NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0219881)

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Record Information

Version

2.0

Created at

2022-09-05 21:01:13 UTC

Updated at

2022-09-05 21:01:13 UTC

NP-MRD ID

NP0219881

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Coriandrinol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. (2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Ampelopsis glandulosa, Betula pendula, Elliottia paniculata, Epimedium diphyllum, Lyonia ovalifolia, Machilus thunbergii, Prunus ssiori, Saraca asoca, Ulmus davidiana and Viburnum dilatatum. Coriandrinol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533007131513392D          

 53 57  0  0  1  0            999 V2000
   -2.4048    2.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8858    0.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2094    1.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876    2.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640    2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511    1.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3921    1.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0812    2.0435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1390    1.2383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8587    2.0142    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0466    2.1594    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5148    1.5287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7951    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4829    1.7238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905    2.6449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7663    2.9353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026    1.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.6076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533    2.2692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703    2.8077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314   -0.5086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557    0.8111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6708    1.8690    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5784    2.7901    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3269    1.3835    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2345    2.3046    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    0.8980    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 21  4  1  1  0  0  0
 21  8  1  0  0  0  0
 22  7  1  0  0  0  0
 22  9  1  6  0  0  0
 22 20  1  0  0  0  0
 23 10  2  0  0  0  0
 23 18  1  0  0  0  0
 24 14  1  0  0  0  0
 24 18  1  0  0  0  0
 25 11  1  0  0  0  0
 26 12  1  0  0  0  0
 26 21  1  0  0  0  0
 27 13  1  0  0  0  0
 27 25  1  0  0  0  0
 28 15  1  0  0  0  0
 28 25  1  0  0  0  0
 29 19  1  1  0  0  0
 30 29  1  0  0  0  0
 31 30  1  0  0  0  0
 32 31  1  0  0  0  0
 33 32  1  0  0  0  0
 34  5  1  6  0  0  0
 34 16  1  0  0  0  0
 34 23  1  0  0  0  0
 34 28  1  0  0  0  0
 35  6  1  6  0  0  0
 35 17  1  0  0  0  0
 35 26  1  0  0  0  0
 35 27  1  0  0  0  0
 36 19  1  0  0  0  0
 30 37  1  6  0  0  0
 31 38  1  6  0  0  0
 32 39  1  6  0  0  0
 40 24  1  0  0  0  0
 33 40  1  1  0  0  0
 41 29  1  0  0  0  0
 41 33  1  0  0  0  0
 21 42  1  6  0  0  0
 22 43  1  1  0  0  0
 44 24  1  0  0  0  0
 25 45  1  6  0  0  0
 46 26  1  0  0  0  0
 27 47  1  1  0  0  0
 28 48  1  1  0  0  0
 29 49  1  6  0  0  0
 30 50  1  1  0  0  0
 31 51  1  6  0  0  0
 32 52  1  1  0  0  0
 33 53  1  6  0  0  0
M  END


  Mrv1533007131513392D          

 53 57  0  0  1  0            999 V2000
   -2.4048    2.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8858    0.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2094    1.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876    2.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640    2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511    1.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3921    1.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0812    2.0435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1390    1.2383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8587    2.0142    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0466    2.1594    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5148    1.5287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7951    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4829    1.7238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905    2.6449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7663    2.9353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026    1.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.6076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533    2.2692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703    2.8077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314   -0.5086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557    0.8111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6708    1.8690    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5784    2.7901    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3269    1.3835    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2345    2.3046    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    0.8980    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 21  4  1  1  0  0  0
 21  8  1  0  0  0  0
 22  7  1  0  0  0  0
 22  9  1  6  0  0  0
 22 20  1  0  0  0  0
 23 10  2  0  0  0  0
 23 18  1  0  0  0  0
 24 14  1  0  0  0  0
 24 18  1  0  0  0  0
 25 11  1  0  0  0  0
 26 12  1  0  0  0  0
 26 21  1  0  0  0  0
 27 13  1  0  0  0  0
 27 25  1  0  0  0  0
 28 15  1  0  0  0  0
 28 25  1  0  0  0  0
 29 19  1  1  0  0  0
 30 29  1  0  0  0  0
 31 30  1  0  0  0  0
 32 31  1  0  0  0  0
 33 32  1  0  0  0  0
 34  5  1  6  0  0  0
 34 16  1  0  0  0  0
 34 23  1  0  0  0  0
 34 28  1  0  0  0  0
 35  6  1  6  0  0  0
 35 17  1  0  0  0  0
 35 26  1  0  0  0  0
 35 27  1  0  0  0  0
 36 19  1  0  0  0  0
 30 37  1  6  0  0  0
 31 38  1  6  0  0  0
 32 39  1  6  0  0  0
 40 24  1  0  0  0  0
 33 40  1  1  0  0  0
 41 29  1  0  0  0  0
 41 33  1  0  0  0  0
 21 42  1  6  0  0  0
 22 43  1  1  0  0  0
 44 24  1  0  0  0  0
 25 45  1  6  0  0  0
 46 26  1  0  0  0  0
 27 47  1  1  0  0  0
 28 48  1  1  0  0  0
 29 49  1  6  0  0  0
 30 50  1  1  0  0  0
 31 51  1  6  0  0  0
 32 52  1  1  0  0  0
 33 53  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0219881

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](C)(CC[C@@]([H])(CC)C(C)C)C1([H])CC[C@@]2([H])[C@]3([H])CC=C4CC([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C35H60O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h10,20-22,24-33,36-39H,7-9,11-19H2,1-6H3/t21-,22-,24?,25+,26?,27+,28+,29-,30-,31+,32-,33-,34+,35-/m1/s1

> <INCHI_KEY>
NPJICTMALKLTFW-QYDWNGEASA-N

> <FORMULA>
C35H60O6

> <MOLECULAR_WEIGHT>
576.859

> <EXACT_MASS>
576.438989652

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
101

> <JCHEM_AVERAGE_POLARIZABILITY>
69.48196546849644

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1S,2R,10S,11S,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
5.71

> <JCHEM_LOGP>
6.073641146333333

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200090025428626

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210561282115878

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083542853919

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
162.17939999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1S,2R,10S,11S,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -4.489   4.820   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.653   1.172   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.124   2.177   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.558   4.447   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.487   2.489   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.791   3.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.963   5.030   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.452   2.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.493   4.025   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.541  -1.585   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.025  -1.314   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.495   0.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.770  -0.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.519   1.947   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.971   2.761   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.003   2.218   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.455   3.032   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.049  -0.678   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.575   2.040   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.599   2.388   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.978   3.020   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.018   3.815   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.533  -0.407   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.042   0.499   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.502   0.135   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.923   1.804   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.986   0.406   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.494   1.312   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.059   2.311   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.536   3.760   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.020   4.031   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.028   2.854   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.551   1.405   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.010   1.041   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.462   1.854   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      19.568   3.218   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      17.529   4.937   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      14.497   5.479   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      12.512   3.125   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      13.558   0.228   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      16.067   1.134   0.000  0.00  0.00           O+0
HETATM   42  H   UNK     0       1.033   4.236   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.438   5.241   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      12.565  -0.949   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.509  -1.043   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.411   1.514   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.978   1.583   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       8.017  -0.136   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      18.052   3.489   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0      16.013   5.208   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      15.544   2.583   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0      13.504   4.302   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0      13.035   1.676   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5   34                                                            
CONECT    6   35                                                            
CONECT    7    1   22                                                       
CONECT    8    9   21                                                       
CONECT    9    8   22                                                       
CONECT   10   11   23                                                       
CONECT   11   10   25                                                       
CONECT   12   13   26                                                       
CONECT   13   12   27                                                       
CONECT   14   16   24                                                       
CONECT   15   17   28                                                       
CONECT   16   14   34                                                       
CONECT   17   15   35                                                       
CONECT   18   23   24                                                       
CONECT   19   29   36                                                       
CONECT   20    2    3   22                                                  
CONECT   21    4    8   26   42                                             
CONECT   22    7    9   20   43                                             
CONECT   23   10   18   34                                                  
CONECT   24   14   18   40   44                                             
CONECT   25   11   27   28   45                                             
CONECT   26   12   21   35   46                                             
CONECT   27   13   25   35   47                                             
CONECT   28   15   25   34   48                                             
CONECT   29   19   30   41   49                                             
CONECT   30   29   31   37   50                                             
CONECT   31   30   32   38   51                                             
CONECT   32   31   33   39   52                                             
CONECT   33   32   40   41   53                                             
CONECT   34    5   16   23   28                                             
CONECT   35    6   17   26   27                                             
CONECT   36   19                                                            
CONECT   37   30                                                            
CONECT   38   31                                                            
CONECT   39   32                                                            
CONECT   40   24   33                                                       
CONECT   41   29   33                                                       
CONECT   42   21                                                            
CONECT   43   22                                                            
CONECT   44   24                                                            
CONECT   45   25                                                            
CONECT   46   26                                                            
CONECT   47   27                                                            
CONECT   48   28                                                            
CONECT   49   29                                                            
CONECT   50   30                                                            
CONECT   51   31                                                            
CONECT   52   32                                                            
CONECT   53   33                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  114    0
END

View in JSmol

Synonyms

Value	Source
beta-Sitosterol glucutonide	MeSH
beta-Sitosterol glucoside	MeSH
beta-Sitosterol-beta-D-glycoside	MeSH
Daucosterol	MeSH
Lyoniside	MeSH
Sitosterol beta-D-glucoside	MeSH
beta-Sitosteryl-beta-D-glucopyranoside	MeSH
Eleutheroside a	MeSH
Sitosterol glucuronide	MeSH

Chemical Formula

C₃₅H₆₀O₆

Average Mass

576.8590 Da

Monoisotopic Mass

576.43899 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(1S,2R,10S,11S,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(1S,2R,10S,11S,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

[H][C@@](C)(CC[C@@]([H])(CC)C(C)C)C1([H])CC[C@@]2([H])[C@]3([H])CC=C4CC([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C35H60O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h10,20-22,24-33,36-39H,7-9,11-19H2,1-6H3/t21-,22-,24?,25+,26?,27+,28+,29-,30-,31+,32-,33-,34+,35-/m1/s1

InChI Key

NPJICTMALKLTFW-QYDWNGEASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ampelopsis glandulosa	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Elliottia paniculata	LOTUS Database	35616633
Epimedium diphyllum	LOTUS Database	35616633
Lyonia ovalifolia	LOTUS Database	35616633
Machilus thunbergii	LOTUS Database	35616633
Prunus ssiori	LOTUS Database	35616633
Saraca asoca	LOTUS Database	35616633
Ulmus davidiana	LOTUS Database	35616633
Viburnum dilatatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Triterpenoid
Stigmastane-skeleton
Steroidal glycoside
Delta-5-steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Secondary alcohol
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	5.71	ALOGPS
logP	6.07	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	162.18 m³·mol⁻¹	ChemAxon
Polarizability	69.48 Å³	ChemAxon
Number of Rings	5	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005190

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

71628

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0219881)

MOL for NP0219881 ((2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0219881 ((2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0219881 ((2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0219881 ((2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0219881 ((2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0219881 ((2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0219881 ((2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0219881 ((2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0219881 ((2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0219881 ((2r,3r,4s,5s,6r)-2-{[(3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)