NP-MRD: Showing NP-Card for (2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester (NP0331660)

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Record Information

Version

2.0

Created at

2023-05-31 12:01:07 UTC

Updated at

2025-02-11 15:45:35 UTC

NP-MRD ID

NP0331660

Natural Product DOI

https://doi.org/10.57994/0651

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester

Description

(2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester was first documented in 2023 (PMID: 37200063). Based on a literature review very few articles have been published on (2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305312314012D          

 41 45  0  0  1  0            999 V2000
    2.0329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.6039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.0329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6829    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.7474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4454    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    3.4618    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2704    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    3.4618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9204    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    2.7474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7454    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0954   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3684   -3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7553   -3.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409   -3.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2124   -2.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  6  0  0  0
  6 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 21 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 36 40  1  0  0  0  0
 35 41  1  0  0  0  0
  2 41  1  0  0  0  0
M  END


  Mrv1652305312314012D          

 41 45  0  0  1  0            999 V2000
    2.0329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.6039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.0329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6829    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.7474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4454    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    3.4618    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2704    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    3.4618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9204    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    2.7474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7454    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0954   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3684   -3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7553   -3.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409   -3.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2124   -2.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  6  0  0  0
  6 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 21 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 36 40  1  0  0  0  0
 35 41  1  0  0  0  0
  2 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331660

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC(O[C@H]3O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]3O)[C@@]3(C)C(=C[C@H](O)C[C@@]3([H])[C@]1(C)C[C@H](OC2=O)C1=COC=C1)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O12/c1-26-9-16(12-4-5-36-11-12)37-24(34)14(26)8-19(39-25-22(32)21(31)20(30)17(10-28)38-25)27(2)15(23(33)35-3)6-13(29)7-18(26)27/h4-6,11,13-14,16-22,25,28-32H,7-10H2,1-3H3/t13-,14-,16-,17-,18-,19?,20-,21+,22-,25+,26+,27-/m0/s1

> <INCHI_KEY>
XUOAZZCHOKUHCF-AKSXVTHESA-N

> <FORMULA>
C27H36O12

> <MOLECULAR_WEIGHT>
552.573

> <EXACT_MASS>
552.220676599

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.553322657505085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,4aR,6aR,9R,10aS,10bS)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4-oxo-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4H,4aH,5H,6H,6aH,9H,10H,10aH,10bH-naphtho[2,1-c]pyran-7-carboxylate

> <JCHEM_LOGP>
-0.40653183599999976

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.190541617164953

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.209430837763989

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8613848056347795

> <JCHEM_POLAR_SURFACE_AREA>
185.35

> <JCHEM_REFRACTIVITY>
131.00459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,4aR,6aR,9R,10aS,10bS)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4-oxo-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4aH,5H,6H,9H,10H,10aH-naphtho[2,1-c]pyran-7-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-23         0                                  
HETATM    1  O   UNK     0       3.795   1.127   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       5.335   1.127   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.185   2.461   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.415   3.795   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.875   3.795   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.105   5.128   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.565   5.128   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.795   6.462   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.875   6.462   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.105   7.796   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.415   6.462   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.185   7.796   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.185   5.128   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.725   5.128   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.955   1.127   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.495   1.127   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.725   2.461   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.495   3.795   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.035   1.127   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       7.645  -0.206   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.795  -4.207   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.421  -5.614   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.277  -6.645   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.943  -5.875   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.263  -4.368   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.795  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   41                                                  
CONECT    3    2    4    5   32                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8   18                                                  
CONECT   18   17                                                            
CONECT   19    6   20   21   30                                             
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22                                                            
CONECT   26   21   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   19   31   32                                             
CONECT   31   30                                                            
CONECT   32   30    3   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   41                                                  
CONECT   36   35   37   40                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   36                                                       
CONECT   41   35    2                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
(2R,5R,6R,8R,9S,10S,12S)-15,16-Epoxy-2-hydroxy-6-O-(-D-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-Oate methyl ester	Generator

Chemical Formula

C₂₇H₃₆O₁₂

Average Mass

552.5730 Da

Monoisotopic Mass

552.22068 Da

IUPAC Name

methyl (2S,4aR,6aR,9R,10aS,10bS)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4-oxo-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4H,4aH,5H,6H,6aH,9H,10H,10aH,10bH-naphtho[2,1-c]pyran-7-carboxylate

Traditional Name

methyl (2S,4aR,6aR,9R,10aS,10bS)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4-oxo-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4aH,5H,6H,9H,10H,10aH-naphtho[2,1-c]pyran-7-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC(O[C@H]3O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]3O)[C@@]3(C)C(=C[C@H](O)C[C@@]3([H])[C@]1(C)C[C@H](OC2=O)C1=COC=C1)C(=O)OC

InChI Identifier

InChI=1S/C27H36O12/c1-26-9-16(12-4-5-36-11-12)37-24(34)14(26)8-19(39-25-22(32)21(31)20(30)17(10-28)38-25)27(2)15(23(33)35-3)6-13(29)7-18(26)27/h4-6,11,13-14,16-22,25,28-32H,7-10H2,1-3H3/t13-,14-,16-,17-,18-,19?,20-,21+,22-,25+,26+,27-/m0/s1

InChI Key

XUOAZZCHOKUHCF-AKSXVTHESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400, CD₃OD, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Tinospora crispa		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Clerodane diterpenoid
Diterpenoid
Diterpene lactone
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Naphthopyran
Fatty alcohol ester
Alkyl glycoside
Naphthalene
Fatty alcohol
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Fatty acyl
Pyran
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Furan
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.41	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	185.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	131 m³·mol⁻¹	ChemAxon
Polarizability	55.55 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1021/acs.jnatprod.3c00114

Showing NP-Card for (2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester (NP0331660)

MOL for NP0331660 ((2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester)

3D MOL for NP0331660 ((2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester)

3D SDF for NP0331660 ((2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester)

3D-SDF for NP0331660 ((2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester)

PDB for NP0331660 ((2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester)

3D PDB for NP0331660 ((2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester)

SMILES for NP0331660 ((2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester)

INCHI for NP0331660 ((2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester)

Structure for NP0331660 ((2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester)

3D Structure for NP0331660 ((2R,5R,6R,8R,9S,10S,12S)-15,16-epoxy-2-hydroxy-6-O-(-d-glucopyranosyl)cleroda-3,13(16),14-trien-17,12-olid-18-oic acid methyl ester)