NP-MRD: Showing NP-Card for (4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid (NP0310155)

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Record Information

Version

2.0

Created at

2022-09-11 05:15:59 UTC

Updated at

2022-09-11 05:15:59 UTC

NP-MRD ID

NP0310155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid

Description

(4R)-4-[(1S,2R,5R,6R,9R,10R,13S,15S)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]Nonadec-18-en-5-yl]pentanoic acid belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid. (4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid is found in Mallotus macrostachyus. Based on a literature review very few articles have been published on (4R)-4-[(1S,2R,5R,6R,9R,10R,13S,15S)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]Nonadec-18-en-5-yl]pentanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112207162D          

 29 33  0  0  1  0            999 V2000
    7.1213    3.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5930    2.5572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4150    2.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7654    3.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5874    3.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9378    4.1911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0591    2.7673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427    1.8103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6410    1.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0770    0.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3301    0.8361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4651    0.8325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9691    0.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0405   -0.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3444    0.5405    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5107    0.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866    1.0806    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3617    1.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4961    1.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3169    1.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649    1.3010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4943    0.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7585    1.4241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1109    2.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9231    2.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4325    1.6547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7315    2.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0479    0.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7908    0.6315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  2  0  0  0  0
  5  7  1  0  0  0  0
  8  2  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  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  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  1  0  0  0
 15 28  1  6  0  0  0
 28 29  1  0  0  0  0
 12 29  1  6  0  0  0
M  END

     RDKit          3D

 65 69  0  0  0  0  0  0  0  0999 V2000
    3.8663   -1.6566    1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6768   -0.9109   -0.2083 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9538   -0.1092   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2293    0.8682    0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4817    1.5876    0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1295    1.3590   -0.7701 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0128    2.5694    1.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5442    0.0432   -0.2273 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5231    0.7004   -1.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583    0.9212   -1.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3614    0.5889   -0.6888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0880    0.4085   -0.7330 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5898   -0.5014   -1.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9378   -0.6195   -1.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5436    0.2819   -0.7158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0254    0.2939   -0.7757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5588    1.2662    0.2232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7531    0.8276    0.8085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5615    1.6189    1.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7538    0.4275    1.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0265   -0.2545    0.6257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3557   -1.7469    0.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5623   -0.0101    0.6550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7840   -1.1300    1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000   -0.9014    1.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1701   -0.5728   -0.1769 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0684   -1.7997   -1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0265    1.5395   -0.9242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7357    1.6230   -0.9639 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3921   -1.1185    1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9598   -1.6970    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5444   -2.7122    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5910   -1.5924   -1.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7982   -0.8294   -0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9332    0.4026   -1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3898    0.3738    1.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4500    1.6267    0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5938    3.4731    1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5968    0.8066    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9164   -0.0201   -2.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0943    1.6329   -1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9420    2.0307   -2.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7264    0.3331   -2.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724    1.4386    0.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666   -1.0135   -2.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007   -1.2617   -2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3796   -0.7526   -0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3596    0.4977   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8170    2.2151   -0.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1385    1.6047    1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9474    2.4812    1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1591    1.9484    2.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9752    0.8291    2.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3919   -0.2345    2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4537   -1.8559    0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8957   -2.0578    1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705   -2.2993   -0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3797    0.8954    1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533   -2.1155    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583   -1.1632    2.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566   -0.1888    1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711   -1.8918    1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991   -1.6633   -2.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8429   -2.5225   -0.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1034   -2.3110   -0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  5  6  2  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 26  1  0
 26 27  1  6
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  1  6
 21 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  0
 17 16  1  0
 15 16  1  1
 15 28  1  0
 28 29  1  0
 12 29  1  6
 12 13  1  0
 13 14  2  0
 26  8  1  0
 12 23  1  0
 12 11  1  0
 15 21  1  0
 14 15  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 27 63  1  0
 27 64  1  0
 27 65  1  0
 25 61  1  0
 25 62  1  0
 24 59  1  0
 24 60  1  0
 23 58  1  1
 22 55  1  0
 22 56  1  0
 22 57  1  0
 20 53  1  0
 20 54  1  0
 19 51  1  0
 19 52  1  0
 17 49  1  6
 18 50  1  0
 16 47  1  0
 16 48  1  0
 13 45  1  0
 14 46  1  0
M  END


  Mrv1652309112207162D          

 29 33  0  0  1  0            999 V2000
    7.1213    3.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5930    2.5572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4150    2.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7654    3.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5874    3.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9378    4.1911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0591    2.7673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427    1.8103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6410    1.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0770    0.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3301    0.8361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4651    0.8325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9691    0.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0405   -0.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3444    0.5405    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5107    0.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866    1.0806    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3617    1.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4961    1.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3169    1.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649    1.3010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4943    0.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7585    1.4241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1109    2.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9231    2.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4325    1.6547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7315    2.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0479    0.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7908    0.6315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  2  0  0  0  0
  5  7  1  0  0  0  0
  8  2  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  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  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  1  0  0  0
 15 28  1  6  0  0  0
 28 29  1  0  0  0  0
 12 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0310155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC(O)=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@H](O)C[C@@]33OO[C@@]21C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O5/c1-15(4-7-20(26)27)17-5-6-18-21(17,2)10-9-19-22(3)11-8-16(25)14-23(22)12-13-24(18,19)29-28-23/h12-13,15-19,25H,4-11,14H2,1-3H3,(H,26,27)/t15-,16+,17-,18-,19-,21-,22-,23-,24+/m1/s1

> <INCHI_KEY>
ACAXZYDRDZTBIF-MAVOBODLSA-N

> <FORMULA>
C24H36O5

> <MOLECULAR_WEIGHT>
404.547

> <EXACT_MASS>
404.256274259

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.132804581620555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2R,5R,6R,9R,10R,13S,15S)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-5-yl]pentanoic acid

> <JCHEM_LOGP>
3.9264432166666676

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.149025482692775

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.492225890900448

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7336162538743682

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
109.07370000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2R,5R,6R,9R,10R,13S,15S)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-5-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      13.293   6.037   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.174   4.773   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.708   4.904   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.362   6.298   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.896   6.429   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      18.550   7.823   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      18.777   5.166   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.520   3.379   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.263   2.031   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.210   0.907   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.816   1.561   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.202   1.554   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.276   0.045   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.542  -0.194   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.243   1.009   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.687   0.579   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.082   2.017   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.542   1.999   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.659   3.487   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.191   3.639   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.214   2.429   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.389   1.433   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.882   2.658   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.540   4.100   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.056   4.368   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.007   3.089   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.565   4.524   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.556   0.988   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.943   1.179   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   26                                                  
CONECT   12   11   13   23   29                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21   28                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   12   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    8   11   27                                             
CONECT   27   26                                                            
CONECT   28   15   29                                                       
CONECT   29   28   12                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
(4R)-4-[(1S,2R,5R,6R,9R,10R,13S,15S)-13-Hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0,.0,.0,]nonadec-18-en-5-yl]pentanoate	Generator

Chemical Formula

C₂₄H₃₆O₅

Average Mass

404.5470 Da

Monoisotopic Mass

404.25627 Da

IUPAC Name

(4R)-4-[(1S,2R,5R,6R,9R,10R,13S,15S)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-5-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,5R,6R,9R,10R,13S,15S)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-5-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CCC(O)=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@H](O)C[C@@]33OO[C@@]21C=C3

InChI Identifier

InChI=1S/C24H36O5/c1-15(4-7-20(26)27)17-5-6-18-21(17,2)10-9-19-22(3)11-8-16(25)14-23(22)12-13-24(18,19)29-28-23/h12-13,15-19,25H,4-11,14H2,1-3H3,(H,26,27)/t15-,16+,17-,18-,19-,21-,22-,23-,24+/m1/s1

InChI Key

ACAXZYDRDZTBIF-MAVOBODLSA-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
Mallotus macrostachyus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Bile acids, alcohols and derivatives

Alternative Parents

Substituents

Bile acid, alcohol, or derivatives
Ortho-dioxane
Cyclic alcohol
Secondary alcohol
Dialkyl peroxide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
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	3.93	ChemAxon
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.07 m³·mol⁻¹	ChemAxon
Polarizability	46.13 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

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

162866611

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid (NP0310155)

MOL for NP0310155 ((4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid)

3D MOL for NP0310155 ((4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid)

3D SDF for NP0310155 ((4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid)

3D-SDF for NP0310155 ((4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid)

PDB for NP0310155 ((4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid)

3D PDB for NP0310155 ((4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid)

SMILES for NP0310155 ((4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid)

INCHI for NP0310155 ((4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid)

Structure for NP0310155 ((4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid)

3D Structure for NP0310155 ((4r)-4-[(1s,2r,5r,6r,9r,10r,13s,15s)-13-hydroxy-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-5-yl]pentanoic acid)