NP-MRD: Showing NP-Card for (+)-Excavatolide A (NP0080601)

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Record Information

Version

2.0

Created at

2022-04-29 01:36:32 UTC

Updated at

2022-04-29 01:36:32 UTC

NP-MRD ID

NP0080601

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Excavatolide A

Description

(1R,2S,3S,7S,8R,9S,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]Octadec-4-en-9-yl acetate belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (+)-Excavatolide A is found in Braiareum stechei, Briareum excavatum and Briareum stechei. Based on a literature review very few articles have been published on (1R,2S,3S,7S,8R,9S,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]Octadec-4-en-9-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203362D          

 33 36  0  0  1  0            999 V2000
    5.5801    1.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120    1.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2897    1.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9354    1.1618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4035    0.4825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2259    0.5482    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6940   -0.1311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5163   -0.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9845   -0.7448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8706    0.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2363   -0.3525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5209   -0.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790   -0.6333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8473   -0.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6425   -1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2313   -0.2697    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4801    0.5531    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3071    0.8591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0911    1.2932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9470    2.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1253    1.7035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3088    1.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    2.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9038    1.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7054    2.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5392    0.1428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346   -0.4836    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -1.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5294   -2.1110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1050   -1.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9515   -0.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8216    2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 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  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 17 24  1  6  0  0  0
 21 25  1  6  0  0  0
 18 26  1  6  0  0  0
 13 26  1  1  0  0  0
 16 27  1  6  0  0  0
 11 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  5 32  1  1  0  0  0
  3 33  1  0  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
   -2.8694   -0.2069    3.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5719   -0.0175    2.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1706   -0.1459    1.7070 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.9089    2.7624    0.7731 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144    3.3585    1.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9353    0.8892   -0.6130 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6566    2.0289   -1.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713    0.7496   -0.6128 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7420   -0.5182   -0.0484 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5690   -0.7457    1.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826   -2.1347    1.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1483    0.2129    1.5584 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9724    0.6786   -2.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3688   -0.5705   -2.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2157   -1.0367   -2.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6338   -2.3141   -2.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3984   -0.4073   -1.0561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0542   -0.3824   -1.4723 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4803    0.8327   -1.9701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9676   -0.8965   -0.3518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1882   -1.0933    0.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5477   -2.2742   -0.7235 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9517   -3.3710    0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9958   -2.1488   -0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8049   -3.0533   -0.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3016   -0.8195   -0.7155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1845   -0.0665   -0.2084 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5749    0.3338    1.1823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1524   -0.2999    1.6839 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7937    1.8468    2.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3008    0.9157    1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958    5.3013    1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4348    5.2690    2.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5811    5.0525    0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137    2.6505   -1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5190    2.7585   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873    1.6929   -2.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743    1.5853   -0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6436   -2.6201    0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9061   -2.7770    1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9451   -2.1662    2.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0703    0.4775   -1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638    1.5671   -2.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453   -1.1493   -3.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422   -2.8455   -1.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5025   -2.9326   -3.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0135   -2.1396   -3.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4993   -1.1133   -0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1710   -1.1051   -2.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3008   -2.4199   -1.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6473    1.4614    1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 28  1  0
 28 29  2  0
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 31 32  1  0
 32 33  1  0
 32  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
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 10 12  1  0
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 17 18  1  0
 18 19  2  0
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 22 24  1  0
 24 25  1  1
 12 13  1  0
 13 14  1  0
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 14 16  2  0
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 24 31  1  0
 25  3  1  0
 21 10  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 26 59  1  6
 31 63  1  6
 32 64  1  6
  1 34  1  0
  1 35  1  0
  3 36  1  1
  4 37  1  0
  4 38  1  0
  5 39  1  1
  8 40  1  0
  8 41  1  0
  8 42  1  0
 11 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  1
 17 50  1  0
 17 51  1  0
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  1
 22 57  1  6
 23 58  1  0
 15 47  1  0
 15 48  1  0
 15 49  1  0
M  END


  Mrv1652304292203362D          

 33 36  0  0  1  0            999 V2000
    5.5801    1.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120    1.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2897    1.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9354    1.1618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4035    0.4825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2259    0.5482    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6940   -0.1311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5163   -0.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9845   -0.7448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8706    0.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2363   -0.3525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5209   -0.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790   -0.6333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8473   -0.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6425   -1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2313   -0.2697    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4801    0.5531    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3071    0.8591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0911    1.2932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9470    2.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1253    1.7035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3088    1.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    2.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9038    1.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7054    2.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5392    0.1428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346   -0.4836    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -1.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5294   -2.1110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1050   -1.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9515   -0.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8216    2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 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  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 17 24  1  6  0  0  0
 21 25  1  6  0  0  0
 18 26  1  6  0  0  0
 13 26  1  1  0  0  0
 16 27  1  6  0  0  0
 11 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  5 32  1  1  0  0  0
  3 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080601

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@@H]3C[C@H](OC(C)=O)[C@@]4(C)[C@H](CC=C(C)[C@@H]4[C@H](O)[C@]12O3)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H31ClO8/c1-10-7-8-16(30-13(4)26)23(6)17(31-14(5)27)9-15-11(2)19(25)21-24(33-15,20(28)18(10)23)12(3)22(29)32-21/h7,12,15-21,28H,2,8-9H2,1,3-6H3/t12-,15-,16-,17-,18+,19-,20-,21-,23+,24+/m0/s1

> <INCHI_KEY>
KCKRPJJFBBQDGW-VAYLNUNKSA-N

> <FORMULA>
C24H31ClO8

> <MOLECULAR_WEIGHT>
482.95

> <EXACT_MASS>
482.1707457

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.38136703202125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,7S,8R,9S,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadec-4-en-9-yl acetate

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
1.6679693356666672

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.575745921432969

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4217687339652185

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
116.3325

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,7S,8R,9S,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadec-4-en-9-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      10.416   2.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.542   3.682   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.007   3.560   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.346   2.169   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.220   0.901   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.755   1.023   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.629  -0.245   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.164  -0.122   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.038  -1.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.825   1.269   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908  -0.658   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.572  -1.499   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.001  -1.182   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.448  -1.580   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.066  -3.072   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.299  -0.503   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.763   1.032   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.307   1.604   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.770   2.414   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.501   3.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.967   3.180   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.443   3.490   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.804   4.892   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.687   2.151   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.050   4.275   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.740   0.267   0.000  0.00  0.00           O+0
HETATM   27 Cl   UNK     0       0.811  -0.903   0.000  0.00  0.00          Cl+0
HETATM   28  O   UNK     0       9.176  -1.532   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.053  -3.067   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.322  -3.940   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.663  -3.728   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.243  -0.251   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.134   4.828   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6   11   32                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   27                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19   21   26                                             
CONECT   19   18    4   20                                                  
CONECT   20   19                                                            
CONECT   21   18   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17                                                       
CONECT   25   21                                                            
CONECT   26   18   13                                                       
CONECT   27   16                                                            
CONECT   28   11   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    5                                                            
CONECT   33    3                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3S,7S,8R,9S,11S,13S,14R,17R)-7-(Acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0,.0,]octadec-4-en-9-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₁ClO₈

Average Mass

482.9500 Da

Monoisotopic Mass

482.17075 Da

IUPAC Name

(1R,2S,3S,7S,8R,9S,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadec-4-en-9-yl acetate

Traditional Name

(1R,2S,3S,7S,8R,9S,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadec-4-en-9-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@@H]3C[C@H](OC(C)=O)[C@@]4(C)[C@H](CC=C(C)[C@@H]4[C@H](O)[C@]12O3)OC(C)=O

InChI Identifier

InChI=1S/C24H31ClO8/c1-10-7-8-16(30-13(4)26)23(6)17(31-14(5)27)9-15-11(2)19(25)21-24(33-15,20(28)18(10)23)12(3)22(29)32-21/h7,12,15-21,28H,2,8-9H2,1,3-6H3/t12-,15-,16-,17-,18+,19-,20-,21-,23+,24+/m0/s1

InChI Key

KCKRPJJFBBQDGW-VAYLNUNKSA-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
Braiareum stechei	-	KNApSAcK
Briareum excavatum	-	KNApSAcK
Briareum stechei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Furopyran
Pyran
Oxane
Gamma butyrolactone
Tetrahydrofuran
Furan
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Alcohol
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	2.62	ALOGPS
logP	1.67	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.58	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.33 m³·mol⁻¹	ChemAxon
Polarizability	48.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162929039

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Excavatolide A (NP0080601)

MOL for NP0080601 ((+)-Excavatolide A)

3D MOL for NP0080601 ((+)-Excavatolide A)

3D SDF for NP0080601 ((+)-Excavatolide A)

3D-SDF for NP0080601 ((+)-Excavatolide A)

PDB for NP0080601 ((+)-Excavatolide A)

3D PDB for NP0080601 ((+)-Excavatolide A)

SMILES for NP0080601 ((+)-Excavatolide A)

INCHI for NP0080601 ((+)-Excavatolide A)

Structure for NP0080601 ((+)-Excavatolide A)

3D Structure for NP0080601 ((+)-Excavatolide A)