NP-MRD: Showing NP-Card for 3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid (NP0306850)

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Record Information

Version

2.0

Created at

2022-09-10 23:35:26 UTC

Updated at

2022-09-10 23:35:26 UTC

NP-MRD ID

NP0306850

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

Description

Dammarenolic acid, also known as dammarenolate, belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. 3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid is found in Aglaia rubiginosa and Shorea robusta. 3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid was first documented in 2008 (PMID: 18972843). Based on a literature review a small amount of articles have been published on Dammarenolic acid (PMID: 20730953) (PMID: 19962871) (PMID: 22557341).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201352D          

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M  END

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M  END


  Mrv1652309112201352D          

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    5.4214   -0.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3669   -1.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6267   -1.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5722   -2.7841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9411   -1.5021    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 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
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  1  0  0  0
  9 27  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306850

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(C)(O)[C@H]1CC[C@@]2(C)C1CCC1[C@](C)(CCC(O)=O)C(CC[C@]21C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O3/c1-20(2)10-9-16-30(8,33)24-14-18-28(6)23(24)11-12-25-27(5,17-15-26(31)32)22(21(3)4)13-19-29(25,28)7/h10,22-25,33H,3,9,11-19H2,1-2,4-8H3,(H,31,32)/t22?,23?,24-,25?,27+,28-,29-,30?/m0/s1

> <INCHI_KEY>
SITSHJMXTJRDSK-JCTUZHSZSA-N

> <FORMULA>
C30H50O3

> <MOLECULAR_WEIGHT>
458.727

> <EXACT_MASS>
458.37599547

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
56.280955058978016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3S,6R,9aS,9bS)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid

> <JCHEM_LOGP>
7.011873540666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.966705621244582

> <JCHEM_PKA_STRONGEST_BASIC>
-0.39746422425291283

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
137.49890000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3S,6R,9aS,9bS)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      12.002   1.983   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.191   0.674   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.919  -0.683   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.845   2.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.551  -1.070   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.545  -2.246   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.556   0.106   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.375  -2.064   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.074  -1.543   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.250  -2.537   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.700  -2.016   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.876  -3.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.973  -0.500   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.039   2.042   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.242   2.392   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.846  -2.127   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.120  -1.444   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.018  -2.980   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.637  -3.660   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.535  -5.197   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       7.357  -2.804   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   25                                             
CONECT    8    7                                                            
CONECT    9    7   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   13   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   12    7   26                                             
CONECT   26   25                                                            
CONECT   27    9    4   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
Dammarenolate	Generator

Chemical Formula

C₃₀H₅₀O₃

Average Mass

458.7270 Da

Monoisotopic Mass

458.37600 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(C)(O)[C@H]1CC[C@@]2(C)C1CCC1[C@](C)(CCC(O)=O)C(CC[C@]21C)C(C)=C

InChI Identifier

InChI=1S/C30H50O3/c1-20(2)10-9-16-30(8,33)24-14-18-28(6)23(24)11-12-25-27(5,17-15-26(31)32)22(21(3)4)13-19-29(25,28)7/h10,22-25,33H,3,9,11-19H2,1-2,4-8H3,(H,31,32)/t22?,23?,24-,25?,27+,28-,29-,30?/m0/s1

InChI Key

SITSHJMXTJRDSK-JCTUZHSZSA-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
Aglaia rubiginosa	LOTUS Database	35616633
Shorea robusta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Carbocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Tertiary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

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

35466751

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57347487

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ukiya M, Kikuchi T, Tokuda H, Tabata K, Kimura Y, Arai T, Ezaki Y, Oseto O, Suzuki T, Akihisa T: Antitumor-promoting effects and cytotoxic activities of dammar resin triterpenoids and their derivatives. Chem Biodivers. 2010 Aug;7(8):1871-84. doi: 10.1002/cbdv.201000107. [PubMed:20730953 ]
Esimone CO, Eck G, Nworu CS, Hoffmann D, Uberla K, Proksch P: Dammarenolic acid, a secodammarane triterpenoid from Aglaia sp. shows potent anti-retroviral activity in vitro. Phytomedicine. 2010 Jun;17(7):540-7. doi: 10.1016/j.phymed.2009.10.015. Epub 2009 Dec 4. [PubMed:19962871 ]
Poornima B: Comparative phytochemical analysis of Shorea robusta Gaertn (oleoresin) WSR to its seasonal collection. Anc Sci Life. 2009 Jul;29(1):26-8. [PubMed:22557341 ]
Esimone CO, Eck G, Duong TN, Uberla K, Proksch P, Grunwald T: Potential anti-respiratory syncytial virus lead compounds from Aglaia species. Pharmazie. 2008 Oct;63(10):768-73. [PubMed:18972843 ]
LOTUS database [Link]

Showing NP-Card for 3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid (NP0306850)

MOL for NP0306850 (3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

3D MOL for NP0306850 (3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

3D SDF for NP0306850 (3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

3D-SDF for NP0306850 (3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

PDB for NP0306850 (3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

3D PDB for NP0306850 (3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

SMILES for NP0306850 (3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

INCHI for NP0306850 (3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

Structure for NP0306850 (3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

3D Structure for NP0306850 (3-[(3s,6r,9as,9bs)-3-(2-hydroxy-6-methylhept-5-en-2-yl)-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)