NP-MRD: Showing NP-Card for (1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0152821)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 09:22:37 UTC

Updated at

2022-09-02 09:22:37 UTC

NP-MRD ID

NP0152821

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid

Description

Mussaenosidic acid, also known as mussaenosidate, 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. (1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid is found in Cistanche tubulosa, Gardenia jasminoides, Kickxia abhaica, Kickxia elatine, Melampyrum cristatum, Plantago alpina, Plantago arborescens, Utricularia vulgaris and Vitex agnus-castus. (1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid was first documented in 2016 (PMID: 26828611). Based on a literature review a small amount of articles have been published on Mussaenosidic acid (PMID: 26207992) (PMID: 28550715) (PMID: 28507520).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211222D          

 26 28  0  0  1  0            999 V2000
    0.4243   -1.7779    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
    1.4743   -2.1191    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
    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
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.3646    0.0000 O   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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
 13 26  1  0  0  0  0
 26  6  1  6  0  0  0
  2 26  1  0  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -2.3509   -0.9739   -2.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4380   -1.4694   -1.0699 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8292   -2.7203   -1.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -1.5061   -0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1650   -0.2937    0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8352    0.3552    0.4566 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7778    1.7589    0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5969    2.7943    0.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599    2.4377    1.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5642    4.1183    0.3516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807    2.1465   -0.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1931    1.2041   -1.5649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6168    0.2127   -0.7431 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1911    0.6826    0.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4881    0.2128    0.2327 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7571   -0.5985    1.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -1.1749    1.0953 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2156   -2.4432    1.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4826   -2.9250    1.5384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0344   -0.1376    1.4624 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2626   -0.5666    0.9688 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6669    1.2388    0.9829 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4635    2.0729    2.0914 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208    1.2656    0.0294 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0529    1.2149   -1.2772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7750   -0.5194   -0.0965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9040   -0.0185   -2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066   -1.7422   -3.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3343   -0.9508   -2.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2630   -3.2809   -0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0774   -2.4635   -0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5690   -1.4878   -1.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8763    0.3966   -0.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6800   -0.6447    1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7557    0.3566    1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0753    4.8355    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9526    3.2100   -1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0428   -0.4848   -1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5515   -0.4879   -0.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0336   -1.4144    0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094   -2.2679    2.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922   -3.2079    1.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1644   -2.6504    2.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1138   -0.1451    2.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0317   -0.1151    1.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5869    1.6493    0.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0977    2.9444    1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676    2.2968    0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6568    0.4320   -1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276   -1.1463    0.7089 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
  6 26  1  0
 26 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 13 12  1  0
 12 11  1  0
 11  7  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
 26  2  1  0
 24 15  1  0
  7  6  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  1
 26 50  1  1
 13 38  1  6
 15 39  1  6
 17 40  1  6
 18 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  1
 21 45  1  0
 22 46  1  6
 23 47  1  0
 24 48  1  6
 25 49  1  0
 11 37  1  0
 10 36  1  0
M  END


  Mrv1652309022211222D          

 26 28  0  0  1  0            999 V2000
    0.4243   -1.7779    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
    1.4743   -2.1191    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
    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
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.3646    0.0000 O   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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
 13 26  1  0  0  0  0
 26  6  1  6  0  0  0
  2 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(O)CC[C@H]2[C@@H]1[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC=C2C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O10/c1-16(23)3-2-6-7(13(21)22)5-24-14(9(6)16)26-15-12(20)11(19)10(18)8(4-17)25-15/h5-6,8-12,14-15,17-20,23H,2-4H2,1H3,(H,21,22)/t6-,8-,9-,10-,11+,12-,14+,15+,16+/m1/s1

> <INCHI_KEY>
VLCHQFXSBHIBRV-NJPMDSMTSA-N

> <FORMULA>
C16H24O10

> <MOLECULAR_WEIGHT>
376.358

> <EXACT_MASS>
376.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.108890691494864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <ALOGPS_LOGP>
-1.82

> <JCHEM_LOGP>
-2.0396898606666674

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.20531729306329

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.257302060368095

> <JCHEM_PKA_STRONGEST_BASIC>
-2.969944069865554

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
82.51110000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.17e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.792  -3.319   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       2.752  -3.956   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  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.258   2.547   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.590   2.547   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.259  -2.843   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   26                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24                                                            
CONECT   26   13    6    2                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
Mussaenosidate	Generator

Chemical Formula

C₁₆H₂₄O₁₀

Average Mass

376.3580 Da

Monoisotopic Mass

376.13695 Da

IUPAC Name

(1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

Traditional Name

(1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@]1(O)CC[C@H]2[C@@H]1[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC=C2C(O)=O

InChI Identifier

InChI=1S/C16H24O10/c1-16(23)3-2-6-7(13(21)22)5-24-14(9(6)16)26-15-12(20)11(19)10(18)8(4-17)25-15/h5-6,8-12,14-15,17-20,23H,2-4H2,1H3,(H,21,22)/t6-,8-,9-,10-,11+,12-,14+,15+,16+/m1/s1

InChI Key

VLCHQFXSBHIBRV-NJPMDSMTSA-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
Cistanche tubulosa	LOTUS Database	35616633
Gardenia jasminoides	LOTUS Database	35616633
Kickxia abhaica	LOTUS Database	35616633
Kickxia elatine	LOTUS Database	35616633
Melampyrum cristatum	LOTUS Database	35616633
Plantago alpina	LOTUS Database	35616633
Plantago arborescens	LOTUS Database	35616633
Utricularia vulgaris	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
Vinylogous ester
Tertiary alcohol
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Carboxylic acid
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Primary alcohol
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	-1.8	ALOGPS
logP	-2	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.51 m³·mol⁻¹	ChemAxon
Polarizability	36.11 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

C00010629

Chemspider ID

10264396

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21633105

PDB ID

Not Available

ChEBI ID

167726

Good Scents ID

Not Available

References

General References

Venditti A, Frezza C, Sciubba F, Foddai S, Serafini M, Nicoletti M, Bianco A: Secoiridoids and other chemotaxonomically relevant compounds in Pedicularis: phytochemical analysis and comparison of Pedicularis rostratocapitata Crantz and Pedicularis verticillata L. from Dolomites. Nat Prod Res. 2016 Aug;30(15):1698-705. doi: 10.1080/14786419.2015.1136307. Epub 2016 Feb 1. [PubMed:26828611 ]
Venditti A, Frezza C, Serafini M, Bianco A: Iridoids and phenylethanoid from Pedicularis kerneri Dalla Torre growing in Dolomites, Italy. Nat Prod Res. 2016;30(3):327-31. doi: 10.1080/14786419.2015.1060230. Epub 2015 Jul 24. [PubMed:26207992 ]
Kroll-Moller P, Pedersen KD, Gousiadou C, Kokubun T, Albach D, Taskova R, Garnock-Jones PJ, Gotfredsen CH, Jensen SR: Iridoid glucosides in the genus Veronica (Plantaginaceae) from New Zealand. Phytochemistry. 2017 Aug;140:174-180. doi: 10.1016/j.phytochem.2017.04.025. Epub 2017 May 24. [PubMed:28550715 ]
Amin A, Tuenter E, Foubert K, Iqbal J, Cos P, Maes L, Exarchou V, Apers S, Pieters L: In Vitro and In Silico Antidiabetic and Antimicrobial Evaluation of Constituents from Kickxia ramosissima (Nanorrhinum ramosissimum). Front Pharmacol. 2017 May 1;8:232. doi: 10.3389/fphar.2017.00232. eCollection 2017. [PubMed:28507520 ]
LOTUS database [Link]

Showing NP-Card for (1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid (NP0152821)

MOL for NP0152821 ((1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D MOL for NP0152821 ((1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D SDF for NP0152821 ((1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D-SDF for NP0152821 ((1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

PDB for NP0152821 ((1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D PDB for NP0152821 ((1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

SMILES for NP0152821 ((1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

INCHI for NP0152821 ((1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

Structure for NP0152821 ((1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid)

3D Structure for NP0152821 ((1s,4as,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylic acid)