NP-MRD: Showing NP-Card for Harpagide (NP0137152)

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Record Information

Version

2.0

Created at

2022-05-30 16:43:16 UTC

Updated at

2022-05-30 16:43:16 UTC

NP-MRD ID

NP0137152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Harpagide

Description

2-({4A,5,7-trihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Harpagide is found in Ajuga decumbens, Ajuga nipponensis, Ajuga pyramidalis, Ajuga reptans, Ajuga taiwanensis, Angelonia integerrima, Betonica macrantha, Betonica officinalis, Caryopteris incana, Clerodendrum indicum, Clerodendrum trichotomum, Harpagophytum procumbens, Harpagophytum zeyheri, Lagochilus platycalyx, Lamium galeobdolon, Leonurus turkestanicus, Penstemon serrulatus, Physostegia virginiana, Rogeria adenophylla, Scrophularia buergeriana, Scrophularia canina, Scrophularia cryptophila, Scrophularia ilwensis, Scrophularia leucoclada, Scrophularia ningpoensis, Scrophularia nodosa, Scrophularia racemosa, Scrophularia scorodonia, Scrophularia umbrosa, Scrophularia variegata, Stachys iberica, Stachys palustris, Stachys spinosa, Stachys subcrenata, Stachys sylvatica, Teucrium orientale, Triaenophora rupestris, Verbascum densiflorum, Verbascum thapsus and Vitex agnus-castus. 2-({4A,5,7-trihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
   -1.5458    0.9366    2.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218    0.0657    1.2071 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4554   -1.2128    1.3850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246   -0.0812    1.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1152    0.7095    0.1810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0141    1.6829    0.6755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0050    1.3336   -0.5993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2136    1.1249   -1.9846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9395    2.7658   -0.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    3.3771   -0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6307    2.6068   -0.6999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769    1.2655   -0.3680 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2551    0.5553   -1.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125   -0.0063   -0.8198 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3943   -1.4015   -0.8166 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2379   -1.8118    0.2246 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2570   -3.3062    0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6909   -3.9743   -0.7401 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5937   -1.1950    0.1429 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9094   -0.4065    1.2503 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136   -0.3792   -1.0962 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1065   -1.2823   -2.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6627    0.5261   -1.4373 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6003    0.6185   -2.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842    0.5761   -0.1835 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4810    0.8363    2.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074    0.6393    3.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7548    2.0084    2.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830   -1.7606    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003    0.2373    2.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8330   -1.1513    1.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7504    0.0533   -0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6560    1.8933   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3553    0.9475   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7973    3.3370   -0.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6221    4.4093   -0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0237    1.2437    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4398    0.2864    0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7552   -1.4060    1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514   -3.6502    0.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9285   -3.5152    1.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4517   -4.5729   -0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3401   -2.0240    0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855   -0.8668    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6980    0.2700   -0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0518   -1.2402   -2.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8188    1.5551   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261   -0.2678   -3.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7812   -0.3491   -0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12 25  1  0
 25  2  1  0
 25  7  1  0
 23 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  6
  6 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  1
 14 38  1  1
 16 39  1  1
 17 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  6
 20 44  1  0
 21 45  1  1
 22 46  1  0
 23 47  1  1
 24 48  1  0
 25 49  1  6
M  END


  Mrv1533004161513102D          

 25 27  0  0  0  0            999 V2000
    1.4743   -2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -1.7779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    0.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
  2 25  1  0  0  0  0
  7 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(O)CC(O)C2(O)C=COC(OC3OC(CO)C(O)C(O)C3O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3

> <INCHI_KEY>
XUWSHXDEJOOIND-UHFFFAOYSA-N

> <FORMULA>
C15H24O10

> <MOLECULAR_WEIGHT>
364.347

> <EXACT_MASS>
364.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.699000666290395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-({4a,5,7-trihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-2.18

> <JCHEM_LOGP>
-4.202633549999998

> <ALOGPS_LOGS>
-0.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.774164501389873

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.117364889911116

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760235146

> <JCHEM_POLAR_SURFACE_AREA>
169.29999999999998

> <JCHEM_REFRACTIVITY>
79.20390000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.90e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({4a,5,7-trihydroxy-7-methyl-1H,5H,6H,7aH-cyclopenta[c]pyran-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.752  -3.956   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.792  -3.319   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.429   0.999   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.259  -2.843   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   25                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   25                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   12    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
Harpagide	MeSH
Myoporoside	MeSH
Ajugol	MeSH
Leonuride	MeSH

Chemical Formula

C₁₅H₂₄O₁₀

Average Mass

364.3470 Da

Monoisotopic Mass

364.13695 Da

IUPAC Name

2-({4a,5,7-trihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-({4a,5,7-trihydroxy-7-methyl-1H,5H,6H,7aH-cyclopenta[c]pyran-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CC1(O)CC(O)C2(O)C=COC(OC3OC(CO)C(O)C(O)C3O)C12

InChI Identifier

InChI=1S/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3

InChI Key

XUWSHXDEJOOIND-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ajuga decumbens	LOTUS Database	35616633
Ajuga nipponensis	LOTUS Database	35616633
Ajuga pyramidalis	LOTUS Database	35616633
Ajuga reptans	LOTUS Database	35616633
Ajuga taiwanensis	LOTUS Database	35616633
Angelonia integerrima	LOTUS Database	35616633
Betonica macrantha	LOTUS Database	35616633
Betonica officinalis	LOTUS Database	35616633
Caryopteris incana	LOTUS Database	35616633
Clerodendrum indicum	LOTUS Database	35616633
Clerodendrum trichotomum	LOTUS Database	35616633
Harpagophytum procumbens	LOTUS Database	35616633
Harpagophytum zeyheri	LOTUS Database	35616633
Lagochilus platycalyx	LOTUS Database	35616633
Lamiastrum galeobdolon	LOTUS Database	35616633
Leonurus turkestanicus	LOTUS Database	35616633
Penstemon serrulatus	LOTUS Database	35616633
Physostegia virginiana	LOTUS Database	35616633
Rogeria adenophylla	LOTUS Database	35616633
Scrophularia buergeriana	LOTUS Database	35616633
Scrophularia canina	LOTUS Database	35616633
Scrophularia cryptophila	LOTUS Database	35616633
Scrophularia ilwensis	LOTUS Database	35616633
Scrophularia leucoclada	LOTUS Database	35616633
Scrophularia ningpoensis	LOTUS Database	35616633
Scrophularia nodosa	LOTUS Database	35616633
Scrophularia racemosa	LOTUS Database	35616633
Scrophularia scorodonia	LOTUS Database	35616633
Scrophularia umbrosa	LOTUS Database	35616633
Scrophularia variegata	LOTUS Database	35616633
Stachys iberica	LOTUS Database	35616633
Stachys palustris	LOTUS Database	35616633
Stachys spinosa	LOTUS Database	35616633
Stachys subcrenata	LOTUS Database	35616633
Stachys sylvatica	LOTUS Database	35616633
Teucrium orientale	LOTUS Database	35616633
Triaenophora rupestris	LOTUS Database	35616633
Verbascum densiflorum	LOTUS Database	35616633
Verbascum thapsus	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	-2.2	ALOGPS
logP	-4.2	ChemAxon
logS	-0.28	ALOGPS
pKa (Strongest Acidic)	12.12	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	169.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.2 m³·mol⁻¹	ChemAxon
Polarizability	34.7 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

4678529

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Harpagide (NP0137152)

MOL for NP0137152 (Harpagide)

3D MOL for NP0137152 (Harpagide)

3D SDF for NP0137152 (Harpagide)

3D-SDF for NP0137152 (Harpagide)

PDB for NP0137152 (Harpagide)

3D PDB for NP0137152 (Harpagide)

SMILES for NP0137152 (Harpagide)

INCHI for NP0137152 (Harpagide)

Structure for NP0137152 (Harpagide)

3D Structure for NP0137152 (Harpagide)