NP-MRD: Showing NP-Card for Daldinin D (NP0003956)

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Record Information

Version

2.0

Created at

2020-12-09 01:29:27 UTC

Updated at

2021-07-15 16:47:50 UTC

NP-MRD ID

NP0003956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Daldinin D

Provided By

NPAtlas

Description

(3R,3'R,4R,6'S,7S)-3',4-bis(acetyloxy)-6',7-dimethyl-6,8-dioxo-4,6,7,8-tetrahydrospiro[2-benzopyran-3,2'-oxane]-7-yl acetate belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Daldinin D is found in Penicillium thymicola. Daldinin D was first documented in 2001 (PMID: 11754624). Based on a literature review very few articles have been published on (3R,3'R,4R,6'S,7S)-3',4-bis(acetyloxy)-6',7-dimethyl-6,8-dioxo-4,6,7,8-tetrahydrospiro[2-benzopyran-3,2'-oxane]-7-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117513D          

 55 57  0  0  0  0            999 V2000
   -2.9105   -3.4449   -2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839   -2.4060   -0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9375   -2.7247   -0.0336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6628   -1.1262   -1.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9147   -0.1434   -0.0572 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6669    1.0417   -0.6010 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0230    1.8752    0.6296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7650    2.2255    1.3481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1286    3.4075    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    1.2298    1.6216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805    0.2553    0.7131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3083   -0.8981    1.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1536   -1.0625    2.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9341   -0.4139    1.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2000   -0.5184    2.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2622   -0.9361    3.5676 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559   -0.1231    1.6532 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4583    0.3712    2.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -1.2446    0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1445   -1.1953    0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6946   -2.4079   -0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7566   -0.1025    0.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502    0.9833    0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202    1.8493    0.4368 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299    1.0518    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7910    0.4002    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047    0.5453   -0.2007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5378   -0.1719   -1.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6383    0.4290   -2.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758   -0.3194   -3.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001    1.6965   -2.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4020   -3.0368   -2.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9275   -3.7703   -2.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5705    0.6888   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7100    1.2260    1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0485   -1.6714    3.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4159   -0.2097    2.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7688    1.4376    2.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0960    0.3306    3.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756   -2.4635   -1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4117   -3.3369    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8052   -2.3085   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5755    1.6258   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627    0.0908   -4.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942   -1.3470   -3.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6815   -0.4213   -4.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 11  5  1  0  0  0  0
 26 14  1  0  0  0  0
 27 11  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  5 35  1  1  0  0  0
  6 36  1  0  0  0  0
  6 37  1  0  0  0  0
  7 38  1  0  0  0  0
  7 39  1  0  0  0  0
  8 40  1  1  0  0  0
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  9 43  1  0  0  0  0
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 25 51  1  0  0  0  0
 27 52  1  6  0  0  0
 30 53  1  0  0  0  0
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 30 55  1  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
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   -2.7650    2.2255    1.3481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1286    3.4075    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    1.2298    1.6216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805    0.2553    0.7131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3083   -0.8981    1.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2000   -0.5184    2.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4583    0.3712    2.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -1.2446    0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6946   -2.4079   -0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0202    1.8493    0.4368 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6489    4.3640    0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
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 25 51  1  0
 27 52  1  6
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 30 55  1  0
M  END


  Mrv1652306242117513D          

 55 57  0  0  0  0            999 V2000
   -2.9105   -3.4449   -2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839   -2.4060   -0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9375   -2.7247   -0.0336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6628   -1.1262   -1.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9147   -0.1434   -0.0572 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6669    1.0417   -0.6010 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0230    1.8752    0.6296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7650    2.2255    1.3481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1286    3.4075    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    1.2298    1.6216 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2000   -0.5184    2.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0202    1.8493    0.4368 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7910    0.4002    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047    0.5453   -0.2007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5378   -0.1719   -1.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6758   -0.3194   -3.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001    1.6965   -2.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4489   -4.3427   -1.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6035   -0.6177    0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5705    0.6888   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028    1.6621   -1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    2.7821    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7100    1.2260    1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896    2.6742    2.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6489    4.3640    0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    3.3327   -0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0911    3.5072    0.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0485   -1.6714    3.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4159   -0.2097    2.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7688    1.4376    2.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0960    0.3306    3.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756   -2.4635   -1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4117   -3.3369    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8052   -2.3085   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584    1.6811   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755    1.6258   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627    0.0908   -4.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942   -1.3470   -3.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6815   -0.4213   -4.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 11  5  1  0  0  0  0
 26 14  1  0  0  0  0
 27 11  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  5 35  1  1  0  0  0
  6 36  1  0  0  0  0
  6 37  1  0  0  0  0
  7 38  1  0  0  0  0
  7 39  1  0  0  0  0
  8 40  1  1  0  0  0
  9 41  1  0  0  0  0
  9 42  1  0  0  0  0
  9 43  1  0  0  0  0
 13 44  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 21 48  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
 25 51  1  0  0  0  0
 27 52  1  6  0  0  0
 30 53  1  0  0  0  0
 30 54  1  0  0  0  0
 30 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003956

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C2C(=O)[C@@](OC(=O)C([H])([H])[H])(C(=O)C([H])=C2[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]2(O1)O[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]2([H])OC(=O)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O10/c1-10-6-7-17(28-11(2)22)21(30-10)19(29-12(3)23)14-8-16(25)20(5,31-13(4)24)18(26)15(14)9-27-21/h8-10,17,19H,6-7H2,1-5H3/t10-,17+,19+,20-,21-/m0/s1

> <INCHI_KEY>
FHJLYQODAHDGIV-YNDOHWJBSA-N

> <FORMULA>
C21H24O10

> <MOLECULAR_WEIGHT>
436.413

> <EXACT_MASS>
436.136946973

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.31237343100442

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3'R,4R,6'S,7S)-3',7-bis(acetyloxy)-6',7-dimethyl-6,8-dioxo-4,6,7,8-tetrahydrospiro[2-benzopyran-3,2'-oxane]-4-yl acetate

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.3895199399999996

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.9192956630533375

> <JCHEM_PKA_STRONGEST_BASIC>
-4.285543374185632

> <JCHEM_POLAR_SURFACE_AREA>
131.50000000000003

> <JCHEM_REFRACTIVITY>
102.21559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3'R,4R,6'S,7S)-3',7-bis(acetyloxy)-6',7-dimethyl-6,8-dioxo-4H-spiro[2-benzopyran-3,2'-oxane]-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -2.9105   -3.4449   -2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839   -2.4060   -0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9375   -2.7247   -0.0336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6628   -1.1262   -1.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9147   -0.1434   -0.0572 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6669    1.0417   -0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0230    1.8752    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7650    2.2255    1.3481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1286    3.4075    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    1.2298    1.6216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805    0.2553    0.7131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3083   -0.8981    1.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1536   -1.0625    2.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9341   -0.4139    1.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2000   -0.5184    2.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2622   -0.9361    3.5676 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559   -0.1231    1.6532 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4583    0.3712    2.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -1.2446    0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1445   -1.1953    0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6946   -2.4079   -0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7566   -0.1025    0.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502    0.9833    0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202    1.8493    0.4368 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299    1.0518    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7910    0.4002    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047    0.5453   -0.2007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5378   -0.1719   -1.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6383    0.4290   -2.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758   -0.3194   -3.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001    1.6965   -2.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4020   -3.0368   -2.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9275   -3.7703   -2.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489   -4.3427   -1.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6035   -0.6177    0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5705    0.6888   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028    1.6621   -1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    2.7821    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7100    1.2260    1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896    2.6742    2.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6489    4.3640    0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    3.3327   -0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0911    3.5072    0.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0485   -1.6714    3.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4159   -0.2097    2.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7688    1.4376    2.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0960    0.3306    3.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756   -2.4635   -1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4117   -3.3369    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8052   -2.3085   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584    1.6811   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755    1.6258   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627    0.0908   -4.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942   -1.3470   -3.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6815   -0.4213   -4.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 11 10  1  1
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  6
 19 20  1  0
 20 21  1  0
 20 22  2  0
 17 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 11  5  1  0
 26 14  1  0
 27 11  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  1
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  1
  9 41  1  0
  9 42  1  0
  9 43  1  0
 13 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 25 51  1  0
 27 52  1  6
 30 53  1  0
 30 54  1  0
 30 55  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  C   UNK     0      -2.910  -3.445  -2.014  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.184  -2.406  -0.986  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.938  -2.725  -0.034  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.663  -1.126  -1.019  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.915  -0.143  -0.057  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.667   1.042  -0.601  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.023   1.875   0.630  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.765   2.225   1.348  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.129   3.408   0.605  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.910   1.230   1.622  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.681   0.255   0.713  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.308  -0.898   1.458  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.154  -1.063   2.164  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.934  -0.414   1.715  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.200  -0.518   2.383  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.262  -0.936   3.568  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.456  -0.123   1.653  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.458   0.371   2.646  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.000  -1.245   0.978  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.144  -1.195   0.228  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.695  -2.408  -0.478  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.757  -0.103   0.124  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.150   0.983   0.693  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.020   1.849   0.437  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.830   1.052   0.054  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.791   0.400   0.528  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.505   0.545  -0.201  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.538  -0.172  -1.389  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.638   0.429  -2.627  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.676  -0.319  -3.912  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.700   1.696  -2.624  0.00  0.00           O+0
HETATM   32  H   UNK     0      -2.402  -3.037  -2.905  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.928  -3.770  -2.383  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.449  -4.343  -1.593  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.603  -0.618   0.705  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.571   0.689  -1.122  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.103   1.662  -1.293  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.534   2.782   0.289  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.710   1.226   1.235  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.090   2.674   2.337  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.649   4.364   0.907  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.262   3.333  -0.481  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.091   3.507   0.944  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.049  -1.671   3.052  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.416  -0.210   2.618  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.769   1.438   2.453  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.096   0.331   3.691  0.00  0.00           H+0
HETATM   48  H   UNK     0       5.276  -2.463  -1.514  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.412  -3.337   0.030  0.00  0.00           H+0
HETATM   50  H   UNK     0       6.805  -2.309  -0.618  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.758   1.681  -0.847  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.576   1.626  -0.459  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.063   0.091  -4.652  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.294  -1.347  -3.678  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.682  -0.421  -4.319  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   11   35                                             
CONECT    6    5    7   36   37                                             
CONECT    7    6    8   38   39                                             
CONECT    8    7    9   10   40                                             
CONECT    9    8   41   42   43                                             
CONECT   10    8   11                                                       
CONECT   11   10   12    5   27                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   44                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   23                                             
CONECT   18   17   45   46   47                                             
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   48   49   50                                             
CONECT   22   20                                                            
CONECT   23   17   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   51                                                  
CONECT   26   25   27   14                                                  
CONECT   27   26   28   11   52                                             
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   53   54   55                                             
CONECT   31   29                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    5                                                            
CONECT   36    6                                                            
CONECT   37    6                                                            
CONECT   38    7                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43    9                                                            
CONECT   44   13                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   21                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   25                                                            
CONECT   52   27                                                            
CONECT   53   30                                                            
CONECT   54   30                                                            
CONECT   55   30                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
   -2.9105   -3.4449   -2.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839   -2.4060   -0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9375   -2.7247   -0.0336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6628   -1.1262   -1.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9147   -0.1434   -0.0572 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6669    1.0417   -0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0230    1.8752    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7650    2.2255    1.3481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1286    3.4075    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    1.2298    1.6216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805    0.2553    0.7131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3083   -0.8981    1.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1536   -1.0625    2.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9341   -0.4139    1.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2000   -0.5184    2.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2622   -0.9361    3.5676 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559   -0.1231    1.6532 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4583    0.3712    2.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -1.2446    0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1445   -1.1953    0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6946   -2.4079   -0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7566   -0.1025    0.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502    0.9833    0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202    1.8493    0.4368 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299    1.0518    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7910    0.4002    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047    0.5453   -0.2007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5378   -0.1719   -1.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6383    0.4290   -2.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758   -0.3194   -3.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001    1.6965   -2.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4020   -3.0368   -2.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9275   -3.7703   -2.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489   -4.3427   -1.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6035   -0.6177    0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5705    0.6888   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028    1.6621   -1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    2.7821    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7100    1.2260    1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896    2.6742    2.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6489    4.3640    0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    3.3327   -0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0911    3.5072    0.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0485   -1.6714    3.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4159   -0.2097    2.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7688    1.4376    2.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0960    0.3306    3.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756   -2.4635   -1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4117   -3.3369    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8052   -2.3085   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584    1.6811   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755    1.6258   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627    0.0908   -4.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942   -1.3470   -3.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6815   -0.4213   -4.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 11 10  1  1
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  6
 19 20  1  0
 20 21  1  0
 20 22  2  0
 17 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 11  5  1  0
 26 14  1  0
 27 11  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  1
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  1
  9 41  1  0
  9 42  1  0
  9 43  1  0
 13 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 25 51  1  0
 27 52  1  6
 30 53  1  0
 30 54  1  0
 30 55  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3R,3'r,4R,6's,7S)-3',4-Bis(acetyloxy)-6',7-dimethyl-6,8-dioxo-4,6,7,8-tetrahydrospiro[2-benzopyran-3,2'-oxane]-7-yl acetic acid	Generator

Chemical Formula

C₂₁H₂₄O₁₀

Average Mass

436.4130 Da

Monoisotopic Mass

436.13695 Da

IUPAC Name

(3R,3'R,4R,6'S,7S)-3',7-bis(acetyloxy)-6',7-dimethyl-6,8-dioxo-4,6,7,8-tetrahydrospiro[2-benzopyran-3,2'-oxane]-4-yl acetate

Traditional Name

(3R,3'R,4R,6'S,7S)-3',7-bis(acetyloxy)-6',7-dimethyl-6,8-dioxo-4H-spiro[2-benzopyran-3,2'-oxane]-4-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@H](OC(C)=O)[C@]2(OC=C3C(=O)[C@@](C)(OC(C)=O)C(=O)C=C3[C@H]2OC(C)=O)O1

InChI Identifier

InChI=1S/C21H24O10/c1-10-6-7-17(28-11(2)22)21(30-10)19(29-12(3)23)14-8-16(25)20(5,31-13(4)24)18(26)15(14)9-27-21/h8-10,17,19H,6-7H2,1-5H3/t10-,17+,19+,20-,21-/m0/s1

InChI Key

FHJLYQODAHDGIV-YNDOHWJBSA-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
Penicillium thymicola	NPAtlas	11754624

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Tricarboxylic acid or derivatives
Ketal
Cyclohexenone
Alpha-acyloxy ketone
Oxane
Vinylogous ester
Cyclic ketone
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.73	ALOGPS
logP	1.39	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.92	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	131.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	102.22 m³·mol⁻¹	ChemAxon
Polarizability	42.31 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	Yes	ChemAxon

External Links

NPAtlas ID

NPA017709

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9319709

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11144599

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Romero Ariza M, Larsen TO, Petersen BO, Duus JO, Christophersen C, Barrero AF: A novel alkaloid serantrypinone and the spiro azaphilone daldinin D from Penicillium thymicola. J Nat Prod. 2001 Dec;64(12):1590-2. doi: 10.1021/np0101550. [PubMed:11754624 ]

Showing NP-Card for Daldinin D (NP0003956)

MOL for NP0003956 (Daldinin D)

3D MOL for NP0003956 (Daldinin D)

3D SDF for NP0003956 (Daldinin D)

3D-SDF for NP0003956 (Daldinin D)

PDB for NP0003956 (Daldinin D)

3D PDB for NP0003956 (Daldinin D)

SMILES for NP0003956 (Daldinin D)

INCHI for NP0003956 (Daldinin D)

Structure for NP0003956 (Daldinin D)

3D Structure for NP0003956 (Daldinin D)