NP-MRD: Showing NP-Card for 2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid (NP0186963)

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Record Information

Version

2.0

Created at

2022-09-04 02:58:30 UTC

Updated at

2022-09-04 02:58:30 UTC

NP-MRD ID

NP0186963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid

Description

Isocephalosporin P1 belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. 2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid is found in Sarocladium strictum. 2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid was first documented in 2015 (PMID: 25824664). Based on a literature review very few articles have been published on Isocephalosporin P1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042204582D          

 41 44  0  0  1  0            999 V2000
    5.3073   -1.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9380   -0.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7139   -1.1987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7927   -0.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850   -0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1814   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1220   -1.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -2.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736   -2.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296   -2.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4978   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1539   -1.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.7875    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893    3.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784    3.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6848    4.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3739    5.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5020    4.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175    2.1564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4220    0.7409    0.0000 O   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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 22 20  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
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 28 29  1  0  0  0  0
 22 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  1  0  0  0
  9 31  1  1  0  0  0
  5 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
M  END

     RDKit          3D

 91 94  0  0  0  0  0  0  0  0999 V2000
    2.8175    5.7462    2.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1662    4.4220    2.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6508    3.9885    3.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918    3.6055    1.2523 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4845    2.4175    1.3202 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1665    2.3193    0.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269    0.8614    0.3165 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4863    0.6024   -1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0947    0.2044    1.2190 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1233   -1.2251    1.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259   -1.7475    1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619   -1.1608    0.3876 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3609    0.3291    0.6035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7364    0.6819    2.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792    0.9998   -0.2717 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.0775    0.6160   -1.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8855   -1.7556   -0.5873 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1247   -0.9788   -0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9822   -3.1786   -0.1757 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.1216   -3.6379    0.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9873   -2.7522    1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -1.9186    0.1870 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3837   -2.8582   -1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1941    1.1310    0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3985    0.9059    0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9053   -0.4392    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2091   -0.6326   -1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7270   -2.0277   -1.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9224   -2.2485   -1.7599 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7796   -1.1043   -2.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4189   -3.6415   -1.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3451    1.9731    0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5653    1.6326   -0.0555 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799    3.3131    0.2906 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9158    5.6865    2.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7357    6.2590    1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3163    6.3887    3.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    2.1959    2.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    2.9253   -0.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6573    2.7922    1.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2715    5.0106   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7760    4.9259   -2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8092    1.0277   -1.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5337   -3.5925   -1.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
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 41 91  1  0
M  END


  Mrv1652309042204582D          

 41 44  0  0  1  0            999 V2000
    5.3073   -1.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9380   -0.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850   -0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1814   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1220   -1.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -2.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736   -2.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296   -2.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4978   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1539   -1.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8069    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893    3.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784    3.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6848    4.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3739    5.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5020    4.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175    2.1564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4220    0.7409    0.0000 O   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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 22 20  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 22 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  1  0  0  0
  9 31  1  1  0  0  0
  5 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@H](O)CC[C@]2(C)[C@@H]3CC[C@H]4\C([C@H](C[C@]4(C)[C@@]3(C)[C@@H](OC(C)=O)[C@H](O)[C@@H]12)OC(C)=O)=C(/CCC=C(C)C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H50O8/c1-17(2)10-9-11-21(30(38)39)26-22-12-13-25-31(6)15-14-23(36)18(3)27(31)28(37)29(41-20(5)35)33(25,8)32(22,7)16-24(26)40-19(4)34/h10,18,22-25,27-29,36-37H,9,11-16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,23-,24+,25+,27-,28-,29+,31-,32+,33-/m1/s1

> <INCHI_KEY>
GDJVSKALKNUTRX-VALXSNPUSA-N

> <FORMULA>
C33H50O8

> <MOLECULAR_WEIGHT>
574.755

> <EXACT_MASS>
574.35056857

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
64.40541487530285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1S,2R,5R,6S,7S,8R,9R,10S,11S,13S,14Z,15R)-9,13-bis(acetyloxy)-5,8-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-ylidene]-6-methylhept-5-enoic acid

> <JCHEM_LOGP>
3.944043079666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.846514367658912

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.434299526514637

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8230594918337566

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
154.48230000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S,2R,5R,6S,7S,8R,9R,10S,11S,13S,14Z,15R)-9,13-bis(acetyloxy)-5,8-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-ylidene]-6-methylhept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       9.907  -2.707   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.084  -1.714   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.533  -2.237   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.813  -0.198   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.505  -1.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.939  -1.292   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.828  -2.491   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.305  -3.939   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.297  -5.117   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.789  -4.210   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.796  -3.033   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.287  -2.127   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.698   0.228   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.373   2.489   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.882   3.020   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.302   4.447   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.247   5.662   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.666   7.089   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.612   8.305   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.031   9.731   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.137   8.094   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.407   2.809   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      12.353   4.025   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      11.988   1.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   13                                             
CONECT    8    7                                                            
CONECT    9    7   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12    7   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   29                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   22   12   30                                             
CONECT   30   29                                                            
CONECT   31    9    5   32                                                  
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   32   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₅₀O₈

Average Mass

574.7550 Da

Monoisotopic Mass

574.35057 Da

IUPAC Name

2-[(1S,2R,5R,6S,7S,8R,9R,10S,11S,13S,14Z,15R)-9,13-bis(acetyloxy)-5,8-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-ylidene]-6-methylhept-5-enoic acid

Traditional Name

2-[(1S,2R,5R,6S,7S,8R,9R,10S,11S,13S,14Z,15R)-9,13-bis(acetyloxy)-5,8-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-ylidene]-6-methylhept-5-enoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@H](O)CC[C@]2(C)[C@@H]3CC[C@H]4\C([C@H](C[C@]4(C)[C@@]3(C)[C@@H](OC(C)=O)[C@H](O)[C@@H]12)OC(C)=O)=C(/CCC=C(C)C)C(O)=O

InChI Identifier

InChI=1S/C33H50O8/c1-17(2)10-9-11-21(30(38)39)26-22-12-13-25-31(6)15-14-23(36)18(3)27(31)28(37)29(41-20(5)35)33(25,8)32(22,7)16-24(26)40-19(4)34/h10,18,22-25,27-29,36-37H,9,11-16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,23-,24+,25+,27-,28-,29+,31-,32+,33-/m1/s1

InChI Key

GDJVSKALKNUTRX-VALXSNPUSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Acremonium strictum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid esters

Alternative Parents

Substituents

Steroid ester
3-hydroxysteroid
6-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Tricarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.94	ChemAxon
pKa (Strongest Acidic)	4.43	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	154.48 m³·mol⁻¹	ChemAxon
Polarizability	64.41 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

58992445

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

118728786

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang S, Wang S, Zhang Q, Chang CW, Zhan J: Three new fusidic acid derivatives and their antibacterial activity. Bioorg Med Chem Lett. 2015 May 1;25(9):1920-4. doi: 10.1016/j.bmcl.2015.03.033. Epub 2015 Mar 20. [PubMed:25824664 ]
LOTUS database [Link]

Showing NP-Card for 2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid (NP0186963)

MOL for NP0186963 (2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid)

3D MOL for NP0186963 (2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid)

3D SDF for NP0186963 (2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid)

3D-SDF for NP0186963 (2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid)

PDB for NP0186963 (2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid)

3D PDB for NP0186963 (2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid)

SMILES for NP0186963 (2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid)

INCHI for NP0186963 (2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid)

Structure for NP0186963 (2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid)

3D Structure for NP0186963 (2-[(1z,2s,3as,3bs,4r,5r,5as,6s,7r,9ar,9bs,11ar)-2,4-bis(acetyloxy)-5,7-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid)