NP-MRD: Showing NP-Card for Spirolide C (NP0335815)

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Record Information

Version

2.0

Created at

2024-09-11 03:22:10 UTC

Updated at

2024-09-11 03:22:11 UTC

NP-MRD ID

NP0335815

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spirolide C

Description

Spirolide C belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. Spirolide C was first documented in 2020 (PMID: 33261221). Based on a literature review a significant number of articles have been published on Spirolide C (PMID: 33774286) (PMID: 33744630) (PMID: 33379060) (PMID: 38479322) (PMID: 37999494) (PMID: 37689146).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262305542D          

 51 57  0  0  0  0            999 V2000
   -1.8809    0.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8809    0.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1676   -0.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556    0.1567    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4556    0.9813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1676    1.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2123    0.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0067    0.7175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284    1.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353    2.1977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1230    2.3408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4968    1.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7552   -0.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5957   -0.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009    3.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164    2.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6247   -0.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3394    0.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0541   -0.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369    0.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042    0.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4238    1.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637    0.2075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3490    0.0783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015   -0.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4905   -1.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849   -1.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050   -0.1140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -0.9346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8630   -1.4335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6216   -1.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7221   -0.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898   -0.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8714   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012   -1.8253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0232   -1.7429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7626   -2.2513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -1.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405   -1.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405   -2.0975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6742   -0.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7552   -2.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1676   -1.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8272   -2.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221   -0.4481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3820   -1.9133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2116   -2.7228    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9263   -3.1353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5366   -2.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4583   -3.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263   -3.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  3 43  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 12  1  1  0  0  0
  7  8  2  0  0  0  0
  7 17  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  1  0  0  0
 11 12  1  0  0  0  0
 11 15  1  6  0  0  0
 13 39  2  0  0  0  0
 14 24  1  0  0  0  0
 14 27  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
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 21  1  6  0  0  0
 23 28  1  0  0  0  0
 23 32  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 45  2  0  0  0  0
 26 27  2  0  0  0  0
 26 44  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 29 36  1  1  0  0  0
 30 31  1  0  0  0  0
 30 37  1  0  0  0  0
 30 38  1  6  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 46  1  1  0  0  0
 35 49  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 40 42  1  6  0  0  0
 40 50  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 50  1  1  0  0  0
 48 49  1  0  0  0  0
 48 51  1  1  0  0  0
M  END


  Mrv2104 05262305542D          

 51 57  0  0  0  0            999 V2000
   -1.8809    0.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8809    0.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1676   -0.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556    0.1567    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4556    0.9813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1676    1.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2123    0.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0067    0.7175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284    1.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353    2.1977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1230    2.3408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4968    1.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7552   -0.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5957   -0.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009    3.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164    2.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6247   -0.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3394    0.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0541   -0.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369    0.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042    0.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4238    1.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637    0.2075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3490    0.0783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015   -0.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4905   -1.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849   -1.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050   -0.1140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -0.9346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8630   -1.4335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6216   -1.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7221   -0.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898   -0.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8714   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012   -1.8253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0232   -1.7429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7626   -2.2513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -1.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405   -1.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405   -2.0975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6742   -0.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7552   -2.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1676   -1.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8272   -2.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221   -0.4481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3820   -1.9133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2116   -2.7228    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9263   -3.1353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5366   -2.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4583   -3.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263   -3.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  3 43  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 12  1  1  0  0  0
  7  8  2  0  0  0  0
  7 17  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  1  0  0  0
 11 12  1  0  0  0  0
 11 15  1  6  0  0  0
 13 39  2  0  0  0  0
 14 24  1  0  0  0  0
 14 27  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
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 21  1  6  0  0  0
 23 28  1  0  0  0  0
 23 32  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 45  2  0  0  0  0
 26 27  2  0  0  0  0
 26 44  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 29 36  1  1  0  0  0
 30 31  1  0  0  0  0
 30 37  1  0  0  0  0
 30 38  1  6  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 46  1  1  0  0  0
 35 49  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 40 42  1  6  0  0  0
 40 50  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 50  1  1  0  0  0
 48 49  1  0  0  0  0
 48 51  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0335815

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@]23CC[C@]4(O2)O[C@@H](CC[C@@]4(C)O)CC(=C)CCCC2=NC[C@H](C)[C@@H](C)C[C@@]22CCC(C4OC(=O)C(C)=C4)=C(C)[C@@H]2\C=C(C)\[C@@H](O)C[C@H]1O3

> <INCHI_IDENTIFIER>
InChI=1/C43H63NO7/c1-25-10-9-11-38-41(22-28(4)30(6)24-44-38)15-13-33(37-20-27(3)39(46)48-37)31(7)34(41)19-26(2)35(45)21-36-29(5)23-42(50-36)16-17-43(51-42)40(8,47)14-12-32(18-25)49-43/h19-20,28-30,32,34-37,45,47H,1,9-18,21-24H2,2-8H3/b26-19+/t28-,29+,30-,32-,34-,35-,36+,37?,40+,41+,42-,43+/s2

> <INCHI_KEY>
BDNZANPABAQRBQ-YPVYZADFNA-N

> <FORMULA>
C43H63NO7

> <MOLECULAR_WEIGHT>
705.977

> <EXACT_MASS>
705.460453373

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
114

> <JCHEM_AVERAGE_POLARIZABILITY>
80.58489113082254

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(1R,4S,6R,7R,9S,10E,12S,17R,19S,20R,29S,32R)-9,32-dihydroxy-6,10,13,19,20,32-hexamethyl-27-methylidene-33,34,35-trioxa-22-azahexacyclo[27.3.1.1^{1,4}.1^{4,7}.0^{12,17}.0^{17,23}]pentatriaconta-10,13,22-trien-14-yl]-3-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
7.074737167935092

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.116798805601675

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.059462697501653

> <JCHEM_PKA_STRONGEST_BASIC>
8.243411748539389

> <JCHEM_POLAR_SURFACE_AREA>
106.81000000000002

> <JCHEM_REFRACTIVITY>
200.48280000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1R,4S,6R,7R,9S,10E,12S,17R,19S,20R,29S,32R)-9,32-dihydroxy-6,10,13,19,20,32-hexamethyl-27-methylidene-33,34,35-trioxa-22-azahexacyclo[27.3.1.1^{1,4}.1^{4,7}.0^{12,17}.0^{17,23}]pentatriaconta-10,13,22-trien-14-yl]-3-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -3.511   1.832   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.511   0.293   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.180  -0.477   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.850   0.293   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.850   1.832   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.180   2.599   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.396   0.929   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.879   1.339   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.480   2.753   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.746   4.102   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.230   4.369   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.927   3.348   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.410  -1.606   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.845  -0.477   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.188   5.853   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.644   5.352   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.166  -0.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.500   0.364   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.834  -0.405   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.922   0.682   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.541   1.524   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.524   2.171   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.586   0.387   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.251   0.146   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -7.283  -0.998   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.516  -2.332   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.012  -2.014   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.169  -0.213   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.982  -1.745   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.211  -2.676   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.627  -2.070   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.815  -0.539   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.648  -0.970   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.493  -1.993   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.109  -3.407   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.643  -3.253   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       7.024  -4.202   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.440  -3.600   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.076  -2.376   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.076  -3.915   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.259  -1.606   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -1.410  -4.685   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.180  -2.014   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -7.144  -3.738   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -8.815  -0.836   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       2.580  -3.571   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       2.262  -5.083   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       3.596  -5.853   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.735  -4.818   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.855  -5.711   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       3.596  -7.393   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4   43                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7   12                                             
CONECT    6    1    5                                                       
CONECT    7    5    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   15                                                  
CONECT   12    5   11                                                       
CONECT   13    4   39                                                       
CONECT   14    2   24   27                                                  
CONECT   15   11                                                            
CONECT   16   10                                                            
CONECT   17    7   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   23                                                       
CONECT   22   20                                                            
CONECT   23   21   28   32                                                  
CONECT   24   14   25                                                       
CONECT   25   24   26   45                                                  
CONECT   26   25   27   44                                                  
CONECT   27   14   26                                                       
CONECT   28   23   29                                                       
CONECT   29   28   30   33   36                                             
CONECT   30   29   31   37   38                                             
CONECT   31   30   32                                                       
CONECT   32   23   31                                                       
CONECT   33   29   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   46   49                                             
CONECT   36   29   35                                                       
CONECT   37   30                                                            
CONECT   38   30                                                            
CONECT   39   13   40   41                                                  
CONECT   40   39   42   50                                                  
CONECT   41   39                                                            
CONECT   42   40                                                            
CONECT   43    3                                                            
CONECT   44   26                                                            
CONECT   45   25                                                            
CONECT   46   35   47                                                       
CONECT   47   46   48   50                                                  
CONECT   48   47   49   51                                                  
CONECT   49   35   48                                                       
CONECT   50   40   47                                                       
CONECT   51   48                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  114    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₆₃NO₇

Average Mass

705.9770 Da

Monoisotopic Mass

705.46045 Da

IUPAC Name

5-[(1R,4S,6R,7R,9S,10E,12S,17R,19S,20R,29S,32R)-9,32-dihydroxy-6,10,13,19,20,32-hexamethyl-27-methylidene-33,34,35-trioxa-22-azahexacyclo[27.3.1.1^{1,4}.1^{4,7}.0^{12,17}.0^{17,23}]pentatriaconta-10,13,22-trien-14-yl]-3-methyl-2,5-dihydrofuran-2-one

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@]23CC[C@]4(O2)O[C@@H](CC[C@@]4(C)O)CC(=C)CCCC2=NC[C@H](C)[C@@H](C)C[C@@]22CCC(C4OC(=O)C(C)=C4)=C(C)[C@@H]2\C=C(C)\[C@@H](O)C[C@H]1O3

InChI Identifier

InChI=1/C43H63NO7/c1-25-10-9-11-38-41(22-28(4)30(6)24-44-38)15-13-33(37-20-27(3)39(46)48-37)31(7)34(41)19-26(2)35(45)21-36-29(5)23-42(50-36)16-17-43(51-42)40(8,47)14-12-32(18-25)49-43/h19-20,28-30,32,34-37,45,47H,1,9-18,21-24H2,2-8H3/b26-19+/t28-,29+,30-,32-,34-,35-,36+,37?,40+,41+,42-,43+/s2

InChI Key

BDNZANPABAQRBQ-YPVYZADFNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azepines

Sub Class

Not Available

Direct Parent

Azepines

Alternative Parents

Substituents

Azepine
Ketal
2-furanone
Oxane
Dihydrofuran
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketimine
Lactone
Secondary alcohol
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Hydrocarbon derivative
Alcohol
Imine
Organopnictogen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Organic nitrogen compound
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	7.07	ChemAxon
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	8.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.81 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	200.48 m³·mol⁻¹	ChemAxon
Polarizability	80.58 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shang L, Xu Y, Leaw CP, Lim PT, Wang J, Chen J, Deng Y, Hu Z, Tang YZ: Potent allelopathy and non-PSTs, non-spirolides toxicity of the dinoflagellate Alexandrium leei to phytoplankton, finfish and zooplankton observed from laboratory bioassays. Sci Total Environ. 2021 Aug 1;780:146484. doi: 10.1016/j.scitotenv.2021.146484. Epub 2021 Mar 17. [PubMed:33774286 ]
Lamas JP, Arevalo F, Morono A, Correa J, Rossignoli AE, Blanco J: Gymnodimine A in mollusks from the north Atlantic Coast of Spain: Prevalence, concentration, and relationship with spirolides. Environ Pollut. 2021 Jun 15;279:116919. doi: 10.1016/j.envpol.2021.116919. Epub 2021 Mar 11. [PubMed:33744630 ]
Varriale F, Tartaglione L, Cinti S, Milandri A, Dall'Ara S, Calfapietra A, Dell'Aversano C: Development of a data dependent acquisition-based approach for the identification of unknown fast-acting toxins and their ester metabolites. Talanta. 2021 Mar 1;224:121842. doi: 10.1016/j.talanta.2020.121842. Epub 2020 Nov 5. [PubMed:33379060 ]
Tang J, He X, Chen J, Cao W, Han T, Xu Q, Sun C: Occurrence and distribution of phycotoxins in the Antarctic Ocean. Mar Pollut Bull. 2024 Apr;201:116250. doi: 10.1016/j.marpolbul.2024.116250. Epub 2024 Mar 13. [PubMed:38479322 ]
Rossignoli AE, Ben-Gigirey B, Cid M, Marino C, Martin H, Garrido S, Rodriguez F, Blanco J: Lipophilic Shellfish Poisoning Toxins in Marine Invertebrates from the Galician Coast. Toxins (Basel). 2023 Oct 27;15(11):631. doi: 10.3390/toxins15110631. [PubMed:37999494 ]
Sheng C, He X, Shen N, Han T, Chen J, Liu C, Li X: Occurrence and phase distribution of lipophilic marine algal toxins in the bottom boundary layer and sediment-porewater system of two mariculture sites. Chemosphere. 2023 Nov;341:140109. doi: 10.1016/j.chemosphere.2023.140109. Epub 2023 Sep 7. [PubMed:37689146 ]
Blanco J, Arevalo F, Morono A, Correa J, Rossignoli AE, Lamas JP: Spirolides in Bivalve Mollusk of the Galician (NW Spain) Coast: Interspecific, Spatial, Temporal Variation and Presence of an Isomer of 13-Desmethyl Spirolide C. Toxins (Basel). 2022 Dec 24;15(1):13. doi: 10.3390/toxins15010013. [PubMed:36668833 ]
Wang J, Li R, Liu B, Zhang Q, Wang X, Zhu Y, Zhang Y: Occurrence and distribution of lipophilic marine algal toxins in the coastal seawater of Southeast China and the South China Sea. Mar Pollut Bull. 2023 Feb;187:114584. doi: 10.1016/j.marpolbul.2023.114584. Epub 2023 Jan 13. [PubMed:36642003 ]
Earl ADW, Li FF, Ma C, Furkert DP, Brimble MA: Stereoselective synthesis of the spirocyclic core of 13-desmethyl spirolide C using an aza-Claisen rearrangement and an exo-selective Diels-Alder cycloaddition. Org Biomol Chem. 2023 Feb 8;21(6):1222-1234. doi: 10.1039/d2ob01992b. [PubMed:36633001 ]
Rossignoli AE, Lamas JP, Marino C, Martin H, Blanco J: Enzymatic Biotransformation of 13-desmethyl Spirolide C by Two Infaunal Mollusk Species: The Limpet Patella vulgata and the Cockle Cerastoderma edule. Toxins (Basel). 2022 Dec 2;14(12):848. doi: 10.3390/toxins14120848. [PubMed:36548745 ]
Nieva JA, Krock B, Tillmann U, Tebben J, Zurhelle C, Bickmeyer U: Gymnodimine A and 13-desMethyl Spirolide C Alter Intracellular Calcium Levels via Acetylcholine Receptors. Toxins (Basel). 2020 Nov 27;12(12):751. doi: 10.3390/toxins12120751. [PubMed:33261221 ]
Otero P, Vale C, Boente-Juncal A, Costas C, Louzao MC, Botana LM: Detection of Cyclic Imine Toxins in Dietary Supplements of Green Lipped Mussels (Perna canaliculus) and in Shellfish Mytilus chilensis. Toxins (Basel). 2020 Sep 24;12(10):613. doi: 10.3390/toxins12100613. [PubMed:32987858 ]
Bacchiocchi S, Siracusa M, Campacci D, Ciriaci M, Dubbini A, Tavoloni T, Stramenga A, Gorbi S, Piersanti A: Cyclic Imines (CIs) in Mussels from North-Central Adriatic Sea: First Evidence of Gymnodimine A in Italy. Toxins (Basel). 2020 Jun 4;12(6):370. doi: 10.3390/toxins12060370. [PubMed:32512714 ]
Liu Y, Zhang P, Du S, Lin Z, Zhou Y, Chen L, Yu R, Zhang L: Occurrence and distribution of lipophilic phycotoxins in a subtropical bay of the South China Sea. Chemosphere. 2020 Mar;243:125352. doi: 10.1016/j.chemosphere.2019.125352. Epub 2019 Nov 14. [PubMed:31759209 ]

Showing NP-Card for Spirolide C (NP0335815)

MOL for NP0335815 (Spirolide C)

3D MOL for NP0335815 (Spirolide C)

3D SDF for NP0335815 (Spirolide C)

3D-SDF for NP0335815 (Spirolide C)

PDB for NP0335815 (Spirolide C)

3D PDB for NP0335815 (Spirolide C)

SMILES for NP0335815 (Spirolide C)

INCHI for NP0335815 (Spirolide C)

Structure for NP0335815 (Spirolide C)

3D Structure for NP0335815 (Spirolide C)