NP-MRD: Showing NP-Card for (2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid (NP0217503)

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Record Information

Version

2.0

Created at

2022-09-05 17:52:22 UTC

Updated at

2022-09-05 17:52:22 UTC

NP-MRD ID

NP0217503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid

Description

Solidagonal acid belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid was first documented in 2008 (PMID: 18389472). Based on a literature review very few articles have been published on Solidagonal acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052219522D          

 23 24  0  0  1  0            999 V2000
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1075    0.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    0.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9806    0.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109    1.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287    2.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3233    1.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8536    1.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715    2.5117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6661    1.5932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8371   -1.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  3  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0217503

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@]2(C)[C@H](CC(C=O)=C2C)[C@@]1(C)CC\C(C)=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-13(10-18(22)23)6-8-19(4)14(2)7-9-20(5)15(3)16(12-21)11-17(19)20/h10,12,14,17H,6-9,11H2,1-5H3,(H,22,23)/b13-10+/t14-,17-,19+,20+/m1/s1

> <INCHI_KEY>
JIKPDGHCTOSDJA-OHGCEXCKSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.374292759597346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-[(3aR,6R,7S,7aR)-2-formyl-3,3a,6,7-tetramethyl-3a,4,5,6,7,7a-hexahydro-1H-inden-7-yl]-3-methylpent-2-enoic acid

> <JCHEM_LOGP>
4.253520267333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.96017859372028

> <JCHEM_PKA_STRONGEST_BASIC>
-4.364517385014759

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
93.46649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-[(3aR,4S,5R,7aR)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3H-inden-4-yl]-3-methylpent-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.090  -2.637   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.934   1.417   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.914   1.417   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.430   1.149   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.420   2.329   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.894   3.776   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.937   2.062   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.927   3.241   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.400   4.689   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.443   2.974   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.429  -3.604   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9   10   18                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    8   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2    7   23                                             
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4570 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

(2E)-5-[(3aR,6R,7S,7aR)-2-formyl-3,3a,6,7-tetramethyl-3a,4,5,6,7,7a-hexahydro-1H-inden-7-yl]-3-methylpent-2-enoic acid

Traditional Name

(2E)-5-[(3aR,4S,5R,7aR)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3H-inden-4-yl]-3-methylpent-2-enoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@]2(C)[C@H](CC(C=O)=C2C)[C@@]1(C)CC\C(C)=C\C(O)=O

InChI Identifier

InChI=1S/C20H30O3/c1-13(10-18(22)23)6-8-19(4)14(2)7-9-20(5)15(3)16(12-21)11-17(19)20/h10,12,14,17H,6-9,11H2,1-5H3,(H,22,23)/b13-10+/t14-,17-,19+,20+/m1/s1

InChI Key

JIKPDGHCTOSDJA-OHGCEXCKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Bicyclic monoterpenoid
11-noriridane monoterpenoid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
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	4.25	ChemAxon
pKa (Strongest Acidic)	4.96	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.47 m³·mol⁻¹	ChemAxon
Polarizability	37.37 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

101285195

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Faizi S, Khan RA, Mughal NR, Malik MS, Sajjadi KE, Ahmad A: Antimicrobial activity of various parts of Polyalthia longifolia var. pendula: isolation of active principles from the leaves and the berries. Phytother Res. 2008 Jul;22(7):907-12. doi: 10.1002/ptr.2414. [PubMed:18389472 ]
LOTUS database [Link]

Showing NP-Card for (2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid (NP0217503)

MOL for NP0217503 ((2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid)

3D MOL for NP0217503 ((2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid)

3D SDF for NP0217503 ((2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid)

3D-SDF for NP0217503 ((2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid)

PDB for NP0217503 ((2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid)

3D PDB for NP0217503 ((2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid)

SMILES for NP0217503 ((2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid)

INCHI for NP0217503 ((2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid)

Structure for NP0217503 ((2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid)

3D Structure for NP0217503 ((2e)-5-[(3ar,4s,5r,7ar)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3h-inden-4-yl]-3-methylpent-2-enoic acid)