NP-MRD: Showing NP-Card for (1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate (NP0196030)

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Record Information

Version

2.0

Created at

2022-09-04 14:00:55 UTC

Updated at

2022-09-04 14:00:55 UTC

NP-MRD ID

NP0196030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate

Description

Physagulin H belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. (1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate is found in Physalis angulata. (1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate was first documented in 2021 (PMID: 33957208). Based on a literature review very few articles have been published on Physagulin H.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042216002D          

 38 44  0  0  1  0            999 V2000
    4.2302   -1.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9079   -1.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394   -2.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -1.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7227   -0.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4282   -0.0436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0292    0.5215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2393    0.7595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3934    1.5700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7685    2.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1723    1.8418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3264    2.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1054    2.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2595    3.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7302    2.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5092    2.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5761    1.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2010    1.0362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7972    1.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171    0.8281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8142    1.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9180    1.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0995    1.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803    0.6203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2795   -0.0366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9602   -0.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -0.9012    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3234   -1.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6426   -0.2443    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8242   -0.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250    0.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442    1.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4627    1.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819    1.9340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618    0.5164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2811    1.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0979    0.0673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8599   -0.7226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  6  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 24 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  1  0  0  0
 25 37  1  0  0  0  0
  5 37  1  0  0  0  0
 20 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END


  Mrv1652309042216002D          

 38 44  0  0  1  0            999 V2000
    4.2302   -1.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9079   -1.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394   -2.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -1.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7227   -0.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4282   -0.0436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0292    0.5215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2393    0.7595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3934    1.5700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7685    2.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1723    1.8418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3264    2.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1054    2.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2595    3.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7302    2.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5092    2.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5761    1.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2010    1.0362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7972    1.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171    0.8281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8142    1.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9180    1.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0995    1.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803    0.6203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2795   -0.0366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9602   -0.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -0.9012    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3234   -1.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6426   -0.2443    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8242   -0.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250    0.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442    1.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4627    1.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819    1.9340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618    0.5164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2811    1.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0979    0.0673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8599   -0.7226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  6  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 24 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  1  0  0  0
 25 37  1  0  0  0  0
  5 37  1  0  0  0  0
 20 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0196030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]([C@H]1CC(C)=C(C)C(=O)O1)[C@]12O[C@H]1[C@H](OC(C)=O)[C@]1(O)[C@@H]3C[C@H]4O[C@]44CC=CC(=O)[C@]4(C)[C@H]3CC[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O8/c1-14-12-20(36-25(33)15(14)2)16(3)30-24(38-30)23(35-17(4)31)29(34)19-13-22-28(37-22)10-7-8-21(32)27(28,6)18(19)9-11-26(29,30)5/h7-8,16,18-20,22-24,34H,9-13H2,1-6H3/t16-,18+,19-,20-,22-,23+,24+,26+,27+,28-,29-,30+/m1/s1

> <INCHI_KEY>
OZZNUJSEIHDCFJ-UXNBTRKISA-N

> <FORMULA>
C30H38O8

> <MOLECULAR_WEIGHT>
526.626

> <EXACT_MASS>
526.256668184

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.71535303398991

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,7S,9R,11R,12S,13S,14S,16R,17S)-16-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0^{2,7}.0^{7,9}.0^{12,17}.0^{14,16}]nonadec-4-en-13-yl acetate

> <JCHEM_LOGP>
3.3474890336666654

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.650497648274918

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.091221533460466

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6281843394281683

> <JCHEM_POLAR_SURFACE_AREA>
114.96

> <JCHEM_REFRACTIVITY>
135.14929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,7S,9R,11R,12S,13S,14S,16R,17S)-16-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0^{2,7}.0^{7,9}.0^{12,17}.0^{14,16}]nonadec-4-en-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.896  -2.193   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.161  -3.071   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.034  -4.606   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.555  -2.415   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.682  -0.880   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.999  -0.081   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.121   0.974   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.647   1.418   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.934   2.931   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.768   3.936   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.388   3.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.676   4.951   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.130   5.458   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.418   6.971   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.296   4.453   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.750   4.960   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.009   2.940   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.175   1.934   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      14.555   2.432   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.112   1.546   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.853   2.896   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.180   2.772   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.652   2.578   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.057   1.158   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.988  -0.068   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.392  -1.488   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.865  -1.682   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.337  -1.876   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.933  -0.456   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.405  -0.650   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.473   0.576   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.069   1.996   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.597   2.190   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.193   3.610   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.529   0.964   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.125   2.384   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.516   0.126   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.072  -1.349   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    8                                                       
CONECT    8    7    6    9   20                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11                                                       
CONECT   20    8   21   22   37                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   35                                                  
CONECT   25   24   26   37                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   27   30   35                                             
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   24   29   36                                             
CONECT   36   35                                                            
CONECT   37   25    5   20   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₈O₈

Average Mass

526.6260 Da

Monoisotopic Mass

526.25667 Da

IUPAC Name

(1S,2R,7S,9R,11R,12S,13S,14S,16R,17S)-16-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0^{2,7}.0^{7,9}.0^{12,17}.0^{14,16}]nonadec-4-en-13-yl acetate

Traditional Name

(1S,2R,7S,9R,11R,12S,13S,14S,16R,17S)-16-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0^{2,7}.0^{7,9}.0^{12,17}.0^{14,16}]nonadec-4-en-13-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]([C@H]1CC(C)=C(C)C(=O)O1)[C@]12O[C@H]1[C@H](OC(C)=O)[C@]1(O)[C@@H]3C[C@H]4O[C@]44CC=CC(=O)[C@]4(C)[C@H]3CC[C@]21C

InChI Identifier

InChI=1S/C30H38O8/c1-14-12-20(36-25(33)15(14)2)16(3)30-24(38-30)23(35-17(4)31)29(34)19-13-22-28(37-22)10-7-8-21(32)27(28,6)18(19)9-11-26(29,30)5/h7-8,16,18-20,22-24,34H,9-13H2,1-6H3/t16-,18+,19-,20-,22-,23+,24+,26+,27+,28-,29-,30+/m1/s1

InChI Key

OZZNUJSEIHDCFJ-UXNBTRKISA-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
Physalis angulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
Steroid ester
5,6-epoxysteroid
Naphthopyran
Naphthalene
Dihydropyranone
Cyclohexenone
Oxepane
Dicarboxylic acid or derivatives
Oxane
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	3.35	ChemAxon
pKa (Strongest Acidic)	13.09	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	114.96 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	135.15 m³·mol⁻¹	ChemAxon
Polarizability	55.72 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00057555

Chemspider ID

76772791

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101273381

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang L, Lu S, Wang L, Xin M, Xu Y, Wang G, Chen D, Chen L, Liu S, Zhao F: Anti-inflammatory effects of three withanolides isolated from Physalis angulata L. in LPS-activated RAW 264.7 cells through blocking NF-kappaB signaling pathway. J Ethnopharmacol. 2021 Aug 10;276:114186. doi: 10.1016/j.jep.2021.114186. Epub 2021 May 4. [PubMed:33957208 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate (NP0196030)

MOL for NP0196030 ((1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate)

3D MOL for NP0196030 ((1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate)

3D SDF for NP0196030 ((1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate)

3D-SDF for NP0196030 ((1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate)

PDB for NP0196030 ((1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate)

3D PDB for NP0196030 ((1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate)

SMILES for NP0196030 ((1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate)

INCHI for NP0196030 ((1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate)

Structure for NP0196030 ((1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate)

3D Structure for NP0196030 ((1s,2r,7s,9r,11r,12s,13s,14s,16r,17s)-16-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-12-hydroxy-2,17-dimethyl-3-oxo-8,15-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁷.0¹⁴,¹⁶]nonadec-4-en-13-yl acetate)