
 14 15  1  0
 12 13  1  0
  9 11  2  0
 15 16  2  0
 21 22  1  0
  5  3  1  6
 11 12  1  0
 12 14  2  0
  3  2  1  0
 17 15  1  0
  2  1  1  0
 14  7  1  0
  3  4  2  0
  5 17  1  0
  9 10  1  0
  5  6  1  0
 17 32  1  1
  8 26  1  0
 11 30  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  6
 13 31  1  0
 22 38  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₆

Average Mass

304.2980 Da

Monoisotopic Mass

304.09469 Da

IUPAC Name

methyl (4R,4aS,9aR)-4,8-dihydroxy-6-methyl-9-oxo-4,4a,9,9a-tetrahydro-1H-xanthene-4a-carboxylate

Traditional Name

methyl (4R,4aS,9aR)-4,8-dihydroxy-6-methyl-9-oxo-4,9a-dihydro-1H-xanthene-4a-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(O[C@]3(C(=O)OC([H])([H])[H])[C@]([H])(O[H])C([H])=C([H])C([H])([H])[C@@]3([H])C2=O)=C([H])C(=C1[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C16H16O6/c1-8-6-10(17)13-11(7-8)22-16(15(20)21-2)9(14(13)19)4-3-5-12(16)18/h3,5-7,9,12,17-18H,4H2,1-2H3/t9-,12+,16-/m0/s1

InChI Key

SQQVLPAZXRNECF-DUZHOBMZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Neurospora micropertusa	LOTUS Database	35616633
Neurospora santi-florii	JEOL database	Fujimoto, H., et al, Chem. Pharm. Bull. 54, 550 (2006)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Beta-hydroxy acid
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Hydroxy acid
Methyl ester
Vinylogous acid
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
Carbonyl group
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	1.53	ALOGPS
logP	2.21	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	8.8	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.62 m³·mol⁻¹	ChemAxon
Polarizability	30.15 Å³	ChemAxon
Number of Rings	3	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8884947

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10709606

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fujimoto, H., et al. (2006). Fujimoto, H., et al, Chem. Pharm. Bull. 54, 550 (2006). Chem. Pharm. Bull..

Showing NP-Card for (4R,4aS,9aR)-1,9a-dihydronidulalin A (NP0029529)

MOL for NP0029529 ((4R,4aS,9aR)-1,9a-dihydronidulalin A)

3D MOL for NP0029529 ((4R,4aS,9aR)-1,9a-dihydronidulalin A)

3D SDF for NP0029529 ((4R,4aS,9aR)-1,9a-dihydronidulalin A)

3D-SDF for NP0029529 ((4R,4aS,9aR)-1,9a-dihydronidulalin A)

PDB for NP0029529 ((4R,4aS,9aR)-1,9a-dihydronidulalin A)

3D PDB for NP0029529 ((4R,4aS,9aR)-1,9a-dihydronidulalin A)

SMILES for NP0029529 ((4R,4aS,9aR)-1,9a-dihydronidulalin A)

INCHI for NP0029529 ((4R,4aS,9aR)-1,9a-dihydronidulalin A)

Structure for NP0029529 ((4R,4aS,9aR)-1,9a-dihydronidulalin A)

3D Structure for NP0029529 ((4R,4aS,9aR)-1,9a-dihydronidulalin A)