NP-MRD: Showing NP-Card for (1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate (NP0284877)

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Record Information

Version

2.0

Created at

2022-09-09 12:47:35 UTC

Updated at

2022-09-09 12:47:35 UTC

NP-MRD ID

NP0284877

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate

Description

(17S,18S,20R,22R)-4beta-Acetoxy-5,6beta:18,20-Diepoxy-18,22-dihydroxy-1-oxo-5beta-ergosta-2,24-diene-26-oic acid delta-lactone 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,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate is found in Dunalia brachyacantha. Based on a literature review very few articles have been published on (17S,18S,20R,22R)-4beta-Acetoxy-5,6beta:18,20-Diepoxy-18,22-dihydroxy-1-oxo-5beta-ergosta-2,24-diene-26-oic acid delta-lactone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092214472D          

 38 44  0  0  1  0            999 V2000
    1.7580   -2.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546   -1.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -1.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0734   -1.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700   -1.2587    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2477   -0.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7443    0.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5631    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0597    0.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8854   -0.7005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3819   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -0.8011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2008   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0196   -0.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3419   -1.0024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3564   -0.1775    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6976    0.3191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1454    0.0636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6185   -0.6122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2412   -0.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2218   -1.1749    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0108   -0.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6141   -1.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4031   -1.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4284   -2.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0318   -2.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6395   -2.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4538   -3.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0361   -1.9787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1219   -1.2710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1075   -2.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3185   -2.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8453   -1.6612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0265   -1.5606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5299   -2.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7111   -2.1188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8923   -2.0182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888   -1.3593    0.0000 C   0  0  2  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  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 21 29  1  1  0  0  0
 19 30  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 33 32  1  1  0  0  0
 15 33  1  0  0  0  0
 33 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 38 37  1  1  0  0  0
  5 38  1  0  0  0  0
 36 38  1  0  0  0  0
 10 38  1  0  0  0  0
M  END


  Mrv1652309092214472D          

 38 44  0  0  1  0            999 V2000
    1.7580   -2.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546   -1.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -1.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0734   -1.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700   -1.2587    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2477   -0.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7443    0.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5631    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0597    0.7178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8854   -0.7005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3819   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -0.8011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2008   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0196   -0.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3419   -1.0024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3564   -0.1775    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6976    0.3191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1454    0.0636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6185   -0.6122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2412   -0.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2218   -1.1749    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0108   -0.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6141   -1.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4031   -1.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4284   -2.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0318   -2.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6395   -2.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4538   -3.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0361   -1.9787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1219   -1.2710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1075   -2.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3185   -2.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8453   -1.6612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0265   -1.5606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5299   -2.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7111   -2.1188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8923   -2.0182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888   -1.3593    0.0000 C   0  0  2  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  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 21 29  1  1  0  0  0
 19 30  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 33 32  1  1  0  0  0
 15 33  1  0  0  0  0
 33 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 38 37  1  1  0  0  0
  5 38  1  0  0  0  0
 36 38  1  0  0  0  0
 10 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0284877

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C=CC(=O)[C@]2(C)[C@H]3CC[C@]45[C@@H](O)O[C@](C)([C@H]4CC[C@H]5[C@@H]3C[C@H]3O[C@@]123)[C@H]1CC(C)=C(C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O8/c1-14-12-23(36-25(33)15(14)2)28(5)20-7-6-19-17-13-24-30(37-24)22(35-16(3)31)9-8-21(32)27(30,4)18(17)10-11-29(19,20)26(34)38-28/h8-9,17-20,22-24,26,34H,6-7,10-13H2,1-5H3/t17-,18+,19+,20-,22+,23-,24-,26+,27+,28-,29-,30-/m1/s1

> <INCHI_KEY>
UCLKYVACLANLCC-ZZONCJOWSA-N

> <FORMULA>
C30H38O8

> <MOLECULAR_WEIGHT>
526.626

> <EXACT_MASS>
526.256668184

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
56.37790580757259

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,6R,8S,9R,12S,13R,17S,18S,20R)-6-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0^{2,9}.0^{5,9}.0^{13,18}.0^{18,20}]henicos-15-en-17-yl acetate

> <JCHEM_LOGP>
3.7392331203333304

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.122144353899877

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.48879992290868

> <JCHEM_PKA_STRONGEST_BASIC>
-4.009545245493042

> <JCHEM_POLAR_SURFACE_AREA>
111.66000000000001

> <JCHEM_REFRACTIVITY>
135.31709999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,6R,8S,9R,12S,13R,17S,18S,20R)-6-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0^{2,9}.0^{5,9}.0^{13,18}.0^{18,20}]henicos-15-en-17-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       3.282  -4.621   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.209  -3.392   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.607  -1.974   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.737  -3.579   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.664  -2.350   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.062  -0.932   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.989   0.298   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.518   0.110   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.445   1.340   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.119  -1.308   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.046  -0.078   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.648  -1.495   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.575  -0.266   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.103  -0.453   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.705  -1.871   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.732  -0.331   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.502   0.596   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      15.205   0.119   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.088  -1.143   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.250  -0.133   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.214  -2.193   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.687  -1.743   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.813  -2.793   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.286  -2.343   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.466  -4.294   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.593  -5.344   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.994  -4.744   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      17.647  -6.245   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      16.867  -3.694   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.161  -2.373   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.134  -3.912   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.661  -4.362   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.778  -3.101   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.249  -2.913   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.323  -4.143   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.794  -3.955   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       7.266  -3.767   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.192  -2.537   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   38                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   38                                             
CONECT   11   10                                                            
CONECT   12   10   13   34                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   30   33                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   30                                             
CONECT   20   19                                                            
CONECT   21   19   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   21                                                       
CONECT   30   19   15   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   15   34                                                  
CONECT   34   33   12   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36   38                                                       
CONECT   38   37    5   36   10                                             
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Value	Source
(17S,18S,20R,22R)-4b-Acetoxy-5,6beta:18,20-diepoxy-18,22-dihydroxy-1-oxo-5b-ergosta-2,24-diene-26-Oate delta-lactone	Generator
(17S,18S,20R,22R)-4b-Acetoxy-5,6beta:18,20-diepoxy-18,22-dihydroxy-1-oxo-5b-ergosta-2,24-diene-26-Oic acid delta-lactone	Generator
(17S,18S,20R,22R)-4beta-Acetoxy-5,6beta:18,20-diepoxy-18,22-dihydroxy-1-oxo-5beta-ergosta-2,24-diene-26-Oate delta-lactone	Generator
(17S,18S,20R,22R)-4Β-acetoxy-5,6beta:18,20-diepoxy-18,22-dihydroxy-1-oxo-5β-ergosta-2,24-diene-26-Oate δ-lactone	Generator
(17S,18S,20R,22R)-4Β-acetoxy-5,6beta:18,20-diepoxy-18,22-dihydroxy-1-oxo-5β-ergosta-2,24-diene-26-Oic acid δ-lactone	Generator

Chemical Formula

C₃₀H₃₈O₈

Average Mass

526.6260 Da

Monoisotopic Mass

526.25667 Da

IUPAC Name

(1S,2S,5S,6R,8S,9R,12S,13R,17S,18S,20R)-6-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0^{2,9}.0^{5,9}.0^{13,18}.0^{18,20}]henicos-15-en-17-yl acetate

Traditional Name

(1S,2S,5S,6R,8S,9R,12S,13R,17S,18S,20R)-6-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0^{2,9}.0^{5,9}.0^{13,18}.0^{18,20}]henicos-15-en-17-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C=CC(=O)[C@]2(C)[C@H]3CC[C@]45[C@@H](O)O[C@](C)([C@H]4CC[C@H]5[C@@H]3C[C@H]3O[C@@]123)[C@H]1CC(C)=C(C)C(=O)O1

InChI Identifier

InChI=1S/C30H38O8/c1-14-12-23(36-25(33)15(14)2)28(5)20-7-6-19-17-13-24-30(37-24)22(35-16(3)31)9-8-21(32)27(30,4)18(17)10-11-29(19,20)26(34)38-28/h8-9,17-20,22-24,26,34H,6-7,10-13H2,1-5H3/t17-,18+,19+,20-,22+,23-,24-,26+,27+,28-,29-,30-/m1/s1

InChI Key

UCLKYVACLANLCC-ZZONCJOWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dunalia brachyacantha	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
Dihydropyranone
Oxepane
Cyclohexenone
Dicarboxylic acid or derivatives
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Ether
Oxirane
Organoheterocyclic compound
Dialkyl ether
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxide
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	3.74	ChemAxon
pKa (Strongest Acidic)	11.49	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	135.32 m³·mol⁻¹	ChemAxon
Polarizability	56.38 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

Not Available

Chemspider ID

10279050

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21670292

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate (NP0284877)

MOL for NP0284877 ((1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate)

3D MOL for NP0284877 ((1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate)

3D SDF for NP0284877 ((1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate)

3D-SDF for NP0284877 ((1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate)

PDB for NP0284877 ((1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate)

3D PDB for NP0284877 ((1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate)

SMILES for NP0284877 ((1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate)

INCHI for NP0284877 ((1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate)

Structure for NP0284877 ((1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate)

3D Structure for NP0284877 ((1s,2s,5s,6r,8s,9r,12s,13r,17s,18s,20r)-6-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-8-hydroxy-6,13-dimethyl-14-oxo-7,19-dioxahexacyclo[10.9.0.0²,⁹.0⁵,⁹.0¹³,¹⁸.0¹⁸,²⁰]henicos-15-en-17-yl acetate)