NP-MRD: Showing NP-Card for [14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid (NP0322657)

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Record Information

Version

2.0

Created at

2022-09-12 01:33:03 UTC

Updated at

2022-09-12 01:33:03 UTC

NP-MRD ID

NP0322657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid

Description

[14-({4,5-Dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icos-18-en-16-yl]oxidanesulfonic acid belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. [14-({4,5-Dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icos-18-en-16-yl]oxidanesulfonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231523502D          

 66 73  0  0  0  0            999 V2000
    1.7004   -1.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -0.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293   -1.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339   -2.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8507   -2.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3696   -3.2172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1820   -1.7915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030   -1.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7151   -1.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3313   -2.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1513   -1.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4826   -1.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3026   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7913   -1.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6112   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0999   -2.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7686   -3.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9486   -3.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6173   -3.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1060   -4.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9260   -4.4822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4147   -5.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0834   -5.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5720   -6.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2634   -5.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9321   -6.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7747   -5.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9547   -5.4195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6234   -6.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1121   -6.8398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7808   -7.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2695   -8.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9608   -7.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6295   -8.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4721   -7.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6521   -7.1123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8034   -6.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3148   -5.6012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4600   -2.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1286   -3.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6400   -2.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3087   -3.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4887   -3.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -2.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5915   -3.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791   -2.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4669   -3.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3853   -3.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9199   -2.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4086   -2.8803    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7439   -3.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0733   -2.3916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8973   -3.5450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4079   -0.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911    0.3283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6864    1.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9696    1.5618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9650    2.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2482    2.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    3.6202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    2.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6725    3.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939    2.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    2.8113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3986    1.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1153    1.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  0  0  0  0
 18 39  1  0  0  0  0
 14 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 11 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 10 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
  8 46  1  0  0  0  0
 46 47  1  0  0  0  0
  5 47  1  0  0  0  0
 47 48  1  0  0  0  0
 16 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  2  0  0  0  0
 50 53  1  0  0  0  0
  2 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 58 61  1  0  0  0  0
 61 62  1  0  0  0  0
 61 63  1  0  0  0  0
 63 64  1  0  0  0  0
 63 65  1  0  0  0  0
 56 65  1  0  0  0  0
 65 66  1  0  0  0  0
M  END

     RDKit          3D

138145  0  0  0  0  0  0  0  0999 V2000
  -11.7191   -0.7823    0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2808   -1.2835    0.6681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.5861   -0.6184   -0.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2080   -0.8167   -0.2187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4984   -0.2891   -1.2615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6227    0.7504   -0.8783 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2347    0.3002   -1.3199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2898    1.2779   -1.1497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    1.0041   -0.2390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3809    2.0429    0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3465    3.4616    0.3232 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6168    4.0127    0.2371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6670    5.4743    1.0592 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.2078    6.6079    0.1522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0795    5.7358    1.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6317    5.4771    2.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7179    3.5039   -1.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6711    2.4750   -1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4481    2.8035   -1.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348    1.7898   -1.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4783    0.6325   -0.8041 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5826    0.5918    0.2234 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8702    0.1794   -0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035   -0.2107    0.7425 C   0  0  2  0  0  0  0  0  0  0  0  0
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    7.4068   -3.6690    3.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9834   -2.5252    1.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0325    1.9477   -1.6821 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004231523502D          

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M  END
> <DATABASE_ID>
NP0322657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1(O)OC2CC3C4CC=C5CC(CC(OC6OCC(O)C(O)C6OC6OC(C)C(O)C(O)C6O)C5(C)C4CCC3(C)C2C1C)OS(O)(=O)=O)COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C44H72O21S/c1-18(16-58-39-36(52)35(51)33(49)28(15-45)61-39)8-11-44(54)19(2)30-27(64-44)14-25-23-7-6-21-12-22(65-66(55,56)57)13-29(43(21,5)24(23)9-10-42(25,30)4)62-41-38(32(48)26(46)17-59-41)63-40-37(53)34(50)31(47)20(3)60-40/h6,18-20,22-41,45-54H,7-17H2,1-5H3,(H,55,56,57)

> <INCHI_KEY>
KQYLGZBUZREODJ-UHFFFAOYSA-N

> <FORMULA>
C44H72O21S

> <MOLECULAR_WEIGHT>
969.1

> <EXACT_MASS>
968.428680512

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
138

> <JCHEM_AVERAGE_POLARIZABILITY>
100.05356171829817

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.79

> <JCHEM_LOGP>
-1.118279451666666

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.572198179531762

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.5848937197186972

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483772987566265

> <JCHEM_POLAR_SURFACE_AREA>
330.51

> <JCHEM_REFRACTIVITY>
224.97340000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       3.174  -2.467   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.503  -1.690   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.841  -2.452   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.850  -3.992   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.188  -4.755   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.290  -6.006   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.806  -3.344   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.339  -3.497   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.668  -2.719   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.818  -3.743   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.349  -3.573   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.968  -2.163   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.498  -1.993   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.410  -3.234   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.941  -3.065   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.853  -4.305   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.235  -5.716   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.704  -5.885   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.086  -7.296   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.998  -8.536   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      18.529  -8.367   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      19.441  -9.608   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.822 -11.018   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      19.734 -12.259   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      17.292 -11.188   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.673 -12.598   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      16.379  -9.947   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.849 -10.116   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.230 -11.527   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      15.143 -12.768   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.524 -14.178   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.436 -15.419   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.993 -14.348   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.375 -15.758   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      12.081 -13.107   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.551 -13.276   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      12.700 -11.696   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.788 -10.456   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      15.792  -4.645   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      15.173  -6.055   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      14.261  -4.814   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.643  -6.225   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.112  -6.394   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.200  -5.153   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      10.438  -6.491   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.668  -5.001   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       8.338  -5.779   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       8.186  -7.311   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      20.384  -4.136   0.000  0.00  0.00           O+0
HETATM   50  S   UNK     0      21.296  -5.377   0.000  0.00  0.00           S+0
HETATM   51  O   UNK     0      20.055  -6.289   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      22.537  -4.464   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      22.208  -6.617   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       4.495  -0.150   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       3.157   0.613   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       3.148   2.153   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       1.810   2.915   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       1.801   4.455   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       0.463   5.218   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       0.455   6.758   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0       3.131   5.233   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       3.122   6.773   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       4.469   4.470   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       5.798   5.248   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0       4.477   2.930   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0       5.815   2.168   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   54                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   47                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   46                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   44                                                  
CONECT   11   10   12   41                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   39                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   49                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   39                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   29   38                                                  
CONECT   38   37                                                            
CONECT   39   18   14   40   41                                             
CONECT   40   39                                                            
CONECT   41   39   11   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   10   45   46                                             
CONECT   45   44                                                            
CONECT   46   44    8   47                                                  
CONECT   47   46    5   48                                                  
CONECT   48   47                                                            
CONECT   49   16   50                                                       
CONECT   50   49   51   52   53                                             
CONECT   51   50                                                            
CONECT   52   50                                                            
CONECT   53   50                                                            
CONECT   54    2   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57   65                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59   61                                                  
CONECT   59   58   60                                                       
CONECT   60   59                                                            
CONECT   61   58   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   64   65                                                  
CONECT   64   63                                                            
CONECT   65   63   56   66                                                  
CONECT   66   65                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  146    0
END

View in JSmol

Synonyms

Value	Source
[14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0,.0,.0,]icos-18-en-16-yl]oxidanesulfonate	Generator
[14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0,.0,.0,]icos-18-en-16-yl]oxidanesulphonate	Generator
[14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0,.0,.0,]icos-18-en-16-yl]oxidanesulphonic acid	Generator
[14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonate	Generator
[14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulphonate	Generator
[14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulphonic acid	Generator

Chemical Formula

C₄₄H₇₂O₂₁S

Average Mass

969.1000 Da

Monoisotopic Mass

968.42868 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(CCC1(O)OC2CC3C4CC=C5CC(CC(OC6OCC(O)C(O)C6OC6OC(C)C(O)C(O)C6O)C5(C)C4CCC3(C)C2C1C)OS(O)(=O)=O)COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C44H72O21S/c1-18(16-58-39-36(52)35(51)33(49)28(15-45)61-39)8-11-44(54)19(2)30-27(64-44)14-25-23-7-6-21-12-22(65-66(55,56)57)13-29(43(21,5)24(23)9-10-42(25,30)4)62-41-38(32(48)26(46)17-59-41)63-40-37(53)34(50)31(47)20(3)60-40/h6,18-20,22-41,45-54H,7-17H2,1-5H3,(H,55,56,57)

InChI Key

KQYLGZBUZREODJ-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxo-delta-1,4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
6-hydroxysteroid
Hydroxysteroid
Delta-1,4-steroid
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
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	-0.79	ALOGPS
logP	-1.1	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	-1.6	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	330.51 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	224.97 m³·mol⁻¹	ChemAxon
Polarizability	100.05 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid (NP0322657)

MOL for NP0322657 ([14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid)

3D MOL for NP0322657 ([14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid)

3D SDF for NP0322657 ([14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid)

3D-SDF for NP0322657 ([14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid)

PDB for NP0322657 ([14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid)

3D PDB for NP0322657 ([14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid)

SMILES for NP0322657 ([14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid)

INCHI for NP0322657 ([14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid)

Structure for NP0322657 ([14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid)

3D Structure for NP0322657 ([14-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxidanesulfonic acid)