NP-MRD: Showing NP-Card for Pachypodol (NP0043941)

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Record Information

Version

1.0

Created at

2021-06-22 17:41:56 UTC

Updated at

2021-06-22 17:41:56 UTC

NP-MRD ID

NP0043941

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pachypodol

Description

Pachypodol belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, pachypodol is considered to be a flavonoid. Pachypodol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Pachypodol is found in Aeonium lindleyi, Artemisia annua, Blumea balsamifera, Bosistoa medicinalis, Chiliadenus montanus, Chromolaena morii, Croton schiedeanus, Duguetia confinis, Duguetia staudtii, Eleutherococcus brachypus, Erythranthe lewisii, Eupomatia laurina, Grindelia hirsutula, Grindelia pulchella, Rhododendron tomentosum, Melicope madagascariensis, Melicope semecarpifolia, Melicope triphylla, Miliusa balansae, Osyris alba, Physalis coztomatl, Plectranthus montanus, Psiadia dentata, Scapholeberis mucronata, Sida galheirensis, Trichophorum cespitosum, Varronia multispicata, Chiliadenus iphionoides and Vitex peduncularis. It was first documented in 1999 (PMID: 10374246). Based on a literature review a significant number of articles have been published on pachypodol (PMID: 10725128) (PMID: 11141110) (PMID: 11199132) (PMID: 16478239).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043941
     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    6.5751   -1.6430    0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442   -2.0538    0.0629 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2414   -1.0761    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5682    0.2256    0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236    1.1595    0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8577    2.4464    0.7870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2185    0.7720    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627    1.6413    0.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    2.8460    0.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1623    1.1751    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1796    2.1036    0.3730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4988    2.7854   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090   -0.1278    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172   -0.6863   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7809   -2.0109   -0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9529   -2.6781   -0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612   -2.0771   -0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3756   -2.7377   -0.7371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1322   -0.7918   -0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3065   -0.1446    0.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3283    1.1886    0.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9175   -0.1115    0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6698   -0.9271   -0.0412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859   -0.5438    0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9284   -1.4575    0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2946   -2.4355   -0.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6882   -1.2516    1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7658   -0.7758   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6012    0.5518    0.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3628    3.2453    0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3251    3.5016   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209    2.0340   -1.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260    3.3822   -1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656   -2.5366   -0.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9299   -3.6921   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2279   -2.2696   -0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9958    1.9010   -0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6545    1.2266    1.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3303    1.4692    1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711    0.8632    0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6802   -2.4901   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
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 13 23  1  0
 23 24  1  0
 24 25  2  0
 25  3  1  0
 24  7  1  0
 22 14  1  0
  1 26  1  0
  1 27  1  0
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  4 29  1  0
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 16 35  1  0
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 21 37  1  0
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 21 39  1  0
 22 40  1  0
 25 41  1  0
M  END


  Mrv1652306222119412D          

 25 27  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
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 16 17  2  0  0  0  0
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 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043941

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C(OC)=C(OC2=C1)C1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-11(19)13(6-9)23-2/h4-8,19-20H,1-3H3

> <INCHI_KEY>
KQFUXLQBMQGNRT-UHFFFAOYSA-N

> <FORMULA>
C18H16O7

> <MOLECULAR_WEIGHT>
344.319

> <EXACT_MASS>
344.089602855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
34.54021322753183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.5609149653333327

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.033627675812705

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.15012214258131

> <JCHEM_PKA_STRONGEST_BASIC>
-4.401144008315609

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
90.57800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pachypodol

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043941
     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    6.5751   -1.6430    0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442   -2.0538    0.0629 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2414   -1.0761    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5682    0.2256    0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236    1.1595    0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8577    2.4464    0.7870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2185    0.7720    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627    1.6413    0.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    2.8460    0.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1623    1.1751    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1796    2.1036    0.3730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4988    2.7854   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090   -0.1278    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172   -0.6863   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7809   -2.0109   -0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9529   -2.6781   -0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612   -2.0771   -0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3756   -2.7377   -0.7371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1322   -0.7918   -0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3065   -0.1446    0.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3283    1.1886    0.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9175   -0.1115    0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6698   -0.9271   -0.0412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859   -0.5438    0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9284   -1.4575    0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2946   -2.4355   -0.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6882   -1.2516    1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7658   -0.7758   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6012    0.5518    0.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3628    3.2453    0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3251    3.5016   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209    2.0340   -1.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260    3.3822   -1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656   -2.5366   -0.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9299   -3.6921   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2279   -2.2696   -0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9958    1.9010   -0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6545    1.2266    1.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3303    1.4692    1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711    0.8632    0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6802   -2.4901   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 13 23  1  0
 23 24  1  0
 24 25  2  0
 25  3  1  0
 24  7  1  0
 22 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 25 41  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14                                                            
CONECT   16   10   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
CONECT   23   18   24                                                       
CONECT   24   23                                                            
CONECT   25    5                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    NP0043941
HETATM    1  C1  UNL     1       6.575  -1.643   0.228  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.244  -2.054   0.063  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.241  -1.076   0.173  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.568   0.226   0.431  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.524   1.159   0.531  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.858   2.446   0.787  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.218   0.772   0.372  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.163   1.641   0.457  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.301   2.846   0.684  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.162   1.175   0.281  1.00  0.00           C  
HETATM   11  O4  UNL     1      -1.180   2.104   0.373  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.499   2.785  -0.865  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.409  -0.128   0.031  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.717  -0.686  -0.157  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.781  -2.011  -0.635  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.953  -2.678  -0.824  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.161  -2.077  -0.551  1.00  0.00           C  
HETATM   18  O5  UNL     1      -5.376  -2.738  -0.737  1.00  0.00           O  
HETATM   19  C14 UNL     1      -4.132  -0.792  -0.086  1.00  0.00           C  
HETATM   20  O6  UNL     1      -5.307  -0.145   0.202  1.00  0.00           O  
HETATM   21  C15 UNL     1      -5.328   1.189   0.687  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.917  -0.111   0.107  1.00  0.00           C  
HETATM   23  O7  UNL     1       0.670  -0.927  -0.041  1.00  0.00           O  
HETATM   24  C17 UNL     1       1.886  -0.544   0.110  1.00  0.00           C  
HETATM   25  C18 UNL     1       2.928  -1.457   0.015  1.00  0.00           C  
HETATM   26  H1  UNL     1       7.295  -2.435  -0.009  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.688  -1.252   1.267  1.00  0.00           H  
HETATM   28  H3  UNL     1       6.766  -0.776  -0.461  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.601   0.552   0.561  1.00  0.00           H  
HETATM   30  H5  UNL     1       3.363   3.245   0.899  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.325   3.502  -0.714  1.00  0.00           H  
HETATM   32  H7  UNL     1      -1.721   2.034  -1.632  1.00  0.00           H  
HETATM   33  H8  UNL     1      -0.626   3.382  -1.206  1.00  0.00           H  
HETATM   34  H9  UNL     1      -0.866  -2.537  -0.867  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.930  -3.692  -1.193  1.00  0.00           H  
HETATM   36  H11 UNL     1      -6.228  -2.270  -0.529  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.996   1.901  -0.100  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.655   1.227   1.584  1.00  0.00           H  
HETATM   39  H14 UNL     1      -6.330   1.469   1.045  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.971   0.863   0.491  1.00  0.00           H  
HETATM   41  H16 UNL     1       2.680  -2.490  -0.190  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   25
CONECT    4    5   29
CONECT    5    6    7    7
CONECT    6   30
CONECT    7    8   24
CONECT    8    9    9   10
CONECT   10   11   13   13
CONECT   11   12
CONECT   12   31   32   33
CONECT   13   14   23
CONECT   14   15   15   22
CONECT   15   16   34
CONECT   16   17   17   35
CONECT   17   18   19
CONECT   18   36
CONECT   19   20   22   22
CONECT   20   21
CONECT   21   37   38   39
CONECT   22   40
CONECT   23   24
CONECT   24   25   25
CONECT   25   41
END

NP0043941
     RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
    6.5751   -1.6430    0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442   -2.0538    0.0629 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2414   -1.0761    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5682    0.2256    0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236    1.1595    0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8577    2.4464    0.7870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2185    0.7720    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627    1.6413    0.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3010    2.8460    0.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1623    1.1751    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1796    2.1036    0.3730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4988    2.7854   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090   -0.1278    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172   -0.6863   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7809   -2.0109   -0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9529   -2.6781   -0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612   -2.0771   -0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3756   -2.7377   -0.7371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1322   -0.7918   -0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3065   -0.1446    0.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3283    1.1886    0.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9175   -0.1115    0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6698   -0.9271   -0.0412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859   -0.5438    0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9284   -1.4575    0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2946   -2.4355   -0.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6882   -1.2516    1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7658   -0.7758   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6012    0.5518    0.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3628    3.2453    0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3251    3.5016   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209    2.0340   -1.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260    3.3822   -1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656   -2.5366   -0.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9299   -3.6921   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2279   -2.2696   -0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9958    1.9010   -0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6545    1.2266    1.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3303    1.4692    1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711    0.8632    0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6802   -2.4901   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 13 23  1  0
 23 24  1  0
 24 25  2  0
 25  3  1  0
 24  7  1  0
 22 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 25 41  1  0
M  END

View in JSmol

Synonyms

Value	Source
5,4'-Dihydroxy-3,7,3'-quercetol trimethyl ether	ChEBI
5,4'-Dihydroxy-3,7,3'-trimethoxyflavone	ChEBI
Quercetin 3,7,3'-trimethyl ether	ChEBI
4',5-Dihydroxy-3,3',7-trimethoxyflavone	MeSH

Chemical Formula

C₁₈H₁₆O₇

Average Mass

344.3190 Da

Monoisotopic Mass

344.08960 Da

IUPAC Name

5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one

Traditional Name

pachypodol

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C(OC)=C(OC2=C1)C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-11(19)13(6-9)23-2/h4-8,19-20H,1-3H3

InChI Key

KQFUXLQBMQGNRT-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Adenosma capitatum	KNApSAcK Database	22123792
Aeonium lindleyi	LOTUS Database	35616633
Agastache rugosa	KNApSAcK Database	22123792
Agastache rugosus	KNApSAcK Database	22123792
Artemisia annua	Linigton's dataset	Lai-King Sy, Geoffrey D. Brown. Three sesquiterpenes from Artemisia annua. Phytochemistry Volume ...
Begonia glabra	KNApSAcK Database	22123792
Betula nigra	KNApSAcK Database	22123792
Blumea balsamifera	LOTUS Database	35616633
Bosistoa floydii	KNApSAcK Database	22123792
Bosistoa medicinalis	LOTUS Database	35616633
Chiliadenus montanus	LOTUS Database	35616633
Chromolaena morii	LOTUS Database	35616633
Chrysothamnus viscidiflorus	KNApSAcK Database	22123792
Cordia multispicata	KNApSAcK Database	22123792
Croton schiedeanus	LOTUS Database	35616633
Duguetia confinis	LOTUS Database	35616633
Duguetia staudtii	LOTUS Database	35616633
Eleutherococcus brachypus	LOTUS Database	35616633
Erythranthe lewisii	LOTUS Database	35616633
Euodia glabra	KNApSAcK Database	22123792
Euodia merrillii	KNApSAcK Database	22123792
Euodia viticina	KNApSAcK Database	22123792
Eupomatia laurina	LOTUS Database	35616633
Flourensia cernua	KNApSAcK Database	22123792
Grindelia hirsutula	LOTUS Database	35616633
Grindelia pulchella	LOTUS Database	35616633
Grindelia robusta	KNApSAcK Database	22123792
Grindelia squarrosa	KNApSAcK Database	22123792
Grindelia tarapacana	KNApSAcK Database	22123792
Heliotropium sinuatum	KNApSAcK Database	22123792
Heterotheca villosa	KNApSAcK Database	22123792
Jasonia montana	KNApSAcK Database	22123792
Larrea cuneifolia	KNApSAcK Database	22123792
Ledum palustre	LOTUS Database	35616633
Macaranga triloba	KNApSAcK Database	22123792
Melicope elleryana	KNApSAcK Database	22123792
Melicope madagascariensis	LOTUS Database	35616633
Melicope semecarpifolia	LOTUS Database	35616633
Melicope ternata	KNApSAcK Database	22123792
Melicope triphylla	LOTUS Database	35616633
Microtoena prainiana	KNApSAcK Database	22123792
Miliusa balansae	LOTUS Database	35616633
Mimulus lewisii	KNApSAcK Database	22123792
Mirabilis viscosa	KNApSAcK Database	22123792
Nothofagus cunninghamii	KNApSAcK Database	22123792
Osyris alba	LOTUS Database	35616633
Petunia surfinia	KNApSAcK Database	22123792
Physalis coztomatl	LOTUS Database	35616633
Plectranthus montanus	LOTUS Database	35616633
Pogostemon cablin	KNApSAcK Database	22123792
Psiadia dentata	LOTUS Database	35616633
Salpiglossis sinuata	KNApSAcK Database	22123792
Scapholeberis mucronata	LOTUS Database	35616633
Senecio viscosissimus	KNApSAcK Database	22123792
Senecio viscosus	KNApSAcK Database	22123792
Sida galheirensis	Plant	KNApSAcK
Solanum pubescens	KNApSAcK Database	22123792
Trichophorum cespitosum	LOTUS Database	35616633
Varronia multispicata	LOTUS Database	35616633
Varthemia iphionoides	LOTUS Database	35616633
Viscum album	KNApSAcK Database	22123792
Viscum cruciatum	KNApSAcK Database	22123792
Vitex peduncularis	LOTUS Database	35616633
Xanthocephalum gymnospermoides	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
3-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
3-methoxychromone
Chromone
Methoxyphenol
Benzopyran
1-benzopyran
Phenoxy compound
Methoxybenzene
Anisole
Phenol ether
Phenol
Pyranone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:70007 )
trimethoxyflavone (CHEBI:70007 )
flavonols (C10117 )
Flavones and Flavonols (C10117 )
Flavones and Flavonols (LMPK12112754 )

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	2.9	ALOGPS
logP	2.56	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.15	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.58 m³·mol⁻¹	ChemAxon
Polarizability	34.54 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00004646

Chemspider ID

4444996

KEGG Compound ID

C10117

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pachypodol

METLIN ID

Not Available

PubChem Compound

5281677

PDB ID

Not Available

ChEBI ID

70007

Good Scents ID

Not Available

References

General References

Yang Y, Kinoshita K, Koyama K, Takahashi K, Tai T, Nunoura Y, Watanabe K: Anti-emetic principles of Pogostemon cablin (Blanco) Benth. Phytomedicine. 1999 May;6(2):89-93. doi: 10.1016/S0944-7113(99)80041-5. [PubMed:10374246 ]
Miyazawa M, Okuno Y, Nakamura S, Kosaka H: Antimutagenic activity of flavonoids from Pogostemon cablin. J Agric Food Chem. 2000 Mar;48(3):642-7. doi: 10.1021/jf990160y. [PubMed:10725128 ]
Orabi KY, Mossa JS, Muhammed I, Alloush MH, Galal AM, El-Feraly FS, McPhail AT: New eudesmane sesquiterpenes from Plectranthus cylindraceus. J Nat Prod. 2000 Dec;63(12):1665-8. doi: 10.1021/np000124p. [PubMed:11141110 ]
Puripattanavong J, Weber S, Brecht V, Frahm AW: Phytochemical investigation of Aglaia andamanica. Planta Med. 2000 Dec;66(8):740-5. doi: 10.1055/s-2000-9901. [PubMed:11199132 ]
Gonzalez-Vazquez R, King Diaz B, Aguilar MI, Diego N, Lotina-Hennsen B: Pachypodol from Croton ciliatoglanduliferus Ort. as water-splitting enzyme inhibitor on thylakoids. J Agric Food Chem. 2006 Feb 22;54(4):1217-21. doi: 10.1021/jf051897s. [PubMed:16478239 ]
Lai-King Sy, Geoffrey D. Brown (1998). Lai-King Sy, Geoffrey D. Brown. Three sesquiterpenes from Artemisia annua. Phytochemistry Volume 48, Issue 7, August 1998, Pages 1207-1211 DOI: 10.1016/S0031-9422(97)01047-9. Phytochemistry.

Showing NP-Card for Pachypodol (NP0043941)

MOL for NP0043941 (Pachypodol)

3D MOL for NP0043941 (Pachypodol)

3D SDF for NP0043941 (Pachypodol)

3D-SDF for NP0043941 (Pachypodol)

PDB for NP0043941 (Pachypodol)

3D PDB for NP0043941 (Pachypodol)

SMILES for NP0043941 (Pachypodol)

INCHI for NP0043941 (Pachypodol)

Structure for NP0043941 (Pachypodol)

3D Structure for NP0043941 (Pachypodol)