NP-MRD: Showing NP-Card for Vernolide B (NP0072553)

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Record Information

Version

2.0

Created at

2022-04-28 17:53:35 UTC

Updated at

2022-04-28 17:53:35 UTC

NP-MRD ID

NP0072553

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vernolide B

Description

Vernolide-B belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Vernolide B is found in Vernonia cinerea . Vernolide B was first documented in 2003 (PMID: 12672998). Based on a literature review very few articles have been published on Vernolide-B (PMID: 16254828).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219532D          

 31 33  0  0  1  0            999 V2000
   -0.1434    0.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393   -0.6778    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6600   -1.2213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4816   -1.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1903   -0.8737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5154   -0.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3370   -0.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621    0.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4666    0.7506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0414    1.1114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327    0.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7120    1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904    1.3074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1817    0.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077    2.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167    0.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -0.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5843   -0.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0066   -1.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315   -1.5848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041   -2.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8110   -1.4172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6507   -2.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8697   -2.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2714   -2.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317   -4.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3349   -1.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -1.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6579   -1.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 13 15  1  1  0  0  0
 13 16  1  0  0  0  0
  2 16  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  5 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
  3 29  1  1  0  0  0
  2 30  1  1  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
    5.6378   -1.7134   -1.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1937   -1.4157   -1.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5342   -0.8670   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2991   -0.5358    0.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1096   -0.6007   -0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5063   -0.8989   -1.8229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634   -0.0309    0.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0090    0.2177    0.1352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6957   -0.7209    1.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4267   -1.8082    0.3477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9030   -3.1762    0.5595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8879   -1.5824    0.5124 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4859   -1.9806    1.6572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5796   -3.2695    2.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6208   -1.9699   -0.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2753   -0.8205   -1.6696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2870    0.3098   -0.6907 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7695    0.7672   -0.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592    1.4717   -1.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6300    2.1494   -0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367    3.5116    0.0519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6544    3.7910    0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3678    4.9137    1.4101 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1751    2.5926    1.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    2.5712    1.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3669    3.5002    1.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8217    3.4490    0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8324    4.4973   -0.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4631    2.6143   -0.8098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117    1.6361    0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0229   -0.1674    0.5436 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7504   -2.7336   -1.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2164   -0.9526   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0200   -1.7285   -2.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6238   -1.6562   -2.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373   -1.3149    0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8787    0.4087    0.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6394   -0.3209    1.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3028   -0.1236   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993   -0.0811    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121   -1.1561    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2243   -1.5813   -0.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379   -3.3298   -0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4140   -3.3505    1.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6322   -3.9237    0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1702   -3.2887    2.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0522   -3.9658    1.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5693   -3.6281    2.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366   -2.9430   -1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7091   -1.9671   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -0.9487   -2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1085   -0.6966   -2.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8135    1.7009   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3310   -0.0619   -0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0925    0.9361   -1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5787    1.7983   -2.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2158    2.7233    2.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9305    1.5799    1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5013    5.5011   -0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0466    4.4314   -1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7469    4.2379    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 12 13  1  1
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 31  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 24 30  2  0
 30  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  2  1  1  0
 31 12  1  0
 30 20  1  0
 10 12  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 18 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 25 57  1  0
 25 58  1  0
 28 59  1  0
 28 60  1  0
 28 61  1  0
  8 39  1  6
  9 40  1  0
  9 41  1  0
 10 42  1  6
 11 43  1  0
 11 44  1  0
 11 45  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  2 35  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END


  Mrv1652304282219532D          

 31 33  0  0  1  0            999 V2000
   -0.1434    0.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393   -0.6778    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6600   -1.2213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4816   -1.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1903   -0.8737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5154   -0.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3370   -0.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621    0.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4666    0.7506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0414    1.1114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327    0.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7120    1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904    1.3074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1817    0.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077    2.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167    0.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -0.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5843   -0.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0066   -1.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315   -1.5848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041   -2.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8110   -1.4172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6507   -2.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8697   -2.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2714   -2.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317   -4.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3349   -1.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -1.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6579   -1.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 13 15  1  1  0  0  0
 13 16  1  0  0  0  0
  2 16  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  5 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
  3 29  1  1  0  0  0
  2 30  1  1  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072553

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@]12CC[C@@](C)(O1)\C=C1\OC(=O)C(COC(C)=O)=C1[C@H](C[C@H]2C)OC(=O)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O8/c1-7-13(2)20(25)29-17-10-14(3)23(27-6)9-8-22(5,31-23)11-18-19(17)16(21(26)30-18)12-28-15(4)24/h7,11,14,17H,8-10,12H2,1-6H3/b13-7+,18-11+/t14-,17+,22-,23+/m1/s1

> <INCHI_KEY>
CIBBPLMBWXKCDP-RRPNGBMBSA-N

> <FORMULA>
C23H30O8

> <MOLECULAR_WEIGHT>
434.485

> <EXACT_MASS>
434.194067926

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.33386170410634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8S,10R,11S)-6-[(acetyloxy)methyl]-11-methoxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-8-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
2.984079745999999

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.056466388203797

> <JCHEM_POLAR_SURFACE_AREA>
97.36

> <JCHEM_REFRACTIVITY>
112.9658

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,10R,11S)-6-[(acetyloxy)methyl]-11-methoxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-8-yl (2E)-2-methylbut-2-enoate

> <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      -0.268   0.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.073  -1.265   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.232  -2.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.766  -2.419   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.089  -1.631   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.695  -0.216   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.229  -0.355   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.836   1.060   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.338   1.401   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.677   2.075   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.354   1.286   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.196   2.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.662   2.440   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.339   1.652   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.321   3.942   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.405   0.786   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.017  -1.678   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.557  -1.657   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.346  -2.980   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.886  -2.958   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.594  -4.324   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.247  -2.645   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.948  -4.156   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.490  -4.652   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.107  -5.171   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.807  -6.681   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.966  -7.696   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.564  -4.674   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.625  -3.695   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.249  -2.054   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.228  -3.593   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3   16   30                                             
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13    1                                                       
CONECT   15   13                                                            
CONECT   16   13    2                                                       
CONECT   17    7   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    5   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29    3                                                            
CONECT   30    2   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₈

Average Mass

434.4850 Da

Monoisotopic Mass

434.19407 Da

IUPAC Name

(1R,8S,10R,11S)-6-[(acetyloxy)methyl]-11-methoxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-8-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1R,8S,10R,11S)-6-[(acetyloxy)methyl]-11-methoxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-2,6-dien-8-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CO[C@@]12CC[C@@](C)(O1)\C=C1\OC(=O)C(COC(C)=O)=C1[C@H](C[C@H]2C)OC(=O)C(\C)=C\C

InChI Identifier

InChI=1S/C23H30O8/c1-7-13(2)20(25)29-17-10-14(3)23(27-6)9-8-22(5,31-23)11-18-19(17)16(21(26)30-18)12-28-15(4)24/h7,11,14,17H,8-10,12H2,1-6H3/b13-7+,18-11+/t14-,17+,22-,23+/m1/s1

InChI Key

CIBBPLMBWXKCDP-RRPNGBMBSA-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
Cyanthillium cinereum	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
Ketal
Fatty acid ester
2-furanone
Fatty acyl
Dihydrofuran
Enol ester
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	3.07	ALOGPS
logP	2.98	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	97.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.97 m³·mol⁻¹	ChemAxon
Polarizability	45.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

28507519

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70692803

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen X, Zhan ZJ, Zhang XW, Ding J, Yue JM: Sesquiterpene lactones with potent cytotoxic activities from Vernonia chinensis. Planta Med. 2005 Oct;71(10):949-54. doi: 10.1055/s-2005-871212. [PubMed:16254828 ]
Kuo YH, Kuo YJ, Yu AS, Wu MD, Ong CW, Yang Kuo LM, Huang JT, Chen CF, Li SY: Two novel sesquiterpene lactones, cytotoxic vernolide-A and -B, from Vernonia cinerea. Chem Pharm Bull (Tokyo). 2003 Apr;51(4):425-6. doi: 10.1248/cpb.51.425. [PubMed:12672998 ]

Showing NP-Card for Vernolide B (NP0072553)

MOL for NP0072553 (Vernolide B)

3D MOL for NP0072553 (Vernolide B)

3D SDF for NP0072553 (Vernolide B)

3D-SDF for NP0072553 (Vernolide B)

PDB for NP0072553 (Vernolide B)

3D PDB for NP0072553 (Vernolide B)

SMILES for NP0072553 (Vernolide B)

INCHI for NP0072553 (Vernolide B)

Structure for NP0072553 (Vernolide B)

3D Structure for NP0072553 (Vernolide B)