NP-MRD: Showing NP-Card for [(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid (NP0150586)

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Record Information

Version

2.0

Created at

2022-09-02 06:43:58 UTC

Updated at

2022-09-02 06:43:58 UTC

NP-MRD ID

NP0150586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid

Description

[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid is found in Apis cerana.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08131209032D          

 37 40  0  0  0  0            999 V2000
   -2.9793   -5.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3119   -5.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7330   -5.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981   -4.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8192   -4.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7307   -4.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5729   -4.4035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2380   -3.4337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9770   -4.4403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -3.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -2.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820   -2.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169   -3.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495   -2.7994    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.4991   -1.7306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351   -2.0117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432   -1.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  9  4  1  1  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 17  7  1  0  0  0  0
 18 14  1  0  0  0  0
 19  5  2  0  0  0  0
 19 14  1  0  0  0  0
 20  5  1  0  0  0  0
 20 15  2  0  0  0  0
 21  6  2  0  0  0  0
 21 10  1  0  0  0  0
 22  6  1  0  0  0  0
 22 15  1  0  0  0  0
 16 22  1  1  0  0  0
 23  8  1  0  0  0  0
 24 11  1  0  0  0  0
 12 25  1  6  0  0  0
 13 26  1  6  0  0  0
 27 17  2  0  0  0  0
 30  4  1  0  0  0  0
 31  9  1  0  0  0  0
 31 16  1  0  0  0  0
 32 17  1  0  0  0  0
 33 28  1  0  0  0  0
 33 29  2  0  0  0  0
 33 30  1  0  0  0  0
 33 32  1  0  0  0  0
  9 34  1  6  0  0  0
 12 35  1  1  0  0  0
 13 36  1  1  0  0  0
 16 37  1  6  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -9.2912   -0.0560    0.0441 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0837    0.3133   -0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1252    1.0086   -1.7583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0162    1.3863   -2.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8165    1.0536   -1.9115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6671    0.3604   -0.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8394   -0.0135   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4504   -0.6780    0.9770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0888   -0.7214    1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6049   -0.0814   -0.0737 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2442    0.1093   -0.4358 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4087   -0.9345   -0.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439   -0.4464   -0.3412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0774   -1.1574    0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1924   -0.6529    0.1797 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3962   -1.4075    1.0675 P   0  0  2  0  0  5  0  0  0  0  0  0
    1.9733   -2.8699    1.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4446   -0.7495    2.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9058   -1.4053    0.3114 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529   -0.5457    0.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7331    0.2508    1.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2313   -0.5966   -0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3895   -1.5415   -1.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5898   -1.5846   -1.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6195   -0.7257   -1.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4578    0.1843   -0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4902    1.0403   -0.0345 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2385    0.2615    0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1783    1.2096    1.2970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1472    1.0281   -0.0728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9535    1.7647   -1.2494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5968    1.2672    0.3356 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0767    2.4789   -0.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1301    0.5500    0.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3417   -1.0012    0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0727    1.9507   -3.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469   -1.2103    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0693    0.2865   -1.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737   -0.6194   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3021   -0.9760    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0569   -2.2328    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4002    0.2432    2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5804   -2.1855   -1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7911   -2.2890   -2.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5751   -0.7769   -1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3855    1.7192    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4501    1.4373    1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4432    1.3270    0.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012    2.2545   -1.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6941    1.1022    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6119    2.8713    0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 14 15  1  0
 16 15  1  6
 16 18  1  0
 16 17  2  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 28  2  0
 28 29  1  0
 28 26  1  0
 26 27  1  0
 26 25  2  0
 25 24  1  0
 24 23  2  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
 11 32  1  0
 32 33  1  0
 32 30  1  0
 30 31  1  0
 30 13  1  0
 23 22  1  0
  6 10  1  0
  6  7  1  0
 13 39  1  6
 14 40  1  0
 14 41  1  0
 18 42  1  0
 29 47  1  0
 27 46  1  0
 25 45  1  0
 24 44  1  0
 23 43  1  0
 11 38  1  6
  9 37  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
 32 50  1  1
 33 51  1  0
 30 48  1  1
 31 49  1  0
M  END


  Mrv0541 08131209032D          

 37 40  0  0  0  0            999 V2000
   -2.9793   -5.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3119   -5.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7330   -5.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981   -4.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8192   -4.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7307   -4.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5729   -4.4035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2380   -3.4337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9770   -4.4403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -3.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -2.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820   -2.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169   -3.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495   -2.7994    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.4991   -1.7306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351   -2.0117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432   -1.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  9  4  1  1  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 17  7  1  0  0  0  0
 18 14  1  0  0  0  0
 19  5  2  0  0  0  0
 19 14  1  0  0  0  0
 20  5  1  0  0  0  0
 20 15  2  0  0  0  0
 21  6  2  0  0  0  0
 21 10  1  0  0  0  0
 22  6  1  0  0  0  0
 22 15  1  0  0  0  0
 16 22  1  1  0  0  0
 23  8  1  0  0  0  0
 24 11  1  0  0  0  0
 12 25  1  6  0  0  0
 13 26  1  6  0  0  0
 27 17  2  0  0  0  0
 30  4  1  0  0  0  0
 31  9  1  0  0  0  0
 31 16  1  0  0  0  0
 32 17  1  0  0  0  0
 33 28  1  0  0  0  0
 33 29  2  0  0  0  0
 33 30  1  0  0  0  0
 33 32  1  0  0  0  0
  9 34  1  6  0  0  0
 12 35  1  1  0  0  0
 13 36  1  1  0  0  0
 16 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0150586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(COP(O)(=O)OC(=O)C2=C(O)C(O)=CC=C2)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C17H18N5O10P/c18-14-10-15(20-5-19-14)22(6-21-10)16-13(26)12(25)9(31-16)4-30-33(28,29)32-17(27)7-2-1-3-8(23)11(7)24/h1-3,5-6,9,12-13,16,23-26H,4H2,(H,28,29)(H2,18,19,20)/t9-,12-,13-,16-/m1/s1

> <INCHI_KEY>
ULPVJDOMCRTJSN-RVXWVPLUSA-N

> <FORMULA>
C17H18N5O10P

> <MOLECULAR_WEIGHT>
483.3261

> <EXACT_MASS>
483.079128333

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
42.44883313547041

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(2,3-dihydroxybenzoyloxy)phosphinic acid

> <ALOGPS_LOGP>
-0.59

> <JCHEM_LOGP>
-2.5633935969859616

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.251717743095863

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.7783191307957664

> <JCHEM_PKA_STRONGEST_BASIC>
4.9884435819175

> <JCHEM_POLAR_SURFACE_AREA>
232.59999999999994

> <JCHEM_REFRACTIVITY>
107.85229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   34  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1    8                                                       
CONECT    4    9   30                                                       
CONECT    5   19   20                                                       
CONECT    6   21   22                                                       
CONECT    7    2   11   17                                                  
CONECT    8    3   11   23                                                  
CONECT    9    4   12   31   34                                             
CONECT   10   14   15   21                                                  
CONECT   11    7    8   24                                                  
CONECT   12    9   13   25   35                                             
CONECT   13   12   16   26   36                                             
CONECT   14   10   18   19                                                  
CONECT   15   10   20   22                                                  
CONECT   16   13   22   31   37                                             
CONECT   17    7   27   32                                                  
CONECT   18   14                                                            
CONECT   19    5   14                                                       
CONECT   20    5   15                                                       
CONECT   21    6   10                                                       
CONECT   22    6   15   16                                                  
CONECT   23    8                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   13                                                            
CONECT   27   17                                                            
CONECT   28   33                                                            
CONECT   29   33                                                            
CONECT   30    4   33                                                       
CONECT   31    9   16                                                       
CONECT   32   17   33                                                       
CONECT   33   28   29   30   32                                             
CONECT   34    9                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   16                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(2,3-Dihydroxybenzoyl)adenylate	ChEBI
Adenosine 5'-(2,3-dihydroxybenzoyl hydrogen phosphate)	ChEBI
Adenosine 5'-(2,3-dihydroxybenzoyl hydrogen phosphoric acid)	Generator

Chemical Formula

C₁₇H₁₈N₅O₁₀P

Average Mass

483.3261 Da

Monoisotopic Mass

483.07913 Da

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(2,3-dihydroxybenzoyloxy)phosphinic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(COP(O)(=O)OC(=O)C2=C(O)C(O)=CC=C2)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C17H18N5O10P/c18-14-10-15(20-5-19-14)22(6-21-10)16-13(26)12(25)9(31-16)4-30-33(28,29)32-17(27)7-2-1-3-8(23)11(7)24/h1-3,5-6,9,12-13,16,23-26H,4H2,(H,28,29)(H2,18,19,20)/t9-,12-,13-,16-/m1/s1

InChI Key

ULPVJDOMCRTJSN-RVXWVPLUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside monophosphates

Alternative Parents

Substituents

Purine ribonucleoside monophosphate
Pentose-5-phosphate
Pentose phosphate
N-glycosyl compound
Glycosyl compound
Salicylic acid or derivatives
6-aminopurine
Pentose monosaccharide
Monosaccharide phosphate
Imidazopyrimidine
Purine
Benzoic acid or derivatives
Catechol
Benzoyl
Acyl phosphate
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monoalkyl phosphate
Aminopyrimidine
Monocyclic benzene moiety
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Imidolactam
Benzenoid
Alkyl phosphate
Phosphoric acid ester
Pyrimidine
Azole
Tetrahydrofuran
Heteroaromatic compound
Imidazole
Vinylogous acid
Secondary alcohol
Amino acid or derivatives
1,2-diol
Carboxylic acid salt
Azacycle
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Amine
Organic salt
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Primary amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

adenosine 5'-phosphate (CHEBI:15572 )

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	-0.59	ALOGPS
logP	-2.6	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.78	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	232.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	107.85 m³·mol⁻¹	ChemAxon
Polarizability	42.45 Å³	ChemAxon
Number of Rings	4	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

C04030

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440201

PDB ID

Not Available

ChEBI ID

15572

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid (NP0150586)

MOL for NP0150586 ([(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid)

3D MOL for NP0150586 ([(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid)

3D SDF for NP0150586 ([(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid)

3D-SDF for NP0150586 ([(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid)

PDB for NP0150586 ([(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid)

3D PDB for NP0150586 ([(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid)

SMILES for NP0150586 ([(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid)

INCHI for NP0150586 ([(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid)

Structure for NP0150586 ([(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid)

3D Structure for NP0150586 ([(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid)