NP-MRD: Showing NP-Card for (5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione (NP0219559)

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Record Information

Version

1.0

Created at

2022-09-05 20:35:41 UTC

Updated at

2022-09-05 20:35:41 UTC

NP-MRD ID

NP0219559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione

Description

Jaborosalactone 3 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. (5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione is found in Jaborosa runcinata. It was first documented in 2014 (PMID: 24878636). Based on a literature review very few articles have been published on Jaborosalactone 3 (PMID: 24314746).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222352D          

 35 40  0  0  1  0            999 V2000
    2.2796    2.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788    1.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6695    1.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0236    2.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417    2.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9932    1.6143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6972    1.1842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4217    1.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1257    1.1487    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8502    1.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1052    0.3240    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8297    0.7186    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8092   -0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7887   -0.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0642   -1.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3602   -0.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6357   -1.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3807   -0.0707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6562   -0.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6767    0.3595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9522   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771    0.4172    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2574   -0.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2687    1.2197    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9239    0.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864    0.1818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8231   -0.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3930   -1.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7097   -1.9105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5905   -0.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639   -1.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5247   -0.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    0.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872    0.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625    0.7694    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  3 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  1  0  0  0
 22 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 26 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END


  Mrv1652309052222352D          

 35 40  0  0  1  0            999 V2000
    2.2796    2.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788    1.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6695    1.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0236    2.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417    2.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9932    1.6143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6972    1.1842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4217    1.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1257    1.1487    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8502    1.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1052    0.3240    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8297    0.7186    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8092   -0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7887   -0.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0642   -1.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3602   -0.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6357   -1.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3807   -0.0707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6562   -0.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6767    0.3595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9522   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771    0.4172    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2574   -0.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2687    1.2197    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9239    0.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864    0.1818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8231   -0.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3930   -1.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7097   -1.9105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5905   -0.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639   -1.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5247   -0.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    0.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872    0.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625    0.7694    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  3 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  1  0  0  0
 22 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 26 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0219559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)[C@]2(OC1=O)C(=O)C(C)=C1CC[C@H]3[C@@H]4C[C@@H](O)[C@@]5(Cl)CC=CC(=O)[C@]5(C)[C@H]4C[C@@]2(O)[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C28H33ClO6/c1-13-15(3)28(35-23(13)33)22(32)14(2)17-8-9-18-16-11-21(31)26(29)10-6-7-20(30)25(26,5)19(16)12-27(28,34)24(17,18)4/h6-7,16,18-19,21,31,34H,8-12H2,1-5H3/t16-,18-,19-,21+,24+,25-,26-,27+,28-/m0/s1

> <INCHI_KEY>
MVBGXFNBAXISLW-TWZBKPIQSA-N

> <FORMULA>
C28H33ClO6

> <MOLECULAR_WEIGHT>
501.02

> <EXACT_MASS>
500.1965665

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
51.31944325936058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2R,2'S,4'R,5'R,10'S,11'S,13'R,20'S)-5'-chloro-4',13'-dihydroxy-3,4,10',16',20'-pentamethyl-5H-spiro[furan-2,14'-pentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{17,20}]icosane]-7',16'-diene-5,9',15'-trione

> <JCHEM_LOGP>
4.049106005333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.913865019012125

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.915513100052916

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2906084355442093

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
131.1967

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'S,4'R,5'R,10'S,11'S,13'R,20'S)-5'-chloro-4',13'-dihydroxy-3,4,10',16',20'-pentamethylspiro[furan-2,14'-pentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{17,20}]icosane]-7',16'-diene-5,9',15'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       4.255   3.955   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.374   2.896   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.850   3.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.511   4.726   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.038   4.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.321   3.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.635   2.211   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.987   2.947   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.301   2.144   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.654   2.881   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.263   0.605   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0      14.615   1.341   0.000  0.00  0.00          Cl+0
HETATM   13  C   UNK     0      14.577  -0.198   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.539  -1.738   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.187  -2.474   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.872  -1.671   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.520  -2.408   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.911  -0.132   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.558  -0.869   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.596   0.671   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.244  -0.066   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.611   0.779   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.947  -0.724   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.968   2.277   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.191   1.341   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.135   0.339   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.136  -0.830   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.334  -2.144   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.925  -3.566   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.836  -1.787   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.666  -2.789   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.713  -0.252   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.399   0.551   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.016   1.398   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.477   1.436   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   18                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    7   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24   26                                             
CONECT   23   22                                                            
CONECT   24   22    3    6   25                                             
CONECT   25   24                                                            
CONECT   26   22   27   32   34                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   26   33                                                  
CONECT   33   32                                                            
CONECT   34   26    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₃ClO₆

Average Mass

501.0200 Da

Monoisotopic Mass

500.19657 Da

IUPAC Name

(1'S,2R,2'S,4'R,5'R,10'S,11'S,13'R,20'S)-5'-chloro-4',13'-dihydroxy-3,4,10',16',20'-pentamethyl-5H-spiro[furan-2,14'-pentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{17,20}]icosane]-7',16'-diene-5,9',15'-trione

Traditional Name

(1'S,2R,2'S,4'R,5'R,10'S,11'S,13'R,20'S)-5'-chloro-4',13'-dihydroxy-3,4,10',16',20'-pentamethylspiro[furan-2,14'-pentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{17,20}]icosane]-7',16'-diene-5,9',15'-trione

CAS Registry Number

Not Available

SMILES

CC1=C(C)[C@]2(OC1=O)C(=O)C(C)=C1CC[C@H]3[C@@H]4C[C@@H](O)[C@@]5(Cl)CC=CC(=O)[C@]5(C)[C@H]4C[C@@]2(O)[C@]13C

InChI Identifier

InChI=1S/C28H33ClO6/c1-13-15(3)28(35-23(13)33)22(32)14(2)17-8-9-18-16-11-21(31)26(29)10-6-7-20(30)25(26,5)19(16)12-27(28,34)24(17,18)4/h6-7,16,18-19,21,31,34H,8-12H2,1-5H3/t16-,18-,19-,21+,24+,25-,26-,27+,28-/m0/s1

InChI Key

MVBGXFNBAXISLW-TWZBKPIQSA-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
Jaborosa runcinata	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
5-halo-steroid
Halo-steroid
12-hydroxysteroid
6-hydroxysteroid
Hydroxysteroid
1-oxosteroid
Oxosteroid
Cyclohexenone
Alpha-acyloxy ketone
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Lactone
Ketone
Halohydrin
Carboxylic acid ester
Chlorohydrin
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organohalogen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Alkyl chloride
Carbonyl group
Organochloride
Organooxygen compound
Alkyl halide
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	4.05	ChemAxon
pKa (Strongest Acidic)	12.92	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	131.2 m³·mol⁻¹	ChemAxon
Polarizability	51.32 Å³	ChemAxon
Number of Rings	6	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

8680973

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10505572

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang H, Cao CM, Gallagher RJ, Day VW, Montenegro G, Timmermann BN: Withanolides from Jaborosa caulescens var. bipinnatifida. Phytochemistry. 2014 Feb;98:232-5. doi: 10.1016/j.phytochem.2013.11.005. Epub 2013 Dec 5. [PubMed:24314746 ]
Garcia ME, Nicotra VE, Oberti JC, Rios-Luci C, Leon LG, Marler L, Li G, Pezzuto JM, van Breemen RB, Padron JM, Hueso-Falcon I, Estevez-Braun A: Antiproliferative and quinone reductase-inducing activities of withanolides derivatives. Eur J Med Chem. 2014 Jul 23;82:68-81. doi: 10.1016/j.ejmech.2014.05.045. Epub 2014 May 20. [PubMed:24878636 ]
LOTUS database [Link]

Showing NP-Card for (5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione (NP0219559)

MOL for NP0219559 ((5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione)

3D MOL for NP0219559 ((5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione)

3D SDF for NP0219559 ((5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione)

3D-SDF for NP0219559 ((5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione)

PDB for NP0219559 ((5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione)

3D PDB for NP0219559 ((5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione)

SMILES for NP0219559 ((5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione)

INCHI for NP0219559 ((5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione)

Structure for NP0219559 ((5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione)

3D Structure for NP0219559 ((5r,5ar,6as,6bs,10ar,11r,12as,12bs,12cs)-10a-chloro-5a,11-dihydroxy-3,3',4',6b,12c-pentamethyl-2,6,6a,10,11,12,12a,12b-octahydro-1h-spiro[cyclohexa[j]aceanthrylene-5,2'-furan]-4,5',7-trione)