NP-MRD: Showing NP-Card for (2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid (NP0307301)

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Record Information

Version

2.0

Created at

2022-09-11 00:20:06 UTC

Updated at

2022-09-11 00:20:07 UTC

NP-MRD ID

NP0307301

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid

Description

{[5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[(2-{5,11-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl}-6-hydroxy-6-methylheptan-3-yl)oxy]phosphinic acid belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. (2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid is found in Locusta migratoria. {[5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[(2-{5,11-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl}-6-hydroxy-6-methylheptan-3-yl)oxy]phosphinic acid is a strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191515262D          

 54 60  0  0  0  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -1.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -1.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4585   -1.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0053   -0.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.3082   -4.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339   -2.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3962   -3.4536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025   -4.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7198   -3.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2914   -4.5869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0338   -4.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9210   -3.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5158   -2.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1088   -3.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7490   -2.5222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613   -4.6161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8742   -5.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6863   -5.5786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0753   -4.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8763   -4.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4480   -5.2483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1056   -3.8609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5340   -3.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7330   -3.4638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5037   -4.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  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
 19 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 23 32  1  0  0  0  0
 26 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 42 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 38 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 33 53  1  0  0  0  0
 36 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END


  Mrv1533004191515262D          

 54 60  0  0  0  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -1.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -1.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4585   -1.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0053   -0.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.3082   -4.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339   -2.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3962   -3.4536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025   -4.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7198   -3.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2914   -4.5869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0338   -4.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9210   -3.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5158   -2.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1088   -3.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7490   -2.5222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613   -4.6161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8742   -5.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6863   -5.5786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0753   -4.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8763   -4.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4480   -5.2483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1056   -3.8609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5340   -3.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7330   -3.4638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5037   -4.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  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
 19 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 23 32  1  0  0  0  0
 26 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 42 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 38 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 33 53  1  0  0  0  0
 36 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307301

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C(CCC(C)(C)O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=NC2=C(N)N=CN=C12)C1CCC2(O)C3=CC(=O)C4CC(O)CCC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C37H56N5O11P/c1-19(21-8-13-37(48)23-15-25(44)24-14-20(43)6-11-35(24,4)22(23)7-12-36(21,37)5)26(9-10-34(2,3)47)53-54(49,50)51-16-27-29(45)30(46)33(52-27)42-18-41-28-31(38)39-17-40-32(28)42/h15,17-22,24,26-27,29-30,33,43,45-48H,6-14,16H2,1-5H3,(H,49,50)(H2,38,39,40)

> <INCHI_KEY>
UQJHEPIKTHIJFC-UHFFFAOYSA-N

> <FORMULA>
C37H56N5O11P

> <MOLECULAR_WEIGHT>
777.853

> <EXACT_MASS>
777.371394641

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
79.37360695740719

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[(2-{5,11-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-14-yl}-6-hydroxy-6-methylheptan-3-yl)oxy]phosphinic acid

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
-1.2245783431335953

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.436398781102355

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.881077010793756

> <JCHEM_PKA_STRONGEST_BASIC>
4.988619922118634

> <JCHEM_POLAR_SURFACE_AREA>
252.82999999999998

> <JCHEM_REFRACTIVITY>
196.35270000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2-{5,11-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-14-yl}-6-hydroxy-6-methylheptan-3-yl)oxyphosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.571  -2.589   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.997  -2.008   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.856  -3.169   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.010  -1.162   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.312  -6.868   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0       0.786  -6.657   0.000  0.00  0.00           P+0
HETATM   12  O   UNK     0       0.575  -8.183   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.997  -5.132   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.740  -6.447   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.685  -7.663   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.210  -7.452   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.277  -8.562   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.663  -7.890   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.452  -6.365   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.563  -5.298   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.937  -6.094   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.265  -4.708   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      -7.021  -8.617   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -7.232 -10.142   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      -8.748 -10.413   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -9.474  -9.055   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.969  -8.686   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0     -12.036  -9.797   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0     -11.397  -7.207   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0     -10.330  -6.097   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      -8.835  -6.466   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      -8.407  -7.945   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   16   22                                                  
CONECT   22   21                                                            
CONECT   23   18   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   23   26                                                  
CONECT   33    2   34   53                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38   53                                             
CONECT   37   36                                                            
CONECT   38   36   39   50                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   48                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   42   49   50                                             
CONECT   49   48                                                            
CONECT   50   48   38   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   33   36   54                                             
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  120    0
END

View in JSmol

Synonyms

Value	Source
{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[(2-{5,11-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0,.0,]heptadec-9-en-14-yl}-6-hydroxy-6-methylheptan-3-yl)oxy]phosphinate	Generator
{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[(2-{5,11-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-14-yl}-6-hydroxy-6-methylheptan-3-yl)oxy]phosphinate	Generator

Chemical Formula

C₃₇H₅₆N₅O₁₁P

Average Mass

777.8530 Da

Monoisotopic Mass

777.37139 Da

IUPAC Name

{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[(2-{5,11-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-14-yl}-6-hydroxy-6-methylheptan-3-yl)oxy]phosphinic acid

Traditional Name

[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2-{5,11-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-14-yl}-6-hydroxy-6-methylheptan-3-yl)oxyphosphinic acid

CAS Registry Number

Not Available

SMILES

CC(C(CCC(C)(C)O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=NC2=C(N)N=CN=C12)C1CCC2(O)C3=CC(=O)C4CC(O)CCC4(C)C3CCC12C

InChI Identifier

InChI=1S/C37H56N5O11P/c1-19(21-8-13-37(48)23-15-25(44)24-14-20(43)6-11-35(24,4)22(23)7-12-36(21,37)5)26(9-10-34(2,3)47)53-54(49,50)51-16-27-29(45)30(46)33(52-27)42-18-41-28-31(38)39-17-40-32(28)42/h15,17-22,24,26-27,29-30,33,43,45-48H,6-14,16H2,1-5H3,(H,49,50)(H2,38,39,40)

InChI Key

UQJHEPIKTHIJFC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Locusta migratoria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Cholesterol-skeleton
Cholesterol
Steroidal glycoside
Cholestane-skeleton
Ecdysteroid
Trihydroxy bile acid, alcohol, or derivatives
25-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
Purine ribonucleoside monophosphate
Bile acid, alcohol, or derivatives
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-hydroxy-delta-7-steroid
6-oxosteroid
3-hydroxysteroid
Delta-7-steroid
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
6-aminopurine
Purine
Imidazopyrimidine
Cyclohexenone
Aminopyrimidine
Dialkyl phosphate
Pyrimidine
Phosphoric acid ester
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Imidolactam
Tertiary alcohol
Imidazole
Cyclic alcohol
Azole
Tetrahydrofuran
Heteroaromatic compound
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Azacycle
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Alcohol
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.42	ALOGPS
logP	-1.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	1.88	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	252.83 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	196.35 m³·mol⁻¹	ChemAxon
Polarizability	79.37 Å³	ChemAxon
Number of Rings	7	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

73830896

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid (NP0307301)

MOL for NP0307301 ((2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid)

3D MOL for NP0307301 ((2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid)

3D SDF for NP0307301 ((2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid)

3D-SDF for NP0307301 ((2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid)

PDB for NP0307301 ((2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid)

3D PDB for NP0307301 ((2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid)

SMILES for NP0307301 ((2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid)

INCHI for NP0307301 ((2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid)

Structure for NP0307301 ((2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid)

3D Structure for NP0307301 ((2-{3a,7-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-6-methylheptan-3-yl)oxy([5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid)