NP-MRD: Showing NP-Card for Sargassopenilline C (NP0013575)

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Record Information

Version

2.0

Created at

2021-01-05 22:53:52 UTC

Updated at

2021-07-15 17:14:51 UTC

NP-MRD ID

NP0013575

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sargassopenilline C

Provided By

NPAtlas

Description

Sargassopenilline C is found in Penicillium and Penicillium thomii. Sargassopenilline C was first documented in 2014 (PMID: 25501795). Based on a literature review very few articles have been published on Sargassopenilline C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119373D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242119373D          

 58 60  0  0  0  0            999 V2000
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   -2.5916   -4.5873   -0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5066   -4.1629    0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8559   -5.1358   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6112   -0.6781   -1.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933    0.1018    2.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361    1.7314    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7791    2.6769    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4676    4.7464    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4536    3.9279   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1636    4.2696   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197    3.2100   -1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9307    2.2654    0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699    1.2815   -2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5448    0.5028   -2.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8893   -0.9041   -1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6328   -0.8646    3.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9286   -2.5594    2.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0869   -1.3158    2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460   -1.6840    1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -2.1248    0.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6935   -1.3302    1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9302    2.5269   -0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7421    1.4173    1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9752    1.2171   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -1.8908   -1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7275   -0.4396   -2.4128 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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  7 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 24 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 10  5  1  0  0  0  0
 32  6  1  0  0  0  0
 17 10  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  5 36  1  6  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
 12 39  1  1  0  0  0
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 13 42  1  0  0  0  0
 14 43  1  0  0  0  0
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 15 45  1  6  0  0  0
 16 46  1  0  0  0  0
 17 47  1  6  0  0  0
 20 48  1  0  0  0  0
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 20 50  1  0  0  0  0
 25 51  1  0  0  0  0
 25 52  1  0  0  0  0
 25 53  1  0  0  0  0
 28 54  1  0  0  0  0
 28 55  1  0  0  0  0
 28 56  1  0  0  0  0
 32 57  1  0  0  0  0
 32 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0013575

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])[C@@]([H])(O[C@@]2(OC([H])([H])C3=C(C([H])([H])C(=O)[C@@](OC(=O)C([H])([H])[H])(C3=O)C([H])([H])[H])[C@@]2([H])OC(=O)C([H])([H])[H])[C@@]1([H])OC(=O)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O11/c1-9-6-15(25)19(30-11(3)23)21(31-9)18(29-10(2)22)13-7-16(26)20(5,32-12(4)24)17(27)14(13)8-28-21/h9,15,18-19,25H,6-8H2,1-5H3/t9-,15-,18+,19-,20+,21+/m0/s1

> <INCHI_KEY>
BLUKNYPPXACRML-SGEUHFFASA-N

> <FORMULA>
C21H26O11

> <MOLECULAR_WEIGHT>
454.428

> <EXACT_MASS>
454.147511657

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.32397627024498

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3'S,4R,4'S,6'S,7R)-4,7-bis(acetyloxy)-4'-hydroxy-6',7-dimethyl-6,8-dioxo-1,4,5,6,7,8-hexahydrospiro[2-benzopyran-3,2'-oxane]-3'-yl acetate

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.026005595666666544

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.913816042867527

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.209133448985746

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2739586958414826

> <JCHEM_POLAR_SURFACE_AREA>
151.73000000000002

> <JCHEM_REFRACTIVITY>
103.30969999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3'S,4R,4'S,6'S,7R)-4,7-bis(acetyloxy)-4'-hydroxy-6',7-dimethyl-6,8-dioxo-4,5-dihydro-1H-spiro[2-benzopyran-3,2'-oxane]-3'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
   -1.5436   -4.3317   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146   -3.0300   -0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1789    0.2963    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999    0.6627    1.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582    0.3272    1.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0151    1.6173   -0.6486 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4430    3.9436   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2980    2.3623   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657    1.1431   -1.3092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6250    0.8460   -1.7690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -0.0144   -0.4898 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5094   -0.1695    0.7210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -1.3079    0.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0249   -1.4817    2.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2580   -2.2144    0.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    0.6667    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649    1.5678    1.8780 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7262   -0.0063    0.4191 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9303   -1.3390    1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8519    0.8434    0.5091 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1008    0.5267    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2670    1.4756    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2724   -0.5976   -0.5002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3470   -0.2411   -1.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    0.0062   -1.8904 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121   -0.7733   -1.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -4.5873   -0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5066   -4.1629    0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8559   -5.1358   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6112   -0.6781   -1.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933    0.1018    2.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361    1.7314    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7791    2.6769    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4676    4.7464    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4536    3.9279   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1636    4.2696   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197    3.2100   -1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9307    2.2654    0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699    1.2815   -2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5448    0.5028   -2.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8893   -0.9041   -1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6328   -0.8646    3.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9286   -2.5594    2.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0869   -1.3158    2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460   -1.6840    1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -2.1248    0.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6935   -1.3302    1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9302    2.5269   -0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7421    1.4173    1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9752    1.2171   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -1.8908   -1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7275   -0.4396   -2.4128 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  2  0
  7  8  1  0
  8  9  1  0
 10  9  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
  7 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 24 26  1  6
 26 27  1  0
 27 28  1  0
 27 29  2  0
 24 30  1  0
 30 31  2  0
 30 32  1  0
 10  5  1  0
 32  6  1  0
 17 10  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  6
  8 37  1  0
  8 38  1  0
 12 39  1  1
 13 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  6
 16 46  1  0
 17 47  1  6
 20 48  1  0
 20 49  1  0
 20 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 32 57  1  0
 32 58  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      -1.544  -4.332  -0.215  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.215  -3.030  -0.865  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.364  -2.963  -2.108  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.767  -1.927  -0.190  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.449  -0.681  -0.783  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.971  -0.353  -0.446  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.179   0.296   0.686  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.100   0.663   1.606  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.158   0.327   1.198  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.365   0.356  -0.173  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.015   1.617  -0.649  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.831   2.592  -0.103  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.443   3.944  -0.674  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.298   2.362  -0.452  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.366   1.143  -1.309  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.625   0.846  -1.769  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.776  -0.014  -0.490  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.509  -0.170   0.721  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.253  -1.308   0.998  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.025  -1.482   2.261  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.258  -2.214   0.126  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.549   0.667   1.038  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.765   1.568   1.878  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.726  -0.006   0.419  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.930  -1.339   1.064  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.852   0.843   0.509  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.101   0.527   0.045  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.267   1.476   0.166  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.272  -0.598  -0.500  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.347  -0.241  -1.015  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.140   0.006  -1.890  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.012  -0.773  -1.391  0.00  0.00           C+0
HETATM   33  H   UNK     0      -2.592  -4.587  -0.467  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.507  -4.163   0.885  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.856  -5.136  -0.531  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.611  -0.678  -1.872  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.293   0.102   2.568  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.236   1.731   1.878  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.779   2.677   0.985  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.468   4.746   0.096  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.454   3.928  -1.147  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.164   4.270  -1.469  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.720   3.210  -1.038  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.931   2.265   0.455  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.670   1.282  -2.160  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.545   0.503  -2.698  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.889  -0.904  -1.143  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.633  -0.865   3.083  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.929  -2.559   2.573  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.087  -1.316   2.057  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.946  -1.684   1.497  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.213  -2.125   0.332  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.694  -1.330   1.856  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.930   2.527  -0.064  0.00  0.00           H+0
HETATM   55  H   UNK     0       7.742   1.417   1.146  0.00  0.00           H+0
HETATM   56  H   UNK     0       7.975   1.217  -0.664  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.126  -1.891  -1.436  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.728  -0.440  -2.413  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10   36                                             
CONECT    6    5    7   32                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9   37   38                                             
CONECT    9    8   10                                                       
CONECT   10    9   11    5   17                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14   39                                             
CONECT   13   12   40   41   42                                             
CONECT   14   12   15   43   44                                             
CONECT   15   14   16   17   45                                             
CONECT   16   15   46                                                       
CONECT   17   15   18   10   47                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   48   49   50                                             
CONECT   21   19                                                            
CONECT   22    7   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   30                                             
CONECT   25   24   51   52   53                                             
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   54   55   56                                             
CONECT   29   27                                                            
CONECT   30   24   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    6   57   58                                             
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    5                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39   12                                                            
CONECT   40   13                                                            
CONECT   41   13                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   28                                                            
CONECT   55   28                                                            
CONECT   56   28                                                            
CONECT   57   32                                                            
CONECT   58   32                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

RDKit          3D

58 60  0  0  0  0  0  0  0  0999 V2000
   -1.5436   -4.3317   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146   -3.0300   -0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3641   -2.9630   -2.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669   -1.9267   -0.1899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4492   -0.6809   -0.7825 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9705   -0.3530   -0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789    0.2963    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999    0.6627    1.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582    0.3272    1.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3648    0.3559   -0.1732 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0151    1.6173   -0.6486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310    2.5924   -0.1028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4430    3.9436   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2980    2.3623   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657    1.1431   -1.3092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6250    0.8460   -1.7690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -0.0144   -0.4898 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5094   -0.1695    0.7210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -1.3079    0.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0249   -1.4817    2.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2580   -2.2144    0.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    0.6667    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649    1.5678    1.8780 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7262   -0.0063    0.4191 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9303   -1.3390    1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8519    0.8434    0.5091 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1008    0.5267    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2670    1.4756    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2724   -0.5976   -0.5002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3470   -0.2411   -1.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    0.0062   -1.8904 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121   -0.7733   -1.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -4.5873   -0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5066   -4.1629    0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8559   -5.1358   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6112   -0.6781   -1.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933    0.1018    2.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361    1.7314    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7791    2.6769    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4676    4.7464    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4536    3.9279   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1636    4.2696   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197    3.2100   -1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9307    2.2654    0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699    1.2815   -2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5448    0.5028   -2.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8893   -0.9041   -1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6328   -0.8646    3.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9286   -2.5594    2.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0869   -1.3158    2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460   -1.6840    1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -2.1248    0.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6935   -1.3302    1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9302    2.5269   -0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7421    1.4173    1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9752    1.2171   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -1.8908   -1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7275   -0.4396   -2.4128 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  2  0
  7  8  1  0
  8  9  1  0
 10  9  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
  7 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 24 26  1  6
 26 27  1  0
 27 28  1  0
 27 29  2  0
 24 30  1  0
 30 31  2  0
 30 32  1  0
 10  5  1  0
 32  6  1  0
 17 10  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  6
  8 37  1  0
  8 38  1  0
 12 39  1  1
 13 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  6
 16 46  1  0
 17 47  1  6
 20 48  1  0
 20 49  1  0
 20 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 32 57  1  0
 32 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3R,3's,4's,6's)-3',4-Bis(acetyloxy)-4'-hydroxy-6',7-dimethyl-6,8-dioxo-1,4,5,6,7,8-hexahydrospiro[2-benzopyran-3,2'-oxane]-7-yl acetic acid	Generator

Chemical Formula

C₂₁H₂₆O₁₁

Average Mass

454.4280 Da

Monoisotopic Mass

454.14751 Da

IUPAC Name

(3R,3'S,4R,4'S,6'S,7R)-4,7-bis(acetyloxy)-4'-hydroxy-6',7-dimethyl-6,8-dioxo-1,4,5,6,7,8-hexahydrospiro[2-benzopyran-3,2'-oxane]-3'-yl acetate

Traditional Name

(3R,3'S,4R,4'S,6'S,7R)-4,7-bis(acetyloxy)-4'-hydroxy-6',7-dimethyl-6,8-dioxo-4,5-dihydro-1H-spiro[2-benzopyran-3,2'-oxane]-3'-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@H](O)[C@H](OC(C)=O)[C@]2(OCC3=C(CC(=O)C(C)(OC(C)=O)C3=O)C2OC(C)=O)O1

InChI Identifier

InChI=1S/C21H26O11/c1-9-6-15(25)19(30-11(3)23)21(31-9)18(29-10(2)22)13-7-16(26)20(5,32-12(4)24)17(27)14(13)8-28-21/h9,15,18-19,25H,6-8H2,1-5H3/t9-,15-,18?,19-,20?,21+/m0/s1

InChI Key

BLUKNYPPXACRML-SGEUHFFASA-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	NPAtlas	25501795
Penicillium thomii	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	0.87	ALOGPS
logP	0.026	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	151.73 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.31 m³·mol⁻¹	ChemAxon
Polarizability	44.32 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

NPA007286

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34982095

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585136

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhuravleva OI, Sobolevskaya MP, Afiyatullov SSh, Kirichuk NN, Denisenko VA, Dmitrenok PS, Yurchenko EA, Dyshlovoy SA: Sargassopenillines A-G, 6,6-spiroketals from the alga-derived fungi Penicillium thomii and Penicillium lividum. Mar Drugs. 2014 Dec 9;12(12):5930-43. doi: 10.3390/md12125930. [PubMed:25501795 ]

Showing NP-Card for Sargassopenilline C (NP0013575)

MOL for NP0013575 (Sargassopenilline C)

3D MOL for NP0013575 (Sargassopenilline C)

3D SDF for NP0013575 (Sargassopenilline C)

3D-SDF for NP0013575 (Sargassopenilline C)

PDB for NP0013575 (Sargassopenilline C)

3D PDB for NP0013575 (Sargassopenilline C)

SMILES for NP0013575 (Sargassopenilline C)

INCHI for NP0013575 (Sargassopenilline C)

Structure for NP0013575 (Sargassopenilline C)

3D Structure for NP0013575 (Sargassopenilline C)