NP-MRD: Showing NP-Card for Decaspirone G (NP0006704)

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Record Information

Version

2.0

Created at

2020-12-09 03:39:13 UTC

Updated at

2021-07-15 16:55:34 UTC

NP-MRD ID

NP0006704

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Decaspirone G

Provided By

NPAtlas

Description

(4S,4aR,8R,8aS)-4,8-dihydroxy-4a,5,8,8a-tetrahydro-4H-2',4'-dioxaspiro[naphthalene-1,3'-tricyclo[7.3.1.0⁵,¹³]Tridecane]-1'(12'),5',7',9'(13'),10'-pentaen-5-one belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Decaspirone G is found in Drepanospora viridis, Helicoma and Helicoma viridis. Decaspirone G was first documented in 2006 (PMID: 17190440). Based on a literature review very few articles have been published on (4S,4aR,8R,8aS)-4,8-dihydroxy-4a,5,8,8a-tetrahydro-4H-2',4'-dioxaspiro[naphthalene-1,3'-tricyclo[7.3.1.0⁵,¹³]Tridecane]-1'(12'),5',7',9'(13'),10'-pentaen-5-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118303D          

 41 45  0  0  0  0            999 V2000
   -4.4685   -0.6263    1.9266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7438   -0.0233    1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089    1.1109    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    1.9137   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770    1.6783   -0.4140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4893    2.2659    0.7166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8354    0.2026   -0.3639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3600   -0.4529    0.8959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1811   -1.9330    0.8364 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4138   -2.5327    0.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403   -2.3807   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777   -1.5803   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3424   -0.1278   -0.3989 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3328    0.6632   -1.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7307    0.6277   -1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924    0.9350   -2.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8703    0.9013   -2.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    0.5646   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518    0.2590   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3276   -0.0852    1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -0.3958    2.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345   -0.3552    2.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -0.0129    0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    0.2929   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245    0.0327    0.8878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3809    1.2396    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9854    2.7293   -0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049    2.0771   -1.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    2.1243    1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212   -0.2992   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7143   -0.0529    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9282   -2.2935    1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4644   -2.6109   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -3.4331   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.9301   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9806    1.2000   -3.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4829    1.1363   -3.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5937    0.5241   -1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274   -0.1040    1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1225   -0.6620    3.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120   -0.5868    3.0208 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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  8  2  1  0  0  0  0
 25 13  1  0  0  0  0
 13  7  1  0  0  0  0
 24 15  1  0  0  0  0
 24 19  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  6  0  0  0
  6 29  1  0  0  0  0
  7 30  1  6  0  0  0
  8 31  1  1  0  0  0
  9 32  1  1  0  0  0
 10 33  1  0  0  0  0
 11 34  1  0  0  0  0
 12 35  1  0  0  0  0
 16 36  1  0  0  0  0
 17 37  1  0  0  0  0
 18 38  1  0  0  0  0
 20 39  1  0  0  0  0
 21 40  1  0  0  0  0
 22 41  1  0  0  0  0
M  END

     RDKit          3D

 41 45  0  0  0  0  0  0  0  0999 V2000
   -4.4685   -0.6263    1.9266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7438   -0.0233    1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089    1.1109    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    1.9137   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770    1.6783   -0.4140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4893    2.2659    0.7166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8354    0.2026   -0.3639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3600   -0.4529    0.8959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1811   -1.9330    0.8364 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4138   -2.5327    0.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403   -2.3807   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777   -1.5803   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3424   -0.1278   -0.3989 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3328    0.6632   -1.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7307    0.6277   -1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924    0.9350   -2.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8703    0.9013   -2.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    0.5646   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518    0.2590   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3276   -0.0852    1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -0.3958    2.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345   -0.3552    2.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -0.0129    0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    0.2929   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245    0.0327    0.8878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3809    1.2396    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9854    2.7293   -0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049    2.0771   -1.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    2.1243    1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212   -0.2992   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7143   -0.0529    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9282   -2.2935    1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4644   -2.6109   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -3.4331   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.9301   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9806    1.2000   -3.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4829    1.1363   -3.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5937    0.5241   -1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274   -0.1040    1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1225   -0.6620    3.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120   -0.5868    3.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  6
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  8  2  1  0
 25 13  1  0
 13  7  1  0
 24 15  1  0
 24 19  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  0
  7 30  1  6
  8 31  1  1
  9 32  1  1
 10 33  1  0
 11 34  1  0
 12 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END


  Mrv1652306242118303D          

 41 45  0  0  0  0            999 V2000
   -4.4685   -0.6263    1.9266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7438   -0.0233    1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089    1.1109    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    1.9137   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770    1.6783   -0.4140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4893    2.2659    0.7166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8354    0.2026   -0.3639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3600   -0.4529    0.8959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1811   -1.9330    0.8364 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4138   -2.5327    0.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403   -2.3807   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777   -1.5803   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3424   -0.1278   -0.3989 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3328    0.6632   -1.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7307    0.6277   -1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924    0.9350   -2.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8703    0.9013   -2.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    0.5646   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518    0.2590   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3276   -0.0852    1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -0.3958    2.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345   -0.3552    2.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -0.0129    0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    0.2929   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245    0.0327    0.8878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3809    1.2396    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9854    2.7293   -0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049    2.0771   -1.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    2.1243    1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212   -0.2992   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7143   -0.0529    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9282   -2.2935    1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4644   -2.6109   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -3.4331   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.9301   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9806    1.2000   -3.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4829    1.1363   -3.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5937    0.5241   -1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274   -0.1040    1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1225   -0.6620    3.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120   -0.5868    3.0208 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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  8  2  1  0  0  0  0
 25 13  1  0  0  0  0
 13  7  1  0  0  0  0
 24 15  1  0  0  0  0
 24 19  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  6  0  0  0
  6 29  1  0  0  0  0
  7 30  1  6  0  0  0
  8 31  1  1  0  0  0
  9 32  1  1  0  0  0
 10 33  1  0  0  0  0
 11 34  1  0  0  0  0
 12 35  1  0  0  0  0
 16 36  1  0  0  0  0
 17 37  1  0  0  0  0
 18 38  1  0  0  0  0
 20 39  1  0  0  0  0
 21 40  1  0  0  0  0
 22 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006704

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])=C([H])C2(OC3=C([H])C([H])=C([H])C4=C([H])C([H])=C([H])C(O2)=C34)[C@]2([H])[C@]([H])(O[H])C([H])=C([H])C(=O)[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c21-12-7-8-14(23)19-18(12)13(22)9-10-20(19)24-15-5-1-3-11-4-2-6-16(25-20)17(11)15/h1-10,13-14,18-19,22-23H/t13-,14+,18-,19+/m0/s1

> <INCHI_KEY>
WKESGSKGMIPHTP-QABNGEJJSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.343

> <EXACT_MASS>
336.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
33.66866606046733

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,4aR,8R,8aS)-4,8-dihydroxy-4a,5,8,8a-tetrahydro-4H-2',4'-dioxaspiro[naphthalene-1,3'-tricyclo[7.3.1.0^{5,13}]tridecane]-1'(12'),5',7',9'(13'),10'-pentaen-5-one

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
2.562519443666667

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.999393247807188

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.105136818870387

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0836749243775223

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
91.3694

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,8R,8aS)-4,8-dihydroxy-4,4a,8,8a-tetrahydro-2',4'-dioxaspiro[naphthalene-1,3'-tricyclo[7.3.1.0^{5,13}]tridecane]-1'(12'),5',7',9'(13'),10'-pentaen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 45  0  0  0  0  0  0  0  0999 V2000
   -4.4685   -0.6263    1.9266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7438   -0.0233    1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089    1.1109    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    1.9137   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770    1.6783   -0.4140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4893    2.2659    0.7166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8354    0.2026   -0.3639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3600   -0.4529    0.8959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1811   -1.9330    0.8364 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4138   -2.5327    0.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403   -2.3807   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777   -1.5803   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3424   -0.1278   -0.3989 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3328    0.6632   -1.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7307    0.6277   -1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924    0.9350   -2.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8703    0.9013   -2.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    0.5646   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518    0.2590   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3276   -0.0852    1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -0.3958    2.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345   -0.3552    2.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -0.0129    0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    0.2929   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245    0.0327    0.8878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3809    1.2396    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9854    2.7293   -0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049    2.0771   -1.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    2.1243    1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212   -0.2992   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7143   -0.0529    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9282   -2.2935    1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4644   -2.6109   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -3.4331   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.9301   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9806    1.2000   -3.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4829    1.1363   -3.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5937    0.5241   -1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274   -0.1040    1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1225   -0.6620    3.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120   -0.5868    3.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  6
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  8  2  1  0
 25 13  1  0
 13  7  1  0
 24 15  1  0
 24 19  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  0
  7 30  1  6
  8 31  1  1
  9 32  1  1
 10 33  1  0
 11 34  1  0
 12 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  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      -4.468  -0.626   1.927  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.744  -0.023   1.100  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.309   1.111   0.351  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.537   1.914  -0.361  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.077   1.678  -0.414  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.489   2.266   0.717  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.835   0.203  -0.364  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.360  -0.453   0.896  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.181  -1.933   0.836  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.414  -2.533   0.534  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.140  -2.381  -0.122  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.278  -1.580  -0.710  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.342  -0.128  -0.399  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.333   0.663  -1.356  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.731   0.628  -1.293  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.492   0.935  -2.417  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.870   0.901  -2.360  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.530   0.565  -1.196  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.752   0.259  -0.077  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.328  -0.085   1.118  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.608  -0.396   2.252  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.235  -0.355   2.171  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.613  -0.013   0.985  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.355   0.293  -0.133  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.225   0.033   0.888  0.00  0.00           O+0
HETATM   26  H   UNK     0      -5.381   1.240   0.423  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.985   2.729  -0.893  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.605   2.077  -1.312  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.083   2.124   1.490  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.321  -0.299  -1.233  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.714  -0.053   1.732  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.928  -2.293   1.869  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.464  -2.611  -0.451  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.093  -3.433  -0.347  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.461  -1.930  -1.395  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.981   1.200  -3.334  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.483   1.136  -3.221  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.594   0.524  -1.101  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.427  -0.104   1.135  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.122  -0.662   3.173  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.612  -0.587   3.021  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5   27                                                  
CONECT    5    4    6    7   28                                             
CONECT    6    5   29                                                       
CONECT    7    5    8   13   30                                             
CONECT    8    7    9    2   31                                             
CONECT    9    8   10   11   32                                             
CONECT   10    9   33                                                       
CONECT   11    9   12   34                                                  
CONECT   12   11   13   35                                                  
CONECT   13   12   14   25    7                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   36                                                  
CONECT   17   16   18   37                                                  
CONECT   18   17   19   38                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21   39                                                  
CONECT   21   20   22   40                                                  
CONECT   22   21   23   41                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   15   19                                                  
CONECT   25   23   13                                                       
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   11                                                            
CONECT   35   12                                                            
CONECT   36   16                                                            
CONECT   37   17                                                            
CONECT   38   18                                                            
CONECT   39   20                                                            
CONECT   40   21                                                            
CONECT   41   22                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

RDKit          3D

41 45  0  0  0  0  0  0  0  0999 V2000
   -4.4685   -0.6263    1.9266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7438   -0.0233    1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089    1.1109    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    1.9137   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770    1.6783   -0.4140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4893    2.2659    0.7166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8354    0.2026   -0.3639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3600   -0.4529    0.8959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1811   -1.9330    0.8364 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4138   -2.5327    0.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403   -2.3807   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777   -1.5803   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3424   -0.1278   -0.3989 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3328    0.6632   -1.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7307    0.6277   -1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924    0.9350   -2.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8703    0.9013   -2.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    0.5646   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518    0.2590   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3276   -0.0852    1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080   -0.3958    2.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345   -0.3552    2.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -0.0129    0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    0.2929   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245    0.0327    0.8878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3809    1.2396    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9854    2.7293   -0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049    2.0771   -1.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    2.1243    1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212   -0.2992   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7143   -0.0529    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9282   -2.2935    1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4644   -2.6109   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -3.4331   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.9301   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9806    1.2000   -3.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4829    1.1363   -3.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5937    0.5241   -1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274   -0.1040    1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1225   -0.6620    3.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120   -0.5868    3.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  6
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  8  2  1  0
 25 13  1  0
 13  7  1  0
 24 15  1  0
 24 19  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  0
  7 30  1  6
  8 31  1  1
  9 32  1  1
 10 33  1  0
 11 34  1  0
 12 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆O₅

Average Mass

336.3430 Da

Monoisotopic Mass

336.09977 Da

IUPAC Name

(4S,4aR,8R,8aS)-4,8-dihydroxy-4a,5,8,8a-tetrahydro-4H-2',4'-dioxaspiro[naphthalene-1,3'-tricyclo[7.3.1.0^{5,13}]tridecane]-1'(12'),5',7',9'(13'),10'-pentaen-5-one

Traditional Name

(4S,4aR,8R,8aS)-4,8-dihydroxy-4,4a,8,8a-tetrahydro-2',4'-dioxaspiro[naphthalene-1,3'-tricyclo[7.3.1.0^{5,13}]tridecane]-1'(12'),5',7',9'(13'),10'-pentaen-5-one

CAS Registry Number

Not Available

SMILES

O[C@H]1C=CC2(OC3=CC=CC4=C3C(O2)=CC=C4)[C@@H]2[C@H](O)C=CC(=O)[C@@H]12

InChI Identifier

InChI=1S/C20H16O5/c21-12-7-8-14(23)19-18(12)13(22)9-10-20(19)24-15-5-1-3-11-4-2-6-16(25-20)17(11)15/h1-10,13-14,18-19,22-23H/t13-,14+,18-,19+/m0/s1

InChI Key

WKESGSKGMIPHTP-QABNGEJJSA-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
Drepanospora viridis	LOTUS Database	35616633
Helicoma	NPAtlas	17190440
Helicoma viridis	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Ketal
Cyclohexenone
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Acetal
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	2	ALOGPS
logP	2.56	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.11	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.37 m³·mol⁻¹	ChemAxon
Polarizability	33.67 Å³	ChemAxon
Number of Rings	5	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

NPA000433

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78436296

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583207

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hu H, Guo H, Li E, Liu X, Zhou Y, Che Y: Decaspirones F-I, bioactive secondary metabolites from the saprophytic fungus Helicoma viridis. J Nat Prod. 2006 Dec;69(12):1672-5. doi: 10.1021/np0603830. [PubMed:17190440 ]

Showing NP-Card for Decaspirone G (NP0006704)

MOL for NP0006704 (Decaspirone G)

3D MOL for NP0006704 (Decaspirone G)

3D SDF for NP0006704 (Decaspirone G)

3D-SDF for NP0006704 (Decaspirone G)

PDB for NP0006704 (Decaspirone G)

3D PDB for NP0006704 (Decaspirone G)

SMILES for NP0006704 (Decaspirone G)

INCHI for NP0006704 (Decaspirone G)

Structure for NP0006704 (Decaspirone G)

3D Structure for NP0006704 (Decaspirone G)