NP-MRD: Showing NP-Card for (-)-Erythrolide K (NP0080252)

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Record Information

Version

2.0

Created at

2022-04-29 01:18:09 UTC

Updated at

2022-04-29 01:18:09 UTC

NP-MRD ID

NP0080252

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Erythrolide K

Description

(3S,4R,7R,8S,10S,12Z,16S)-10-(acetyloxy)-8-chloro-3-hydroxy-4,16,17-trimethyl-9-methylidene-5,15-dioxo-6-oxatricyclo[12.2.1.0³,⁷]Heptadeca-1,12,14(17)-trien-16-yl acetate 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. (-)-Erythrolide K is found in Erythropodium caribaeorum. Based on a literature review very few articles have been published on (3S,4R,7R,8S,10S,12Z,16S)-10-(acetyloxy)-8-chloro-3-hydroxy-4,16,17-trimethyl-9-methylidene-5,15-dioxo-6-oxatricyclo[12.2.1.0³,⁷]Heptadeca-1,12,14(17)-trien-16-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203182D          

 33 35  0  0  1  0            999 V2000
    2.0071   -0.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -0.8459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4490   -0.0973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2985   -0.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296    0.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262   -0.2823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6919   -1.1066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3027   -1.6275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3542   -2.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0509   -2.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6232   -2.7552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9265   -2.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955   -2.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988   -2.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332   -1.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2642   -1.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9609   -1.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -3.5795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2855   -4.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2511   -4.8457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165   -3.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1196   -1.1661    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4652   -1.3940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9775   -0.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8018   -0.7817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5208   -0.0603    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8082    0.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8466    0.5338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875    0.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5080    0.7256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2501    1.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091    1.9089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9333    0.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  2  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 22  1  1  0  0  0
  7 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  1  0  0  0
  6 28  1  1  0  0  0
  3 29  1  6  0  0  0
  3 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -4.0239    0.9628   -1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8905    0.4487   -0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0436   -0.7741    0.0739 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5858   -1.8579   -0.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8305   -2.3992   -0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2157   -3.5562   -1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5580   -1.8868    0.4351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8540   -1.0975    0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -2.4711    0.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0412   -2.6245    1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9304   -1.6111    1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0007   -0.2823    1.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5105    0.4002    3.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7480    0.0859    0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182    0.8302   -0.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5534    1.9316   -0.3550 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6064    2.5950   -1.6147 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873    3.0959    0.5504 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0827    3.9223   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415    3.9320    0.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4192    5.0703    1.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1908    3.2966   -0.3225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8960    1.8831   -0.1152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5974    1.0556   -1.1371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5558   -0.1388   -1.9502 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0828   -0.7022    0.6466 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9994   -0.1199    1.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7128   -0.8671   -0.5506 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757   -1.5313   -1.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1129   -1.5979   -2.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1440   -2.0763   -1.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3904   -1.9610    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0031   -3.0337    1.2108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9634    0.5261   -0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0007    1.8398   -1.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8486   -0.4693    0.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6125   -4.4276   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0264   -3.3897   -2.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2715   -3.8031   -1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0729   -0.5118    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0364   -0.9275    1.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529   -3.2331    0.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1617   -3.7090    1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5247    0.7897    2.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5261   -0.1874    3.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796    1.3040    3.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8575    0.5922   -1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5023    2.4899   -2.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2576    2.8135    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6236    4.5382   -0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    4.6247    0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8725    3.2563   -0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2527    1.7969    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8144    1.7814   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8396    0.9908    1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8070   -0.5445    2.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0391   -0.3513    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7756   -2.4920   -2.9196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -1.5014   -3.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7940   -0.7173   -2.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24  2  1  0
  2  1  2  3
  2  3  1  0
  3  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  6
 14 26  1  0
 26 27  1  0
 26 28  1  6
 28 29  1  0
 29 30  1  0
 29 31  2  0
 26 32  1  0
 32 33  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
 16 18  1  0
 16 23  1  0
 32 11  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 18 49  1  1
 23 53  1  1
 24 54  1  6
  1 34  1  0
  1 35  1  0
  3 36  1  1
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 15 47  1  0
 17 48  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 30 58  1  0
 30 59  1  0
 30 60  1  0
  6 37  1  0
  6 38  1  0
  6 39  1  0
M  END


  Mrv1652304292203182D          

 33 35  0  0  1  0            999 V2000
    2.0071   -0.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -0.8459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4490   -0.0973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2985   -0.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296    0.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262   -0.2823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6919   -1.1066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3027   -1.6275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3542   -2.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0509   -2.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6232   -2.7552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9265   -2.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955   -2.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988   -2.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332   -1.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2642   -1.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9609   -1.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -3.5795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2855   -4.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2511   -4.8457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165   -3.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1196   -1.1661    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4652   -1.3940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9775   -0.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8018   -0.7817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5208   -0.0603    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8082    0.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8466    0.5338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875    0.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5080    0.7256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2501    1.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091    1.9089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9333    0.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  2  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 22  1  1  0  0  0
  7 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  1  0  0  0
  6 28  1  1  0  0  0
  3 29  1  6  0  0  0
  3 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080252

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@H](C\C=C/C3=C(C)/C(=C\[C@]12O)/[C@](C)(OC(C)=O)C3=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H27ClO8/c1-11-16-8-7-9-18(31-14(4)26)12(2)19(25)21-24(30,13(3)22(29)32-21)10-17(11)23(6,20(16)28)33-15(5)27/h7-8,10,13,18-19,21,30H,2,9H2,1,3-6H3/b8-7-,17-10+/t13-,18-,19-,21-,23-,24-/m0/s1

> <INCHI_KEY>
IQMWVLDTBJYWTA-ZHMHLXBNSA-N

> <FORMULA>
C24H27ClO8

> <MOLECULAR_WEIGHT>
478.92

> <EXACT_MASS>
478.1394455

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.59199449447074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R,7R,8S,10S,12Z,16S)-10-(acetyloxy)-8-chloro-3-hydroxy-4,16,17-trimethyl-9-methylidene-5,15-dioxo-6-oxatricyclo[12.2.1.0^{3,7}]heptadeca-1,12,14(17)-trien-16-yl acetate

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.132657221666666

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.86524299884708

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7325427123042862

> <JCHEM_POLAR_SURFACE_AREA>
116.20000000000002

> <JCHEM_REFRACTIVITY>
119.38629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R,7R,8S,10S,12Z,16S)-10-(acetyloxy)-8-chloro-3-hydroxy-4,16,17-trimethyl-9-methylidene-5,15-dioxo-6-oxatricyclo[12.2.1.0^{3,7}]heptadeca-1,12,14(17)-trien-16-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       3.747  -1.482   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.210  -1.579   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.572  -0.182   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.157  -0.416   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.522   0.298   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.822  -0.527   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.758  -2.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.898  -3.038   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.994  -4.429   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.295  -5.254   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.630  -5.143   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.329  -4.318   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.965  -5.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.664  -4.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.729  -2.668   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.093  -1.955   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.394  -2.779   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.566  -6.682   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.866  -7.507   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.802  -9.045   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.231  -6.793   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0      11.423  -2.177   0.000  0.00  0.00          Cl+0
HETATM   23  O   UNK     0      10.202  -2.602   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.158  -1.395   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.697  -1.459   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.306  -0.113   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.842   1.331   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.047   0.996   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.337   0.739   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.682   1.354   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.067   2.027   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.177   3.563   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.342   1.164   0.000  0.00  0.00           C+0
CONECT    1    2    3   15                                                  
CONECT    2    1                                                            
CONECT    3    1    4   29   30                                             
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   26   28                                             
CONECT    7    6    8   23                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    1   16                                                  
CONECT   16   15    4   17                                                  
CONECT   17   16                                                            
CONECT   18   11   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    8                                                            
CONECT   23    7   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    6   27                                                  
CONECT   27   26                                                            
CONECT   28    6                                                            
CONECT   29    3                                                            
CONECT   30    3   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
(3S,4R,7R,8S,10S,12Z,16S)-10-(Acetyloxy)-8-chloro-3-hydroxy-4,16,17-trimethyl-9-methylidene-5,15-dioxo-6-oxatricyclo[12.2.1.0,]heptadeca-1,12,14(17)-trien-16-yl acetic acid	Generator

Chemical Formula

C₂₄H₂₇ClO₈

Average Mass

478.9200 Da

Monoisotopic Mass

478.13945 Da

IUPAC Name

(3S,4R,7R,8S,10S,12Z,16S)-10-(acetyloxy)-8-chloro-3-hydroxy-4,16,17-trimethyl-9-methylidene-5,15-dioxo-6-oxatricyclo[12.2.1.0^{3,7}]heptadeca-1,12,14(17)-trien-16-yl acetate

Traditional Name

(3S,4R,7R,8S,10S,12Z,16S)-10-(acetyloxy)-8-chloro-3-hydroxy-4,16,17-trimethyl-9-methylidene-5,15-dioxo-6-oxatricyclo[12.2.1.0^{3,7}]heptadeca-1,12,14(17)-trien-16-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@H](C\C=C/C3=C(C)/C(=C\[C@]12O)/[C@](C)(OC(C)=O)C3=O)OC(C)=O

InChI Identifier

InChI=1S/C24H27ClO8/c1-11-16-8-7-9-18(31-14(4)26)12(2)19(25)21-24(30,13(3)22(29)32-21)10-17(11)23(6,20(16)28)33-15(5)27/h7-8,10,13,18-19,21,30H,2,9H2,1,3-6H3/b8-7-,17-10+/t13-,18-,19-,21-,23-,24-/m0/s1

InChI Key

IQMWVLDTBJYWTA-ZHMHLXBNSA-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
Erythropodium caribaeorum	-	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
Tricarboxylic acid or derivatives
Alpha-acyloxy ketone
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Alkyl halide
Organohalogen compound
Organochloride
Organooxygen 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	2.51	ALOGPS
logP	2.13	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	119.39 m³·mol⁻¹	ChemAxon
Polarizability	46.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

10477153

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21774957

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Erythrolide K (NP0080252)

MOL for NP0080252 ((-)-Erythrolide K)

3D MOL for NP0080252 ((-)-Erythrolide K)

3D SDF for NP0080252 ((-)-Erythrolide K)

3D-SDF for NP0080252 ((-)-Erythrolide K)

PDB for NP0080252 ((-)-Erythrolide K)

3D PDB for NP0080252 ((-)-Erythrolide K)

SMILES for NP0080252 ((-)-Erythrolide K)

INCHI for NP0080252 ((-)-Erythrolide K)

Structure for NP0080252 ((-)-Erythrolide K)

3D Structure for NP0080252 ((-)-Erythrolide K)