NP-MRD: Showing NP-Card for (2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid (NP0150685)

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Record Information

Version

2.0

Created at

2022-09-02 06:52:45 UTC

Updated at

2022-09-02 06:52:45 UTC

NP-MRD ID

NP0150685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid

Description

(2R)-2-[(4aR,5R,6S,7S,8aR)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]propanoic acid belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on (2R)-2-[(4aR,5R,6S,7S,8aR)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022208522D          

 27 28  0  0  1  0            999 V2000
    2.1434   -0.4125    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   -0.4125    0.0000 C   0  0  1  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 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
   -1.4289   -1.6500    0.0000 O   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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    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  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   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
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  6  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 27  1  0  0  0  0
  3 27  1  0  0  0  0
M  END

     RDKit          3D

 51 52  0  0  0  0  0  0  0  0999 V2000
    0.3138   -2.4195   -2.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0344   -2.1198   -1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9511   -1.0484   -0.9931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2491   -1.3025   -1.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7557   -2.5468   -1.2826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0296   -2.6566    0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9734   -3.3374    0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610   -1.9319    0.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2426   -2.1272    2.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567   -0.9566    0.4966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6263    0.4747    0.7767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1177    0.4748    2.0812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4138    1.3390    0.6291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6910    2.7981    0.5244 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3788    3.2174   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946    3.3485    1.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8545    4.1161    2.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7414    3.0320    1.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4650    0.8926   -0.4921 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4542   -0.0501   -0.0991 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8194    0.1830   -0.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0997    1.2748   -0.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8317   -0.7800    0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151   -1.9165    0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2640   -0.4914   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667    0.6836    0.5088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3828    0.2453   -1.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217   -3.1890   -2.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1568   -1.9043   -3.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220   -2.6534   -0.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0266   -1.3234   -2.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9656   -0.4868   -1.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641   -2.8284    2.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6158   -1.6078    3.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2245   -1.1753    1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280    0.6784    0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3722    0.7556    2.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870    1.2000    1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    3.3096    0.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7129    3.2007   -1.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3439    2.7168   -0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6378    4.3102   -0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4241    3.7561    1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9373    1.7897   -0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695   -2.1220    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2451   -2.6323    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9215   -1.2922    0.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4956   -0.3968   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2955    0.6236    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3118    0.0049   -2.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1971    0.8709   -1.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  1  0
 13 19  1  0
 19 27  1  0
 27  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  3
  8 10  1  0
 10 11  1  0
 11 12  1  0
  3  2  1  1
  2  1  2  3
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  3
 23 25  1  0
 25 26  1  0
 14 16  1  0
 16 18  1  0
 16 17  2  0
 11 13  1  0
 10  3  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 14 39  1  6
 13 38  1  1
 19 44  1  6
 27 50  1  0
 27 51  1  0
  4 31  1  0
  4 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  1
 11 36  1  6
 12 37  1  0
  2 30  1  0
  1 28  1  0
  1 29  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
 26 49  1  0
 18 43  1  0
M  END


  Mrv1652309022208522D          

 27 28  0  0  1  0            999 V2000
    2.1434   -0.4125    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   -0.4125    0.0000 C   0  0  1  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 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
   -1.4289   -1.6500    0.0000 O   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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    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  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   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
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  6  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 27  1  0  0  0  0
  3 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]([C@@H]1[C@H](C[C@@]2(COC(=O)C(=C)[C@@H]2[C@H]1O)C=C)OC(=O)C(=C)CO)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O8/c1-5-19-6-12(27-17(24)9(2)7-20)13(10(3)16(22)23)15(21)14(19)11(4)18(25)26-8-19/h5,10,12-15,20-21H,1-2,4,6-8H2,3H3,(H,22,23)/t10-,12+,13-,14-,15+,19-/m1/s1

> <INCHI_KEY>
DXPZBIQCCNPZKD-HPQSTYCASA-N

> <FORMULA>
C19H24O8

> <MOLECULAR_WEIGHT>
380.393

> <EXACT_MASS>
380.147117733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.06092481145055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-[(4aR,5R,6S,7S,8aR)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]propanoic acid

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.7986363229999999

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.347547292510871

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.165789069427225

> <JCHEM_PKA_STRONGEST_BASIC>
-2.844108411662874

> <JCHEM_POLAR_SURFACE_AREA>
130.35999999999999

> <JCHEM_REFRACTIVITY>
93.15689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(4aR,5R,6S,7S,8aR)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10   27                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-[(4AR,5R,6S,7S,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]propanoate	Generator

Chemical Formula

C₁₉H₂₄O₈

Average Mass

380.3930 Da

Monoisotopic Mass

380.14712 Da

IUPAC Name

(2R)-2-[(4aR,5R,6S,7S,8aR)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]propanoic acid

Traditional Name

(2R)-2-[(4aR,5R,6S,7S,8aR)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H]([C@@H]1[C@H](C[C@@]2(COC(=O)C(=C)[C@@H]2[C@H]1O)C=C)OC(=O)C(=C)CO)C(O)=O

InChI Identifier

InChI=1S/C19H24O8/c1-5-19-6-12(27-17(24)9(2)7-20)13(10(3)16(22)23)15(21)14(19)11(4)18(25)26-8-19/h5,10,12-15,20-21H,1-2,4,6-8H2,3H3,(H,22,23)/t10-,12+,13-,14-,15+,19-/m1/s1

InChI Key

DXPZBIQCCNPZKD-HPQSTYCASA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Benzopyran
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Delta valerolactone
Delta_valerolactone
Hydroxy acid
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Primary alcohol
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	0.53	ALOGPS
logP	0.8	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	93.16 m³·mol⁻¹	ChemAxon
Polarizability	37.06 Å³	ChemAxon
Number of Rings	2	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

162961538

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid (NP0150685)

MOL for NP0150685 ((2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid)

3D MOL for NP0150685 ((2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid)

3D SDF for NP0150685 ((2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid)

3D-SDF for NP0150685 ((2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid)

PDB for NP0150685 ((2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid)

3D PDB for NP0150685 ((2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid)

SMILES for NP0150685 ((2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid)

INCHI for NP0150685 ((2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid)

Structure for NP0150685 ((2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid)

3D Structure for NP0150685 ((2r)-2-[(4ar,5r,6s,7s,8ar)-8a-ethenyl-5-hydroxy-7-{[2-(hydroxymethyl)prop-2-enoyl]oxy}-4-methylidene-3-oxo-hexahydro-2-benzopyran-6-yl]propanoic acid)