NP-MRD: Showing NP-Card for (1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid (NP0295744)

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Record Information

Version

2.0

Created at

2022-09-10 04:54:19 UTC

Updated at

2022-09-10 04:54:19 UTC

NP-MRD ID

NP0295744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid

Description

CHEMBL486853 belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid is found in Ilex paraguariensis. Based on a literature review very few articles have been published on CHEMBL486853.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102206542D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102206542D          

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 11 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
  9 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  3  0  0  0  0
M  END
> <DATABASE_ID>
NP0295744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@](C)(CCC#N)[C@@H](CC[C@@]34C)C(C)=C)[C@@H]2[C@H]1C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H45NO2/c1-19(2)22-12-14-29(7)24(27(22,5)13-8-18-31)10-9-23-25-21(4)20(3)11-15-30(25,26(32)33)17-16-28(23,29)6/h9,20-22,24-25H,1,8,10-17H2,2-7H3,(H,32,33)/t20-,21+,22+,24-,25+,27+,28-,29-,30+/m1/s1

> <INCHI_KEY>
SXPZSMMJUUHTBE-MTCIRRIFSA-N

> <FORMULA>
C30H45NO2

> <MOLECULAR_WEIGHT>
451.695

> <EXACT_MASS>
451.345029693

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.110875516469235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4aR,4bS,6aS,9R,10S,10aS,12aR)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydrochrysene-6a-carboxylic acid

> <JCHEM_LOGP>
6.810925214999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.77147362551407

> <JCHEM_POLAR_SURFACE_AREA>
61.089999999999996

> <JCHEM_REFRACTIVITY>
134.53279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4aR,4bS,6aS,9R,10S,10aS,12aR)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.861  -4.123   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.357  -5.578   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.365  -6.742   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.155  -5.869   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.659  -7.324   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.171  -7.615   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.180  -6.451   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.684  -7.906   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.676  -4.996   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.684  -3.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.196  -4.123   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.700  -5.578   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.212  -5.869   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.220  -4.705   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.716  -3.250   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.733  -4.996   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.741  -3.832   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.237  -6.451   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.229  -7.615   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.716  -7.324   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.220  -8.779   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.212  -9.943   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.733  -9.070   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.708  -8.488   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.196  -8.197   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.692  -6.742   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.560  -8.276   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.163  -4.705   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.401  -3.183   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.035  -3.657   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.379  -2.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.250  -1.107   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      -0.878  -0.059   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   26                                             
CONECT    8    7                                                            
CONECT    9    7   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   13   21   24                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   12    7   27                                             
CONECT   27   26                                                            
CONECT   28    9    4   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₅NO₂

Average Mass

451.6950 Da

Monoisotopic Mass

451.34503 Da

IUPAC Name

(1S,2S,4aR,4bS,6aS,9R,10S,10aS,12aR)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydrochrysene-6a-carboxylic acid

Traditional Name

(1S,2S,4aR,4bS,6aS,9R,10S,10aS,12aR)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@](C)(CCC#N)[C@@H](CC[C@@]34C)C(C)=C)[C@@H]2[C@H]1C)C(O)=O

InChI Identifier

InChI=1S/C30H45NO2/c1-19(2)22-12-14-29(7)24(27(22,5)13-8-18-31)10-9-23-25-21(4)20(3)11-15-30(25,26(32)33)17-16-28(23,29)6/h9,20-22,24-25H,1,8,10-17H2,2-7H3,(H,32,33)/t20-,21+,22+,24-,25+,27+,28-,29-,30+/m1/s1

InChI Key

SXPZSMMJUUHTBE-MTCIRRIFSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ilex paraguariensis	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
Steroid acid
3-carboxy steroid
Steroid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonitrile
Nitrile
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
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	6.81	ChemAxon
pKa (Strongest Acidic)	4.77	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	134.53 m³·mol⁻¹	ChemAxon
Polarizability	54.11 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23331806

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44562528

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid (NP0295744)

MOL for NP0295744 ((1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid)

3D MOL for NP0295744 ((1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid)

3D SDF for NP0295744 ((1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid)

3D-SDF for NP0295744 ((1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid)

PDB for NP0295744 ((1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid)

3D PDB for NP0295744 ((1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid)

SMILES for NP0295744 ((1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid)

INCHI for NP0295744 ((1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid)

Structure for NP0295744 ((1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid)

3D Structure for NP0295744 ((1s,2s,4ar,4bs,6as,9r,10s,10as,12ar)-1-(2-cyanoethyl)-1,4a,4b,9,10-pentamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysene-6a-carboxylic acid)