NP-MRD: Showing NP-Card for Doronine (NP0051158)

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Record Information

Version

2.0

Created at

2022-04-27 22:34:05 UTC

Updated at

2022-04-27 22:34:05 UTC

NP-MRD ID

NP0051158

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Doronine

Description

(1R,4R,6R,7R)-4-[(1R)-1-chloroethyl]-4-hydroxy-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]Heptadec-11-en-7-yl acetate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Doronine is found in Doronicum macrophyllum, Jacobaea ambigua, Senecio doronicum, Senecio inaequidens and Senecio othonnae. Based on a literature review very few articles have been published on (1R,4R,6R,7R)-4-[(1R)-1-chloroethyl]-4-hydroxy-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]Heptadec-11-en-7-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200342D          

 31 32  0  0  1  0            999 V2000
    0.9325   -1.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7556   -1.0722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694   -0.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9520   -0.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2190   -1.1521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8559   -1.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0754   -2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4725   -1.7011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8356   -2.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587   -2.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0218   -3.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -1.8130    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9418   -1.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018   -1.1841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0387   -0.4433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2156   -0.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2460   -1.2118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525    0.3534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0294    0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664   -0.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233    0.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8764    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9610    1.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5447    0.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2249   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2918   -2.6196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6502   -2.4440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3696   -3.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4624   -2.2991    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0424   -1.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  1  9  1  0  0  0  0
  9 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
 13 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  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 16 21  1  1  0  0  0
 16 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 15 26  1  6  0  0  0
 13 27  1  1  0  0  0
 13 28  1  6  0  0  0
 28 29  1  0  0  0  0
 28 30  1  6  0  0  0
  6 31  1  0  0  0  0
M  END

     RDKit          3D

 61 62  0  0  0  0  0  0  0  0999 V2000
    6.2325   -1.0252    1.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0124   -1.0376    0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0896   -0.7897   -1.0274 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779   -1.3225    0.6759 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5845   -1.3675   -0.0045 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4843   -2.4849   -1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5055   -1.6840    1.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -2.0381    2.1903 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1903   -1.6235    0.8052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7293   -2.2385   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8560   -1.3741   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8978   -2.2412   -0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3731   -2.2289   -0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7928   -1.0344    0.5325 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2430   -1.0703    0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3924    0.1727   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148    0.8985    0.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2094    1.2576   -0.0823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2264    1.8722    0.6140 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0260    1.6802    1.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4199    1.1566    2.1281 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1697    2.0913    0.1568 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8318    2.3595   -1.1420 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659    3.4244    0.7436 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5699    4.4666    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1115    3.2371    2.4515 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3313    1.1149    0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1313   -0.0959   -0.6610 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6175    0.1516   -2.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137    0.0160   -0.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4150    0.4377   -1.9757 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1178   -0.7146    0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2918   -2.0552    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9706   -0.3529    1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900   -2.2158   -1.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4555   -2.7140   -1.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1810   -3.4255   -0.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412   -3.0997    0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2938   -2.8403   -0.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5213   -3.2389   -0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8995   -2.3339   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6648   -3.0915    0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6772   -1.4399   -0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5981   -1.6888    1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6343   -0.0374    0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491   -0.0836   -1.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2702    0.8315   -0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8764    1.8346    1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0741    0.2453    1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573    2.0134   -0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595    2.7246   -1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5556    3.7876    0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865    4.7313   -0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9056    5.3286    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3645    4.0191    1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4836    0.7881    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223    1.6627   -0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0039   -0.1949   -0.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9047   -0.7233   -2.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3660    1.0023   -2.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7555    0.6010   -2.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 26  1  0
 24 22  1  0
 22 23  1  6
 22 27  1  0
 27 28  1  0
 28 29  1  0
 28  5  1  0
  5  6  1  0
  5  4  1  1
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 18 30  1  0
 30 31  2  0
 20 22  1  0
 30 11  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 24 52  1  6
 23 51  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  6
 29 59  1  0
 29 60  1  0
 29 61  1  0
  6 35  1  0
  6 36  1  0
  6 37  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  6
M  END


  Mrv1652304282200342D          

 31 32  0  0  1  0            999 V2000
    0.9325   -1.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7556   -1.0722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694   -0.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9520   -0.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2190   -1.1521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8559   -1.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0754   -2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4725   -1.7011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8356   -2.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587   -2.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0218   -3.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -1.8130    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9418   -1.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018   -1.1841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0387   -0.4433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2156   -0.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2460   -1.2118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525    0.3534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0294    0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664   -0.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233    0.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8764    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9610    1.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5447    0.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2249   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2918   -2.6196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6502   -2.4440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3696   -3.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4624   -2.2991    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0424   -1.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  1  9  1  0  0  0  0
  9 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
 13 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  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 16 21  1  1  0  0  0
 16 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 15 26  1  6  0  0  0
 13 27  1  1  0  0  0
 13 28  1  6  0  0  0
 28 29  1  0  0  0  0
 28 30  1  6  0  0  0
  6 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051158

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](Cl)[C@@]1(O)C[C@@H](C)[C@@](C)(OC(C)=O)C(=O)OCC2=CCN(C)CC[C@@H](OC1=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30ClNO8/c1-12-10-21(28,13(2)22)19(27)30-16-7-9-23(5)8-6-15(17(16)25)11-29-18(26)20(12,4)31-14(3)24/h6,12-13,16,28H,7-11H2,1-5H3/t12-,13-,16-,20-,21+/m1/s1

> <INCHI_KEY>
VGRSISYREBBIAL-YLRKQKNVSA-N

> <FORMULA>
C21H30ClNO8

> <MOLECULAR_WEIGHT>
459.92

> <EXACT_MASS>
459.1659946

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.26737451027867

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R,6R,7R)-4-[(1R)-1-chloroethyl]-4-hydroxy-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.5484572509999994

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.91479271023806

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.48368204688604

> <JCHEM_PKA_STRONGEST_BASIC>
6.930382273181841

> <JCHEM_POLAR_SURFACE_AREA>
119.44000000000001

> <JCHEM_REFRACTIVITY>
111.2954

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,6R,7R)-4-[(1R)-1-chloroethyl]-4-hydroxy-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.741  -1.897   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.277  -2.001   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.063  -0.514   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.394  -0.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.777  -0.693   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.276  -2.151   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.598  -3.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.141  -4.032   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.882  -3.175   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.560  -4.558   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.096  -4.663   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.774  -6.045   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.955  -3.384   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.491  -3.489   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.350  -2.210   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.672  -0.827   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.136  -0.723   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.193  -2.262   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.458   0.660   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.922   0.764   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.031  -0.102   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.830   0.704   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.236   1.334   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.394   2.865   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.484   0.431   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.886  -2.315   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.278  -4.890   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.947  -4.562   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.423  -6.010   0.000  0.00  0.00           C+0
HETATM   30 Cl   UNK     0       6.463  -4.292   0.000  0.00  0.00          Cl+0
HETATM   31  C   UNK     0      -3.812  -2.248   0.000  0.00  0.00           C+0
CONECT    1    2    3    9                                                  
CONECT    2    1                                                            
CONECT    3    1    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    1   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   27   28                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17   21   22                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    3                                                       
CONECT   21   16                                                            
CONECT   22   16   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   15                                                            
CONECT   27   13                                                            
CONECT   28   13   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    6                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
(1R,4R,6R,7R)-4-[(1R)-1-Chloroethyl]-4-hydroxy-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetic acid	Generator

Chemical Formula

C₂₁H₃₀ClNO₈

Average Mass

459.9200 Da

Monoisotopic Mass

459.16599 Da

IUPAC Name

(1R,4R,6R,7R)-4-[(1R)-1-chloroethyl]-4-hydroxy-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

Traditional Name

(1R,4R,6R,7R)-4-[(1R)-1-chloroethyl]-4-hydroxy-6,7,14-trimethyl-3,8,17-trioxo-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-en-7-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H](Cl)[C@@]1(O)C[C@@H](C)[C@@](C)(OC(C)=O)C(=O)OCC2=CCN(C)CC[C@@H](OC1=O)C2=O

InChI Identifier

InChI=1S/C21H30ClNO8/c1-12-10-21(28,13(2)22)19(27)30-16-7-9-23(5)8-6-15(17(16)25)11-29-18(26)20(12,4)31-14(3)24/h6,12-13,16,28H,7-11H2,1-5H3/t12-,13-,16-,20-,21+/m1/s1

InChI Key

VGRSISYREBBIAL-YLRKQKNVSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Doronicum macrophyllum	Plant	KNApSAcK
Jacobaea ambigua	LOTUS Database	35616633
Senecio doronicum	Plant	KNApSAcK
Senecio inaequidens	LOTUS Database	35616633
Senecio othonnae	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Alpha-acyloxy ketone
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Lactone
Ketone
Halohydrin
Chlorohydrin
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Amine
Alkyl halide
Alkyl chloride
Alcohol
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	1.34	ALOGPS
logP	1.55	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.48	ChemAxon
pKa (Strongest Basic)	6.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	119.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.3 m³·mol⁻¹	ChemAxon
Polarizability	45.27 Å³	ChemAxon
Number of Rings	2	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

442719

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Doronine (NP0051158)

MOL for NP0051158 (Doronine)

3D MOL for NP0051158 (Doronine)

3D SDF for NP0051158 (Doronine)

3D-SDF for NP0051158 (Doronine)

PDB for NP0051158 (Doronine)

3D PDB for NP0051158 (Doronine)

SMILES for NP0051158 (Doronine)

INCHI for NP0051158 (Doronine)

Structure for NP0051158 (Doronine)

3D Structure for NP0051158 (Doronine)