NP-MRD: Showing NP-Card for (1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate (NP0306659)

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Record Information

Version

2.0

Created at

2022-09-10 23:16:44 UTC

Updated at

2022-09-10 23:16:44 UTC

NP-MRD ID

NP0306659

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate

Description

(1S,3R,5R,6S,7S,9R,10R,11S,13S,14R,19R,21S,23S,24R,25S)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(2-oxo-2H-pyran-5-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]Pentacos-17-en-11-yl acetate belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. (1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate is found in Drimia calcarata. Based on a literature review very few articles have been published on (1S,3R,5R,6S,7S,9R,10R,11S,13S,14R,19R,21S,23S,24R,25S)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(2-oxo-2H-pyran-5-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]Pentacos-17-en-11-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112201162D          

 46 52  0  0  1  0            999 V2000
    7.3236   -2.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0505   -2.8784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0760   -3.7030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3099   -4.0091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9197   -4.7360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1361   -4.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5208   -5.0276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3525   -4.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6892   -5.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4728   -6.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0881   -5.5436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7362   -6.0541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5608   -6.0285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1760   -5.4789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2941   -4.6624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1017   -4.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8596   -3.9611    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3701   -3.3129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6091   -4.8052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1635   -4.1943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0739   -6.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2903   -6.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1220   -5.3192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7372   -4.7696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5689   -3.9619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1841   -3.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7852   -3.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6169   -2.8963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1700   -4.2535    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9181   -3.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498   -4.1640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9402   -3.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1152   -3.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7055   -2.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1208   -2.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7111   -1.2997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458   -2.0190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555   -2.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113   -4.9164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2037   -5.0848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9457   -5.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4953   -6.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380   -6.0367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6223   -5.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3383   -5.0611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4213   -5.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  6  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  6  0  0  0
 13 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  1  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 24 23  1  6  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 32 38  2  0  0  0  0
 31 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 39 44  1  0  0  0  0
 44 45  1  0  0  0  0
 23 45  1  0  0  0  0
 29 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END


  Mrv1652309112201162D          

 46 52  0  0  1  0            999 V2000
    7.3236   -2.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0505   -2.8784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0760   -3.7030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3099   -4.0091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9197   -4.7360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1361   -4.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5208   -5.0276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3525   -4.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6892   -5.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4728   -6.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0881   -5.5436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7362   -6.0541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5608   -6.0285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1760   -5.4789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2941   -4.6624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1017   -4.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8596   -3.9611    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3701   -3.3129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6091   -4.8052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1635   -4.1943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0739   -6.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2903   -6.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1220   -5.3192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7372   -4.7696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5689   -3.9619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1841   -3.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7852   -3.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6169   -2.8963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1700   -4.2535    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9181   -3.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498   -4.1640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9402   -3.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1152   -3.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7055   -2.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1208   -2.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7111   -1.2997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458   -2.0190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555   -2.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113   -4.9164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2037   -5.0848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9457   -5.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4953   -6.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380   -6.0367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6223   -5.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3383   -5.0611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4213   -5.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  6  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  6  0  0  0
 13 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  1  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 24 23  1  6  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 32 38  2  0  0  0  0
 31 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 39 44  1  0  0  0  0
 44 45  1  0  0  0  0
 23 45  1  0  0  0  0
 29 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0306659

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]12O[C@@H]3C[C@]4(C)[C@H]5[C@H](O)C(=O)[C@]6(C)[C@H]([C@H](C[C@]6(O)[C@@H]5CCC4=C[C@H]3O[C@H](O[C@@H](C)[C@H]1O)[C@@H]2O)OC(C)=O)C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O13/c1-14-26(37)33(41-5)28(39)29(43-14)45-19-10-17-7-8-18-24(30(17,3)11-20(19)46-33)25(36)27(38)31(4)23(16-6-9-22(35)42-13-16)21(44-15(2)34)12-32(18,31)40/h6,9-10,13-14,18-21,23-26,28-29,36-37,39-40H,7-8,11-12H2,1-5H3/t14-,18+,19+,20+,21-,23-,24+,25-,26+,28-,29-,30-,31-,32-,33-/m0/s1

> <INCHI_KEY>
JEGCJQAXZZCFCS-QDWXTXCPSA-N

> <FORMULA>
C33H42O13

> <MOLECULAR_WEIGHT>
646.686

> <EXACT_MASS>
646.262541412

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
66.50723692145998

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,5R,6S,7S,9R,10R,11S,13S,14R,19R,21S,23S,24R,25S)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(2-oxo-2H-pyran-5-yl)-2,20,22-trioxahexacyclo[19.3.1.0^{3,19}.0^{5,17}.0^{6,14}.0^{9,13}]pentacos-17-en-11-yl acetate

> <JCHEM_LOGP>
0.4425772859999971

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.326088015475932

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.398684110089341

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2870177122643858

> <JCHEM_POLAR_SURFACE_AREA>
187.50999999999996

> <JCHEM_REFRACTIVITY>
156.93300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,5R,6S,7S,9R,10R,11S,13S,14R,19R,21S,23S,24R,25S)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0^{3,19}.0^{5,17}.0^{6,14}.0^{9,13}]pentacos-17-en-11-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      13.671  -4.645   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.028  -5.373   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.075  -6.912   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.645  -7.484   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.917  -8.840   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.454  -8.359   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.306  -9.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.991  -7.877   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.620 -10.892   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.083 -11.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.231 -10.348   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.441 -11.301   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      15.980 -11.253   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.129 -10.227   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      17.349  -8.703   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.856  -8.389   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.538  -7.394   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.491  -6.184   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.070  -8.970   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      17.105  -7.829   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.471 -11.918   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.009 -11.437   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.694  -9.929   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.843  -8.903   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.529  -7.396   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.677  -6.370   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.066  -6.914   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.752  -5.406   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.917  -7.940   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.447  -6.473   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.386  -7.773   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.622  -6.436   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.082  -6.430   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.317  -5.093   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.092  -3.763   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.327  -2.426   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       3.632  -3.769   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.397  -5.106   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.754  -9.177   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.247  -9.492   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.765 -10.954   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.791 -12.103   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       0.258 -11.269   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       4.895 -10.212   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.232  -9.447   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       6.387 -10.980   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17   19                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   24                                             
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    3   18                                                  
CONECT   18   17                                                            
CONECT   19   13    3   20                                                  
CONECT   20   19                                                            
CONECT   21    9   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   45                                                  
CONECT   24   23    7   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   45                                             
CONECT   30   29                                                            
CONECT   31   29   32   39                                                  
CONECT   32   31   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   32                                                       
CONECT   39   31   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   39   45                                                       
CONECT   45   44   23   29   46                                             
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  104    0
END

View in JSmol

Synonyms

Value	Source
(1S,3R,5R,6S,7S,9R,10R,11S,13S,14R,19R,21S,23S,24R,25S)-7,13,24,25-Tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(2-oxo-2H-pyran-5-yl)-2,20,22-trioxahexacyclo[19.3.1.0,.0,.0,.0,]pentacos-17-en-11-yl acetic acid	Generator

Chemical Formula

C₃₃H₄₂O₁₃

Average Mass

646.6860 Da

Monoisotopic Mass

646.26254 Da

IUPAC Name

Traditional Name

(1S,3R,5R,6S,7S,9R,10R,11S,13S,14R,19R,21S,23S,24R,25S)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0^{3,19}.0^{5,17}.0^{6,14}.0^{9,13}]pentacos-17-en-11-yl acetate

CAS Registry Number

Not Available

SMILES

CO[C@]12O[C@@H]3C[C@]4(C)[C@H]5[C@H](O)C(=O)[C@]6(C)[C@H]([C@H](C[C@]6(O)[C@@H]5CCC4=C[C@H]3O[C@H](O[C@@H](C)[C@H]1O)[C@@H]2O)OC(C)=O)C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C33H42O13/c1-14-26(37)33(41-5)28(39)29(43-14)45-19-10-17-7-8-18-24(30(17,3)11-20(19)46-33)25(36)27(38)31(4)23(16-6-9-22(35)42-13-16)21(44-15(2)34)12-32(18,31)40/h6,9-10,13-14,18-21,23-26,28-29,36-37,39-40H,7-8,11-12H2,1-5H3/t14-,18+,19+,20+,21-,23-,24+,25-,26+,28-,29-,30-,31-,32-,33-/m0/s1

InChI Key

JEGCJQAXZZCFCS-QDWXTXCPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Geschollia calcarata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
Steroid ester
11-hydroxysteroid
11-alpha-hydroxysteroid
Oxosteroid
12-oxosteroid
Hydroxysteroid
14-hydroxysteroid
Delta-4-steroid
Ketal
Pyranone
Dioxepane
1,4-dioxepane
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.44	ChemAxon
pKa (Strongest Acidic)	11.4	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	187.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	156.93 m³·mol⁻¹	ChemAxon
Polarizability	66.51 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

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

163104539

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate (NP0306659)

MOL for NP0306659 ((1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate)

3D MOL for NP0306659 ((1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate)

3D SDF for NP0306659 ((1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate)

3D-SDF for NP0306659 ((1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate)

PDB for NP0306659 ((1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate)

3D PDB for NP0306659 ((1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate)

SMILES for NP0306659 ((1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate)

INCHI for NP0306659 ((1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate)

Structure for NP0306659 ((1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate)

3D Structure for NP0306659 ((1s,3r,5r,6s,7s,9r,10r,11s,13s,14r,19r,21s,23s,24r,25s)-7,13,24,25-tetrahydroxy-1-methoxy-5,9,23-trimethyl-8-oxo-10-(6-oxopyran-3-yl)-2,20,22-trioxahexacyclo[19.3.1.0³,¹⁹.0⁵,¹⁷.0⁶,¹⁴.0⁹,¹³]pentacos-17-en-11-yl acetate)