NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0307702)

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Record Information

Version

2.0

Created at

2022-09-11 01:00:53 UTC

Updated at

2022-09-11 01:00:54 UTC

NP-MRD ID

NP0307702

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Ajugol, also known as harpagide or myoporoside, 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. (2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Ajuga genevensis, Angelonia integerrima, Asystasia gangetica, Betonica macrantha, Cistanche salsa, Cistanche tubulosa, Crescentia cujete, Markhamia stipulata, Penstemon albidus, Penstemon auriberbis, Physostegia virginiana, Rehmannia glutinosa, Scrophularia ilwensis, Scrophularia umbrosa, Stachys grandidentata, Stachys menthifolia, Stachys spinosa, Stereospermum cylindricum, Triaenophora rupestris, Verbascum sinuatum, Verbascum thapsus and Zaluzianskya capensis. (2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol was first documented in 2022 (PMID: 35285206). Based on a literature review a small amount of articles have been published on Ajugol (PMID: 36070589) (PMID: 35534249) (PMID: 35905568) (PMID: 35899121).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112203002D          

 24 26  0  0  1  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  2  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  1  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  2  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  1  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  2  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  2  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  1  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  2  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  1  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  2  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24  7  1  6  0  0  0
  2 24  1  0  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
   -1.3991    1.5603   -0.9946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047    0.7077   -0.4895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3618    0.3377   -1.5578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3582    1.4844    0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3133    0.3557    0.9327 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0421   -0.0813   -0.1515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2782   -0.7318    1.2534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9584   -0.5975    2.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7413   -0.7767    3.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7660   -1.1066    2.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7905   -0.3876    0.9938 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1575   -1.0575    0.2019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2860   -0.2794   -0.0511 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5027   -0.2537   -1.3901 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7009    0.2757   -1.8058 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9276   -0.2040   -3.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9017    0.2282   -4.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8824   -0.1086   -0.9926 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9322    0.7927   -1.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6516   -0.1193    0.4874 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7446   -0.7239    1.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4022   -0.9496    0.7322 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0657   -0.9484    2.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173   -0.4941    0.3058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8925    2.4387   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785    1.9871   -0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525    1.0386   -1.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3199   -0.6602   -1.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8801    2.3173    0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7043    1.7301    1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9052    0.6283    1.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8226    0.4636   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7304   -1.7416    1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7771   -0.3334    3.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5541   -0.6639    4.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    0.6257    1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1311    0.7065    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6734    1.4018   -1.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9306    0.0800   -3.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096   -1.3295   -3.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4896    1.0403   -3.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2621   -1.1024   -1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7945    0.3270   -1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5329    0.9063    0.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4994   -1.6441    1.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5567   -1.9480    0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4210   -1.7907    2.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0542   -1.3998   -0.3826 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  0
  8  9  2  0
  9 10  1  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
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11 24  1  0
 24  2  1  0
 24  7  1  0
 22 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  1
  6 32  1  0
  7 33  1  1
  8 34  1  0
  9 35  1  0
 11 36  1  1
 13 37  1  1
 15 38  1  6
 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
 20 44  1  1
 21 45  1  0
 22 46  1  6
 23 47  1  0
 24 48  1  6
M  END


  Mrv1652309112203002D          

 24 26  0  0  1  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  2  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  1  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  2  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  1  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  2  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  2  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  1  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  2  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  1  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  2  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24  7  1  6  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307702

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(O)C[C@@H](O)[C@@H]2C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O9/c1-15(21)4-7(17)6-2-3-22-13(9(6)15)24-14-12(20)11(19)10(18)8(5-16)23-14/h2-3,6-14,16-21H,4-5H2,1H3/t6-,7+,8+,9+,10+,11-,12+,13-,14-,15-/m0/s1

> <INCHI_KEY>
VELYAQRXBJLJAK-XKKWFBPMSA-N

> <FORMULA>
C15H24O9

> <MOLECULAR_WEIGHT>
348.348

> <EXACT_MASS>
348.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
33.85940509154424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-2.8563025343333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.170933970356305

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.203765093018271

> <JCHEM_PKA_STRONGEST_BASIC>
-2.89682284458896

> <JCHEM_POLAR_SURFACE_AREA>
149.07

> <JCHEM_REFRACTIVITY>
78.06080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         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  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.259  -2.843   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   24                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23                                                  
CONECT   23   22                                                            
CONECT   24   11    7    2                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Harpagide	MeSH
Myoporoside	MeSH
Leonuride	MeSH

Chemical Formula

C₁₅H₂₄O₉

Average Mass

348.3480 Da

Monoisotopic Mass

348.14203 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{[(1S,4aR,5R,7S,7aS)-5,7-dihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5S,6R)-2-{[(1S,4aR,5R,7S,7aS)-5,7-dihydroxy-7-methyl-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

C[C@]1(O)C[C@@H](O)[C@@H]2C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]12

InChI Identifier

InChI=1S/C15H24O9/c1-15(21)4-7(17)6-2-3-22-13(9(6)15)24-14-12(20)11(19)10(18)8(5-16)23-14/h2-3,6-14,16-21H,4-5H2,1H3/t6-,7+,8+,9+,10+,11-,12+,13-,14-,15-/m0/s1

InChI Key

VELYAQRXBJLJAK-XKKWFBPMSA-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 genevensis	LOTUS Database	35616633
Angelonia integerrima	LOTUS Database	35616633
Asystasia gangetica	LOTUS Database	35616633
Betonica macrantha	LOTUS Database	35616633
Cistanche salsa	LOTUS Database	35616633
Cistanche tubulosa	LOTUS Database	35616633
Crescentia cujete	LOTUS Database	35616633
Markhamia stipulata	LOTUS Database	35616633
Penstemon albidus	LOTUS Database	35616633
Penstemon auriberbis	LOTUS Database	35616633
Physostegia virginiana	LOTUS Database	35616633
Rehmannia glutinosa	LOTUS Database	35616633
Scrophularia ilwensis	LOTUS Database	35616633
Scrophularia umbrosa	LOTUS Database	35616633
Stachys grandidentata	LOTUS Database	35616633
Stachys menthifolia	LOTUS Database	35616633
Stachys spinosa	LOTUS Database	35616633
Stereospermum cylindricum	LOTUS Database	35616633
Triaenophora rupestris	LOTUS Database	35616633
Verbascum sinuatum	LOTUS Database	35616633
Verbascum thapsus	LOTUS Database	35616633
Zaluzianskya capensis	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	-2.9	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	149.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.06 m³·mol⁻¹	ChemAxon
Polarizability	33.86 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

C00010600

Chemspider ID

4884665

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6325127

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Han DE, Yue ZS, Li HW, Liu GZ, Cai BR, Tian P: [Anti-depressant components and mechanism of Rehmanniae Radix based on UPLC-Q-Orbitrap HRMS and network pharmacology]. Zhongguo Zhong Yao Za Zhi. 2022 Feb;47(4):1051-1063. doi: 10.19540/j.cnki.cjcmm.20210811.404. [PubMed:35285206 ]
Xiao Y, Tian M, Liu Q, Xu B, Peng Y, Zhao C, Li C: A novel absorbent, HOF-3@PU: Preparation and application for sustainable and efficient purification of catalpol and ajugol from Rehmannia glutinosa leaves. Nat Prod Res. 2022 Sep 7:1-7. doi: 10.1080/14786419.2022.2119968. [PubMed:36070589 ]
Cao ZY, Liu JT, Han YQ, Zhang TJ, Xu J: [Identification of Q-markers for Cistanches Herba based on HPLC-Q-TOF-MS/MS and network pharmacology]. Zhongguo Zhong Yao Za Zhi. 2022 Apr;47(7):1790-1801. doi: 10.19540/j.cnki.cjcmm.20211210.201. [PubMed:35534249 ]
Yi L, Zhou Y, Song J, Tang W, Yu H, Huang X, Shi H, Chen M, Sun J, Wei Y, Dong J: A novel iridoid glycoside leonuride (ajugol) attenuates airway inflammation and remodeling through inhibiting type-2 high cytokine/chemokine activity in OVA-induced asthmatic mice. Phytomedicine. 2022 Oct;105:154345. doi: 10.1016/j.phymed.2022.154345. Epub 2022 Jul 22. [PubMed:35905568 ]
Yao J, Miao Y, Zhang Y, Zhu L, Chen H, Wu X, Yang Y, Dai X, Hu Q, Wan M, Tang W: Dao-Chi Powder Ameliorates Pancreatitis-Induced Intestinal and Cardiac Injuries via Regulating the Nrf2-HO-1-HMGB1 Signaling Pathway in Rats. Front Pharmacol. 2022 Jul 11;13:922130. doi: 10.3389/fphar.2022.922130. eCollection 2022. [PubMed:35899121 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0307702)

MOL for NP0307702 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0307702 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0307702 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0307702 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0307702 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0307702 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0307702 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0307702 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0307702 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0307702 ((2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)