NP-MRD: Showing NP-Card for 3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid (NP0332606)

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Record Information

Version

1.0

Created at

2024-03-08 20:11:16 UTC

Updated at

2024-04-19 10:12:15 UTC

NP-MRD ID

NP0332606

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03082420112D          

 35 38  0  0  1  0            999 V2000
    5.4731   -0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -1.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1154    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4149    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2251   -0.9907    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7946   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0647    0.8802    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.0361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2849   -0.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6160    1.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165    0.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5244    0.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8293   -0.6578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.1921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9845    1.8157    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358    2.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10  2  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  6  0  0  0
 16 14  1  0  0  0  0
  8 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
 20 19  1  0  0  0  0
 20 21  1  6  0  0  0
 22 20  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 31 26  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
M  END


  Mrv2104 03082420112D          

 35 38  0  0  1  0            999 V2000
    5.4731   -0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -1.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1154    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4149    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2251   -0.9907    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7946   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0647    0.8802    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.0361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2849   -0.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6160    1.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165    0.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5244    0.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8293   -0.6578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.1921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9845    1.8157    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358    2.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10  2  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  6  0  0  0
 16 14  1  0  0  0  0
  8 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
 20 19  1  0  0  0  0
 20 21  1  6  0  0  0
 22 20  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 31 26  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332606

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@@](C)(C(O)=O)[C@]2([H])C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O4/c1-16(28)21-17-8-9-19-24(4)12-11-20(29)23(2,3)18(24)10-13-27(19,7)26(17,6)15-14-25(21,5)22(30)31/h17-21,29H,8-15H2,1-7H3,(H,30,31)/t17-,18+,19-,20+,21-,24+,25-,26-,27-/m1/s1

> <INCHI_KEY>
BQIACKUVMRPRQY-MIGYPBRWSA-N

> <FORMULA>
C27H44O4

> <MOLECULAR_WEIGHT>
432.645

> <EXACT_MASS>
432.323959897

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
50.711090034007796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4aR,4bR,6aR,8S,10aR,10bR,12aR)-1-acetyl-8-hydroxy-2,4a,4b,7,7,10a-hexamethyl-octadecahydrochrysene-2-carboxylic acid

> <JCHEM_LOGP>
5.253286210666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.367099964259214

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.595931034868827

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351233186953927

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
121.59339999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4aR,4bR,6aR,8S,10aR,10bR,12aR)-1-acetyl-8-hydroxy-2,4a,4b,7,7,10a-hexamethyl-dodecahydro-1H-chrysene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-MAR-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-24         0                                  
HETATM    1  C   UNK     0      10.216  -1.476   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.346  -2.124   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.415   0.188   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.375   2.516   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       7.887  -1.849   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       6.375  -1.558   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.350  -0.976   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       3.854   1.643   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.398  -0.995   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.150   2.256   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.524   0.312   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.846   1.103   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.548  -1.228   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       1.838   3.389   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0       0.326   3.680   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334   4.844   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.187   3.971   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8    2   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   22                                             
CONECT   15   14                                                            
CONECT   16   14    8   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   31                                             
CONECT   21   20                                                            
CONECT   22   20   14   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   31                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26   20   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₄

Average Mass

432.6450 Da

Monoisotopic Mass

432.32396 Da

IUPAC Name

(1R,2R,4aR,4bR,6aR,8S,10aR,10bR,12aR)-1-acetyl-8-hydroxy-2,4a,4b,7,7,10a-hexamethyl-octadecahydrochrysene-2-carboxylic acid

Traditional Name

(1R,2R,4aR,4bR,6aR,8S,10aR,10bR,12aR)-1-acetyl-8-hydroxy-2,4a,4b,7,7,10a-hexamethyl-dodecahydro-1H-chrysene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@@](C)(C(O)=O)[C@]2([H])C(C)=O

InChI Identifier

InChI=1S/C27H44O4/c1-16(28)21-17-8-9-19-24(4)12-11-20(29)23(2,3)18(24)10-13-27(19,7)26(17,6)15-14-25(21,5)22(30)31/h17-21,29H,8-15H2,1-7H3,(H,30,31)/t17-,18+,19-,20+,21-,24+,25-,26-,27-/m1/s1

InChI Key

BQIACKUVMRPRQY-MIGYPBRWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)	shtwangxin@buu.edu.cn	Beijing Union University	Xin Wang	2024-03-08	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)	shtwangxin@buu.edu.cn	Beijing Union University	Xin Wang	2024-03-08	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)	shtwangxin@buu.edu.cn	Beijing Union University	Xin Wang	2024-03-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)	shtwangxin@buu.edu.cn	Beijing Union University	Xin Wang	2024-03-08	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)	shtwangxin@buu.edu.cn	Beijing Union University	Xin Wang	2024-03-08	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, C5D5N, experimental)	shtwangxin@buu.edu.cn	Beijing Union University	Xin Wang	2024-03-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125.770364779 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500.132693198 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	5.25	ChemAxon
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	121.59 m³·mol⁻¹	ChemAxon
Polarizability	50.71 Å³	ChemAxon
Number of Rings	4	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

Not Available

References

General References

Not Available

Showing NP-Card for 3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid (NP0332606)

MOL for NP0332606 (3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid)

3D MOL for NP0332606 (3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid)

3D SDF for NP0332606 (3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid)

3D-SDF for NP0332606 (3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid)

PDB for NP0332606 (3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid)

3D PDB for NP0332606 (3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid)

SMILES for NP0332606 (3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid)

INCHI for NP0332606 (3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid)

Structure for NP0332606 (3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid)

3D Structure for NP0332606 (3β-hydroxy-19-oxo-20,21-seco-19-norlupan-21-oic acid)