NP-MRD: Showing NP-Card for 3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid (NP0285553)

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Record Information

Version

2.0

Created at

2022-09-09 13:46:18 UTC

Updated at

2022-09-09 13:46:18 UTC

NP-MRD ID

NP0285553

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid

Description

3-[1,4A,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydrochrysen-1-yl]propanoic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid is found in Gentiana macrophylla. 3-[1,4A,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydrochrysen-1-yl]propanoic acid is a weakly acidic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191514412D          

 32 35  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004191514412D          

 32 35  0  0  0  0            999 V2000
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  5  6  1  0  0  0  0
  5  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
  9 11  1  0  0  0  0
 11 12  2  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
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 25  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 11 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285553

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(C)CCC3(C)C(=CCC4C(C)(CCC(O)=O)C(CCC34C)C(C)=C)C2C1C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O2/c1-19(2)22-12-16-30(8)24(28(22,6)15-13-25(31)32)10-9-23-26-21(4)20(3)11-14-27(26,5)17-18-29(23,30)7/h9,20-22,24,26H,1,10-18H2,2-8H3,(H,31,32)

> <INCHI_KEY>
RPPYCVULPFKBOG-UHFFFAOYSA-N

> <FORMULA>
C30H48O2

> <MOLECULAR_WEIGHT>
440.712

> <EXACT_MASS>
440.365430786

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.64853893425576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydrochrysen-1-yl]propanoic acid

> <ALOGPS_LOGP>
7.90

> <JCHEM_LOGP>
7.561283749333334

> <ALOGPS_LOGS>
-6.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.871145598085972

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
133.83629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.32e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       4.652  -1.522   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.172  -6.469   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.685  -6.178   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.197  -5.887   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.709  -5.596   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.551  -1.604   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.680  -0.956   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.652   0.239   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.103   1.678   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.074   2.873   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.582   1.921   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.661  -5.615   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.750  -3.268   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.758  -4.432   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.254  -1.813   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.677  -0.940   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   30                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   25                                             
CONECT   10    9                                                            
CONECT   11    9   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16   17   22                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    9   14   26                                             
CONECT   26   25                                                            
CONECT   27   22   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   11    5   31                                                  
CONECT   31   30    2   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
3-[1,4a,4b,6a,9,10-Hexamethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydrochrysen-1-yl]propanoate	Generator
3-((1S,2S,4AR,4BS,6ar,9R,10S,10ar,12ar)-1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydrochrysen-1-yl)propanoate	Generator

Chemical Formula

C₃₀H₄₈O₂

Average Mass

440.7120 Da

Monoisotopic Mass

440.36543 Da

IUPAC Name

3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydrochrysen-1-yl]propanoic acid

Traditional Name

3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC1CCC2(C)CCC3(C)C(=CCC4C(C)(CCC(O)=O)C(CCC34C)C(C)=C)C2C1C

InChI Identifier

InChI=1S/C30H48O2/c1-19(2)22-12-16-30(8)24(28(22,6)15-13-25(31)32)10-9-23-26-21(4)20(3)11-14-27(26,5)17-18-29(23,30)7/h9,20-22,24,26H,1,10-18H2,2-8H3,(H,31,32)

InChI Key

RPPYCVULPFKBOG-UHFFFAOYSA-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
Gentiana macrophylla	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
Steroid
Carbocyclic fatty acid
Fatty acyl
Monocarboxylic acid or derivatives
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	7.9	ALOGPS
logP	7.56	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	4.87	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.84 m³·mol⁻¹	ChemAxon
Polarizability	54.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

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

12315004

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid (NP0285553)

MOL for NP0285553 (3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid)

3D MOL for NP0285553 (3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid)

3D SDF for NP0285553 (3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid)

3D-SDF for NP0285553 (3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid)

PDB for NP0285553 (3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid)

3D PDB for NP0285553 (3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid)

SMILES for NP0285553 (3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid)

INCHI for NP0285553 (3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid)

Structure for NP0285553 (3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid)

3D Structure for NP0285553 (3-[1,4a,4b,6a,9,10-hexamethyl-2-(prop-1-en-2-yl)-2,3,4,5,6,7,8,9,10,10a,12,12a-dodecahydrochrysen-1-yl]propanoic acid)