NP-MRD: Showing NP-Card for (-)-Praeroside II (NP0063237)

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Record Information

Version

2.0

Created at

2022-04-28 07:41:45 UTC

Updated at

2022-04-28 07:41:45 UTC

NP-MRD ID

NP0063237

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Praeroside II

Description

Praeroside II belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. (-)-Praeroside II is found in Angelica furciijuga, Angelica furcijuga KITAGAWA, Peucedanum japonicum, Peucedanum praeruptorum, Seseli campestre and Seseli devenyense Simonkai. (-)-Praeroside II was first documented in 2003 (PMID: 12926867). Based on a literature review very few articles have been published on Praeroside II.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209412D          

 30 33  0  0  1  0            999 V2000
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7954   -2.9684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0296   -2.9684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4421   -2.2539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0296   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7954   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3045   -1.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3045   -0.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  1  0  0  0
  8  9  1  0  0  0  0
  5 10  1  6  0  0  0
  4 11  1  1  0  0  0
  3 12  1  6  0  0  0
 13  1  1  1  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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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  0  0  0  0
 19 25  1  0  0  0  0
 25 26  2  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  1  0  0  0
 14 29  1  0  0  0  0
 14 30  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -0.4945   -3.1078    0.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981   -1.8659    1.2208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5197   -1.3543    2.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381   -2.0964    1.5616 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6204   -1.8444    0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9265   -2.0608    1.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9551   -1.7901    0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7159   -1.3135   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7106   -1.0295   -1.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4028   -0.5583   -3.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.3639   -3.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8174    0.0669   -4.6672 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1427   -0.6475   -2.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4199   -1.0974   -1.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3850   -1.3701   -0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0039   -1.1306   -1.0269 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5611   -2.2860   -1.6327 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1722   -0.7518    0.1831 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1125   -0.3958   -0.1497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    0.9454    0.1836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3914    0.9834    1.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339    2.2160    1.0885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7794    2.5159    2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4015    3.7592    2.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0061    2.0713   -0.0905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8798    3.1360   -0.1004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1562    1.9764   -1.3288 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6960    0.9768   -2.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7062    1.7326   -1.0484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0035    2.9473   -1.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1536   -3.5429    1.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1497   -2.9057   -0.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2638   -3.9095    0.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6107   -1.5403    2.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1548   -1.9302    3.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718   -0.2885    2.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1070   -2.4284    2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9993   -1.9356    0.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7523   -1.1914   -1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1791   -0.3334   -3.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9515   -0.2713   -1.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508   -3.0201   -1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138    0.1064    0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4842    1.3413    0.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208    3.0197    0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0138    2.5829    3.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4609    1.7044    2.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    4.4493    2.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5240    1.0998    0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6444    2.9020   -0.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2825    2.9307   -1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6033    0.0980   -1.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3063    1.1462   -1.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690    3.6534   -1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 18  2  1  0
 29 20  1  0
 15  5  1  0
 14  8  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 16 41  1  6
 17 42  1  0
 18 43  1  1
 20 44  1  1
 22 45  1  6
 23 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  1
 26 50  1  0
 27 51  1  6
 28 52  1  0
 29 53  1  6
 30 54  1  0
M  END


  Mrv1652304282209412D          

 30 33  0  0  1  0            999 V2000
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7954   -2.9684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0296   -2.9684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4421   -2.2539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0296   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7954   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3045   -1.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3045   -0.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  1  0  0  0
  8  9  1  0  0  0  0
  5 10  1  6  0  0  0
  4 11  1  1  0  0  0
  3 12  1  6  0  0  0
 13  1  1  1  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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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  0  0  0  0
 19 25  1  0  0  0  0
 25 26  2  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  1  0  0  0
 14 29  1  0  0  0  0
 14 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063237

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=CC=C3C=CC(=O)OC3=C2[C@@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O10/c1-20(2)18(29-19-16(26)15(25)13(23)10(7-21)27-19)14(24)12-9(30-20)5-3-8-4-6-11(22)28-17(8)12/h3-6,10,13-16,18-19,21,23-26H,7H2,1-2H3/t10-,13-,14-,15+,16-,18-,19+/m1/s1

> <INCHI_KEY>
QAUDHOGPLBDVAX-GZFODPQLSA-N

> <FORMULA>
C20H24O10

> <MOLECULAR_WEIGHT>
424.402

> <EXACT_MASS>
424.136946973

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
41.686459619544486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(13R,14R)-14-hydroxy-12,12-dimethyl-13-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

> <ALOGPS_LOGP>
-0.41

> <JCHEM_LOGP>
-0.9574381856666669

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.77538220691595

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.119162681428037

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083568056743

> <JCHEM_POLAR_SURFACE_AREA>
155.14

> <JCHEM_REFRACTIVITY>
99.96169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(13R,14R)-14-hydroxy-12,12-dimethyl-13-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

> <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  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.255  -4.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.485  -5.541   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.055  -5.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.825  -4.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.055  -2.874   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.485  -2.874   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.825  -1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.365  -1.540   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.365  -4.207   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.825  -6.875   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.255  -6.875   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.565  -0.206   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.185  -2.874   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.875  -4.207   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.435  -2.263   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.435  -0.817   0.000  0.00  0.00           C+0
CONECT    1    2   13                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8                                                            
CONECT   10    5                                                            
CONECT   11    4                                                            
CONECT   12    3                                                            
CONECT   13    1   14   27                                                  
CONECT   14   13   15   29   30                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19   26                                                  
CONECT   26   25   16   27                                                  
CONECT   27   26   13   28                                                  
CONECT   28   27                                                            
CONECT   29   14                                                            
CONECT   30   14                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₁₀

Average Mass

424.4020 Da

Monoisotopic Mass

424.13695 Da

IUPAC Name

(13R,14R)-14-hydroxy-12,12-dimethyl-13-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

Traditional Name

(13R,14R)-14-hydroxy-12,12-dimethyl-13-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=CC=C3C=CC(=O)OC3=C2[C@@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C20H24O10/c1-20(2)18(29-19-16(26)15(25)13(23)10(7-21)27-19)14(24)12-9(30-20)5-3-8-4-6-11(22)28-17(8)12/h3-6,10,13-16,18-19,21,23-26H,7H2,1-2H3/t10-,13-,14-,15+,16-,18-,19+/m1/s1

InChI Key

QAUDHOGPLBDVAX-GZFODPQLSA-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
Angelica furciijuga	Plant	KNApSAcK
Angelica furcijuga KITAGAWA	Plant	KNApSAcK
Peucedanum japonicum	LOTUS Database	35616633
Peucedanum praeruptorum	Plant	KNApSAcK
Seseli campestre	Plant	KNApSAcK
Seseli devenyense Simonkai	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Pyranochromene
Hexose monosaccharide
2,2-dimethyl-1-benzopyran
Glycosyl compound
O-glycosyl compound
Chromane
1-benzopyran
Benzopyran
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Acetal
Polyol
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	-0.41	ALOGPS
logP	-0.96	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.12	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.96 m³·mol⁻¹	ChemAxon
Polarizability	41.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00020008

Chemspider ID

22912895

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24066895

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hisamoto M, Kikuzaki H, Ohigashi H, Nakatani N: Antioxidant compounds from the leaves of Peucedanum japonicum thunb. J Agric Food Chem. 2003 Aug 27;51(18):5255-61. doi: 10.1021/jf0262458. [PubMed:12926867 ]

Showing NP-Card for (-)-Praeroside II (NP0063237)

MOL for NP0063237 ((-)-Praeroside II)

3D MOL for NP0063237 ((-)-Praeroside II)

3D SDF for NP0063237 ((-)-Praeroside II)

3D-SDF for NP0063237 ((-)-Praeroside II)

PDB for NP0063237 ((-)-Praeroside II)

3D PDB for NP0063237 ((-)-Praeroside II)

SMILES for NP0063237 ((-)-Praeroside II)

INCHI for NP0063237 ((-)-Praeroside II)

Structure for NP0063237 ((-)-Praeroside II)

3D Structure for NP0063237 ((-)-Praeroside II)