NP-MRD: Showing NP-Card for (2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione (NP0278352)

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Record Information

Version

2.0

Created at

2022-09-09 03:20:48 UTC

Updated at

2022-09-09 03:20:48 UTC

NP-MRD ID

NP0278352

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione

Description

CHEMBL457155 belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione is found in Lantana camara. Based on a literature review very few articles have been published on CHEMBL457155.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092205202D          

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M  END

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M  END


  Mrv1652309092205202D          

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  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  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  2  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 24  1  6  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 16  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  6  0  0  0
 35 33  1  6  0  0  0
 12 35  1  0  0  0  0
  8 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0278352

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC(=O)C[C@@H]1[C@@H]2[C@H](C[C@]3(C)C4=CC[C@H]5[C@@]6(C)[C@@H](CC[C@]5(C)[C@H]4CC[C@@]23C)OC6=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O5/c1-16(2)13-17(31)14-18-24-21(34-25(18)32)15-29(5)20-7-8-22-27(3,19(20)9-12-28(24,29)4)11-10-23-30(22,6)26(33)35-23/h7,13,18-19,21-24H,8-12,14-15H2,1-6H3/t18-,19+,21+,22-,23-,24-,27-,28+,29-,30+/m1/s1

> <INCHI_KEY>
UAKRLLAUOQEYFN-PQNCNOJFSA-N

> <FORMULA>
C30H40O5

> <MOLECULAR_WEIGHT>
480.645

> <EXACT_MASS>
480.287574388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.49019165094158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S,7R,8S,9S,12R,13R,16R,19S,20R)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0^{2,9}.0^{4,8}.0^{13,20}.0^{16,19}]docos-1(22)-ene-6,18-dione

> <JCHEM_LOGP>
5.078453235

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.165005037203226

> <JCHEM_PKA_STRONGEST_BASIC>
-4.370961402548799

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
133.44599999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,7R,8S,9S,12R,13R,16R,19S,20R)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0^{2,9}.0^{4,8}.0^{13,20}.0^{16,19}]docos-1(22)-ene-6,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       4.257 -11.197   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.588  -9.693   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.451  -8.654   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.056  -9.228   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.387  -7.724   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.250  -6.685   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.855  -7.258   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.186  -5.754   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.164  -4.602   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.631  -4.752   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.944  -3.274   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.448  -3.605   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.859  -2.989   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.881  -4.141   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.518  -2.739   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.421  -4.152   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.201  -2.824   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.741  -2.835   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.501  -4.174   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.041  -4.186   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.653  -2.695   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.380  -3.425   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      19.790  -1.941   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      20.141  -4.764   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      18.801  -5.525   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.022  -6.853   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.482  -6.842   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.721  -5.503   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.942  -6.831   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.181  -5.491   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.402  -6.819   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.862  -6.808   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.102  -5.469   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.187  -6.708   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.598  -5.138   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   35                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   33                                             
CONECT   15   14                                                            
CONECT   16   14   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21   22   25                                             
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   19   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   16   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   14   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   12    8                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₅

Average Mass

480.6450 Da

Monoisotopic Mass

480.28757 Da

IUPAC Name

(2S,4S,7R,8S,9S,12R,13R,16R,19S,20R)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0^{2,9}.0^{4,8}.0^{13,20}.0^{16,19}]docos-1(22)-ene-6,18-dione

Traditional Name

(2S,4S,7R,8S,9S,12R,13R,16R,19S,20R)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0^{2,9}.0^{4,8}.0^{13,20}.0^{16,19}]docos-1(22)-ene-6,18-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CC(=O)C[C@@H]1[C@@H]2[C@H](C[C@]3(C)C4=CC[C@H]5[C@@]6(C)[C@@H](CC[C@]5(C)[C@H]4CC[C@@]23C)OC6=O)OC1=O

InChI Identifier

InChI=1S/C30H40O5/c1-16(2)13-17(31)14-18-24-21(34-25(18)32)15-29(5)20-7-8-22-27(3,19(20)9-12-28(24,29)4)11-10-23-30(22,6)26(33)35-23/h7,13,18-19,21-24H,8-12,14-15H2,1-6H3/t18-,19+,21+,22-,23-,24-,27-,28+,29-,30+/m1/s1

InChI Key

UAKRLLAUOQEYFN-PQNCNOJFSA-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
Lantana camara	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
Bile acid, alcohol, or derivatives
Delta-7-steroid
Steroid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Acryloyl-group
Beta_propiolactone
Alpha,beta-unsaturated ketone
Tetrahydrofuran
Enone
Carboxylic acid ester
Oxetane
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	5.08	ChemAxon
pKa (Strongest Acidic)	17.17	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	133.45 m³·mol⁻¹	ChemAxon
Polarizability	54.49 Å³	ChemAxon
Number of Rings	6	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

8871443

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10696098

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione (NP0278352)

MOL for NP0278352 ((2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione)

3D MOL for NP0278352 ((2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione)

3D SDF for NP0278352 ((2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione)

3D-SDF for NP0278352 ((2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione)

PDB for NP0278352 ((2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione)

3D PDB for NP0278352 ((2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione)

SMILES for NP0278352 ((2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione)

INCHI for NP0278352 ((2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione)

Structure for NP0278352 ((2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione)

3D Structure for NP0278352 ((2s,4s,7r,8s,9s,12r,13r,16r,19s,20r)-2,9,13,19-tetramethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-5,17-dioxahexacyclo[10.10.0.0²,⁹.0⁴,⁸.0¹³,²⁰.0¹⁶,¹⁹]docos-1(22)-ene-6,18-dione)