NP-MRD: Showing NP-Card for xestospongiene A/B (NP0040182)

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Record Information

Version

2.0

Created at

2021-06-20 22:25:01 UTC

Updated at

2021-06-30 00:13:57 UTC

NP-MRD ID

NP0040182

Secondary Accession Numbers

None

Natural Product Identification

Common Name

xestospongiene A/B

Provided By

JEOL Database JEOL Logo

Description

(5S)-5-[(1E,3S)-10,10-dibromo-3-hydroxydeca-1,9-dien-1-yl]oxolan-2-one belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. xestospongiene A/B is found in Xestospongia testudinaria. xestospongiene A/B was first documented in 2011 (Jiang, W., et al.). Based on a literature review very few articles have been published on (5S)-5-[(1E,3S)-10,10-dibromo-3-hydroxydeca-1,9-dien-1-yl]oxolan-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100253D          

 39 39  0  0  0  0            999 V2000
    3.9564    1.7971   -0.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1947    2.7429   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615    3.3485   -1.5299 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1749    4.6633   -1.0757 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6545    4.3407    0.3115 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2875    3.7280    0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    3.5061   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9491    2.8501   -0.2797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9324    3.7657   -0.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030    1.5252   -1.0389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0504    0.4555   -0.7274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0231    0.0367    0.7438 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0033   -1.0759    0.9833 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1511   -1.4431    2.4635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0855   -2.0850    3.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9201   -1.5870    3.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7363    0.0946    4.7538 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4111   -2.5781    4.5209 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    3.3823    0.8170 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6137    3.4993   -2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146    2.7017   -1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9860    5.3990   -0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4354    5.0778   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993    5.2345    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    3.4320    1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270    3.7955   -1.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314    2.7015    0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008    3.3964   -0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029    1.1186   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0917    1.7231   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2663   -0.4249   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578    0.8082   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689    0.8947    1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0226   -0.3017    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9824   -0.7475    0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2726   -1.9650    0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4588   -0.5586    3.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9735   -2.1624    2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968   -3.0748    2.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
 13 12  1  0  0  0  0
  5 19  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
 17 16  1  0  0  0  0
 10  8  1  0  0  0  0
 19  2  1  0  0  0  0
  8  7  1  0  0  0  0
 16 15  2  3  0  0  0
  7  6  2  0  0  0  0
  6  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  1  2  0  0  0  0
 15 14  1  0  0  0  0
 16 18  1  0  0  0  0
  3  4  1  0  0  0  0
  8  9  1  0  0  0  0
 14 13  1  0  0  0  0
  5 24  1  1  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
 15 39  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
  8 27  1  1  0  0  0
  7 26  1  0  0  0  0
  6 25  1  0  0  0  0
  9 28  1  0  0  0  0
M  END

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    3.9564    1.7971   -0.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1947    2.7429   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615    3.3485   -1.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    4.6633   -1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545    4.3407    0.3115 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2875    3.7280    0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    3.5061   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9491    2.8501   -0.2797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9324    3.7657   -0.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030    1.5252   -1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0504    0.4555   -0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231    0.0367    0.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0033   -1.0759    0.9833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1511   -1.4431    2.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0855   -2.0850    3.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9201   -1.5870    3.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7363    0.0946    4.7538 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4111   -2.5781    4.5209 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    3.3823    0.8170 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6137    3.4993   -2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146    2.7017   -1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9860    5.3990   -0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4354    5.0778   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993    5.2345    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    3.4320    1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270    3.7955   -1.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314    2.7015    0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008    3.3964   -0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029    1.1186   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0917    1.7231   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2663   -0.4249   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578    0.8082   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689    0.8947    1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0226   -0.3017    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9824   -0.7475    0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2726   -1.9650    0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4588   -0.5586    3.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9735   -2.1624    2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968   -3.0748    2.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 13 12  1  0
  5 19  1  0
 12 11  1  0
 11 10  1  0
 17 16  1  0
 10  8  1  0
 19  2  1  0
  8  7  1  0
 16 15  2  3
  7  6  2  0
  6  5  1  0
  2  3  1  0
  2  1  2  0
 15 14  1  0
 16 18  1  0
  3  4  1  0
  8  9  1  0
 14 13  1  0
  5 24  1  1
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
 15 39  1  0
 14 37  1  0
 14 38  1  0
 13 35  1  0
 13 36  1  0
 12 33  1  0
 12 34  1  0
 11 31  1  0
 11 32  1  0
 10 29  1  0
 10 30  1  0
  8 27  1  1
  7 26  1  0
  6 25  1  0
  9 28  1  0
M  END


  Mrv1652306212100253D          

 39 39  0  0  0  0            999 V2000
    3.9564    1.7971   -0.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1947    2.7429   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615    3.3485   -1.5299 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1749    4.6633   -1.0757 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6545    4.3407    0.3115 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2875    3.7280    0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    3.5061   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9491    2.8501   -0.2797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9324    3.7657   -0.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030    1.5252   -1.0389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0504    0.4555   -0.7274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0231    0.0367    0.7438 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0033   -1.0759    0.9833 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1511   -1.4431    2.4635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0855   -2.0850    3.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9201   -1.5870    3.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7363    0.0946    4.7538 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4111   -2.5781    4.5209 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    3.3823    0.8170 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6137    3.4993   -2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146    2.7017   -1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9860    5.3990   -0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4354    5.0778   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993    5.2345    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    3.4320    1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270    3.7955   -1.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314    2.7015    0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008    3.3964   -0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029    1.1186   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0917    1.7231   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2663   -0.4249   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578    0.8082   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689    0.8947    1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0226   -0.3017    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9824   -0.7475    0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2726   -1.9650    0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4588   -0.5586    3.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9735   -2.1624    2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968   -3.0748    2.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
 13 12  1  0  0  0  0
  5 19  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
 17 16  1  0  0  0  0
 10  8  1  0  0  0  0
 19  2  1  0  0  0  0
  8  7  1  0  0  0  0
 16 15  2  3  0  0  0
  7  6  2  0  0  0  0
  6  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  1  2  0  0  0  0
 15 14  1  0  0  0  0
 16 18  1  0  0  0  0
  3  4  1  0  0  0  0
  8  9  1  0  0  0  0
 14 13  1  0  0  0  0
  5 24  1  1  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
 15 39  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
  8 27  1  1  0  0  0
  7 26  1  0  0  0  0
  6 25  1  0  0  0  0
  9 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040182

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C(\[H])=C(/[H])[C@@]1([H])OC(=O)C([H])([H])C1([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])=C(Br)Br

> <INCHI_IDENTIFIER>
InChI=1S/C14H20Br2O3/c15-13(16)6-4-2-1-3-5-11(17)7-8-12-9-10-14(18)19-12/h6-8,11-12,17H,1-5,9-10H2/b8-7+/t11-,12+/m0/s1

> <INCHI_KEY>
MZAQGPQBEPVOJJ-ADYIUWEDSA-N

> <FORMULA>
C14H20Br2O3

> <MOLECULAR_WEIGHT>
396.119

> <EXACT_MASS>
393.977921

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.86123454084905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-5-[(1E,3S)-10,10-dibromo-3-hydroxydeca-1,9-dien-1-yl]oxolan-2-one

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
3.9588187543333326

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.890025532586069

> <JCHEM_PKA_STRONGEST_BASIC>
-2.846902832046853

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
94.17850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-[(1E,3S)-10,10-dibromo-3-hydroxydeca-1,9-dien-1-yl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    3.9564    1.7971   -0.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1947    2.7429   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615    3.3485   -1.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    4.6633   -1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545    4.3407    0.3115 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2875    3.7280    0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    3.5061   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9491    2.8501   -0.2797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9324    3.7657   -0.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030    1.5252   -1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0504    0.4555   -0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231    0.0367    0.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0033   -1.0759    0.9833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1511   -1.4431    2.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0855   -2.0850    3.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9201   -1.5870    3.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7363    0.0946    4.7538 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4111   -2.5781    4.5209 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    3.3823    0.8170 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6137    3.4993   -2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146    2.7017   -1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9860    5.3990   -0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4354    5.0778   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993    5.2345    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    3.4320    1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270    3.7955   -1.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314    2.7015    0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008    3.3964   -0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029    1.1186   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0917    1.7231   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2663   -0.4249   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578    0.8082   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689    0.8947    1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0226   -0.3017    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9824   -0.7475    0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2726   -1.9650    0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4588   -0.5586    3.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9735   -2.1624    2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968   -3.0748    2.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 13 12  1  0
  5 19  1  0
 12 11  1  0
 11 10  1  0
 17 16  1  0
 10  8  1  0
 19  2  1  0
  8  7  1  0
 16 15  2  3
  7  6  2  0
  6  5  1  0
  2  3  1  0
  2  1  2  0
 15 14  1  0
 16 18  1  0
  3  4  1  0
  8  9  1  0
 14 13  1  0
  5 24  1  1
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
 15 39  1  0
 14 37  1  0
 14 38  1  0
 13 35  1  0
 13 36  1  0
 12 33  1  0
 12 34  1  0
 11 31  1  0
 11 32  1  0
 10 29  1  0
 10 30  1  0
  8 27  1  1
  7 26  1  0
  6 25  1  0
  9 28  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0       3.956   1.797  -0.109  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.195   2.743  -0.229  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.761   3.349  -1.530  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.175   4.663  -1.076  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.655   4.341   0.312  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.288   3.728   0.450  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.621   3.506  -0.516  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.949   2.850  -0.280  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.932   3.766  -0.753  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.103   1.525  -1.039  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.050   0.456  -0.727  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.023   0.037   0.744  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.003  -1.076   0.983  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.151  -1.443   2.463  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.085  -2.085   3.030  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.920  -1.587   3.957  0.00  0.00           C+0
HETATM   17 Br   UNK     0      -1.736   0.095   4.754  0.00  0.00          Br+0
HETATM   18 Br   UNK     0      -3.411  -2.578   4.521  0.00  0.00          Br+0
HETATM   19  O   UNK     0       2.594   3.382   0.817  0.00  0.00           O+0
HETATM   20  H   UNK     0       3.614   3.499  -2.196  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.015   2.702  -1.998  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.986   5.399  -0.992  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.435   5.078  -1.766  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.699   5.234   0.944  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.041   3.432   1.470  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.427   3.796  -1.545  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.131   2.701   0.790  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.801   3.396  -0.520  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.103   1.119  -0.837  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.092   1.723  -2.120  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.266  -0.425  -1.346  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.058   0.808  -1.032  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.769   0.895   1.375  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.023  -0.302   1.040  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.982  -0.748   0.612  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.273  -1.965   0.402  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.459  -0.559   3.030  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.974  -2.162   2.564  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.297  -3.075   2.627  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   19    3    1                                                  
CONECT    3    2    4   20   21                                             
CONECT    4    5    3   22   23                                             
CONECT    5    4   19    6   24                                             
CONECT    6    7    5   25                                                  
CONECT    7    8    6   26                                                  
CONECT    8   10    7    9   27                                             
CONECT    9    8   28                                                       
CONECT   10   11    8   29   30                                             
CONECT   11   12   10   31   32                                             
CONECT   12   13   11   33   34                                             
CONECT   13   12   14   35   36                                             
CONECT   14   15   13   37   38                                             
CONECT   15   16   14   39                                                  
CONECT   16   17   15   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    5    2                                                       
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   11                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   78    0
END

RDKit          3D

39 39  0  0  0  0  0  0  0  0999 V2000
    3.9564    1.7971   -0.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1947    2.7429   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615    3.3485   -1.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    4.6633   -1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545    4.3407    0.3115 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2875    3.7280    0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    3.5061   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9491    2.8501   -0.2797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9324    3.7657   -0.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030    1.5252   -1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0504    0.4555   -0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231    0.0367    0.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0033   -1.0759    0.9833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1511   -1.4431    2.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0855   -2.0850    3.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9201   -1.5870    3.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7363    0.0946    4.7538 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4111   -2.5781    4.5209 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    3.3823    0.8170 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6137    3.4993   -2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146    2.7017   -1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9860    5.3990   -0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4354    5.0778   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993    5.2345    0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    3.4320    1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270    3.7955   -1.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314    2.7015    0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008    3.3964   -0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029    1.1186   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0917    1.7231   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2663   -0.4249   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578    0.8082   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689    0.8947    1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0226   -0.3017    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9824   -0.7475    0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2726   -1.9650    0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4588   -0.5586    3.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9735   -2.1624    2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968   -3.0748    2.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 13 12  1  0
  5 19  1  0
 12 11  1  0
 11 10  1  0
 17 16  1  0
 10  8  1  0
 19  2  1  0
  8  7  1  0
 16 15  2  3
  7  6  2  0
  6  5  1  0
  2  3  1  0
  2  1  2  0
 15 14  1  0
 16 18  1  0
  3  4  1  0
  8  9  1  0
 14 13  1  0
  5 24  1  1
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
 15 39  1  0
 14 37  1  0
 14 38  1  0
 13 35  1  0
 13 36  1  0
 12 33  1  0
 12 34  1  0
 11 31  1  0
 11 32  1  0
 10 29  1  0
 10 30  1  0
  8 27  1  1
  7 26  1  0
  6 25  1  0
  9 28  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀Br₂O₃

Average Mass

396.1190 Da

Monoisotopic Mass

393.97792 Da

IUPAC Name

(5S)-5-[(1E,3S)-10,10-dibromo-3-hydroxydeca-1,9-dien-1-yl]oxolan-2-one

Traditional Name

(5S)-5-[(1E,3S)-10,10-dibromo-3-hydroxydeca-1,9-dien-1-yl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]([H])(C(\[H])=C(/[H])[C@@]1([H])OC(=O)C([H])([H])C1([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])=C(Br)Br

InChI Identifier

InChI=1S/C14H20Br2O3/c15-13(16)6-4-2-1-3-5-11(17)7-8-12-9-10-14(18)19-12/h6-8,11-12,17H,1-5,9-10H2/b8-7+/t11-,12+/m0/s1

InChI Key

MZAQGPQBEPVOJJ-ADYIUWEDSA-N

Experimental Spectra

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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xestospongia testudinaria	JEOL database	Jiang, W., et al, Tetrahedron 67, 58 (2011).

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Oxolane
Carboxylic acid ester
Ketene acetal or derivatives
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Bromoalkene
Vinyl bromide
Vinyl halide
Haloalkene
Organohalogen compound
Organobromide
Organooxygen compound
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	4.15	ALOGPS
logP	3.96	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.89	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	94.18 m³·mol⁻¹	ChemAxon
Polarizability	32.86 Å³	ChemAxon
Number of Rings	1	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

27025216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51002847

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jiang, W., et al. (2011). Jiang, W., et al, Tetrahedron 67, 58 (2011).. Tetrahedron.

Showing NP-Card for xestospongiene A/B (NP0040182)

MOL for NP0040182 (xestospongiene A/B)

3D MOL for NP0040182 (xestospongiene A/B)

3D SDF for NP0040182 (xestospongiene A/B)

3D-SDF for NP0040182 (xestospongiene A/B)

PDB for NP0040182 (xestospongiene A/B)

3D PDB for NP0040182 (xestospongiene A/B)

SMILES for NP0040182 (xestospongiene A/B)

INCHI for NP0040182 (xestospongiene A/B)

Structure for NP0040182 (xestospongiene A/B)

3D Structure for NP0040182 (xestospongiene A/B)