NP-MRD: Showing NP-Card for cladiellin A (NP0038901)

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Record Information

Version

2.0

Created at

2021-06-20 21:28:13 UTC

Updated at

2021-06-30 00:11:56 UTC

NP-MRD ID

NP0038901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cladiellin A

Provided By

JEOL Database JEOL Logo

Description

(22R)-22-Hydroxy-18,22-epoxycholesta-1,4-diene-3-one belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. cladiellin A is found in Cladiella sp. cladiellin A was first documented in 2005 (Zhang, G.-W., et al.). Based on a literature review very few articles have been published on (22R)-22-Hydroxy-18,22-epoxycholesta-1,4-diene-3-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123283D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202123283D          

 70 74  0  0  0  0            999 V2000
   -4.3626   -2.3247    3.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3094   -1.4844    3.8120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9987   -0.4586    4.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674   -0.8257    2.7850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2006   -0.0669    3.4321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0865    0.3746    2.4514 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8939    1.0649    3.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5026   -0.8149    1.9234 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927   -0.5656    1.0360 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1148    0.1647   -0.2415 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2462   -0.7675   -1.1006 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0773   -1.8963   -1.7387 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3358   -1.3957   -2.5033 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1732   -0.3955   -1.6343 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3499    0.1802   -2.4363 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2351   -0.9212   -3.0105 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4128   -1.8848   -3.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039   -2.0862   -5.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827   -2.9639   -5.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676   -3.1551   -7.1593 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -3.5916   -5.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4074   -3.3947   -4.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2258   -2.5433   -3.1116 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7609   -3.5123   -2.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2429    0.7124   -1.1321 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8237    1.8613   -0.3133 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6116    2.4404    0.4420 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4282    1.4779    0.1733 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6012    1.2872    1.3060 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1356    2.6360    1.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879   -1.7033    2.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0176   -2.8323    3.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8881   -3.0934    2.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7218   -2.1596    4.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2750    0.0717    5.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7103   -0.9492    5.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9495   -0.1424    2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493   -0.7226    4.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5712    0.8058    3.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0761    0.4982    3.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0327   -1.5391    0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3745   -0.0192    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672   -1.2051   -0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2336   -0.1945   -1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3659   -2.6112   -0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4155   -2.4391   -2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9475   -0.8145   -3.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5922   -0.9261   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625    0.8258   -1.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723    0.8101   -3.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7420   -1.4594   -2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0266   -0.4599   -3.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5387   -1.6057   -5.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972   -4.2205   -6.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366   -3.9097   -3.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2887   -2.9960   -1.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4657   -4.2342   -2.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -4.0949   -1.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    1.1780   -2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833    1.5104    0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2926    2.6192   -0.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    3.4437    0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556    2.5420    1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146    1.8849   -0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384    0.7660    0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    2.5012    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4713    3.2483    0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766    3.2048    2.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 25  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 17 18  2  0  0  0  0
 23 22  1  0  0  0  0
 22 21  2  0  0  0  0
 21 19  1  0  0  0  0
 19 18  1  0  0  0  0
 10 25  1  0  0  0  0
 19 20  2  0  0  0  0
 23 24  1  1  0  0  0
 13 14  1  0  0  0  0
 28 29  1  0  0  0  0
 23 13  1  0  0  0  0
 10  9  1  0  0  0  0
 17 16  1  0  0  0  0
 29 30  1  0  0  0  0
 16 15  1  0  0  0  0
 29  6  1  0  0  0  0
 25 26  1  0  0  0  0
  9  8  1  0  0  0  0
  8  6  1  0  0  0  0
 26 27  1  0  0  0  0
  6  5  1  0  0  0  0
 27 28  1  0  0  0  0
  6  7  1  1  0  0  0
 28 10  1  0  0  0  0
  5  4  1  0  0  0  0
 17 23  1  0  0  0  0
  4  2  1  0  0  0  0
 14 15  1  0  0  0  0
  2  1  1  0  0  0  0
 13 12  1  0  0  0  0
  2  3  1  0  0  0  0
 18 55  1  0  0  0  0
 16 53  1  0  0  0  0
 16 54  1  0  0  0  0
 15 51  1  0  0  0  0
 15 52  1  0  0  0  0
 13 49  1  6  0  0  0
 14 50  1  1  0  0  0
 11 45  1  0  0  0  0
 11 46  1  0  0  0  0
 12 47  1  0  0  0  0
 12 48  1  0  0  0  0
 25 61  1  6  0  0  0
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 24 59  1  0  0  0  0
 24 60  1  0  0  0  0
 29 67  1  6  0  0  0
  9 43  1  0  0  0  0
  9 44  1  0  0  0  0
 30 68  1  0  0  0  0
 30 69  1  0  0  0  0
 30 70  1  0  0  0  0
  5 40  1  0  0  0  0
  5 41  1  0  0  0  0
  7 42  1  0  0  0  0
  4 38  1  0  0  0  0
  4 39  1  0  0  0  0
  2 34  1  1  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1(OC([H])([H])[C@]23C([H])([H])C([H])([H])[C@@]4([H])[C@@]([H])(C([H])([H])C([H])([H])C5=C([H])C(=O)C([H])=C([H])[C@]45C([H])([H])[H])[C@]2([H])C([H])([H])C([H])([H])[C@]3([H])[C@]1([H])C([H])([H])[H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O3/c1-17(2)9-14-27(29)18(3)22-7-8-24-21-6-5-19-15-20(28)10-12-25(19,4)23(21)11-13-26(22,24)16-30-27/h10,12,15,17-18,21-24,29H,5-9,11,13-14,16H2,1-4H3/t18-,21+,22+,23-,24-,25-,26-,27+/m0/s1

> <INCHI_KEY>
ZHPAKFYPMMYZNI-QMNNYTQVSA-N

> <FORMULA>
C27H40O3

> <MOLECULAR_WEIGHT>
412.614

> <EXACT_MASS>
412.297745148

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.33581393767551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R,6S,7R,10R,13S,14R)-7-hydroxy-6,14-dimethyl-7-(3-methylbutyl)-8-oxapentacyclo[11.8.0.0^{2,10}.0^{5,10}.0^{14,19}]henicosa-15,18-dien-17-one

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
5.717389846333332

> <ALOGPS_LOGS>
-5.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.863503122661577

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.854642183516182

> <JCHEM_PKA_STRONGEST_BASIC>
-4.174579490317606

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
122.14839999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.61e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,6S,7R,10R,13S,14R)-7-hydroxy-6,14-dimethyl-7-(3-methylbutyl)-8-oxapentacyclo[11.8.0.0^{2,10}.0^{5,10}.0^{14,19}]henicosa-15,18-dien-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 74  0  0  0  0  0  0  0  0999 V2000
   -4.3626   -2.3247    3.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3094   -1.4844    3.8120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9987   -0.4586    4.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674   -0.8257    2.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006   -0.0669    3.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0865    0.3746    2.4514 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8939    1.0649    3.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5026   -0.8149    1.9234 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927   -0.5656    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1148    0.1647   -0.2415 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2462   -0.7675   -1.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773   -1.8963   -1.7387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -1.3957   -2.5033 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1732   -0.3955   -1.6343 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3499    0.1802   -2.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2351   -0.9212   -3.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4128   -1.8848   -3.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039   -2.0862   -5.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827   -2.9639   -5.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676   -3.1551   -7.1593 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -3.5916   -5.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4074   -3.3947   -4.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2258   -2.5433   -3.1116 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7609   -3.5123   -2.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2429    0.7124   -1.1321 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8237    1.8613   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6116    2.4404    0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282    1.4779    0.1733 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6012    1.2872    1.3060 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1356    2.6360    1.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879   -1.7033    2.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0176   -2.8323    3.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8881   -3.0934    2.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7218   -2.1596    4.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5481    0.2826    4.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2750    0.0717    5.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7103   -0.9492    5.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690   -1.6057    2.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9495   -0.1424    2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493   -0.7226    4.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5712    0.8058    3.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0761    0.4982    3.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0327   -1.5391    0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3745   -0.0192    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672   -1.2051   -0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2336   -0.1945   -1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3659   -2.6112   -0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4155   -2.4391   -2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9475   -0.8145   -3.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5922   -0.9261   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625    0.8258   -1.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723    0.8101   -3.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7420   -1.4594   -2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0266   -0.4599   -3.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5387   -1.6057   -5.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972   -4.2205   -6.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366   -3.9097   -3.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2887   -2.9960   -1.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4657   -4.2342   -2.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -4.0949   -1.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    1.1780   -2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833    1.5104    0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2926    2.6192   -0.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    3.4437    0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556    2.5420    1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146    1.8849   -0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384    0.7660    0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    2.5012    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4713    3.2483    0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766    3.2048    2.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 25  1  0
 10 11  1  6
 11 12  1  0
 17 18  2  0
 23 22  1  0
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  3 37  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.363  -2.325   3.085  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.309  -1.484   3.812  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.999  -0.459   4.713  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.367  -0.826   2.785  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.201  -0.067   3.432  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.087   0.375   2.451  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.894   1.065   3.220  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.503  -0.815   1.923  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.593  -0.566   1.036  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.115   0.165  -0.242  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.246  -0.768  -1.101  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.077  -1.896  -1.739  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.336  -1.396  -2.503  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.173  -0.396  -1.634  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.350   0.180  -2.436  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.235  -0.921  -3.010  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.413  -1.885  -3.829  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.704  -2.086  -5.126  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.883  -2.964  -5.984  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.168  -3.155  -7.159  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.699  -3.592  -5.369  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.407  -3.395  -4.077  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.226  -2.543  -3.112  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.761  -3.512  -2.034  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.243   0.712  -1.132  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.824   1.861  -0.313  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.612   2.440   0.442  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.428   1.478   0.173  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.601   1.287   1.306  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.136   2.636   1.798  0.00  0.00           C+0
HETATM   31  H   UNK     0      -4.988  -1.703   2.435  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.018  -2.832   3.801  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.888  -3.093   2.466  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.722  -2.160   4.447  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.548   0.283   4.123  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.275   0.072   5.339  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.710  -0.949   5.386  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.969  -1.606   2.125  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.950  -0.142   2.156  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.749  -0.723   4.190  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.571   0.806   3.982  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.076   0.498   3.988  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.033  -1.539   0.804  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.374  -0.019   1.574  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.567  -1.205  -0.510  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.234  -0.195  -1.905  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.366  -2.611  -0.962  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.416  -2.439  -2.422  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.948  -0.815  -3.357  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.592  -0.926  -0.772  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.963   0.826  -1.796  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.972   0.810  -3.253  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.742  -1.459  -2.201  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.027  -0.460  -3.614  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.539  -1.606  -5.624  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.097  -4.221  -6.014  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.537  -3.910  -3.677  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.289  -2.996  -1.226  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.466  -4.234  -2.466  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.956  -4.095  -1.571  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.790   1.178  -2.023  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.583   1.510   0.394  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.293   2.619  -0.949  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.371   3.444   0.073  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.856   2.542   1.502  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.115   1.885  -0.694  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.438   0.766   0.824  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.996   2.501   2.460  0.00  0.00           H+0
HETATM   69  H   UNK     0      -1.471   3.248   0.954  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.377   3.205   2.343  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    4    1    3   34                                             
CONECT    3    2   35   36   37                                             
CONECT    4    5    2   38   39                                             
CONECT    5    6    4   40   41                                             
CONECT    6   29    8    5    7                                             
CONECT    7    6   42                                                       
CONECT    8    9    6                                                       
CONECT    9   10    8   43   44                                             
CONECT   10   11   25    9   28                                             
CONECT   11   10   12   45   46                                             
CONECT   12   11   13   47   48                                             
CONECT   13   14   23   12   49                                             
CONECT   14   25   13   15   50                                             
CONECT   15   16   14   51   52                                             
CONECT   16   17   15   53   54                                             
CONECT   17   18   16   23                                                  
CONECT   18   17   19   55                                                  
CONECT   19   21   18   20                                                  
CONECT   20   19                                                            
CONECT   21   22   19   56                                                  
CONECT   22   23   21   57                                                  
CONECT   23   22   24   13   17                                             
CONECT   24   23   58   59   60                                             
CONECT   25   14   10   26   61                                             
CONECT   26   25   27   62   63                                             
CONECT   27   26   28   64   65                                             
CONECT   28   29   27   10   66                                             
CONECT   29   28   30    6   67                                             
CONECT   30   29   68   69   70                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    7                                                            
CONECT   43    9                                                            
CONECT   44    9                                                            
CONECT   45   11                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   15                                                            
CONECT   53   16                                                            
CONECT   54   16                                                            
CONECT   55   18                                                            
CONECT   56   21                                                            
CONECT   57   22                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
CONECT   62   26                                                            
CONECT   63   26                                                            
CONECT   64   27                                                            
CONECT   65   27                                                            
CONECT   66   28                                                            
CONECT   67   29                                                            
CONECT   68   30                                                            
CONECT   69   30                                                            
CONECT   70   30                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  148    0
END

RDKit          3D

70 74  0  0  0  0  0  0  0  0999 V2000
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   -3.3094   -1.4844    3.8120 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.1148    0.1647   -0.2415 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2462   -0.7675   -1.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3358   -1.3957   -2.5033 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1732   -0.3955   -1.6343 C   0  0  1  0  0  0  0  0  0  0  0  0
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 14 50  1  1
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 25 61  1  6
 26 62  1  0
 26 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  6
 22 57  1  0
 21 56  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
 29 67  1  6
  9 43  1  0
  9 44  1  0
 30 68  1  0
 30 69  1  0
 30 70  1  0
  5 40  1  0
  5 41  1  0
  7 42  1  0
  4 38  1  0
  4 39  1  0
  2 34  1  1
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₃

Average Mass

412.6140 Da

Monoisotopic Mass

412.29775 Da

IUPAC Name

(1R,2S,5R,6S,7R,10R,13S,14R)-7-hydroxy-6,14-dimethyl-7-(3-methylbutyl)-8-oxapentacyclo[11.8.0.0^{2,10}.0^{5,10}.0^{14,19}]henicosa-15,18-dien-17-one

Traditional Name

(1R,2S,5R,6S,7R,10R,13S,14R)-7-hydroxy-6,14-dimethyl-7-(3-methylbutyl)-8-oxapentacyclo[11.8.0.0^{2,10}.0^{5,10}.0^{14,19}]henicosa-15,18-dien-17-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1(OC([H])([H])[C@]23C([H])([H])C([H])([H])[C@@]4([H])[C@@]([H])(C([H])([H])C([H])([H])C5=C([H])C(=O)C([H])=C([H])[C@]45C([H])([H])[H])[C@]2([H])C([H])([H])C([H])([H])[C@]3([H])[C@]1([H])C([H])([H])[H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C27H40O3/c1-17(2)9-14-27(29)18(3)22-7-8-24-21-6-5-19-15-20(28)10-12-25(19,4)23(21)11-13-26(22,24)16-30-27/h10,12,15,17-18,21-24,29H,5-9,11,13-14,16H2,1-4H3/t18-,21+,22+,23-,24-,25-,26-,27+/m0/s1

InChI Key

ZHPAKFYPMMYZNI-QMNNYTQVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 750 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 750 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Cladiella sp.	JEOL database	Zhang, G.-W., et al, Org. Lett. 7, 991 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

22-hydroxysteroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
Iridoid-skeleton
Oxane
Hemiacetal
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.22	ALOGPS
logP	5.72	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	11.85	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	122.15 m³·mol⁻¹	ChemAxon
Polarizability	49.34 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

29213474

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102210660

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang, G.-W., et al. (2005). Zhang, G.-W., et al, Org. Lett. 7, 991 (2005). Org. Lett..

Showing NP-Card for cladiellin A (NP0038901)

MOL for NP0038901 (cladiellin A)

3D MOL for NP0038901 (cladiellin A)

3D SDF for NP0038901 (cladiellin A)

3D-SDF for NP0038901 (cladiellin A)

PDB for NP0038901 (cladiellin A)

3D PDB for NP0038901 (cladiellin A)

SMILES for NP0038901 (cladiellin A)

INCHI for NP0038901 (cladiellin A)

Structure for NP0038901 (cladiellin A)

3D Structure for NP0038901 (cladiellin A)