NP-MRD: Showing NP-Card for (+)-Foveolin A (NP0077591)

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Record Information

Version

2.0

Created at

2022-04-28 22:43:35 UTC

Updated at

2022-04-28 22:43:35 UTC

NP-MRD ID

NP0077591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Foveolin A

Description

3-[(3S,3aR,5aR,6S,7R,9aR,9bR)-7-(2-hydroxypropan-2-yl)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. (+)-Foveolin A is found in Aglaia foveolata. Based on a literature review very few articles have been published on 3-[(3S,3aR,5aR,6S,7R,9aR,9bR)-7-(2-hydroxypropan-2-yl)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200432D          

 35 38  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652304292200432D          

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    1.4608   -0.0406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3252   -1.2252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -0.9458    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4253   -0.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669    0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333   -1.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8156   -1.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5972   -0.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6695   -2.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4263   -1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555    1.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3749    1.2502    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  4 11  1  6  0  0  0
  4 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  3 17  1  1  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 26 29  1  6  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 24 33  1  6  0  0  0
 20 34  1  6  0  0  0
  2 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0077591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@@H]1CC[C@](C)(O1)[C@H]1CC[C@]2(C)[C@@H]1CC[C@@H]1[C@](C)(CCC(O)=O)[C@@H](CC[C@@]21C)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O5/c1-25(2,33)21-12-17-29(7)22(27(21,5)15-14-24(31)32)10-9-19-20(11-16-28(19,29)6)30(8)18-13-23(35-30)26(3,4)34/h19-23,33-34H,9-18H2,1-8H3,(H,31,32)/t19-,20+,21+,22-,23+,27-,28-,29-,30+/m1/s1

> <INCHI_KEY>
ISCNJOCYZXMPDO-YQUOWJQLSA-N

> <FORMULA>
C30H52O5

> <MOLECULAR_WEIGHT>
492.741

> <EXACT_MASS>
492.381474774

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
57.9197699407466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3S,3aR,5aR,6S,7R,9aR,9bR)-7-(2-hydroxypropan-2-yl)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid

> <ALOGPS_LOGP>
5.41

> <JCHEM_LOGP>
4.987623158333333

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.325328794519496

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.87552100178078

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6729434419781525

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
138.318

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.82e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3S,3aR,5aR,6S,7R,9aR,9bR)-7-(2-hydroxypropan-2-yl)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-decahydrocyclopenta[a]naphthalen-6-yl]propanoic 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       7.384   2.127   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.191   0.674   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.730   0.626   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.239   2.213   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.143  -0.865   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.120  -1.444   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.846  -2.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.182  -2.892   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.188  -4.432   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.524  -5.197   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.857  -5.207   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.039   2.042   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.551  -1.070   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.607  -2.287   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.842  -1.766   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.794  -0.226   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.685   0.204   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.116  -2.631   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.389  -3.497   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.981  -1.358   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.250  -3.905   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.662  -2.136   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.704   2.253   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.300   2.334   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20   35                                             
CONECT    3    2    4   17                                                  
CONECT    4    3    5   11   12                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    4                                                            
CONECT   12    4   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    3   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19    2   21   34                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19   24                                                  
CONECT   24   23   25   28   33                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   26   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33   24                                                            
CONECT   34   20                                                            
CONECT   35    2                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
3-[(3S,3AR,5ar,6S,7R,9ar,9BR)-7-(2-hydroxypropan-2-yl)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate	Generator

Chemical Formula

C₃₀H₅₂O₅

Average Mass

492.7410 Da

Monoisotopic Mass

492.38147 Da

IUPAC Name

3-[(3S,3aR,5aR,6S,7R,9aR,9bR)-7-(2-hydroxypropan-2-yl)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid

Traditional Name

3-[(3S,3aR,5aR,6S,7R,9aR,9bR)-7-(2-hydroxypropan-2-yl)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H]1CC[C@](C)(O1)[C@H]1CC[C@]2(C)[C@@H]1CC[C@@H]1[C@](C)(CCC(O)=O)[C@@H](CC[C@@]21C)C(C)(C)O

InChI Identifier

InChI=1S/C30H52O5/c1-25(2,33)21-12-17-29(7)22(27(21,5)15-14-24(31)32)10-9-19-20(11-16-28(19,29)6)30(8)18-13-23(35-30)26(3,4)34/h19-23,33-34H,9-18H2,1-8H3,(H,31,32)/t19-,20+,21+,22-,23+,27-,28-,29-,30+/m1/s1

InChI Key

ISCNJOCYZXMPDO-YQUOWJQLSA-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
Aglaia foveolata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Carbocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Tetrahydrofuran
Tertiary alcohol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	5.41	ALOGPS
logP	4.99	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.88	ChemAxon
pKa (Strongest Basic)	-0.67	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	138.32 m³·mol⁻¹	ChemAxon
Polarizability	57.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162867735

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Foveolin A (NP0077591)

MOL for NP0077591 ((+)-Foveolin A)

3D MOL for NP0077591 ((+)-Foveolin A)

3D SDF for NP0077591 ((+)-Foveolin A)

3D-SDF for NP0077591 ((+)-Foveolin A)

PDB for NP0077591 ((+)-Foveolin A)

3D PDB for NP0077591 ((+)-Foveolin A)

SMILES for NP0077591 ((+)-Foveolin A)

INCHI for NP0077591 ((+)-Foveolin A)

Structure for NP0077591 ((+)-Foveolin A)

3D Structure for NP0077591 ((+)-Foveolin A)