NP-MRD: Showing NP-Card for 3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid (NP0304298)

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Record Information

Version

2.0

Created at

2022-09-10 19:17:31 UTC

Updated at

2022-09-10 19:17:32 UTC

NP-MRD ID

NP0304298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid

Description

3-Hydroxy-4,24-dimethylene-3,4-seco-28-nor-5alpha-cycloartane-3-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid is found in Pisonia umbellifera. Based on a literature review very few articles have been published on 3-Hydroxy-4,24-dimethylene-3,4-seco-28-nor-5alpha-cycloartane-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102221172D          

 33 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102221172D          

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    1.0087   -1.8371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7934   -2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6673   -3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3818   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6673   -3.8951    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  5  1  1  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 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 19 25  1  0  0  0  0
 26 25  1  1  0  0  0
 12 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  7 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  1  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304298

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H](C(C)=C)[C@@]4(CCC(O)=O)C[C@@]34CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C31H50O2/c1-20(2)22(5)9-10-23(6)25-13-15-29(8)26-12-11-24(21(3)4)30(16-14-27(32)33)19-31(26,30)18-17-28(25,29)7/h20,23-26H,3,5,9-19H2,1-2,4,6-8H3,(H,32,33)/t23-,24+,25-,26+,28-,29+,30-,31+/m1/s1

> <INCHI_KEY>
MPVBOAOGIWZEDP-NNBSIIRNSA-N

> <FORMULA>
C31H50O2

> <MOLECULAR_WEIGHT>
454.739

> <EXACT_MASS>
454.38108085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
56.99355679848239

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(1S,4R,5R,8S,9S,12S,13R)-4,8-dimethyl-5-[(2R)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0^{1,13}.0^{4,8}]tetradecan-13-yl]propanoic acid

> <JCHEM_LOGP>
8.06378608466667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.87271764630199

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
137.36479999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1S,4R,5R,8S,9S,12S,13R)-4,8-dimethyl-5-[(2R)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0^{1,13}.0^{4,8}]tetradecan-13-yl]propanoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

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       7.379  -3.421   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.379  -4.961   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.045  -5.731   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.711  -4.961   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.378  -5.731   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.378  -7.271   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.044  -4.961   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.637  -5.587   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.393  -4.443   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.377  -3.109   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.155  -2.948   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.099  -1.644   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.606  -1.324   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.081   0.140   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.051   1.285   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.527   2.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.033   3.070   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.496   3.894   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.455   0.965   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.776   2.471   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.240   2.947   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.385   1.916   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.849   2.392   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.064   0.410   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.962   0.644   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.931  -0.500   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.438  -0.820   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.913  -2.285   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.883  -3.429   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.348  -3.905   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.712  -5.731   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.046  -4.961   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.712  -7.271   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                                                  
CONECT    6    5                                                            
CONECT    7    5    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   29                                             
CONECT   11   10                                                            
CONECT   12   10   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   15   20   25   26                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   19   26                                                       
CONECT   26   25   12   19   27                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    7   10   30                                             
CONECT   30   29                                                            
CONECT   31    2   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-4,24-dimethylene-3,4-seco-28-nor-5a-cycloartane-3-one	Generator
3-Hydroxy-4,24-dimethylene-3,4-seco-28-nor-5α-cycloartane-3-one	Generator

Chemical Formula

C₃₁H₅₀O₂

Average Mass

454.7390 Da

Monoisotopic Mass

454.38108 Da

IUPAC Name

3-[(1S,4R,5R,8S,9S,12S,13R)-4,8-dimethyl-5-[(2R)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0^{1,13}.0^{4,8}]tetradecan-13-yl]propanoic acid

Traditional Name

3-[(1S,4R,5R,8S,9S,12S,13R)-4,8-dimethyl-5-[(2R)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0^{1,13}.0^{4,8}]tetradecan-13-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H](C(C)=C)[C@@]4(CCC(O)=O)C[C@@]34CC[C@]12C

InChI Identifier

InChI=1S/C31H50O2/c1-20(2)22(5)9-10-23(6)25-13-15-29(8)26-12-11-24(21(3)4)30(16-14-27(32)33)19-31(26,30)18-17-28(25,29)7/h20,23-26H,3,5,9-19H2,1-2,4,6-8H3,(H,32,33)/t23-,24+,25-,26+,28-,29+,30-,31+/m1/s1

InChI Key

MPVBOAOGIWZEDP-NNBSIIRNSA-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
Ceodes umbellifera	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
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	8.06	ChemAxon
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	9	ChemAxon
Refractivity	137.36 m³·mol⁻¹	ChemAxon
Polarizability	56.99 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	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

21377195

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13943213

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid (NP0304298)

MOL for NP0304298 (3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

3D MOL for NP0304298 (3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

3D SDF for NP0304298 (3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

3D-SDF for NP0304298 (3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

PDB for NP0304298 (3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

3D PDB for NP0304298 (3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

SMILES for NP0304298 (3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

INCHI for NP0304298 (3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

Structure for NP0304298 (3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)

3D Structure for NP0304298 (3-[(1s,4r,5r,8s,9s,12s,13r)-4,8-dimethyl-5-[(2r)-6-methyl-5-methylideneheptan-2-yl]-12-(prop-1-en-2-yl)tetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-13-yl]propanoic acid)