NP-MRD: Showing NP-Card for Lophotoxin (NP0076796)

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Record Information

Version

1.0

Created at

2022-04-28 21:59:17 UTC

Updated at

2022-04-28 21:59:17 UTC

NP-MRD ID

NP0076796

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lophotoxin

Description

Lophotoxin belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Lophotoxin is found in Leptogorgia alba, Leptogorgia laxa, Leptogorgia violacea, Lophogorgia peruana and Lophogorgia violacea. It was first documented in 2002 (PMID: 12000299). Based on a literature review a significant number of articles have been published on Lophotoxin (PMID: 18698819) (PMID: 17190454) (PMID: 16032357) (PMID: 15844963).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223592D          

 30 34  0  0  1  0            999 V2000
    3.1744   -0.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256   -0.8313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4824   -1.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2605   -0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9994   -0.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0514   -1.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -0.4878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2336   -2.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4280   -2.4045    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8712   -1.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0656   -1.9735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5088   -1.3647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7232   -0.5681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4020    0.2581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3450   -0.3386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909   -1.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9250   -1.6895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0108    0.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7284    0.4079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5410    0.5506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0112    1.1830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4436    1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739   -0.7807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8168   -2.7601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112   -2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2376   -3.7245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456   -2.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -3.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7360   -3.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3736   -3.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  3  8  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  1  0  0  0
 19 21  1  0  0  0  0
 19 22  1  6  0  0  0
 13 23  1  1  0  0  0
 12 23  1  1  0  0  0
 11 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  9 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
   -2.2730   -2.5406   -2.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4336   -1.8801   -1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6631   -2.0926   -0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4331   -0.8750   -0.5930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9932   -1.3726    0.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -2.0052    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2244   -1.2755   -0.1123 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3386   -1.9119   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2147   -3.1351    0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9303   -3.1875    0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2963   -4.2719    1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8691   -4.2433    2.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4622   -1.2512   -0.9367 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6018   -1.1132   -0.0991 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8408    0.0269   -0.5465 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6586    0.9073   -1.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1359    0.7390    0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2831    1.8400   -0.0122 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8968    1.6171   -1.3332 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5191    1.6500   -1.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0702    1.5390   -2.5905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0516    1.8340   -0.1657 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3081    3.1841    0.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9547    1.9555    0.7511 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4531    1.5310    0.1727 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2360    2.7086   -0.0875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9347    3.3744    0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7079    4.5824    0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8921    2.9371    2.0559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1029    0.4480   -0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0143   -3.2468   -2.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942   -2.3909   -2.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5761   -1.8617   -0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7342   -3.1718    0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6802   -1.4351    0.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6114   -0.8513   -1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   -2.1793    1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9466   -0.5906    1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9582   -3.9134    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -5.1737    1.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6107   -1.6301   -1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0089    1.2605   -2.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5840    0.4183   -1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    1.8102   -0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    1.2258    1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5742    0.0682    1.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7745    2.8281    0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9870    1.8807    1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666    1.3368    1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4257    4.3672   -0.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0275    5.3825    0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2711    5.0253    1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866    0.7827   -1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1495    0.3398   -0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 29  2  0
 27 26  1  0
 26 25  1  0
 25 30  1  0
 30  4  1  0
  4  5  1  0
  5  6  1  0
  6 10  2  0
 10 11  1  0
 11 12  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  6
 23 24  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 22 25  1  0
 24 22  1  0
  7  6  1  0
 15 13  1  0
 24 18  1  0
 28 50  1  0
 28 51  1  0
 28 52  1  0
 25 49  1  1
 30 53  1  0
 30 54  1  0
  4 36  1  6
  5 37  1  0
  5 38  1  0
 11 40  1  0
  9 39  1  0
 13 41  1  6
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  6
 24 48  1  1
  3 33  1  0
  3 34  1  0
  3 35  1  0
  1 31  1  0
  1 32  1  0
M  END


  Mrv1652304282223592D          

 30 34  0  0  1  0            999 V2000
    3.1744   -0.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256   -0.8313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4824   -1.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2605   -0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9994   -0.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0514   -1.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -0.4878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2336   -2.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4280   -2.4045    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8712   -1.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0656   -1.9735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5088   -1.3647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7232   -0.5681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4020    0.2581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3450   -0.3386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909   -1.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9250   -1.6895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0108    0.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7284    0.4079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5410    0.5506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0112    1.1830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4436    1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739   -0.7807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8168   -2.7601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112   -2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2376   -3.7245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456   -2.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -3.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7360   -3.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3736   -3.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  3  8  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  1  0  0  0
 19 21  1  0  0  0  0
 19 22  1  6  0  0  0
 13 23  1  1  0  0  0
 12 23  1  1  0  0  0
 11 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  9 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076796

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@H](CC2=C(C=O)C=C(O2)[C@@H]2O[C@]2(C)C[C@H]2OC(=O)[C@@]11O[C@H]21)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O8/c1-10(2)12-5-14-13(9-23)6-15(27-14)18-21(4,29-18)8-16-19-22(30-19,20(25)28-16)17(7-12)26-11(3)24/h6,9,12,16-19H,1,5,7-8H2,2-4H3/t12-,16-,17+,18+,19-,21-,22-/m1/s1

> <INCHI_KEY>
KGRIGHVGXOOCOY-ALYDTWDZSA-N

> <FORMULA>
C22H24O8

> <MOLECULAR_WEIGHT>
416.426

> <EXACT_MASS>
416.147117733

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.993693089916405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4S,10R,12R,14R,15R)-7-formyl-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-dien-2-yl acetate

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
1.726488488333333

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.971423550880505

> <JCHEM_POLAR_SURFACE_AREA>
107.87

> <JCHEM_REFRACTIVITY>
101.6174

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,10R,12R,14R,15R)-7-formyl-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-dien-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.926  -0.083   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.461  -1.552   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.501  -2.688   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.953  -1.532   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.466  -0.071   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.429  -1.970   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.547  -0.911   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.036  -4.156   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.532  -4.488   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.493  -3.352   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.989  -3.684   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.950  -2.547   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.350  -1.060   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.750   0.482   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.644  -0.632   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.543  -2.169   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.727  -3.154   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.887   1.521   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.226   0.762   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.743   1.028   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.754   2.208   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.695   2.207   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.138  -1.457   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.525  -5.152   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.021  -5.484   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.444  -6.952   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.019  -4.348   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.068  -5.957   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.107  -7.093   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.564  -6.289   0.000  0.00  0.00           C+0
CONECT    1    2    5   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13   16   23                                             
CONECT   13   12   14   23                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19    1   21                                                  
CONECT   21   20   19                                                       
CONECT   22   19                                                            
CONECT   23   13   12                                                       
CONECT   24   11   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    9   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₈

Average Mass

416.4260 Da

Monoisotopic Mass

416.14712 Da

IUPAC Name

(1R,2S,4S,10R,12R,14R,15R)-7-formyl-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-dien-2-yl acetate

Traditional Name

(1R,2S,4S,10R,12R,14R,15R)-7-formyl-12-methyl-17-oxo-4-(prop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.1^{6,9}.0^{1,15}.0^{10,12}]nonadeca-6,8-dien-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@H](CC2=C(C=O)C=C(O2)[C@@H]2O[C@]2(C)C[C@H]2OC(=O)[C@@]11O[C@H]21)C(C)=C

InChI Identifier

InChI=1S/C22H24O8/c1-10(2)12-5-14-13(9-23)6-15(27-14)18-21(4,29-18)8-16-19-22(30-19,20(25)28-16)17(7-12)26-11(3)24/h6,9,12,16-19H,1,5,7-8H2,2-4H3/t12-,16-,17+,18+,19-,21-,22-/m1/s1

InChI Key

KGRIGHVGXOOCOY-ALYDTWDZSA-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
Leptogorgia alba	-	KNApSAcK
Leptogorgia laxa	-	KNApSAcK
Leptogorgia violacea	LOTUS Database	35616633
Lophogorgia peruana	-	KNApSAcK
Lophogorgia violacea	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Aryl-aldehyde
Para-dioxane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Heteroaromatic compound
Tetrahydrofuran
Furan
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Carbonyl group
Aldehyde
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.24	ALOGPS
logP	1.73	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	107.87 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.62 m³·mol⁻¹	ChemAxon
Polarizability	40.99 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039655

Chemspider ID

21256774

KEGG Compound ID

C13680

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108179

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ortega MJ, Zubia E, Sanchez MC, Carballo JL: Cembrane diterpenes from the gorgonian Leptogorgia laxa. J Nat Prod. 2008 Sep;71(9):1637-9. doi: 10.1021/np8002639. Epub 2008 Aug 13. [PubMed:18698819 ]
Sanchez MC, Ortega MJ, Zubia E, Carballo JL: Cembrane diterpenes from the gorgonian Lophogorgia peruana. J Nat Prod. 2006 Dec;69(12):1749-55. doi: 10.1021/np060388x. [PubMed:17190454 ]
Cases M, Gonzalez-Lopez de Turiso F, Hadjisoteriou MS, Pattenden G: Synthetic studies towards furanocembrane diterpenes. A total synthesis of bis-deoxylophotoxin. Org Biomol Chem. 2005 Aug 7;3(15):2786-804. doi: 10.1039/b504545b. Epub 2005 Jun 28. [PubMed:16032357 ]
Gutierrez M, Capson TL, Guzman HM, Gonzalez J, Ortega-Barria E, Quinoa E, Riguera R: Leptolide, a new furanocembranolide diterpene from Leptogorgia alba. J Nat Prod. 2005 Apr;68(4):614-6. doi: 10.1021/np049745z. [PubMed:15844963 ]
Wipf P, Soth MJ: Synthesis of the C(1)-C(18) segment of lophotoxin and pukalide. Control of 2-alkenylfuran (E/Z)-configuration. Org Lett. 2002 May 16;4(10):1787-90. doi: 10.1021/ol025861m. [PubMed:12000299 ]

Showing NP-Card for Lophotoxin (NP0076796)

MOL for NP0076796 (Lophotoxin)

3D MOL for NP0076796 (Lophotoxin)

3D SDF for NP0076796 (Lophotoxin)

3D-SDF for NP0076796 (Lophotoxin)

PDB for NP0076796 (Lophotoxin)

3D PDB for NP0076796 (Lophotoxin)

SMILES for NP0076796 (Lophotoxin)

INCHI for NP0076796 (Lophotoxin)

Structure for NP0076796 (Lophotoxin)

3D Structure for NP0076796 (Lophotoxin)