NP-MRD: Showing NP-Card for Actinidic acid (NP0085373)

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Record Information

Version

2.0

Created at

2022-04-29 05:55:22 UTC

Updated at

2022-04-29 05:55:22 UTC

NP-MRD ID

NP0085373

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Actinidic acid

Description

Actinidic acid, also known as actinidate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Actinidic acid is found in Actinidia chinensis, Actinidia deliciosa cv. Golden King and Rhododendron brachycarpum. Actinidic acid was first documented in 2001 (PMID: 11302196). Based on a literature review a small amount of articles have been published on actinidic acid (PMID: 32315181) (PMID: 18481026).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207552D          

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M  END

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M  END


  Mrv1652304292207552D          

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    5.2520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 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
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 20 23  1  6  0  0  0
 19 24  1  6  0  0  0
 15 25  1  6  0  0  0
 14 26  1  1  0  0  0
 11 27  1  6  0  0  0
 10 28  1  1  0  0  0
  6 29  1  1  0  0  0
  3 30  1  6  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
  3 37  1  0  0  0  0
 35 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0085373

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)C(=C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)[C@H](O)[C@@]2(C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,18,20-24,31-33H,1,8-16H2,2-6H3,(H,34,35)/t18-,20+,21+,22+,23-,24-,26-,27-,28+,29+,30-/m0/s1

> <INCHI_KEY>
FFMVHFPLIIYYNC-QXIFDOFRSA-N

> <FORMULA>
C30H46O5

> <MOLECULAR_WEIGHT>
486.693

> <EXACT_MASS>
486.334524581

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.938413430558896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
4.77

> <JCHEM_LOGP>
3.878484835

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.553793907258104

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.717986532478568

> <JCHEM_PKA_STRONGEST_BASIC>
-2.787482617442854

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
136.61169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic 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  H   UNK     0       8.264  -0.564   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494   3.437   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   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.850   4.366   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       3.644   2.104   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0       6.885   3.635   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.574   3.437   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.804   4.771   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.114  -1.897   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   33                                             
CONECT    3    2    4   30   37                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11   29                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15   28                                             
CONECT   11   10    6   12   27                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20   26                                             
CONECT   15   14   10   16   25                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   14   21   23                                             
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20                                                            
CONECT   24   19                                                            
CONECT   25   15                                                            
CONECT   26   14                                                            
CONECT   27   11                                                            
CONECT   28   10                                                            
CONECT   29    6                                                            
CONECT   30    3   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    2   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36    3                                                       
CONECT   38   35                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
Actinidate	Generator

Chemical Formula

C₃₀H₄₆O₅

Average Mass

486.6930 Da

Monoisotopic Mass

486.33452 Da

IUPAC Name

(1R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

(1R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)C(=C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)[C@H](O)[C@@]2(C)CO

InChI Identifier

InChI=1S/C30H46O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,18,20-24,31-33H,1,8-16H2,2-6H3,(H,34,35)/t18-,20+,21+,22+,23-,24-,26-,27-,28+,29+,30-/m0/s1

InChI Key

FFMVHFPLIIYYNC-QXIFDOFRSA-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
Actinidia chinensis	LOTUS Database	35616633
Actinidia deliciosa cv. Golden King	Plant	KNApSAcK
Rhododendron brachycarpum	LOTUS Database	35616633

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
12-hydroxysteroid
Hydroxysteroid
12-beta-hydroxysteroid
Steroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:71457 )
pentacyclic triterpenoid (CHEBI:71457 )

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	4.77	ALOGPS
logP	3.88	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.61 m³·mol⁻¹	ChemAxon
Polarizability	55.94 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00055210

Chemspider ID

28425456

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70680338

PDB ID

Not Available

ChEBI ID

71457

Good Scents ID

Not Available

References

General References

Ahn JH, Park Y, Yeon SW, Jo YH, Han YK, Turk A, Ryu SH, Hwang BY, Lee KY, Lee MK: Phenylpropanoid-Conjugated Triterpenoids from the Leaves of Actinidia arguta and Their Inhibitory Activity on alpha-Glucosidase. J Nat Prod. 2020 May 22;83(5):1416-1423. doi: 10.1021/acs.jnatprod.9b00643. Epub 2020 Apr 21. [PubMed:32315181 ]
Jang DS, Lee GY, Kim J, Lee YM, Kim JM, Kim YS, Kim JS: A new pancreatic lipase inhibitor isolated from the roots of Actinidia arguta. Arch Pharm Res. 2008 May;31(5):666-70. doi: 10.1007/s12272-001-1210-9. Epub 2008 May 15. [PubMed:18481026 ]
Lahlou EH, Hirai N, Kamo T, Tsuda M, Ohigashi H: Actinidic acid, a new triterpene phytoalexin from unripe kiwi fruit. Biosci Biotechnol Biochem. 2001 Feb;65(2):480-3. doi: 10.1271/bbb.65.480. [PubMed:11302196 ]

Showing NP-Card for Actinidic acid (NP0085373)

MOL for NP0085373 (Actinidic acid)

3D MOL for NP0085373 (Actinidic acid)

3D SDF for NP0085373 (Actinidic acid)

3D-SDF for NP0085373 (Actinidic acid)

PDB for NP0085373 (Actinidic acid)

3D PDB for NP0085373 (Actinidic acid)

SMILES for NP0085373 (Actinidic acid)

INCHI for NP0085373 (Actinidic acid)

Structure for NP0085373 (Actinidic acid)

3D Structure for NP0085373 (Actinidic acid)