NP-MRD: Showing NP-Card for Berkeleyone A (NP0010302)

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Record Information

Version

2.0

Created at

2021-01-05 19:52:03 UTC

Updated at

2021-07-15 17:05:43 UTC

NP-MRD ID

NP0010302

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Berkeleyone A

Provided By

NPAtlas

Description

Berkeleyone A belongs to the class of organic compounds known as 3-alpha-hydroxysteroids. These are steroids carrying a alpha-hydroxyl group at the 3-position of the steroid backbone. Berkeleyone A is found in Penicillium and Talaromyces ruber. Based on a literature review very few articles have been published on berkeleyone A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107373D          

 70 73  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242107373D          

 70 73  0  0  0  0            999 V2000
   -3.5711   -0.9746    1.8828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5516   -0.3367    1.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7545    0.5952    2.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2785    0.6428    3.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2937    0.2037    2.1709 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1277    0.0035    0.7655 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6262   -0.1592    0.5872 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1444   -1.4152    1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031    1.0045    1.2732 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7663    1.0878    0.9584 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1258    1.0023   -0.4647 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4169    0.4253   -0.5519 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2387    0.1913   -1.3418 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9075   -1.1247   -1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    0.9595   -2.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8656   -0.0313   -0.8840 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2652   -1.2351   -1.5465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2118   -1.4023   -1.2981 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6840   -1.0501    0.0597 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.0260   -1.3962   -0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037   -2.5169   -1.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3759   -1.0583   -0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2896   -1.9331   -1.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238    0.8865   -0.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9846    1.0398   -1.8114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248    2.1295    0.1792 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6437    3.3236   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3387    0.3186    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2821    2.0552   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9631    0.8546   -1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9742   -0.9015   -1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4396   -1.4605   -2.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8182   -1.9134   -1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2088    0.7205   -3.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0553    0.7859   -3.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0670    2.0428   -2.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337    0.8458   -1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4052   -1.1058   -2.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144   -2.1767   -1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018   -2.5048   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593   -0.8900   -2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4421   -3.2108    0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8585   -2.9491   -1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2120   -1.9292   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5128   -1.6159   -2.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899    3.2467   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027    4.2411   -0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5666    3.3444   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9260    3.1816   -0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
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  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 11 13  1  0  0  0  0
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 21  2  1  0  0  0  0
 31  3  1  0  0  0  0
 19  6  1  0  0  0  0
 16  7  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  5 38  1  0  0  0  0
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  6 40  1  6  0  0  0
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 29 67  1  0  0  0  0
 29 68  1  0  0  0  0
 29 69  1  0  0  0  0
 30 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010302

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@@]2([H])C([H])([H])[C@]2(C(=O)[C@](O[H])(C(=O)[C@]3(C(=O)OC([H])([H])[H])C2=C([H])[H])C([H])([H])[H])C([H])([H])[H])C1(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O6/c1-14-23(5)13-16-22(4)11-10-17(27)21(2,3)15(22)9-12-24(16,6)26(14,20(30)32-8)19(29)25(7,31)18(23)28/h15-17,27,31H,1,9-13H2,2-8H3/t15-,16+,17-,22-,23-,24+,25+,26+/m1/s1

> <INCHI_KEY>
NNHHTFDBMMPBSL-JFPRQHOTSA-N

> <FORMULA>
C26H38O6

> <MOLECULAR_WEIGHT>
446.584

> <EXACT_MASS>
446.266838944

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
48.1688943588134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2S,5S,7R,10S,11S,13R,15S)-7,15-dihydroxy-2,6,6,10,13,15-hexamethyl-17-methylidene-14,16-dioxotetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadecane-1-carboxylate

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
3.949570821333336

> <ALOGPS_LOGS>
-4.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.489433387285015

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.482276554751381

> <JCHEM_PKA_STRONGEST_BASIC>
-0.835121647808471

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
119.23769999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,5S,7R,10S,11S,13R,15S)-7,15-dihydroxy-2,6,6,10,13,15-hexamethyl-17-methylidene-14,16-dioxotetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadecane-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
   -3.5711   -0.9746    1.8828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5516   -0.3367    1.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7545    0.5952    2.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2785    0.6428    3.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2937    0.2037    2.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1277    0.0035    0.7655 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6262   -0.1592    0.5872 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1444   -1.4152    1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031    1.0045    1.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7663    1.0878    0.9584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1258    1.0023   -0.4647 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4169    0.4253   -0.5519 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2387    0.1913   -1.3418 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9075   -1.1247   -1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    0.9595   -2.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8656   -0.0313   -0.8840 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2652   -1.2351   -1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2118   -1.4023   -1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6840   -1.0501    0.0597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8228   -2.3208    0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0864   -0.4733   -0.0567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0260   -1.3962   -0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037   -2.5169   -1.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3759   -1.0583   -0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2896   -1.9331   -1.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238    0.8865   -0.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9846    1.0398   -1.8114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3248    2.1295    0.1792 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6437    3.3236   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6920    2.4153    0.1924 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1107    0.9690    0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8483   -1.3699    2.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8406   -2.3423    0.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497   -1.3709    1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2451    0.7750    2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7643    1.9449    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3387    0.3186    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1222    2.0673    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2821    2.0552   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9631    0.8546   -1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9742   -0.9015   -1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4396   -1.4605   -2.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8182   -1.9134   -1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2088    0.7205   -3.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0553    0.7859   -3.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0670    2.0428   -2.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337    0.8458   -1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4052   -1.1058   -2.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144   -2.1767   -1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018   -2.5048   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593   -0.8900   -2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8861   -2.5866    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2971   -2.3238    1.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -3.2108    0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8585   -2.9491   -1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2120   -1.9292   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5128   -1.6159   -2.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899    3.2467   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027    4.2411   -0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5666    3.3444   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9260    3.1816   -0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  1
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  6
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  6
 22 23  2  0
 22 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 28 30  1  1
 28 31  1  0
 31 32  2  0
 21  2  1  0
 31  3  1  0
 19  6  1  0
 16  7  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  6
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  6
 12 49  1  0
 14 50  1  0
 14 51  1  0
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 16 56  1  6
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 17 58  1  0
 18 59  1  0
 18 60  1  0
 20 61  1  0
 20 62  1  0
 20 63  1  0
 25 64  1  0
 25 65  1  0
 25 66  1  0
 29 67  1  0
 29 68  1  0
 29 69  1  0
 30 70  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.571  -0.975   1.883  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.552  -0.337   1.375  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.755   0.595   2.210  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.279   0.643   3.630  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.294   0.204   2.171  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.128   0.004   0.766  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.626  -0.159   0.587  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.144  -1.415   1.204  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.303   1.004   1.273  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.766   1.088   0.958  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.126   1.002  -0.465  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.417   0.425  -0.552  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.239   0.191  -1.342  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.908  -1.125  -1.773  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.154   0.960  -2.681  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.866  -0.031  -0.884  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.265  -1.235  -1.547  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.212  -1.402  -1.298  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.684  -1.050   0.060  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.823  -2.321   0.868  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.086  -0.473  -0.057  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.026  -1.396  -0.731  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.704  -2.517  -1.202  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.376  -1.058  -0.886  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.290  -1.933  -1.530  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.124   0.887  -0.618  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.985   1.040  -1.811  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.325   2.130   0.179  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.644   3.324  -0.478  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.692   2.415   0.192  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.857   1.941   1.581  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.540   2.898   2.265  0.00  0.00           O+0
HETATM   33  H   UNK     0      -3.841  -0.826   2.920  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.194  -1.670   1.335  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.674   1.299   4.276  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.208  -0.375   4.054  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.313   1.000   3.674  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.050  -0.605   2.870  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.247   1.112   2.576  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.111   0.969   0.222  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.848  -1.370   2.295  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.841  -2.342   0.729  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.250  -1.371   1.223  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.245   0.775   2.379  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.764   1.945   1.133  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.339   0.319   1.557  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.122   2.067   1.399  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.282   2.055  -0.847  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.963   0.855  -1.241  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.974  -0.902  -1.990  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.440  -1.460  -2.732  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.818  -1.913  -1.038  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.209   0.721  -3.185  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.055   0.786  -3.290  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.067   2.043  -2.376  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.234   0.846  -1.221  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.405  -1.106  -2.645  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.814  -2.177  -1.302  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.402  -2.505  -1.490  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.759  -0.890  -2.101  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.886  -2.587   1.087  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.297  -2.324   1.819  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.442  -3.211   0.283  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.859  -2.949  -1.520  0.00  0.00           H+0
HETATM   65  H   UNK     0      -6.212  -1.929  -0.894  0.00  0.00           H+0
HETATM   66  H   UNK     0      -5.513  -1.616  -2.572  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.690   3.247  -1.566  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.103   4.241  -0.073  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.567   3.344  -0.142  0.00  0.00           H+0
HETATM   70  H   UNK     0      -3.926   3.182  -0.384  0.00  0.00           H+0
CONECT    1    2   33   34                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4    5   31                                             
CONECT    4    3   35   36   37                                             
CONECT    5    3    6   38   39                                             
CONECT    6    5    7   19   40                                             
CONECT    7    6    8    9   16                                             
CONECT    8    7   41   42   43                                             
CONECT    9    7   10   44   45                                             
CONECT   10    9   11   46   47                                             
CONECT   11   10   12   13   48                                             
CONECT   12   11   49                                                       
CONECT   13   11   14   15   16                                             
CONECT   14   13   50   51   52                                             
CONECT   15   13   53   54   55                                             
CONECT   16   13   17    7   56                                             
CONECT   17   16   18   57   58                                             
CONECT   18   17   19   59   60                                             
CONECT   19   18   20   21    6                                             
CONECT   20   19   61   62   63                                             
CONECT   21   19   22   26    2                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   64   65   66                                             
CONECT   26   21   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28   67   68   69                                             
CONECT   30   28   70                                                       
CONECT   31   28   32    3                                                  
CONECT   32   31                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   10                                                            
CONECT   48   11                                                            
CONECT   49   12                                                            
CONECT   50   14                                                            
CONECT   51   14                                                            
CONECT   52   14                                                            
CONECT   53   15                                                            
CONECT   54   15                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   17                                                            
CONECT   58   17                                                            
CONECT   59   18                                                            
CONECT   60   18                                                            
CONECT   61   20                                                            
CONECT   62   20                                                            
CONECT   63   20                                                            
CONECT   64   25                                                            
CONECT   65   25                                                            
CONECT   66   25                                                            
CONECT   67   29                                                            
CONECT   68   29                                                            
CONECT   69   29                                                            
CONECT   70   30                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  146    0
END

RDKit          3D

70 73  0  0  0  0  0  0  0  0999 V2000
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   -2.5516   -0.3367    1.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7545    0.5952    2.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2785    0.6428    3.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2937    0.2037    2.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1277    0.0035    0.7655 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6262   -0.1592    0.5872 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1444   -1.4152    1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031    1.0045    1.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7663    1.0878    0.9584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1258    1.0023   -0.4647 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4169    0.4253   -0.5519 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2387    0.1913   -1.3418 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9075   -1.1247   -1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    0.9595   -2.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8656   -0.0313   -0.8840 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.0260   -1.3962   -0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2821    2.0552   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8585   -2.9491   -1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3
  2  3  1  0
  3  4  1  1
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  5  6  1  0
  6  7  1  0
  7  8  1  1
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  9 10  1  0
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 17 18  1  0
 18 19  1  0
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 21 22  1  6
 22 23  2  0
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 21 26  1  0
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 31 32  2  0
 21  2  1  0
 31  3  1  0
 19  6  1  0
 16  7  1  0
  1 33  1  0
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  4 35  1  0
  4 36  1  0
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  6 40  1  6
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 29 67  1  0
 29 68  1  0
 29 69  1  0
 30 70  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈O₆

Average Mass

446.5840 Da

Monoisotopic Mass

446.26684 Da

IUPAC Name

methyl (1R,2S,5S,7R,10S,11S,13R,15S)-7,15-dihydroxy-2,6,6,10,13,15-hexamethyl-17-methylidene-14,16-dioxotetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadecane-1-carboxylate

Traditional Name

methyl (1R,2S,5S,7R,10S,11S,13R,15S)-7,15-dihydroxy-2,6,6,10,13,15-hexamethyl-17-methylidene-14,16-dioxotetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadecane-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12C(=C)[C@@](C)(C[C@H]3[C@]4(C)CC[C@@H](O)C(C)(C)[C@H]4CC[C@]13C)C(=O)[C@](C)(O)C2=O

InChI Identifier

InChI=1S/C26H38O6/c1-14-23(5)13-16-22(4)11-10-17(27)21(2,3)15(22)9-12-24(16,6)26(14,20(30)32-8)19(29)25(7,31)18(23)28/h15-17,27,31H,1,9-13H2,2-8H3/t15-,16+,17-,22-,23-,24+,25+,26+/m1/s1

InChI Key

NNHHTFDBMMPBSL-JFPRQHOTSA-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
Penicillium	NPAtlas	21916432
Talaromyces ruber	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alpha-hydroxysteroids. These are steroids carrying a alpha-hydroxyl group at the 3-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

3-alpha-hydroxysteroids

Alternative Parents

Substituents

3-alpha-hydroxysteroid
Acyloin
Cyclic alcohol
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

methyl ester (CHEBI:69024 )
diol (CHEBI:69024 )
beta-diketone (CHEBI:69024 )
meroterpenoid (CHEBI:69024 )
cyclic terpene ketone (CHEBI:69024 )
carbopolycyclic compound (CHEBI:69024 )

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	3.42	ALOGPS
logP	3.95	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	11.48	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	119.24 m³·mol⁻¹	ChemAxon
Polarizability	48.17 Å³	ChemAxon
Number of Rings	4	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

NPAtlas ID

NPA012126

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28485232

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57391090

PDB ID

Not Available

ChEBI ID

69024

Good Scents ID

Not Available

References

General References

Showing NP-Card for Berkeleyone A (NP0010302)

MOL for NP0010302 (Berkeleyone A)

3D MOL for NP0010302 (Berkeleyone A)

3D SDF for NP0010302 (Berkeleyone A)

3D-SDF for NP0010302 (Berkeleyone A)

PDB for NP0010302 (Berkeleyone A)

3D PDB for NP0010302 (Berkeleyone A)

SMILES for NP0010302 (Berkeleyone A)

INCHI for NP0010302 (Berkeleyone A)

Structure for NP0010302 (Berkeleyone A)

3D Structure for NP0010302 (Berkeleyone A)