NP-MRD: Showing NP-Card for (3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate (NP0311714)

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Record Information

Version

2.0

Created at

2022-09-11 07:54:05 UTC

Updated at

2022-09-11 07:54:06 UTC

NP-MRD ID

NP0311714

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate

Description

Hebevinoside III belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. Hebevinoside III is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, hebevinoside III has been detected, but not quantified in, mushrooms. (3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate is found in Hebeloma vinosophyllum. This could make hebevinoside III a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308502D          

 56 61  0  0  0  0            999 V2000
   -1.3574    6.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856    5.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1616    4.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6631   -2.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4264    1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4239    1.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377    3.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8218    4.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596    1.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729    4.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1620    5.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9665    3.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1498    3.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9620    3.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5256    3.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7135    3.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3665    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8106    2.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0832    0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3228   -0.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683    5.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493    3.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083   -1.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6180    2.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8983    2.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5544    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8953    0.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1278    2.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3079    0.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2423    2.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571    3.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4271    0.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0838   -0.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7145    0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1468    1.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693    1.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2741    2.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3347    1.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7934    1.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7104    1.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8059    3.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1817    3.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620    2.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843   -1.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226    1.0135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1756   -0.6337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2392    0.6277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2290   -1.0068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4904    0.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6786    2.1796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2000    1.6811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1776   -1.2583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8029    1.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6481    2.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626    0.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0544    2.4700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 14 13  1  0  0  0  0
 16 15  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21 11  2  0  0  0  0
 22  3  1  0  0  0  0
 22 12  1  0  0  0  0
 23  4  1  0  0  0  0
 24 13  1  0  0  0  0
 25 17  2  0  0  0  0
 25 24  1  0  0  0  0
 26 17  1  0  0  0  0
 27 19  1  0  0  0  0
 28 18  1  0  0  0  0
 29 20  1  0  0  0  0
 30 14  1  0  0  0  0
 31 22  1  0  0  0  0
 31 28  1  0  0  0  0
 32 27  1  0  0  0  0
 33 29  1  0  0  0  0
 34 33  1  0  0  0  0
 35 32  1  0  0  0  0
 36 34  1  0  0  0  0
 37 26  1  0  0  0  0
 38 35  1  0  0  0  0
 39 36  1  0  0  0  0
 40  5  1  0  0  0  0
 40  6  1  0  0  0  0
 40 25  1  0  0  0  0
 40 30  1  0  0  0  0
 41  7  1  0  0  0  0
 41 15  1  0  0  0  0
 41 24  1  0  0  0  0
 41 37  1  0  0  0  0
 42  8  1  0  0  0  0
 42 16  1  0  0  0  0
 42 31  1  0  0  0  0
 43  9  1  0  0  0  0
 43 18  1  0  0  0  0
 43 37  1  0  0  0  0
 43 42  1  0  0  0  0
 44 23  2  0  0  0  0
 45 26  1  0  0  0  0
 46 27  1  0  0  0  0
 47 32  1  0  0  0  0
 48 33  1  0  0  0  0
 49 34  1  0  0  0  0
 50 35  1  0  0  0  0
 51 36  1  0  0  0  0
 52 20  1  0  0  0  0
 52 23  1  0  0  0  0
 53 19  1  0  0  0  0
 53 38  1  0  0  0  0
 54 28  1  0  0  0  0
 54 39  1  0  0  0  0
 55 29  1  0  0  0  0
 55 39  1  0  0  0  0
 56 30  1  0  0  0  0
 56 38  1  0  0  0  0
M  END

     RDKit          3D

126131  0  0  0  0  0  0  0  0999 V2000
   -6.7778    7.6451   -1.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3118    6.2287   -1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8353    5.2941   -1.8640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2911    5.9658   -0.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6602    4.8178    0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3711    3.8177    0.8428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5693    2.7479    1.1858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7921    1.5892    0.4790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8479    0.6447    0.9291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9768    0.2241   -0.1153 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6720    0.9661    0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -0.0091   -0.1937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8224   -0.0405   -1.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7374    0.2768    0.1248 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0343    1.4334    1.0475 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4582    2.5692    0.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339    1.5722    1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3637    0.7006    0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9626   -0.5647   -0.1570 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0002   -1.6173   -0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1807   -1.0753   -0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7579    0.2131   -0.1826 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4355    0.7965   -1.2169 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8929   -0.6207   -0.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2066   -0.9036   -0.9325 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1371    0.2384   -0.7363 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2558   -0.2803   -0.0055 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4884    0.6511    1.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6003   -0.9205    0.4706 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9070   -1.0646    1.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864   -2.1528   -0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2591   -1.2979    0.3296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2444   -1.3256    1.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7001   -1.2409   -0.0537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1974   -2.0491   -1.1798 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7236   -1.7490   -1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3196   -3.5619   -0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0498   -4.3237   -1.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1914   -5.7493   -1.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   -6.5100   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1431   -8.0024   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5815    1.7498   -0.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3721    0.6603   -1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6691    1.9308   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6507    1.2547    1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313    0.8694   -2.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164    0.1096   -2.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632   -0.8892   -2.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1839    0.7088   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6077    1.3940    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9389    2.7527   -0.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9881   -0.9773    2.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061308502D          

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M  END
> <DATABASE_ID>
NP0311714

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C)C1C(CC2(C)C3C(O)C=C4C(CCC(OC5OCC(O)C(O)C5O)C4(C)C)C3(C)CCC12C)OC1OC(COC(C)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C43H70O13/c1-21(2)11-10-12-22(3)31-28(54-39-36(51)34(49)33(48)29(55-39)20-52-23(4)44)18-43(9)37-26(45)17-25-24(41(37,7)15-16-42(31,43)8)13-14-30(40(25,5)6)56-38-35(50)32(47)27(46)19-53-38/h11,17,22,24,26-39,45-51H,10,12-16,18-20H2,1-9H3

> <INCHI_KEY>
ZSGIZQTTWRMUOQ-UHFFFAOYSA-N

> <FORMULA>
C43H70O13

> <MOLECULAR_WEIGHT>
795.0081

> <EXACT_MASS>
794.481642326

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
87.85087024437598

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3,4,5-trihydroxy-6-{[9-hydroxy-1,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl]oxy}oxan-2-yl)methyl acetate

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
2.818497272666667

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.461675101523845

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.927843599339278

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6145693604988068

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999996

> <JCHEM_REFRACTIVITY>
205.8579

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3,4,5-trihydroxy-6-{[9-hydroxy-1,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl]oxy}oxan-2-yl)methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.534  12.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.640  10.840   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.302   8.829   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.238  -4.857   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.263   2.259   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.125   2.931   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.230   6.872   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.534   7.623   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.098   3.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.749   8.408   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.169   9.835   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.804   7.192   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.746   6.601   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.262   6.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.714   7.143   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.199   7.414   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.284   2.798   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.513   3.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.355   0.537   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.603  -0.833   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.114  11.050   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.279   7.403   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.509  -3.342   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.754   5.424   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.277   3.975   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.768   3.069   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.871   0.265   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.239   4.708   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.575   0.160   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.786   4.882   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.667   6.187   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.864   1.443   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.023  -0.363   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.200   0.629   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.341   2.891   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.929   2.145   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.245   4.518   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.825   3.162   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.481   2.669   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.793   3.704   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.238   5.695   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.206   6.237   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.729   4.789   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       2.957  -2.818   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       3.776   1.892   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      13.394  -1.183   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      15.380   1.172   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -2.294  -1.879   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -4.649   0.106   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      14.333   4.069   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -4.107   3.138   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       0.332  -2.349   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      10.832   1.985   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      -1.210   4.185   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      -0.304   1.676   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      11.302   4.611   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5   40                                                            
CONECT    6   40                                                            
CONECT    7   41                                                            
CONECT    8   42                                                            
CONECT    9   43                                                            
CONECT   10   11   12                                                       
CONECT   11   10   21                                                       
CONECT   12   10   22                                                       
CONECT   13   14   24                                                       
CONECT   14   13   30                                                       
CONECT   15   16   41                                                       
CONECT   16   15   42                                                       
CONECT   17   25   26                                                       
CONECT   18   28   43                                                       
CONECT   19   27   53                                                       
CONECT   20   29   52                                                       
CONECT   21    1    2   11                                                  
CONECT   22    3   12   31                                                  
CONECT   23    4   44   52                                                  
CONECT   24   13   25   41                                                  
CONECT   25   17   24   40                                                  
CONECT   26   17   37   45                                                  
CONECT   27   19   32   46                                                  
CONECT   28   18   31   54                                                  
CONECT   29   20   33   55                                                  
CONECT   30   14   40   56                                                  
CONECT   31   22   28   42                                                  
CONECT   32   27   35   47                                                  
CONECT   33   29   34   48                                                  
CONECT   34   33   36   49                                                  
CONECT   35   32   38   50                                                  
CONECT   36   34   39   51                                                  
CONECT   37   26   41   43                                                  
CONECT   38   35   53   56                                                  
CONECT   39   36   54   55                                                  
CONECT   40    5    6   25   30                                             
CONECT   41    7   15   24   37                                             
CONECT   42    8   16   31   43                                             
CONECT   43    9   18   37   42                                             
CONECT   44   23                                                            
CONECT   45   26                                                            
CONECT   46   27                                                            
CONECT   47   32                                                            
CONECT   48   33                                                            
CONECT   49   34                                                            
CONECT   50   35                                                            
CONECT   51   36                                                            
CONECT   52   20   23                                                       
CONECT   53   19   38                                                       
CONECT   54   28   39                                                       
CONECT   55   29   39                                                       
CONECT   56   30   38                                                       
MASTER        0    0    0    0    0    0    0    0   56    0  122    0
END

View in JSmol

Synonyms

Value	Source
(3,4,5-Trihydroxy-6-{[9-hydroxy-1,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl]oxy}oxan-2-yl)methyl acetic acid	Generator

Chemical Formula

C₄₃H₇₀O₁₃

Average Mass

795.0081 Da

Monoisotopic Mass

794.48164 Da

IUPAC Name

(3,4,5-trihydroxy-6-{[9-hydroxy-1,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl]oxy}oxan-2-yl)methyl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C)C1C(CC2(C)C3C(O)C=C4C(CCC(OC5OCC(O)C(O)C5O)C4(C)C)C3(C)CCC12C)OC1OC(COC(C)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C43H70O13/c1-21(2)11-10-12-22(3)31-28(54-39-36(51)34(49)33(48)29(55-39)20-52-23(4)44)18-43(9)37-26(45)17-25-24(41(37,7)15-16-42(31,43)8)13-14-30(40(25,5)6)56-38-35(50)32(47)27(46)19-53-38/h11,17,22,24,26-39,45-51H,10,12-16,18-20H2,1-9H3

InChI Key

ZSGIZQTTWRMUOQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hebeloma vinosophyllum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Not Available

Substituents

Not Available

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	3.11	ALOGPS
logP	2.82	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	11.93	ChemAxon
pKa (Strongest Basic)	-0.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	205.86 m³·mol⁻¹	ChemAxon
Polarizability	87.85 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0035982

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014787

KNApSAcK ID

C00023918

Chemspider ID

26503828

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53463009

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate (NP0311714)

MOL for NP0311714 ((3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate)

3D MOL for NP0311714 ((3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate)

3D SDF for NP0311714 ((3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate)

3D-SDF for NP0311714 ((3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate)

PDB for NP0311714 ((3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate)

3D PDB for NP0311714 ((3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate)

SMILES for NP0311714 ((3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate)

INCHI for NP0311714 ((3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate)

Structure for NP0311714 ((3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate)

3D Structure for NP0311714 ((3,4,5-trihydroxy-6-{[4-hydroxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate)