NP-MRD: Showing NP-Card for Manoalide (NP0076839)

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Record Information

Version

2.0

Created at

2022-04-28 22:01:40 UTC

Updated at

2022-04-28 22:01:40 UTC

NP-MRD ID

NP0076839

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Manoalide

Description

Manoalide belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Manoalide is found in Fasciospongia cavernosa, Hyrtios erectus, Luffariaella variabilis, Luffariella sp. and Luffariella variabilis. Manoalide was first documented in 2018 (PMID: 30487463). Based on a literature review a significant number of articles have been published on manoalide (PMID: 35252186) (PMID: 34708672) (PMID: 34328853) (PMID: 33966383) (PMID: 33747349) (PMID: 33371684).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200012D          

 30 32  0  0  1  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -7.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -8.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -9.3620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -8.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -7.9099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4521   -7.6550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -2.4750    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


  Mrv1652304292200012D          

 30 32  0  0  1  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0076839

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CCC1=C(C)CCCC1(C)C)=C/CCC1=CC[C@@H](O[C@H]1O)C1=CC(=O)O[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3/b16-7+/t21-,23-,24-/m1/s1

> <INCHI_KEY>
FGJIDQWRRLDGDB-CPIXEKRISA-N

> <FORMULA>
C25H36O5

> <MOLECULAR_WEIGHT>
416.558

> <EXACT_MASS>
416.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.20356460510826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-5-hydroxy-4-[(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
4.60

> <JCHEM_LOGP>
4.9366320660000005

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.482109871728778

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.449862062678549

> <JCHEM_PKA_STRONGEST_BASIC>
-4.181379152188392

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
119.48259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
manoalide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.246 -14.765   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.770 -16.230   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.675 -17.476   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.770 -16.230   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.246 -14.765   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.711 -14.289   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.206  -0.054   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.483  -1.306   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    1   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   22                                                            
CONECT   30   18                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₅

Average Mass

416.5580 Da

Monoisotopic Mass

416.25627 Da

IUPAC Name

(5R)-5-hydroxy-4-[(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-2,5-dihydrofuran-2-one

Traditional Name

manoalide

CAS Registry Number

Not Available

SMILES

C\C(CCC1=C(C)CCCC1(C)C)=C/CCC1=CC[C@@H](O[C@H]1O)C1=CC(=O)O[C@H]1O

InChI Identifier

InChI=1S/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3/b16-7+/t21-,23-,24-/m1/s1

InChI Key

FGJIDQWRRLDGDB-CPIXEKRISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Hyrtios erectus	LOTUS Database	35616633
Luffariaella variabilis	-	KNApSAcK
Luffariella sp.	-	KNApSAcK
Luffariella variabilis	-	KNApSAcK

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
2-furanone
Pyran
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butenolide (CHEBI:66666 )
lactol (CHEBI:66666 )
sesterterpenoid (CHEBI:66666 )

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	4.6	ALOGPS
logP	4.94	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5.45	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	119.48 m³·mol⁻¹	ChemAxon
Polarizability	47.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00039732

Chemspider ID

4941932

KEGG Compound ID

C17156

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Manoalide

METLIN ID

Not Available

PubChem Compound

6437368

PDB ID

Not Available

ChEBI ID

66666

Good Scents ID

rw1524661

References

General References

Li C, Lin H, He H, Ma M, Jiang W, Zhou R: Inhibition of the NLRP3 Inflammasome Activation by Manoalide Ameliorates Experimental Autoimmune Encephalomyelitis Pathogenesis. Front Cell Dev Biol. 2022 Feb 16;10:822236. doi: 10.3389/fcell.2022.822236. eCollection 2022. [PubMed:35252186 ]
Yeom JH, Kim HY, Lim JH, Yoon KW, Kim HM, Jeong HJ: A calcium channel blocker, manoalide exerts an anti-allergic inflammatory effect through attenuating NF-kappaB activity. Immunopharmacol Immunotoxicol. 2021 Dec;43(6):799-805. doi: 10.1080/08923973.2021.1988101. Epub 2021 Oct 28. [PubMed:34708672 ]
Lai KH, Peng BR, Hsu YM, El-Shazly M, Du YC, Lu MC, Su JH, Liu YC: The Configuration-Dependent Anti-Leukemic Effect of Manoalide Stereoisomers: Reignite Research Interest in these Sponge-Derived Sesterterpenoids. Bioorg Chem. 2021 Sep;114:105150. doi: 10.1016/j.bioorg.2021.105150. Epub 2021 Jul 7. [PubMed:34328853 ]
Kanki D, Imai K, Ise Y, Okada S, Matsunaga S: Oshimalides A and B, Sesterterpenes of the Manoalide Class from a Luffariella sp. Deep-Sea Marine Sponge: Application of Asymmetric Dihydroxylation in Structure Elucidation. J Nat Prod. 2021 May 28;84(5):1676-1680. doi: 10.1021/acs.jnatprod.1c00320. Epub 2021 May 9. [PubMed:33966383 ]
Wang HR, Chen PH, Tang JY, Yen CY, Su YC, Huang MY, Chang HW: Manoalide Shows Mutual Interaction between Cellular and Mitochondrial Reactive Species with Apoptosis in Oral Cancer Cells. Oxid Med Cell Longev. 2021 Mar 2;2021:6667355. doi: 10.1155/2021/6667355. eCollection 2021. [PubMed:33747349 ]
Kaweetripob W, Mahidol C, Tuntiwachwuttikul P, Ruchirawat S, Prawat H: Cytotoxic Sesterterpenes from Thai Marine Sponge Hyrtios erectus. Mar Drugs. 2018 Nov 28;16(12). pii: md16120474. doi: 10.3390/md16120474. [PubMed:30487463 ]
Luo X, Wang Q, Tang X, Xu J, Wang M, Li P, Li G: Cytotoxic Manoalide-Type Sesterterpenes from the Sponge Luffariella variabilis Collected in the South China Sea. J Nat Prod. 2021 Jan 22;84(1):61-70. doi: 10.1021/acs.jnatprod.0c01026. Epub 2020 Dec 28. [PubMed:33371684 ]
Wang HR, Tang JY, Wang YY, Farooqi AA, Yen CY, Yuan SF, Huang HW, Chang HW: Manoalide Preferentially Provides Antiproliferation of Oral Cancer Cells by Oxidative Stress-Mediated Apoptosis and DNA Damage. Cancers (Basel). 2019 Sep 4;11(9). pii: cancers11091303. doi: 10.3390/cancers11091303. [PubMed:31487907 ]
Zhang X, Li PL, Qin GF, Li S, de Voogd NJ, Tang XL, Li GQ: Isolation and Absolute Configurations of Diversiform C17, C21 and C25 Terpenoids from the Marine Sponge Cacospongia sp. Mar Drugs. 2018 Dec 28;17(1). pii: md17010014. doi: 10.3390/md17010014. [PubMed:30597876 ]
Wang Y, Sherchan P, Huang L, Akyol O, McBride DW, Zhang JH: Multiple mechanisms underlying neuroprotection by secretory phospholipase A2 preconditioning in a surgically induced brain injury rat model. Exp Neurol. 2018 Feb;300:30-40. doi: 10.1016/j.expneurol.2017.10.022. Epub 2017 Oct 24. [PubMed:29074417 ]

Showing NP-Card for Manoalide (NP0076839)

MOL for NP0076839 (Manoalide)

3D MOL for NP0076839 (Manoalide)

3D SDF for NP0076839 (Manoalide)

3D-SDF for NP0076839 (Manoalide)

PDB for NP0076839 (Manoalide)

3D PDB for NP0076839 (Manoalide)

SMILES for NP0076839 (Manoalide)

INCHI for NP0076839 (Manoalide)

Structure for NP0076839 (Manoalide)

3D Structure for NP0076839 (Manoalide)