NP-MRD: Showing NP-Card for Bipinnatin H (NP0082554)

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Record Information

Version

2.0

Created at

2022-04-29 03:36:50 UTC

Updated at

2022-04-29 03:36:50 UTC

NP-MRD ID

NP0082554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bipinnatin H

Description

(2S,4S,6S,10S,12R,13S)-13-(acetyloxy)-4,15-dimethyl-12-[(2R)-2-methyloxiran-2-yl]-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]Octadeca-1(16),9(18),14-trien-10-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. Bipinnatin H is found in Pseudopterogorgia bipinnata. Based on a literature review very few articles have been published on (2S,4S,6S,10S,12R,13S)-13-(acetyloxy)-4,15-dimethyl-12-[(2R)-2-methyloxiran-2-yl]-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]Octadeca-1(16),9(18),14-trien-10-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205362D          

 33 37  0  0  1  0            999 V2000
    4.0575   -0.8772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7989   -0.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3722   -1.1083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9852   -1.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1658   -2.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5727   -3.2949    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7795   -3.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1863   -3.6412    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3932   -3.4142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1932   -2.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7864   -2.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5864   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2553   -0.6848    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8230   -0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7361   -1.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5090   -2.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339   -2.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -3.9876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068   -3.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4137   -4.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8069   -2.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3863   -4.4416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6328   -4.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093   -4.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8479   -5.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726   -4.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658   -4.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1590   -3.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7657   -5.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0135   -2.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6904   -2.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1182   -1.4608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3895   -0.1219    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  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  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
  1 13  1  0  0  0  0
 13 14  1  1  0  0  0
  1 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 10 16  2  0  0  0  0
 16 17  1  0  0  0  0
  9 18  1  6  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
 22 23  1  6  0  0  0
 22 24  1  6  0  0  0
 24 25  1  0  0  0  0
 22 25  1  0  0  0  0
  6 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  3 32  1  6  0  0  0
  1 33  1  6  0  0  0
M  END

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
   -0.3047    5.8193    1.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2844    4.3354    1.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164    3.7758    2.4432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0649    3.5381    0.3024 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0931    2.1164    0.3107 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9904    1.5053   -0.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6858    0.3266    0.1430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1220    0.6247    0.4076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2868    1.9240    1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740   -0.3419    0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0984    0.5119   -0.5625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3731   -0.8983   -0.6389 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3648   -1.8734   -0.6674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423   -2.3905   -1.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959   -3.4263   -1.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3153   -1.9146   -2.9349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1660   -1.5412   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013   -1.7835   -0.7073 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -2.3374    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944   -2.4776    1.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0174   -1.9592    1.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9121   -1.8950    2.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1094   -2.7036   -0.5395 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2480   -2.9205   -1.9008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8950   -1.7434   -1.2259 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4037   -1.8765   -1.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2907   -0.5036   -1.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3721    0.6957   -0.9015 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1575    1.6039   -1.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4692    1.5800   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2919    0.8650    1.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961    0.6124    2.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4964    0.4799    0.4585 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5470    6.2494    1.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2388    6.2189    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252    6.2282    1.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315    1.8740    1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5533    1.2026   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7383    2.2865   -0.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1530    0.2484    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1565    2.7753    0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2759    1.9481    1.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5165    1.8318    2.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0491    0.0025    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2709   -1.3667    0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0512   -0.5952   -1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6629   -3.2634   -1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4685   -4.4445   -1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4202   -3.4220   -2.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8420   -2.9141    2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8836   -2.8340    3.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793   -1.7940    2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6200   -1.0530    3.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6842   -3.4898    0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8819   -1.4734   -2.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6291   -2.9612   -1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8007   -1.3975   -0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8730   -0.2765   -2.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554   -0.6210   -2.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3185    1.2568   -1.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1872    2.0559   -2.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12 17  1  0
 17 21  2  0
 21 22  1  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 25 27  1  0
 27 28  1  0
 28 33  1  0
 33 31  1  0
 31 32  2  0
 31 30  1  0
 30 29  2  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 30  5  1  0
 11  8  1  0
 18 17  1  0
 25 23  1  0
 29 28  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  1
  6 38  1  0
  6 39  1  0
  7 40  1  1
 12 46  1  6
 15 47  1  0
 15 48  1  0
 15 49  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 20 50  1  0
 23 54  1  1
 26 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 28 60  1  6
 29 61  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
M  END


  Mrv1652304292205362D          

 33 37  0  0  1  0            999 V2000
    4.0575   -0.8772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7989   -0.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3722   -1.1083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9852   -1.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1658   -2.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5727   -3.2949    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7795   -3.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1863   -3.6412    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3932   -3.4142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1932   -2.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7864   -2.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5864   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2553   -0.6848    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8230   -0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7361   -1.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5090   -2.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339   -2.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -3.9876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068   -3.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4137   -4.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8069   -2.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3863   -4.4416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6328   -4.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093   -4.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8479   -5.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726   -4.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658   -4.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1590   -3.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7657   -5.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0135   -2.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6904   -2.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1182   -1.4608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3895   -0.1219    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  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  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
  1 13  1  0  0  0  0
 13 14  1  1  0  0  0
  1 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 10 16  2  0  0  0  0
 16 17  1  0  0  0  0
  9 18  1  6  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
 22 23  1  6  0  0  0
 22 24  1  6  0  0  0
 24 25  1  0  0  0  0
 22 25  1  0  0  0  0
  6 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  3 32  1  6  0  0  0
  1 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0082554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@H]([C@H](OC(C)=O)C2=C(C)C=C(O2)[C@H]2O[C@@]2(C)C[C@@H]2OC(=O)C1=C2)[C@]1(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O9/c1-11-6-18-21-23(4,33-21)9-14-7-15(22(27)31-14)17(29-12(2)25)8-16(24(5)10-28-24)20(19(11)32-18)30-13(3)26/h6-7,14,16-17,20-21H,8-10H2,1-5H3/t14-,16-,17+,20+,21-,23+,24+/m1/s1

> <INCHI_KEY>
ZKPQWDXTJKFKDU-JSKTUPDSSA-N

> <FORMULA>
C24H28O9

> <MOLECULAR_WEIGHT>
460.479

> <EXACT_MASS>
460.173332482

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.27672287664673

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4S,6S,10S,12R,13S)-13-(acetyloxy)-4,15-dimethyl-12-[(2R)-2-methyloxiran-2-yl]-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1^{6,9}.0^{2,4}]octadeca-1(16),9(18),14-trien-10-yl acetate

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
1.592903256666667

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.225287631318853

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8603668443894414

> <JCHEM_POLAR_SURFACE_AREA>
117.10000000000001

> <JCHEM_REFRACTIVITY>
112.28249999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,6S,10S,12R,13S)-13-(acetyloxy)-4,15-dimethyl-12-[(2R)-2-methyloxiran-2-yl]-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1^{6,9}.0^{2,4}]octadeca-1(16),9(18),14-trien-10-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       7.574  -1.637   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.958  -0.962   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.028  -2.069   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.306  -3.429   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.643  -5.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.536  -6.150   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.055  -5.727   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.948  -6.797   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.467  -6.373   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.094  -4.879   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.201  -3.809   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.828  -2.315   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.077  -1.278   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.136  -0.161   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.241  -2.538   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.817  -4.019   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.370  -4.546   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.360  -7.443   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.879  -7.020   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.772  -8.090   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.506  -5.526   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.321  -8.291   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.915  -8.918   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.857  -8.183   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.183  -9.567   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.909  -7.645   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.389  -8.068   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.497  -6.998   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.763  -9.562   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.225  -4.254   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.489  -5.135   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      11.421  -2.727   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.194  -0.228   0.000  0.00  0.00           C+0
CONECT    1    2   13   14   33                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12    1   14                                                  
CONECT   14   13    1                                                       
CONECT   15   12   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16                                                            
CONECT   18    9   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    8   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   22                                                       
CONECT   26    6   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    5   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3                                                       
CONECT   33    1                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2S,4S,6S,10S,12R,13S)-13-(Acetyloxy)-4,15-dimethyl-12-[(2R)-2-methyloxiran-2-yl]-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1,.0,]octadeca-1(16),9(18),14-trien-10-yl acetic acid	Generator

Chemical Formula

C₂₄H₂₈O₉

Average Mass

460.4790 Da

Monoisotopic Mass

460.17333 Da

IUPAC Name

(2S,4S,6S,10S,12R,13S)-13-(acetyloxy)-4,15-dimethyl-12-[(2R)-2-methyloxiran-2-yl]-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1^{6,9}.0^{2,4}]octadeca-1(16),9(18),14-trien-10-yl acetate

Traditional Name

(2S,4S,6S,10S,12R,13S)-13-(acetyloxy)-4,15-dimethyl-12-[(2R)-2-methyloxiran-2-yl]-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1^{6,9}.0^{2,4}]octadeca-1(16),9(18),14-trien-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@H]([C@H](OC(C)=O)C2=C(C)C=C(O2)[C@H]2O[C@@]2(C)C[C@@H]2OC(=O)C1=C2)[C@]1(C)CO1

InChI Identifier

InChI=1S/C24H28O9/c1-11-6-18-21-23(4,33-21)9-14-7-15(22(27)31-14)17(29-12(2)25)8-16(24(5)10-28-24)20(19(11)32-18)30-13(3)26/h6-7,14,16-17,20-21H,8-10H2,1-5H3/t14-,16-,17+,20+,21-,23+,24+/m1/s1

InChI Key

ZKPQWDXTJKFKDU-JSKTUPDSSA-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
Antillogorgia bipinnata	-	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
2-furanone
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Furan
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.15	ALOGPS
logP	1.59	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.23	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	117.1 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	112.28 m³·mol⁻¹	ChemAxon
Polarizability	46.28 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

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

162983007

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Bipinnatin H (NP0082554)

MOL for NP0082554 (Bipinnatin H)

3D MOL for NP0082554 (Bipinnatin H)

3D SDF for NP0082554 (Bipinnatin H)

3D-SDF for NP0082554 (Bipinnatin H)

PDB for NP0082554 (Bipinnatin H)

3D PDB for NP0082554 (Bipinnatin H)

SMILES for NP0082554 (Bipinnatin H)

INCHI for NP0082554 (Bipinnatin H)

Structure for NP0082554 (Bipinnatin H)

3D Structure for NP0082554 (Bipinnatin H)