NP-MRD: Showing NP-Card for cyclospongiacatechol (NP0043481)

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Record Information

Version

1.0

Created at

2021-06-21 00:52:50 UTC

Updated at

2021-06-30 00:19:11 UTC

NP-MRD ID

NP0043481

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cyclospongiacatechol

Provided By

JEOL Database JEOL Logo

Description

CYCLOSPONGIACATECHOL belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. cyclospongiacatechol is found in Dactylospongia elegans. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on CYCLOSPONGIACATECHOL (PMID: 27466641) (PMID: 27253005) (PMID: 26389468) (PMID: 26389426) (PMID: 26389424) (PMID: 26389377).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102523D          

 60 63  0  0  0  0            999 V2000
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   -3.0057    3.1846    3.9328 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3268    3.2054    5.5042 O   0  0  0  0  0  0  0  0  0  0  0  0
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 21 22  1  6  0  0  0
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 16 17  1  0  0  0  0
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  8  9  2  0  0  0  0
 14 13  1  1  0  0  0
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M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306212102523D          

 60 63  0  0  0  0            999 V2000
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   -0.8958   -3.3941    0.2605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4421   -1.9446    0.4426 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2646   -1.3327   -0.8079 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531   -2.0329   -0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8411    3.9560    4.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663    4.7841    5.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9920    3.1625    5.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4322    2.2443    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516    1.3565    3.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3398    2.6489    5.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    1.9298   -0.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7583    0.4202   -0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671    2.0109   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8893    1.4432   -2.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490    0.9014   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -0.2640   -2.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7544    1.0551   -3.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7001    0.9570   -4.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785   -1.0674   -4.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9273   -1.4326   -3.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5555   -1.0118   -1.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5147   -5.0181   -2.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7088   -4.2303   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4150   -3.6931   -3.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -2.8697   -4.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536   -4.0594   -3.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477   -2.3377   -3.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7175   -3.0148   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0621   -4.6176   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0421   -4.0758    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4613   -3.6995    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -1.3719    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -1.8900    1.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374   -3.0627   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0391   -2.0814   -1.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085   -1.5374   -0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  6  0  0  0
 25 26  1  0  0  0  0
 16 17  1  0  0  0  0
 24 21  1  0  0  0  0
 21 23  1  0  0  0  0
 21 20  1  0  0  0  0
 20 45  1  1  0  0  0
 27 26  1  0  0  0  0
 27 28  1  6  0  0  0
 27 20  1  0  0  0  0
 15 14  1  0  0  0  0
  7  8  1  0  0  0  0
 25 24  1  0  0  0  0
  8  9  2  0  0  0  0
 14 13  1  1  0  0  0
  9 11  1  0  0  0  0
 11  5  2  0  0  0  0
 27 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
 20 19  1  0  0  0  0
  9 10  1  0  0  0  0
 19 18  1  0  0  0  0
 11 12  1  0  0  0  0
 18 16  1  0  0  0  0
  5  3  1  0  0  0  0
 14 16  1  0  0  0  0
  3  4  2  0  0  0  0
 13  8  1  0  0  0  0
  3  2  1  0  0  0  0
  7 15  1  0  0  0  0
  2  1  1  0  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 24 52  1  0  0  0  0
 24 53  1  0  0  0  0
 26 56  1  0  0  0  0
 26 57  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 16 37  1  1  0  0  0
 22 46  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 23 49  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 28 58  1  0  0  0  0
 28 59  1  0  0  0  0
 28 60  1  0  0  0  0
  6 32  1  0  0  0  0
 10 33  1  0  0  0  0
 12 34  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2O[C@@]3(C([H])([H])C2=C([H])C(C(=O)OC([H])([H])[H])=C1O[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]31C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O5/c1-13-7-8-16-21(2,3)9-6-10-22(16,4)23(13)12-14-11-15(20(26)27-5)17(24)18(25)19(14)28-23/h11,13,16,24-25H,6-10,12H2,1-5H3/t13-,16-,22-,23-/m0/s1

> <INCHI_KEY>
QOJXSCYJHFCUEV-VKSPTSCYSA-N

> <FORMULA>
C23H32O5

> <MOLECULAR_WEIGHT>
388.504

> <EXACT_MASS>
388.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.58967852109757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,2'S,4'aS,8'aS)-6,7-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,5',6',7',8',8'a-octahydro-2'H,3H-spiro[1-benzofuran-2,1'-naphthalene]-5-carboxylate

> <ALOGPS_LOGP>
5.52

> <JCHEM_LOGP>
6.032291865333333

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.055887053242074

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.780470458745624

> <JCHEM_PKA_STRONGEST_BASIC>
-4.34781711273684

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
107.03509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,2'S,4'aS,8'aS)-6,7-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'H,3H-spiro[1-benzofuran-2,1'-naphthalene]-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
   -3.8638    3.8071    4.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0057    3.1846    3.9328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7538    2.9426    4.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268    3.2054    5.5042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9081    2.2963    3.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4103    2.0032    2.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5701    1.3944    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7371    1.0828    1.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520    1.3657    2.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435    1.0586    3.0294 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4290    1.9732    3.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105    2.2220    4.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    0.4901    0.4454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4721    0.2510   -0.6382 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8488    1.0164   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0510    0.9226   -1.9323 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5503    0.7237   -2.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2226    0.5592   -3.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105   -0.9427   -3.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6315   -1.5824   -2.0811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1452   -3.0542   -2.2855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0684   -4.0418   -2.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2695   -3.0762   -3.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -3.5607   -0.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958   -3.3941    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -1.9446    0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646   -1.3327   -0.8079 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531   -2.0329   -0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8411    3.9560    4.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663    4.7841    5.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9920    3.1625    5.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4322    2.2443    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516    1.3565    3.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3398    2.6489    5.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    1.9298   -0.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7583    0.4202   -0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671    2.0109   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8893    1.4432   -2.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490    0.9014   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -0.2640   -2.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7544    1.0551   -3.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7001    0.9570   -4.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785   -1.0674   -4.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9273   -1.4326   -3.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5555   -1.0118   -1.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5147   -5.0181   -2.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7088   -4.2303   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4150   -3.6931   -3.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -2.8697   -4.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536   -4.0594   -3.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477   -2.3377   -3.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7175   -3.0148   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0621   -4.6176   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0421   -4.0758    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4613   -3.6995    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -1.3719    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -1.8900    1.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374   -3.0627   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0391   -2.0814   -1.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085   -1.5374   -0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  6
 25 26  1  0
 16 17  1  0
 24 21  1  0
 21 23  1  0
 21 20  1  0
 20 45  1  1
 27 26  1  0
 27 28  1  6
 27 20  1  0
 15 14  1  0
  7  8  1  0
 25 24  1  0
  8  9  2  0
 14 13  1  1
  9 11  1  0
 11  5  2  0
 27 14  1  0
  5  6  1  0
  6  7  2  0
 20 19  1  0
  9 10  1  0
 19 18  1  0
 11 12  1  0
 18 16  1  0
  5  3  1  0
 14 16  1  0
  3  4  2  0
 13  8  1  0
  3  2  1  0
  7 15  1  0
  2  1  1  0
 15 35  1  0
 15 36  1  0
 25 54  1  0
 25 55  1  0
 24 52  1  0
 24 53  1  0
 26 56  1  0
 26 57  1  0
 19 43  1  0
 19 44  1  0
 18 41  1  0
 18 42  1  0
 16 37  1  1
 22 46  1  0
 22 47  1  0
 22 48  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
  6 32  1  0
 10 33  1  0
 12 34  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.864   3.807   4.891  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.006   3.185   3.933  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.754   2.943   4.388  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.327   3.205   5.504  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.908   2.296   3.354  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.410   2.003   2.073  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.570   1.394   1.149  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.737   1.083   1.464  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.252   1.366   2.712  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.543   1.059   3.029  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.429   1.973   3.664  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.010   2.222   4.887  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.425   0.490   0.445  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.472   0.251  -0.638  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.849   1.016  -0.256  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.051   0.923  -1.932  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.550   0.724  -2.195  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.223   0.559  -3.172  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.011  -0.943  -3.343  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.632  -1.582  -2.081  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.145  -3.054  -2.285  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.068  -4.042  -2.772  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.269  -3.076  -3.355  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.782  -3.561  -0.967  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.896  -3.394   0.261  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.442  -1.945   0.443  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.265  -1.333  -0.808  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.653  -2.033  -0.901  0.00  0.00           C+0
HETATM   29  H   UNK     0      -4.841   3.956   4.424  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.466   4.784   5.183  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.992   3.163   5.766  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.432   2.244   1.795  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.652   1.357   3.954  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.340   2.649   5.467  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.992   1.930  -0.843  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.758   0.420  -0.345  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.967   2.011  -1.794  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.889   1.443  -2.950  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.149   0.901  -1.297  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.793  -0.264  -2.586  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.754   1.055  -3.108  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.700   0.957  -4.076  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.679  -1.067  -4.202  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.927  -1.433  -3.620  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.556  -1.012  -1.908  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.515  -5.018  -2.999  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.709  -4.230  -2.033  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.415  -3.693  -3.690  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.885  -2.870  -4.359  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.754  -4.059  -3.396  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.048  -2.338  -3.132  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.717  -3.015  -0.784  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.062  -4.618  -1.063  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.042  -4.076   0.207  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.461  -3.700   1.150  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.337  -1.372   0.704  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.220  -1.890   1.316  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.637  -3.063  -0.539  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.039  -2.081  -1.920  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.409  -1.537  -0.284  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5   11    6    3                                                  
CONECT    6    5    7   32                                                  
CONECT    7    8    6   15                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9   33                                                       
CONECT   11    9    5   12                                                  
CONECT   12   11   34                                                       
CONECT   13   14    8                                                       
CONECT   14   15   13   27   16                                             
CONECT   15   14    7   35   36                                             
CONECT   16   17   18   14   37                                             
CONECT   17   16   38   39   40                                             
CONECT   18   19   16   41   42                                             
CONECT   19   20   18   43   44                                             
CONECT   20   21   45   27   19                                             
CONECT   21   22   24   23   20                                             
CONECT   22   21   46   47   48                                             
CONECT   23   21   49   50   51                                             
CONECT   24   21   25   52   53                                             
CONECT   25   26   24   54   55                                             
CONECT   26   25   27   56   57                                             
CONECT   27   26   28   20   14                                             
CONECT   28   27   58   59   60                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    6                                                            
CONECT   33   10                                                            
CONECT   34   12                                                            
CONECT   35   15                                                            
CONECT   36   15                                                            
CONECT   37   16                                                            
CONECT   38   17                                                            
CONECT   39   17                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   22                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
CONECT   60   28                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

RDKit          3D

60 63  0  0  0  0  0  0  0  0999 V2000
   -3.8638    3.8071    4.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0057    3.1846    3.9328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7538    2.9426    4.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268    3.2054    5.5042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9081    2.2963    3.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4103    2.0032    2.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5701    1.3944    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7371    1.0828    1.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520    1.3657    2.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435    1.0586    3.0294 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4290    1.9732    3.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105    2.2220    4.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    0.4901    0.4454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4721    0.2510   -0.6382 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8488    1.0164   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0510    0.9226   -1.9323 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5503    0.7237   -2.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2226    0.5592   -3.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105   -0.9427   -3.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6315   -1.5824   -2.0811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1452   -3.0542   -2.2855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0684   -4.0418   -2.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2695   -3.0762   -3.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -3.5607   -0.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958   -3.3941    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -1.9446    0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646   -1.3327   -0.8079 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531   -2.0329   -0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8411    3.9560    4.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663    4.7841    5.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9920    3.1625    5.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4322    2.2443    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516    1.3565    3.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3398    2.6489    5.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    1.9298   -0.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7583    0.4202   -0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671    2.0109   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8893    1.4432   -2.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490    0.9014   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -0.2640   -2.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7544    1.0551   -3.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7001    0.9570   -4.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785   -1.0674   -4.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9273   -1.4326   -3.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5555   -1.0118   -1.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5147   -5.0181   -2.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7088   -4.2303   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4150   -3.6931   -3.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -2.8697   -4.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536   -4.0594   -3.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477   -2.3377   -3.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7175   -3.0148   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0621   -4.6176   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0421   -4.0758    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4613   -3.6995    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -1.3719    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -1.8900    1.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374   -3.0627   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0391   -2.0814   -1.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085   -1.5374   -0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  6
 25 26  1  0
 16 17  1  0
 24 21  1  0
 21 23  1  0
 21 20  1  0
 20 45  1  1
 27 26  1  0
 27 28  1  6
 27 20  1  0
 15 14  1  0
  7  8  1  0
 25 24  1  0
  8  9  2  0
 14 13  1  1
  9 11  1  0
 11  5  2  0
 27 14  1  0
  5  6  1  0
  6  7  2  0
 20 19  1  0
  9 10  1  0
 19 18  1  0
 11 12  1  0
 18 16  1  0
  5  3  1  0
 14 16  1  0
  3  4  2  0
 13  8  1  0
  3  2  1  0
  7 15  1  0
  2  1  1  0
 15 35  1  0
 15 36  1  0
 25 54  1  0
 25 55  1  0
 24 52  1  0
 24 53  1  0
 26 56  1  0
 26 57  1  0
 19 43  1  0
 19 44  1  0
 18 41  1  0
 18 42  1  0
 16 37  1  1
 22 46  1  0
 22 47  1  0
 22 48  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
  6 32  1  0
 10 33  1  0
 12 34  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂O₅

Average Mass

388.5040 Da

Monoisotopic Mass

388.22497 Da

IUPAC Name

methyl (2S,2'S,4'aS,8'aS)-6,7-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,5',6',7',8',8'a-octahydro-2'H,3H-spiro[1-benzofuran-2,1'-naphthalene]-5-carboxylate

Traditional Name

methyl (2S,2'S,4'aS,8'aS)-6,7-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'H,3H-spiro[1-benzofuran-2,1'-naphthalene]-5-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C2O[C@@]3(C([H])([H])C2=C([H])C(C(=O)OC([H])([H])[H])=C1O[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]31C([H])([H])[H]

InChI Identifier

InChI=1S/C23H32O5/c1-13-7-8-16-21(2,3)9-6-10-22(16,4)23(13)12-14-11-15(20(26)27-5)17(24)18(25)19(14)28-23/h11,13,16,24-25H,6-10,12H2,1-5H3/t13-,16-,22-,23-/m0/s1

InChI Key

QOJXSCYJHFCUEV-VKSPTSCYSA-N

Experimental Spectra

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

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dactylospongia elegans	JEOL database	Du, L., et al, J. Nat. Prod. 76, 1175 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acid and derivatives

Alternative Parents

Substituents

Salicylic acid or derivatives
Benzofuran
Coumaran
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Methyl ester
Vinylogous acid
Carboxylic acid ester
Oxacycle
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.52	ALOGPS
logP	6.03	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	107.04 m³·mol⁻¹	ChemAxon
Polarizability	43.59 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30770983

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71726095

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Stomach (Gastric) Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389468 ]
Authors unspecified: Childhood Central Nervous System Atypical Teratoid/Rhabdoid Tumor Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389426 ]
Authors unspecified: Cancer Prevention Overview (PDQ(R)): Patient Version. 2002. [PubMed:26389424 ]
Authors unspecified: Acute Myeloid Leukemia Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389377 ]
Authors unspecified: Cervical Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389339 ]
Authors unspecified: Pheochromocytoma and Paraganglioma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389312 ]
Authors unspecified: Prostate Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:26389306 ]
Du, L., et al. (2013). Du, L., et al, J. Nat. Prod. 76, 1175 (2013). J. Nat. Prod..

Showing NP-Card for cyclospongiacatechol (NP0043481)

MOL for NP0043481 (cyclospongiacatechol)

3D MOL for NP0043481 (cyclospongiacatechol)

3D SDF for NP0043481 (cyclospongiacatechol)

3D-SDF for NP0043481 (cyclospongiacatechol)

PDB for NP0043481 (cyclospongiacatechol)

3D PDB for NP0043481 (cyclospongiacatechol)

SMILES for NP0043481 (cyclospongiacatechol)

INCHI for NP0043481 (cyclospongiacatechol)

Structure for NP0043481 (cyclospongiacatechol)

3D Structure for NP0043481 (cyclospongiacatechol)