NP-MRD: Showing NP-Card for (+)-Aceriphyllic acid H (NP0081526)

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Record Information

Version

2.0

Created at

2022-04-29 02:31:55 UTC

Updated at

2022-04-29 02:31:55 UTC

NP-MRD ID

NP0081526

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Aceriphyllic acid H

Description

Aceriphyllic acid H, also known as aceriphyllate H, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (+)-Aceriphyllic acid H is found in Aceriphyllum rossii. Based on a literature review very few articles have been published on Aceriphyllic acid H.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204312D          

 38 42  0  0  1  0            999 V2000
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7770    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
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  4  5  1  0  0  0  0
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  1  6  1  0  0  0  0
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  9 10  1  0  0  0  0
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  9 14  1  0  0  0  0
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  9 19  1  6  0  0  0
  6 20  1  1  0  0  0
  5 21  1  0  0  0  0
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  4 24  1  0  0  0  0
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 34 35  2  0  0  0  0
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 24 37  1  6  0  0  0
  5 38  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292204312D          

 38 42  0  0  1  0            999 V2000
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    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3977    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3689    2.3887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261    1.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907    1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  1  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  6  0  0  0
 12 16  1  1  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  9 19  1  6  0  0  0
  6 20  1  1  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  6  0  0  0
 27 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 24 37  1  6  0  0  0
  5 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081526

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4C[C@@](C)(CC[C@]4(C)CC[C@@]32C)C(O)=O)[C@]1(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H48O6/c1-19(33)38-24-11-12-29(4)22-9-8-20-21-18-28(3,25(34)35)15-14-27(21,2)16-17-30(20,5)31(22,6)13-10-23(29)32(24,7)26(36)37/h8,21-24H,9-18H2,1-7H3,(H,34,35)(H,36,37)/t21-,22+,23+,24+,27+,28+,29+,30+,31+,32-/m0/s1

> <INCHI_KEY>
UFBADNGLONOAHT-GEHWIPNRSA-N

> <FORMULA>
C32H48O6

> <MOLECULAR_WEIGHT>
528.73

> <EXACT_MASS>
528.345089266

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
59.742105417773985

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4aS,6aS,6bR,8aR,9S,10R,12aR,12bR,14bR)-10-(acetyloxy)-2,4a,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2,9-dicarboxylic acid

> <ALOGPS_LOGP>
6.04

> <JCHEM_LOGP>
6.227651442666665

> <ALOGPS_LOGS>
-5.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.848670702558654

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.234042140441326

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0049333117830646

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
144.49319999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4aS,6aS,6bR,8aR,9S,10R,12aR,12bR,14bR)-10-(acetyloxy)-2,4a,6a,6b,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2,9-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.397  -2.103   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.650  -1.380   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.009  -0.657   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.596  -2.919   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.574   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.689   4.459   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.102   2.197   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.746  -1.897   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -4.056  -0.564   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.023   3.635   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6   21   38                                             
CONECT    6    5    1    7   20                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14   19                                             
CONECT   10    9    1   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15   16                                             
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    9                                                            
CONECT   20    6                                                            
CONECT   21    5   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23    4   25   37                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   23   29   32                                             
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28                                                            
CONECT   33   27   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   24                                                            
CONECT   38    5                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
Aceriphyllate H	Generator

Chemical Formula

C₃₂H₄₈O₆

Average Mass

528.7300 Da

Monoisotopic Mass

528.34509 Da

IUPAC Name

(2R,4aS,6aS,6bR,8aR,9S,10R,12aR,12bR,14bR)-10-(acetyloxy)-2,4a,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2,9-dicarboxylic acid

Traditional Name

(2R,4aS,6aS,6bR,8aR,9S,10R,12aR,12bR,14bR)-10-(acetyloxy)-2,4a,6a,6b,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2,9-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4C[C@@](C)(CC[C@]4(C)CC[C@@]32C)C(O)=O)[C@]1(C)C(O)=O

InChI Identifier

InChI=1S/C32H48O6/c1-19(33)38-24-11-12-29(4)22-9-8-20-21-18-28(3,25(34)35)15-14-27(21,2)16-17-30(20,5)31(22,6)13-10-23(29)32(24,7)26(36)37/h8,21-24H,9-18H2,1-7H3,(H,34,35)(H,36,37)/t21-,22+,23+,24+,27+,28+,29+,30+,31+,32-/m0/s1

InChI Key

UFBADNGLONOAHT-GEHWIPNRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Mukdenia rossii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Hydroxysteroid
15-hydroxysteroid
Steroid
Tricarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	6.04	ALOGPS
logP	6.23	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	144.49 m³·mol⁻¹	ChemAxon
Polarizability	59.74 Å³	ChemAxon
Number of Rings	5	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

C00047698

Chemspider ID

24657352

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44254604

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Aceriphyllic acid H (NP0081526)

MOL for NP0081526 ((+)-Aceriphyllic acid H)

3D MOL for NP0081526 ((+)-Aceriphyllic acid H)

3D SDF for NP0081526 ((+)-Aceriphyllic acid H)

3D-SDF for NP0081526 ((+)-Aceriphyllic acid H)

PDB for NP0081526 ((+)-Aceriphyllic acid H)

3D PDB for NP0081526 ((+)-Aceriphyllic acid H)

SMILES for NP0081526 ((+)-Aceriphyllic acid H)

INCHI for NP0081526 ((+)-Aceriphyllic acid H)

Structure for NP0081526 ((+)-Aceriphyllic acid H)

3D Structure for NP0081526 ((+)-Aceriphyllic acid H)