NP-MRD: Showing NP-Card for 3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate (NP0320748)

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Record Information

Version

2.0

Created at

2022-09-11 22:34:53 UTC

Updated at

2022-09-11 22:34:53 UTC

NP-MRD ID

NP0320748

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate

Description

3-Hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. 3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate is found in Centaurea spinosa. 3-Hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191519062D          

 30 30  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 60 60  0  0  0  0  0  0  0  0999 V2000
    5.1826   -0.5577    1.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3380   -0.4601    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9136   -0.3953    0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -0.4320    2.1849 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447   -0.2918    0.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5552   -0.2281    0.2709 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2124   -1.3772   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6395   -1.3404    0.3843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5120   -1.8696    1.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343   -2.3712   -0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0658   -2.1195   -1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1464   -3.7174   -0.0933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2875   -0.0256    0.2870 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4560    0.0842    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692    0.9872    2.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6669   -0.8134    1.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3939   -2.1250    1.2800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3785    1.1448    0.6090 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0759    2.2894    0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0410    1.1366   -0.0234 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1083    1.6316   -1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7089    0.9190   -2.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3548    2.9403   -1.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1764    3.2920   -3.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9796    3.8980   -1.0638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3984    5.1539   -1.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7621   -0.4109   -0.7185 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1014   -1.4405   -1.3991 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2538   -0.4913   -0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7778   -1.6828   -0.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107   -0.5883    2.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2557   -0.6110    1.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697   -0.2809    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835   -1.5443   -1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2442   -2.3148    0.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4346   -1.9309    2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068   -1.3354    2.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8555   -2.9315    1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5042   -3.0001   -2.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3290   -1.2003   -1.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9604   -4.3261   -0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6582    0.1164   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4585    1.0304    2.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8361    1.7155    2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0260   -0.6487    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5127   -0.4664    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -2.4782    1.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1940    1.1019    1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782    2.1162   -0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5975    1.8210    0.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8237    1.3127   -3.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121   -0.0351   -2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1550    5.5431   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5805    5.8978   -1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142    5.0788   -2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227    0.5768   -1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6354   -2.2761   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6928    0.3914   -0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4866   -0.4378   -1.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6864   -1.6231   -0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 23  1  0
 23 24  2  0
 23 21  1  0
 21 22  2  3
 21 20  1  0
 20 18  1  0
 18 19  1  0
 18 13  1  0
 13 14  1  0
 14 15  2  3
 14 16  1  0
 16 17  1  0
 13  8  1  0
  8  9  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
  8 10  1  6
 10 12  1  0
 10 11  2  3
  6 20  1  0
 26 53  1  0
 26 54  1  0
 26 55  1  0
 22 51  1  0
 22 52  1  0
 20 50  1  1
 18 48  1  1
 19 49  1  0
 13 42  1  6
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
  7 34  1  0
  7 35  1  0
  6 33  1  1
  1 31  1  0
  1 32  1  0
 27 56  1  6
 28 57  1  0
 29 58  1  0
 29 59  1  0
 30 60  1  0
 12 41  1  0
 11 39  1  0
 11 40  1  0
M  END


  Mrv1533004191519062D          

 30 30  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320748

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=C)C1C(O)C(C(=C)CO)C(C)(CC1OC(=O)C(=C)C(O)CO)C(O)=C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O9/c1-10(8-22)17-18(26)16(12(3)19(27)29-6)15(7-21(17,5)13(4)24)30-20(28)11(2)14(25)9-23/h14-18,22-26H,1-4,7-9H2,5-6H3

> <INCHI_KEY>
TWXCADQDVNDWNH-UHFFFAOYSA-N

> <FORMULA>
C21H30O9

> <MOLECULAR_WEIGHT>
426.462

> <EXACT_MASS>
426.188982546

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.97871435426788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate

> <ALOGPS_LOGP>
0.12

> <JCHEM_LOGP>
-0.3044938146666672

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.473283989014597

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.63149965332823

> <JCHEM_PKA_STRONGEST_BASIC>
-2.728378430522115

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
107.35919999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.840   3.222   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.797   4.937   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   18                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10   16   17   28                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   15   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoic acid	Generator

Chemical Formula

C₂₁H₃₀O₉

Average Mass

426.4620 Da

Monoisotopic Mass

426.18898 Da

IUPAC Name

3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate

Traditional Name

3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C)C1C(O)C(C(=C)CO)C(C)(CC1OC(=O)C(=C)C(O)CO)C(O)=C

InChI Identifier

InChI=1S/C21H30O9/c1-10(8-22)17-18(26)16(12(3)19(27)29-6)15(7-21(17,5)13(4)24)30-20(28)11(2)14(25)9-23/h14-18,22-26H,1-4,7-9H2,5-6H3

InChI Key

TWXCADQDVNDWNH-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
Centaurea spinosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Elemane sesquiterpenoids

Alternative Parents

Substituents

Elemane sesquiterpenoid
Beta-hydroxy acid
Cyclohexanol
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Hydroxy acid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Enol
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.12	ALOGPS
logP	-0.3	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	107.36 m³·mol⁻¹	ChemAxon
Polarizability	42.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

75072074

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate (NP0320748)

MOL for NP0320748 (3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate)

3D MOL for NP0320748 (3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate)

3D SDF for NP0320748 (3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate)

3D-SDF for NP0320748 (3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate)

PDB for NP0320748 (3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate)

3D PDB for NP0320748 (3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate)

SMILES for NP0320748 (3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate)

INCHI for NP0320748 (3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate)

Structure for NP0320748 (3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate)

3D Structure for NP0320748 (3-hydroxy-5-(1-hydroxyethenyl)-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl 3,4-dihydroxy-2-methylidenebutanoate)