NP-MRD: Showing NP-Card for (2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid (NP0291729)

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Record Information

Version

2.0

Created at

2022-09-09 22:55:41 UTC

Updated at

2022-09-09 22:55:42 UTC

NP-MRD ID

NP0291729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid

Description

Rhabdastrellic acid A, also known as rhabdastrellate a, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid is found in Rhabdastrella globostellata. (2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid was first documented in 2019 (PMID: 31448913). Based on a literature review a small amount of articles have been published on rhabdastrellic acid A (PMID: 33635622) (PMID: 33464048).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200552D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102200552D          

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  2 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 25 33  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0291729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C(/C)C(O)=O)=C/C=C/C(/C)=C1\C(=O)C[C@@H]2[C@]1(C)CCC1C(C)(C)C(=O)CC[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O4/c1-19(11-9-13-21(3)27(33)34)10-8-12-20(2)26-22(31)18-24-29(6)17-15-25(32)28(4,5)23(29)14-16-30(24,26)7/h8-13,23-24H,14-18H2,1-7H3,(H,33,34)/b11-9+,12-8+,19-10+,21-13+,26-20+/t23?,24-,29-,30-/m0/s1

> <INCHI_KEY>
IIPLLKSCMYHUOP-HYCGKRAFSA-N

> <FORMULA>
C30H40O4

> <MOLECULAR_WEIGHT>
464.646

> <EXACT_MASS>
464.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.198538015245965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-10-[(3Z,3aS,9aR,9bS)-3a,6,6,9a-tetramethyl-2,7-dioxo-dodecahydro-1H-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid

> <JCHEM_LOGP>
6.430983686000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.549555891309254

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9462094740918925

> <JCHEM_PKA_STRONGEST_BASIC>
-4.836429803585172

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
141.19649999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E)-10-[(3Z,3aS,9aR,9bS)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1H-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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       7.622  -2.586   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.895  -1.070   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.344  -0.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.520  -1.543   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.969  -1.021   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.145  -2.016   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.872  -3.531   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.594  -1.494   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.770  -2.488   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.220  -1.967   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.396  -2.961   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.123  -4.477   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.845  -2.440   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      21.021  -3.434   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      20.118  -0.924   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.719  -0.076   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.141   2.271   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.406   2.042   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.167  -1.660   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.920  -2.095   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.824  -1.159   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.745   0.674   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.062   2.127   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.601   2.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    2   17   21                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   16   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   25   20   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
Rhabdastrellate a	Generator

Chemical Formula

C₃₀H₄₀O₄

Average Mass

464.6460 Da

Monoisotopic Mass

464.29266 Da

IUPAC Name

(2E,4E,6E,8E)-10-[(3Z,3aS,9aR,9bS)-3a,6,6,9a-tetramethyl-2,7-dioxo-dodecahydro-1H-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid

Traditional Name

(2E,4E,6E,8E)-10-[(3Z,3aS,9aR,9bS)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1H-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C=C(/C)C(O)=O)=C/C=C/C(/C)=C1\C(=O)C[C@@H]2[C@]1(C)CCC1C(C)(C)C(=O)CC[C@]21C

InChI Identifier

InChI=1S/C30H40O4/c1-19(11-9-13-21(3)27(33)34)10-8-12-20(2)26-22(31)18-24-29(6)17-15-25(32)28(4,5)23(29)14-16-30(24,26)7/h8-13,23-24H,14-18H2,1-7H3,(H,33,34)/b11-9+,12-8+,19-10+,21-13+,26-20+/t23?,24-,29-,30-/m0/s1

InChI Key

IIPLLKSCMYHUOP-HYCGKRAFSA-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
Rhabdastrella globostellata	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
Medium-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic ketone
Ketone
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	6.43	ChemAxon
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	141.2 m³·mol⁻¹	ChemAxon
Polarizability	55.2 Å³	ChemAxon
Number of Rings	3	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

9928905

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11754202

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huck CJ, Boyko YD, Sarlah D: Total Synthesis of Stelletins through an Unconventional Annulation Strategy. Acc Chem Res. 2021 Apr 6;54(7):1597-1609. doi: 10.1021/acs.accounts.0c00840. Epub 2021 Feb 26. [PubMed:33635622 ]
Boyko YD, Huck CJ, Ning S, Shved AS, Yang C, Chu T, Tonogai EJ, Hergenrother PJ, Sarlah D: Synthetic Studies on Selective, Proapoptotic Isomalabaricane Triterpenoids Aided by Computational Techniques. J Am Chem Soc. 2021 Feb 3;143(4):2138-2155. doi: 10.1021/jacs.0c12569. Epub 2021 Jan 19. [PubMed:33464048 ]
Boyko YD, Huck CJ, Sarlah D: Total Synthesis of Isomalabaricane Triterpenoids. J Am Chem Soc. 2019 Sep 11;141(36):14131-14135. doi: 10.1021/jacs.9b08487. Epub 2019 Aug 28. [PubMed:31448913 ]
LOTUS database [Link]

Showing NP-Card for (2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid (NP0291729)

MOL for NP0291729 ((2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid)

3D MOL for NP0291729 ((2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid)

3D SDF for NP0291729 ((2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid)

3D-SDF for NP0291729 ((2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid)

PDB for NP0291729 ((2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid)

3D PDB for NP0291729 ((2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid)

SMILES for NP0291729 ((2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid)

INCHI for NP0291729 ((2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid)

Structure for NP0291729 ((2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid)

3D Structure for NP0291729 ((2e,4e,6e,8e)-10-[(3z,3as,9ar,9bs)-3a,6,6,9a-tetramethyl-2,7-dioxo-hexahydro-1h-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid)