NP-MRD: Showing NP-Card for (1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate (NP0247181)

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Record Information

Version

2.0

Created at

2022-09-07 08:55:36 UTC

Updated at

2022-09-07 08:55:36 UTC

NP-MRD ID

NP0247181

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate

Description

Cladocoran A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate is found in Cladocora caespitosa. (1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate was first documented in 2003 (PMID: 12713348). Based on a literature review a small amount of articles have been published on Cladocoran A (PMID: 21953776) (PMID: 12968906).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072210552D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072210552D          

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M  END
> <DATABASE_ID>
NP0247181

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@H]2C(=CCC[C@@]2(C)CCCC(C)=C)[C@]1(C)C[C@@H](OC(C)=O)C1=CC(=O)OC1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O5/c1-17(2)9-7-13-26(5)14-8-10-22-21(26)12-11-18(3)27(22,6)16-23(31-19(4)28)20-15-24(29)32-25(20)30/h10,15,18,21,23,25,30H,1,7-9,11-14,16H2,2-6H3/t18-,21-,23-,25?,26-,27-/m1/s1

> <INCHI_KEY>
LUZPPGGVQBQOEH-UMUHMQMUSA-N

> <FORMULA>
C27H40O5

> <MOLECULAR_WEIGHT>
444.612

> <EXACT_MASS>
444.287574388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.10458279407866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-2-[(1R,2R,4aS,5R)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)ethyl acetate

> <JCHEM_LOGP>
5.602422962333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.731356919351496

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.403165323982756

> <JCHEM_PKA_STRONGEST_BASIC>
-4.303387498546837

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
125.70319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-2-[(1R,2R,4aS,5R)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2H-furan-3-yl)ethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.724   7.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.868   6.059   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.333   6.535   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.548   4.553   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.083   4.077   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.763   2.571   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.298   2.095   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.084   3.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.021   0.735   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.205  -0.571   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.517   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.057   0.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.241   2.149   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.964   3.509   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.503   3.562   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.319   2.256   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.858   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.596   0.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.703  -0.640   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.929   0.127   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.929  -1.413   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.263  -2.183   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.597  -1.413   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.597   0.127   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.930  -2.183   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.596  -2.183   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.189  -1.557   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.158  -2.702   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.373  -2.541   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.928  -4.035   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.435  -3.715   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.579  -4.746   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   13                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   26   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₅

Average Mass

444.6120 Da

Monoisotopic Mass

444.28757 Da

IUPAC Name

(1R)-2-[(1R,2R,4aS,5R)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)ethyl acetate

Traditional Name

(1R)-2-[(1R,2R,4aS,5R)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2H-furan-3-yl)ethyl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@H]2C(=CCC[C@@]2(C)CCCC(C)=C)[C@]1(C)C[C@@H](OC(C)=O)C1=CC(=O)OC1O

InChI Identifier

InChI=1S/C27H40O5/c1-17(2)9-7-13-26(5)14-8-10-22-21(26)12-11-18(3)27(22,6)16-23(31-19(4)28)20-15-24(29)32-25(20)30/h10,15,18,21,23,25,30H,1,7-9,11-14,16H2,2-6H3/t18-,21-,23-,25?,26-,27-/m1/s1

InChI Key

LUZPPGGVQBQOEH-UMUHMQMUSA-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
Cladocora caespitosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Clerodane diterpenoid
Diterpenoid
Diterpene lactone
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.6	ChemAxon
pKa (Strongest Acidic)	5.4	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	125.7 m³·mol⁻¹	ChemAxon
Polarizability	50.1 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	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

9092510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10917258

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Miyaoka H, Yamanishi M, Kajiwara Y, Yamada Y: Total synthesis of cladocorans A and B: a structural revision. J Org Chem. 2003 May 2;68(9):3476-9. doi: 10.1021/jo020743y. [PubMed:12713348 ]
Monti MC, Chini MG, Margarucci L, Riccio R, Bifulco G, Casapullo A: The binding mode of cladocoran A to the human group IIA phospholipase A(2). Chembiochem. 2011 Nov 25;12(17):2686-91. doi: 10.1002/cbic.201100478. Epub 2011 Sep 27. [PubMed:21953776 ]
Marcos IS, Pedrero AB, Sexmero MJ, Diez D, Basabe P, Garcia N, Moro RF, Broughton HB, Mollinedo F, Urones JG: Synthesis of bioactive sesterterpenolides from ent-halimic acid. 15-epi-ent-Cladocoran A and B. J Org Chem. 2003 Sep 19;68(19):7496-504. doi: 10.1021/jo034663l. [PubMed:12968906 ]
LOTUS database [Link]

Showing NP-Card for (1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate (NP0247181)

MOL for NP0247181 ((1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate)

3D MOL for NP0247181 ((1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate)

3D SDF for NP0247181 ((1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate)

3D-SDF for NP0247181 ((1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate)

PDB for NP0247181 ((1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate)

3D PDB for NP0247181 ((1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate)

SMILES for NP0247181 ((1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate)

INCHI for NP0247181 ((1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate)

Structure for NP0247181 ((1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate)

3D Structure for NP0247181 ((1r)-2-[(1r,2r,4as,5r)-1,2,5-trimethyl-5-(4-methylpent-4-en-1-yl)-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]-1-(2-hydroxy-5-oxo-2h-furan-3-yl)ethyl acetate)