NP-MRD: Showing NP-Card for 4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one (NP0269115)

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Record Information

Version

2.0

Created at

2022-09-08 14:27:00 UTC

Updated at

2022-09-08 14:27:01 UTC

NP-MRD ID

NP0269115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one

Description

Cacospongionolide B belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one is found in Fasciospongia cavernosa. 4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one was first documented in 2002 (PMID: 12296709). Based on a literature review a significant number of articles have been published on cacospongionolide B (PMID: 33224302) (PMID: 17315974) (PMID: 17117584) (PMID: 15307744) (PMID: 12721113).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082216272D          

 29 32  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309082216272D          

 29 32  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0269115

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@]2(C)[C@@H](CCCC2=C)[C@]1(C)CCC1=CCC(OC1)C1=CC(=O)OC1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O4/c1-16-6-5-7-21-24(16,3)12-10-17(2)25(21,4)13-11-18-8-9-20(28-15-18)19-14-22(26)29-23(19)27/h8,14,17,20-21,23,27H,1,5-7,9-13,15H2,2-4H3/t17-,20?,21-,23?,24-,25-/m1/s1

> <INCHI_KEY>
CVAZWHZRZNYCOV-ILKJNQADSA-N

> <FORMULA>
C25H36O4

> <MOLECULAR_WEIGHT>
400.559

> <EXACT_MASS>
400.261359639

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.316483752866816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(5-{2-[(1R,2R,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-3,6-dihydro-2H-pyran-2-yl)-5-hydroxy-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
5.0422299676666675

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.731975996757972

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.488879736325379

> <JCHEM_PKA_STRONGEST_BASIC>
-4.205785291637656

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
114.81629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-(5-{2-[(1R,2R,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]ethyl}-3,6-dihydro-2H-pyran-2-yl)-5-hydroxy-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.037  -7.105   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.854  -8.411   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.131  -9.771   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.591  -9.825   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.131 -11.185   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.544 -12.569   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.564 -13.639   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.350 -15.164   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.924 -12.916   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.657 -11.399   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.726 -10.291   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.225  -8.519   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.498  -7.159   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28   20   29                                                       
CONECT   29   28   17                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₄

Average Mass

400.5590 Da

Monoisotopic Mass

400.26136 Da

IUPAC Name

4-(5-{2-[(1R,2R,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-3,6-dihydro-2H-pyran-2-yl)-5-hydroxy-2,5-dihydrofuran-2-one

Traditional Name

4-(5-{2-[(1R,2R,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]ethyl}-3,6-dihydro-2H-pyran-2-yl)-5-hydroxy-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@]2(C)[C@@H](CCCC2=C)[C@]1(C)CCC1=CCC(OC1)C1=CC(=O)OC1O

InChI Identifier

InChI=1S/C25H36O4/c1-16-6-5-7-21-24(16,3)12-10-17(2)25(21,4)13-11-18-8-9-20(28-15-18)19-14-22(26)29-23(19)27/h8,14,17,20-21,23,27H,1,5-7,9-13,15H2,2-4H3/t17-,20?,21-,23?,24-,25-/m1/s1

InChI Key

CVAZWHZRZNYCOV-ILKJNQADSA-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
Fasciospongia cavernosa	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

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
2-furanone
Pyran
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Ether
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	5.04	ChemAxon
pKa (Strongest Acidic)	5.49	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.82 m³·mol⁻¹	ChemAxon
Polarizability	46.32 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

8561727

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10386285

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kolarikova V, Rybackova M, Svoboda M, Kvicala J: Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans. Beilstein J Org Chem. 2020 Nov 13;16:2757-2768. doi: 10.3762/bjoc.16.226. eCollection 2020. [PubMed:33224302 ]
Murelli RP, Cheung AK, Snapper ML: Conformationally restricted (+)-cacospongionolide B analogues. Influence on secretory phospholipase A2 inhibition. J Org Chem. 2007 Mar 2;72(5):1545-52. doi: 10.1021/jo061407a. [PubMed:17315974 ]
Alcaraz MJ, Paya M: Marine sponge metabolites for the control of inflammatory diseases. Curr Opin Investig Drugs. 2006 Nov;7(11):974-9. [PubMed:17117584 ]
Cheung AK, Murelli R, Snapper ML: Total syntheses of (+)- and (-)-cacospongionolide B, cacospongionolide e, and related analogues. Preliminary study of structural features required for phospholipase a2 inhibition. J Org Chem. 2004 Aug 20;69(17):5712-9. doi: 10.1021/jo049285e. [PubMed:15307744 ]
Posadas I, De Rosa S, Terencio MC, Paya M, Alcaraz MJ: Cacospongionolide B suppresses the expression of inflammatory enzymes and tumour necrosis factor-alpha by inhibiting nuclear factor-kappa B activation. Br J Pharmacol. 2003 Apr;138(8):1571-9. doi: 10.1038/sj.bjp.0705189. [PubMed:12721113 ]
Cheung AK, Snapper ML: Total syntheses of (+)- and (-)-cacospongionolide B: new insight into structural requirements for phospholipase A(2) inhibition. J Am Chem Soc. 2002 Oct 2;124(39):11584-5. doi: 10.1021/ja026899x. [PubMed:12296709 ]
LOTUS database [Link]

Showing NP-Card for 4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one (NP0269115)

MOL for NP0269115 (4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one)

3D MOL for NP0269115 (4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one)

3D SDF for NP0269115 (4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one)

3D-SDF for NP0269115 (4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one)

PDB for NP0269115 (4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one)

3D PDB for NP0269115 (4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one)

SMILES for NP0269115 (4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one)

INCHI for NP0269115 (4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one)

Structure for NP0269115 (4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one)

3D Structure for NP0269115 (4-(5-{2-[(1r,2r,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-3,6-dihydro-2h-pyran-2-yl)-5-hydroxy-5h-furan-2-one)