NP-MRD: Showing NP-Card for (1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide (NP0331662)

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Record Information

Version

2.0

Created at

2023-05-31 12:01:21 UTC

Updated at

2025-02-11 15:45:37 UTC

NP-MRD ID

NP0331662

Natural Product DOI

https://doi.org/10.57994/0653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide

Description

(1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide was first documented in 2023 (PMID: 37200063).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120423D          

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M  END

     RDKit          3D

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  Mrv1652306202120423D          

 69 74  0  0  0  0            999 V2000
    3.1846    0.0754    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7315    0.6172    0.4484 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2278    1.0473   -0.9437 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0066    2.2435   -1.5085 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3434    2.7774   -2.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3096    3.7560   -2.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0214    3.9116   -4.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052    3.0977   -4.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6033    2.4160   -4.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    3.3049   -0.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931    3.0328    0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2091    3.7753    1.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615    1.8613    1.3584 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3907    2.3796    1.8275 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7707    1.4070    1.6640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4022   -0.0684    1.9307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1186   -0.1967    3.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904   -0.5284    1.1344 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4957   -1.7117    0.2004 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0869   -2.8204    1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837   -2.4640    1.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6219   -1.0168    1.5180 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7033   -0.7379    2.3860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0089   -0.9579    1.8431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1522   -2.2878    1.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4490   -2.5138    0.7809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4834   -3.9167    0.1588 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6805   -4.1543   -0.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5319   -2.3607    1.8630 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8434   -2.5479    1.3202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4296   -0.9722    2.4971 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3635   -0.8862    3.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0081   -0.7148    2.9932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9269    0.6282    3.4948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7111   -0.8777   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6601   -0.4202   -0.6772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5541   -1.2711   -0.6851 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8840    0.8373   -0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -0.2792    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2252   -0.7607   -0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684    1.3126   -0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012    0.2171   -1.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134    1.9190   -1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617    4.2847   -2.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6754    4.5284   -4.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2910    1.7211   -4.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3367    1.5925    2.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1214    3.3153    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769    2.6547    2.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848    1.7216    2.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1823    1.5297    0.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9696    0.1492    4.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7517    0.3968    3.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899   -1.2310    3.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5661   -0.9686    1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324   -2.0803   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462   -3.8123    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368   -3.1417    2.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1917   -0.2162    1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6277   -1.7888   -0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3853   -4.6878    0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6365   -4.0471   -0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4190   -3.7731   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3977   -3.1217    2.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4540   -2.2293    2.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7370   -0.2002    1.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1418   -0.0512    4.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7838   -1.3751    3.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9801    0.7781    3.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  2  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
  2 13  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 27 28  1  0  0  0  0
 20 21  2  0  0  0  0
  2  3  1  0  0  0  0
 13 11  1  0  0  0  0
 11 10  1  0  0  0  0
 10  4  1  0  0  0  0
  4  3  1  0  0  0  0
 11 12  2  0  0  0  0
 24 33  1  0  0  0  0
  4  5  1  0  0  0  0
 33 31  1  0  0  0  0
  2  1  1  6  0  0  0
 31 29  1  0  0  0  0
 18 55  1  1  0  0  0
  9  8  1  0  0  0  0
 20 19  1  0  0  0  0
 21 22  1  0  0  0  0
 22 16  1  0  0  0  0
 18 19  1  0  0  0  0
  5  9  2  0  0  0  0
  8  7  1  0  0  0  0
  7  6  2  0  0  0  0
  6  5  1  0  0  0  0
 18 16  1  0  0  0  0
 29 26  1  0  0  0  0
 19 37  1  0  0  0  0
 26 25  1  0  0  0  0
 22 35  1  0  0  0  0
 35 37  1  0  0  0  0
 25 24  1  0  0  0  0
 35 36  2  0  0  0  0
 22 23  1  1  0  0  0
 16 17  1  1  0  0  0
 13 47  1  1  0  0  0
 26 27  1  0  0  0  0
 24 23  1  0  0  0  0
 28 63  1  0  0  0  0
 24 59  1  6  0  0  0
 29 64  1  1  0  0  0
 30 65  1  0  0  0  0
 31 66  1  6  0  0  0
 32 67  1  0  0  0  0
 33 68  1  1  0  0  0
 34 69  1  0  0  0  0
 27 61  1  0  0  0  0
 27 62  1  0  0  0  0
 26 60  1  6  0  0  0
 20 57  1  0  0  0  0
 21 58  1  0  0  0  0
 19 56  1  6  0  0  0
 15 50  1  0  0  0  0
 15 51  1  0  0  0  0
 14 48  1  0  0  0  0
 14 49  1  0  0  0  0
  4 43  1  6  0  0  0
  3 41  1  0  0  0  0
  3 42  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  9 46  1  0  0  0  0
  7 45  1  0  0  0  0
  6 44  1  0  0  0  0
 17 52  1  0  0  0  0
 17 53  1  0  0  0  0
 17 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331662

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]1([H])O[C@]([H])(O[C@@]23C([H])=C([H])[C@@]([H])(OC2=O)[C@@]2([H])[C@@]4(C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)[C@@]4([H])C([H])([H])C([H])([H])[C@@]32C([H])([H])[H])C2=C([H])OC([H])=C2[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O11/c1-24-9-15(12-5-8-33-11-12)34-21(31)13(24)3-6-25(2)20(24)14-4-7-26(25,23(32)36-14)37-22-19(30)18(29)17(28)16(10-27)35-22/h4-5,7-8,11,13-20,22,27-30H,3,6,9-10H2,1-2H3/t13-,14-,15+,16+,17+,18-,19+,20+,22-,24+,25-,26+/m1/s1

> <INCHI_KEY>
ZHUNNEPKAYTEID-WVHOZIAZSA-N

> <FORMULA>
C26H32O11

> <MOLECULAR_WEIGHT>
520.531

> <EXACT_MASS>
520.19446185

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.38683455517273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3R,5S,8S,11R,12R)-5-(furan-3-yl)-3,11-dimethyl-12-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6,14-dioxatetracyclo[10.2.2.0^{2,11}.0^{3,8}]hexadec-15-ene-7,13-dione

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
0.3836496759999998

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.199382320383037

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.208737742023375

> <JCHEM_PKA_STRONGEST_BASIC>
-2.864634417941994

> <JCHEM_POLAR_SURFACE_AREA>
165.12

> <JCHEM_REFRACTIVITY>
122.63750000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,5S,8S,11R,12R)-5-(furan-3-yl)-3,11-dimethyl-12-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6,14-dioxatetracyclo[10.2.2.0^{2,11}.0^{3,8}]hexadec-15-ene-7,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 69 74  0  0  0  0  0  0  0  0999 V2000
    3.1846    0.0754    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7315    0.6172    0.4484 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2278    1.0473   -0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0066    2.2435   -1.5085 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3434    2.7774   -2.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3096    3.7560   -2.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0214    3.9116   -4.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052    3.0977   -4.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6033    2.4160   -4.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    3.3049   -0.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931    3.0328    0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2091    3.7753    1.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615    1.8613    1.3584 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3907    2.3796    1.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707    1.4070    1.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4022   -0.0684    1.9307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1186   -0.1967    3.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904   -0.5284    1.1344 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4957   -1.7117    0.2004 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0869   -2.8204    1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837   -2.4640    1.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6219   -1.0168    1.5180 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7033   -0.7379    2.3860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0089   -0.9579    1.8431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1522   -2.2878    1.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4490   -2.5138    0.7809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4834   -3.9167    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6805   -4.1543   -0.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5319   -2.3607    1.8630 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8434   -2.5479    1.3202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4296   -0.9722    2.4971 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3635   -0.8862    3.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0081   -0.7148    2.9932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9269    0.6282    3.4948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7111   -0.8777   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6601   -0.4202   -0.6772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5541   -1.2711   -0.6851 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8840    0.8373   -0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -0.2792    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2252   -0.7607   -0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684    1.3126   -0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012    0.2171   -1.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134    1.9190   -1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617    4.2847   -2.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6754    4.5284   -4.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2910    1.7211   -4.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3367    1.5925    2.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1214    3.3153    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769    2.6547    2.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848    1.7216    2.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1823    1.5297    0.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9696    0.1492    4.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7517    0.3968    3.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899   -1.2310    3.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5661   -0.9686    1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324   -2.0803   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462   -3.8123    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368   -3.1417    2.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1917   -0.2162    1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6277   -1.7888   -0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3853   -4.6878    0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6365   -4.0471   -0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4190   -3.7731   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3977   -3.1217    2.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4540   -2.2293    2.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7370   -0.2002    1.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1418   -0.0512    4.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7838   -1.3751    3.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9801    0.7781    3.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  2  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
  2 13  1  0
 29 30  1  0
 31 32  1  0
 33 34  1  0
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  2  3  1  0
 13 11  1  0
 11 10  1  0
 10  4  1  0
  4  3  1  0
 11 12  2  0
 24 33  1  0
  4  5  1  0
 33 31  1  0
  2  1  1  6
 31 29  1  0
 18 55  1  1
  9  8  1  0
 20 19  1  0
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  5  9  2  0
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 17 52  1  0
 17 53  1  0
 17 54  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.185   0.075   0.294  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.732   0.617   0.448  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.228   1.047  -0.944  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.007   2.244  -1.508  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.343   2.777  -2.743  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.310   3.756  -2.825  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.021   3.912  -4.159  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.805   3.098  -4.910  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.603   2.416  -4.050  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.194   3.305  -0.555  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.493   3.033   0.732  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.209   3.775   1.395  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.762   1.861   1.358  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.391   2.380   1.827  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.771   1.407   1.664  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.402  -0.068   1.931  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.119  -0.197   3.458  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.890  -0.528   1.134  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.496  -1.712   0.200  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.087  -2.820   1.038  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.184  -2.464   1.725  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.622  -1.017   1.518  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.703  -0.738   2.386  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.009  -0.958   1.843  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.152  -2.288   1.353  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.449  -2.514   0.781  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.483  -3.917   0.159  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.681  -4.154  -0.574  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.532  -2.361   1.863  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.843  -2.548   1.320  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.430  -0.972   2.497  0.00  0.00           C+0
HETATM   32  O   UNK     0      -7.364  -0.886   3.585  0.00  0.00           O+0
HETATM   33  C   UNK     0      -5.008  -0.715   2.993  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.927   0.628   3.495  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.711  -0.878  -0.053  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.660  -0.420  -0.677  0.00  0.00           O+0
HETATM   37  O   UNK     0      -0.554  -1.271  -0.685  0.00  0.00           O+0
HETATM   38  H   UNK     0       3.884   0.837  -0.063  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.579  -0.279   1.254  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.225  -0.761  -0.412  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.168   1.313  -0.899  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.301   0.217  -1.658  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.013   1.919  -1.801  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.162   4.285  -2.007  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.675   4.528  -4.710  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.291   1.721  -4.513  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.337   1.593   2.257  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.121   3.315   1.320  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.477   2.655   2.888  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.585   1.722   2.331  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.182   1.530   0.658  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.970   0.149   4.055  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.752   0.397   3.757  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.090  -1.231   3.751  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.566  -0.969   1.885  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.332  -2.080  -0.399  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.346  -3.812   1.067  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.737  -3.142   2.363  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.192  -0.216   1.058  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.628  -1.789  -0.025  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.385  -4.688   0.931  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.636  -4.047  -0.523  0.00  0.00           H+0
HETATM   63  H   UNK     0      -7.419  -3.773  -0.051  0.00  0.00           H+0
HETATM   64  H   UNK     0      -6.398  -3.122   2.643  0.00  0.00           H+0
HETATM   65  H   UNK     0      -8.454  -2.229   2.019  0.00  0.00           H+0
HETATM   66  H   UNK     0      -6.737  -0.200   1.781  0.00  0.00           H+0
HETATM   67  H   UNK     0      -7.142  -0.051   4.046  0.00  0.00           H+0
HETATM   68  H   UNK     0      -4.784  -1.375   3.840  0.00  0.00           H+0
HETATM   69  H   UNK     0      -3.980   0.778   3.687  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2   18   13    3    1                                             
CONECT    3    2    4   41   42                                             
CONECT    4   10    3    5   43                                             
CONECT    5    4    9    6                                                  
CONECT    6    7    5   44                                                  
CONECT    7    8    6   45                                                  
CONECT    8    9    7                                                       
CONECT    9    8    5   46                                                  
CONECT   10   11    4                                                       
CONECT   11   13   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14    2   11   47                                             
CONECT   14   15   13   48   49                                             
CONECT   15   16   14   50   51                                             
CONECT   16   15   22   18   17                                             
CONECT   17   16   52   53   54                                             
CONECT   18    2   55   19   16                                             
CONECT   19   20   18   37   56                                             
CONECT   20   21   19   57                                                  
CONECT   21   20   22   58                                                  
CONECT   22   21   16   35   23                                             
CONECT   23   22   24                                                       
CONECT   24   33   25   23   59                                             
CONECT   25   26   24                                                       
CONECT   26   29   25   27   60                                             
CONECT   27   28   26   61   62                                             
CONECT   28   27   63                                                       
CONECT   29   30   31   26   64                                             
CONECT   30   29   65                                                       
CONECT   31   32   33   29   66                                             
CONECT   32   31   67                                                       
CONECT   33   34   24   31   68                                             
CONECT   34   33   69                                                       
CONECT   35   22   37   36                                                  
CONECT   36   35                                                            
CONECT   37   19   35                                                       
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    3                                                            
CONECT   42    3                                                            
CONECT   43    4                                                            
CONECT   44    6                                                            
CONECT   45    7                                                            
CONECT   46    9                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   15                                                            
CONECT   52   17                                                            
CONECT   53   17                                                            
CONECT   54   17                                                            
CONECT   55   18                                                            
CONECT   56   19                                                            
CONECT   57   20                                                            
CONECT   58   21                                                            
CONECT   59   24                                                            
CONECT   60   26                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   29                                                            
CONECT   65   30                                                            
CONECT   66   31                                                            
CONECT   67   32                                                            
CONECT   68   33                                                            
CONECT   69   34                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  148    0
END

RDKit          3D

69 74  0  0  0  0  0  0  0  0999 V2000
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    1.7315    0.6172    0.4484 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.0066    2.2435   -1.5085 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.6033    2.4160   -4.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    3.3049   -0.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931    3.0328    0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2091    3.7753    1.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615    1.8613    1.3584 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3907    2.3796    1.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707    1.4070    1.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
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 34 69  1  0
 27 61  1  0
 27 62  1  0
 26 60  1  6
 20 57  1  0
 21 58  1  0
 19 56  1  6
 15 50  1  0
 15 51  1  0
 14 48  1  0
 14 49  1  0
  4 43  1  6
  3 41  1  0
  3 42  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  9 46  1  0
  7 45  1  0
  6 44  1  0
 17 52  1  0
 17 53  1  0
 17 54  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₁

Average Mass

520.5310 Da

Monoisotopic Mass

520.19446 Da

IUPAC Name

(1R,2S,3R,5S,8S,11R,12R)-5-(furan-3-yl)-3,11-dimethyl-12-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6,14-dioxatetracyclo[10.2.2.0^{2,11}.0^{3,8}]hexadec-15-ene-7,13-dione

Traditional Name

(1R,2S,3R,5S,8S,11R,12R)-5-(furan-3-yl)-3,11-dimethyl-12-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6,14-dioxatetracyclo[10.2.2.0^{2,11}.0^{3,8}]hexadec-15-ene-7,13-dione

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@]1([H])O[C@]([H])(O[C@@]23C([H])=C([H])[C@@]([H])(OC2=O)[C@@]2([H])[C@@]4(C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)[C@@]4([H])C([H])([H])C([H])([H])[C@@]32C([H])([H])[H])C2=C([H])OC([H])=C2[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C26H32O11/c1-24-9-15(12-5-8-33-11-12)34-21(31)13(24)3-6-25(2)20(24)14-4-7-26(25,23(32)36-14)37-22-19(30)18(29)17(28)16(10-27)35-22/h4-5,7-8,11,13-20,22,27-30H,3,6,9-10H2,1-2H3/t13-,14-,15+,16+,17+,18-,19+,20+,22-,24+,25-,26+/m1/s1

InChI Key

ZHUNNEPKAYTEID-WVHOZIAZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

Classification

Not classified

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	0.55	ALOGPS
logP	0.38	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	165.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.64 m³·mol⁻¹	ChemAxon
Polarizability	51.39 Å³	ChemAxon
Number of Rings	6	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

Not Available

References

General References

DOI: 10.1021/acs.jnatprod.3c00114

Showing NP-Card for (1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide (NP0331662)

MOL for NP0331662 ((1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide)

3D MOL for NP0331662 ((1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide)

3D SDF for NP0331662 ((1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide)

3D-SDF for NP0331662 ((1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide)

PDB for NP0331662 ((1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide)

3D PDB for NP0331662 ((1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide)

SMILES for NP0331662 ((1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide)

INCHI for NP0331662 ((1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide)

Structure for NP0331662 ((1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide)

3D Structure for NP0331662 ((1R,4S,5R,8S,9R,10S,12S)-15,16-epoxy-4-O-(β-d-glucopyranosyl)cleroda-2,13(16),14-triene-17(12),18(1)-diolide)