NP-MRD: Showing NP-Card for methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate (NP0158589)

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Record Information

Version

2.0

Created at

2022-09-02 16:12:30 UTC

Updated at

2022-09-02 16:12:30 UTC

NP-MRD ID

NP0158589

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate

Description

Methyl (1R,2S,4R,5S,7S,9S,12R,14S,15R)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]Icosane-5-carboxylate belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate is found in Sinularia erecta. Based on a literature review very few articles have been published on methyl (1R,2S,4R,5S,7S,9S,12R,14S,15R)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]Icosane-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022218122D          

 31 35  0  0  1  0            999 V2000
    9.0100    1.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1985    1.4171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6639    2.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9409    2.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8525    1.8968    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7893    2.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0454    3.0760    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0852    1.1053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4044    0.6393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0762    0.1605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1291   -0.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4716   -0.8621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7690   -1.2946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1406   -0.7601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3646   -1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4548    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2774   -0.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119    0.5682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3003   -0.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0676    0.6445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4657    1.2088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163    1.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183    2.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6349    1.8528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0108    1.3132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7902    1.0426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5061    2.4211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3014    3.2203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3287    2.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0278    1.9200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7508    1.1429    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  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  2  0  0  0  0
 14 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  6  0  0  0
 20 26  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  1  0  0  0
  9 31  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
    2.9332    1.2361    3.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2155    0.5476    2.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    0.3559    0.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424    0.8088    0.6166 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -0.3327   -0.2716 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0213   -1.5638   -0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6511   -1.1170   -0.9557 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8622   -0.8443   -0.0624 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -1.2684   -1.3006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8123   -0.5771   -1.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697   -2.6610   -1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3908   -2.5532   -0.2615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2394   -1.5126   -0.5916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628   -1.0507    0.5245 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2456   -1.7259    0.5481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563   -1.4262    1.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9631   -2.2747    1.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0252   -2.6046    1.7209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1154    0.4641    0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9219    1.2740    0.6532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6790    2.1440    1.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3975    2.6818    1.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4376    3.0748    2.2505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3139    2.6585   -0.0494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4493    3.5435   -0.4468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5787    2.1919   -0.5081 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8924    2.6227   -0.8541 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0256    3.0455   -0.1040 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    1.5390   -1.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9791    0.3584   -1.5757 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3323   -0.8533   -2.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6583    0.5786    3.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5288    2.0523    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2639    1.6974    3.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294   -2.3356   -1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1458   -2.0591    0.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9466   -0.7648   -2.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4590   -3.4186   -0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5947   -2.9182   -2.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326   -3.4950   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7025   -1.6676    1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0633   -2.7821    0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8242   -1.2552   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6006   -0.6024    2.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6566   -2.0681    2.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750    0.6764   -0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8635    0.6046    1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    0.5538    0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782    1.7683   -1.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    3.5723   -1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345    3.8700    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7104    2.0556   -2.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070    1.3150   -2.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    0.3847   -2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8519   -0.4033   -3.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0723   -1.5405   -2.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  1
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  6
  9 31  1  0
 31 30  1  0
 30 29  1  0
 29 27  1  0
 27 28  1  0
 27 24  1  0
 24 25  1  6
 25 26  1  0
 26 20  1  0
 20 19  1  0
 19 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 12  1  0
 12 11  1  0
 12 13  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 30  5  1  0
 26 24  1  0
 13 14  1  0
 11  9  1  0
 22 24  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  6 36  1  0
 10 37  1  0
 31 55  1  0
 31 56  1  0
 30 54  1  6
 29 52  1  0
 29 53  1  0
 27 50  1  6
 28 51  1  0
 26 49  1  6
 20 48  1  1
 19 46  1  0
 19 47  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 12 40  1  1
 11 38  1  0
 11 39  1  0
M  END


  Mrv1652309022218122D          

 31 35  0  0  1  0            999 V2000
    9.0100    1.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1985    1.4171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6639    2.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9409    2.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8525    1.8968    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7893    2.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0454    3.0760    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0852    1.1053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4044    0.6393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0762    0.1605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1291   -0.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4716   -0.8621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7690   -1.2946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1406   -0.7601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3646   -1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4548    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2774   -0.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119    0.5682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3003   -0.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0676    0.6445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4657    1.2088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163    1.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183    2.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6349    1.8528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0108    1.3132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7902    1.0426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5061    2.4211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3014    3.2203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3287    2.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0278    1.9200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7508    1.1429    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  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  2  0  0  0  0
 14 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  6  0  0  0
 20 26  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  1  0  0  0
  9 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(CCl)O[C@@]2(O)C[C@H]1C[C@H](O)[C@@]13O[C@@H]1[C@H](C[C@]1(C)CC(=O)[C@H](C2)O1)OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H25ClO10/c1-17-5-10(22)11(29-17)7-18(26)4-9(19(8-21,31-18)15(24)27-2)3-13(23)20-14(30-20)12(6-17)28-16(20)25/h9,11-14,23,26H,3-8H2,1-2H3/t9-,11+,12+,13+,14-,17+,18+,19+,20-/m1/s1

> <INCHI_KEY>
YKWUYIMJNDVFPG-JKFCAPMCSA-N

> <FORMULA>
C20H25ClO10

> <MOLECULAR_WEIGHT>
460.86

> <EXACT_MASS>
460.1136247

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.74870793105552

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2S,4R,5S,7S,9S,12R,14S,15R)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1^{4,7}.1^{9,12}.0^{1,15}]icosane-5-carboxylate

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
0.23195318866666703

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.645118593505703

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.91208652553536

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3949901949484422

> <JCHEM_POLAR_SURFACE_AREA>
141.12

> <JCHEM_REFRACTIVITY>
99.61089999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,4R,5S,7S,9S,12R,14S,15R)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1^{4,7}.1^{9,12}.0^{1,15}]icosane-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      16.819   2.923   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.304   2.645   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.306   3.818   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      14.823   5.269   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.791   3.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.673   5.076   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      11.285   5.742   0.000  0.00  0.00          Cl+0
HETATM    8  O   UNK     0      13.226   2.063   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.955   1.193   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.209   0.300   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.441  -0.679   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.214  -1.609   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.902  -2.417   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.729  -1.419   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.147  -2.901   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.316   0.005   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.851  -0.112   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.849   1.061   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.161  -0.274   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.726   1.203   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.603   2.256   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.257   3.650   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.514   4.999   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.785   3.459   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.620   2.451   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.075   1.946   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.411   4.519   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.029   6.011   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.947   4.402   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.252   3.584   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.735   2.133   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    8   30                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11   31                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   19                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   27                                             
CONECT   25   24   26                                                       
CONECT   26   25   20   24                                                  
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29    5   31                                                  
CONECT   31   30    9                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,2S,4R,5S,7S,9S,12R,14S,15R)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1,.1,.0,]icosane-5-carboxylic acid	Generator

Chemical Formula

C₂₀H₂₅ClO₁₀

Average Mass

460.8600 Da

Monoisotopic Mass

460.11362 Da

IUPAC Name

methyl (1R,2S,4R,5S,7S,9S,12R,14S,15R)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1^{4,7}.1^{9,12}.0^{1,15}]icosane-5-carboxylate

Traditional Name

methyl (1R,2S,4R,5S,7S,9S,12R,14S,15R)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1^{4,7}.1^{9,12}.0^{1,15}]icosane-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(CCl)O[C@@]2(O)C[C@H]1C[C@H](O)[C@@]13O[C@@H]1[C@H](C[C@]1(C)CC(=O)[C@H](C2)O1)OC3=O

InChI Identifier

InChI=1S/C20H25ClO10/c1-17-5-10(22)11(29-17)7-18(26)4-9(19(8-21,31-18)15(24)27-2)3-13(23)20-14(30-20)12(6-17)28-16(20)25/h9,11-14,23,26H,3-8H2,1-2H3/t9-,11+,12+,13+,14-,17+,18+,19+,20-/m1/s1

InChI Key

YKWUYIMJNDVFPG-JKFCAPMCSA-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
Sinularia erecta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Para-dioxane
Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Methyl ester
Oxolane
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organohalogen compound
Organic oxide
Organochloride
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alkyl chloride
Hydrocarbon derivative
Alkyl halide
Alcohol
Aldehyde
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.1	ALOGPS
logP	0.23	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	141.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.61 m³·mol⁻¹	ChemAxon
Polarizability	42.75 Å³	ChemAxon
Number of Rings	5	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10481262

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21778545

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate (NP0158589)

MOL for NP0158589 (methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate)

3D MOL for NP0158589 (methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate)

3D SDF for NP0158589 (methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate)

3D-SDF for NP0158589 (methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate)

PDB for NP0158589 (methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate)

3D PDB for NP0158589 (methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate)

SMILES for NP0158589 (methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate)

INCHI for NP0158589 (methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate)

Structure for NP0158589 (methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate)

3D Structure for NP0158589 (methyl (1r,2s,4r,5s,7s,9s,12r,14s,15r)-5-(chloromethyl)-2,7-dihydroxy-12-methyl-10,17-dioxo-6,16,18,19-tetraoxapentacyclo[12.2.2.1⁴,⁷.1⁹,¹².0¹,¹⁵]icosane-5-carboxylate)