NP-MRD: Showing NP-Card for scalaradial (NP0288272)

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Record Information

Version

2.0

Created at

2022-09-09 17:54:18 UTC

Updated at

2022-09-09 17:54:18 UTC

NP-MRD ID

NP0288272

Secondary Accession Numbers

None

Natural Product Identification

Common Name

scalaradial

Description

Scalaradial belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. scalaradial is found in Cacospongia mollior, Glossodoris rufomarginata, Hyrtios erectus, Scalarispongia scalaris and Spongia officinalis. scalaradial was first documented in 2014 (PMID: 24769547). Based on a literature review a small amount of articles have been published on scalaradial (PMID: 29019677) (PMID: 33665446) (PMID: 32708154) (PMID: 26784155).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092219542D          

 31 34  0  0  1  0            999 V2000
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    2.0647    3.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    3.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6850    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4149    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731   -0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -1.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  8 16  1  0  0  0  0
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M  END

     RDKit          3D

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    3.3194   -1.9053   -2.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2173   -1.4270   -1.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309092219542D          

 31 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0288272

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]2(C)[C@@H]2CC=C(C=O)[C@H](C=O)[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O4/c1-17(30)31-23-14-22-25(4)12-7-11-24(2,3)20(25)10-13-26(22,5)21-9-8-18(15-28)19(16-29)27(21,23)6/h8,15-16,19-23H,7,9-14H2,1-6H3/t19-,20-,21-,22+,23-,25-,26-,27+/m0/s1

> <INCHI_KEY>
ADWFEADZGIHPDE-QGERINELSA-N

> <FORMULA>
C27H40O4

> <MOLECULAR_WEIGHT>
428.613

> <EXACT_MASS>
428.292659768

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.19337056774706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,4bR,6S,6aS,7R,10aS,10bR,12aS)-7,8-diformyl-1,1,4a,6a,10b-pentamethyl-1,2,3,4,4a,4b,5,6,6a,7,10,10a,10b,11,12,12a-hexadecahydrochrysen-6-yl acetate

> <JCHEM_LOGP>
4.341926992333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.998697558856549

> <JCHEM_PKA_STRONGEST_BASIC>
-4.975827384169709

> <JCHEM_POLAR_SURFACE_AREA>
60.440000000000005

> <JCHEM_REFRACTIVITY>
121.71789999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,4bR,6S,6aS,7R,10aS,10bR,12aS)-7,8-diformyl-1,1,4a,6a,10b-pentamethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       5.366   5.427   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.854   5.718   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.350   7.173   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.846   4.553   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.375   2.516   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.216  -1.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.346  -2.124   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.375  -1.558   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.350  -0.976   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.691   1.352   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.699   0.188   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.326   3.680   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334   4.844   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.838   3.389   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    7   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27    5   21   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
(+)-Scalaradial	ChEBI
12-(Acetyloxy)-4,4,8-trimethylhomoandrost-16-ene-17,17a-dicarboxaldehyde	MeSH

Chemical Formula

C₂₇H₄₀O₄

Average Mass

428.6130 Da

Monoisotopic Mass

428.29266 Da

IUPAC Name

(4aS,4bR,6S,6aS,7R,10aS,10bR,12aS)-7,8-diformyl-1,1,4a,6a,10b-pentamethyl-1,2,3,4,4a,4b,5,6,6a,7,10,10a,10b,11,12,12a-hexadecahydrochrysen-6-yl acetate

Traditional Name

(4aS,4bR,6S,6aS,7R,10aS,10bR,12aS)-7,8-diformyl-1,1,4a,6a,10b-pentamethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-6-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]2(C)[C@@H]2CC=C(C=O)[C@H](C=O)[C@@]12C

InChI Identifier

InChI=1S/C27H40O4/c1-17(30)31-23-14-22-25(4)12-7-11-24(2,3)20(25)10-13-26(22,5)21-9-8-18(15-28)19(16-29)27(21,23)6/h8,15-16,19-23H,7,9-14H2,1-6H3/t19-,20-,21-,22+,23-,25-,26-,27+/m0/s1

InChI Key

ADWFEADZGIHPDE-QGERINELSA-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
Cacospongia mollior	LOTUS Database	35616633
Glossodoris rufomarginata	LOTUS Database	35616633
Hyrtios erectus	LOTUS Database	35616633
Scalarispongia scalaris	LOTUS Database	35616633
Spongia officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Steroid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

scalarane sesterterpenoid (CHEBI:67731 )

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	4.34	ChemAxon
pKa (Strongest Acidic)	14	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.72 m³·mol⁻¹	ChemAxon
Polarizability	49.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00043907

Chemspider ID

10272825

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21637538

PDB ID

Not Available

ChEBI ID

67731

Good Scents ID

Not Available

References

General References

Starkus JG, Poerzgen P, Layugan K, Kawabata KG, Goto JI, Suzuki S, Myers G, Kelly M, Penner R, Fleig A, Horgen FD: Scalaradial Is a Potent Inhibitor of Transient Receptor Potential Melastatin 2 (TRPM2) Ion Channels. J Nat Prod. 2017 Oct 27;80(10):2741-2750. doi: 10.1021/acs.jnatprod.7b00515. Epub 2017 Oct 11. [PubMed:29019677 ]
Lutfia A, Munir E, Yurnaliza Y, Basyuni M: Chemical analysis and anticancer activity of sesterterpenoid from an endophytic fungus Hypomontagnella monticulosa Zg15SU and its host Zingiber griffithii Baker. Heliyon. 2021 Feb 16;7(2):e06292. doi: 10.1016/j.heliyon.2021.e06292. eCollection 2021 Feb. [PubMed:33665446 ]
Zhou M, Peng BR, Tian W, Su JH, Wang G, Lin T, Zeng D, Sheu JH, Chen H: 12-Deacetyl-12-epi-Scalaradial, a Scalarane Sesterterpenoid from a Marine Sponge Hippospongia sp., Induces HeLa Cells Apoptosis via MAPK/ERK Pathway and Modulates Nuclear Receptor Nur77. Mar Drugs. 2020 Jul 21;18(7):375. doi: 10.3390/md18070375. [PubMed:32708154 ]
Elhady SS, El-Halawany AM, Alahdal AM, Hassanean HA, Ahmed SA: A New Bioactive Metabolite Isolated from the Red Sea Marine Sponge Hyrtios erectus. Molecules. 2016 Jan 15;21(1):82. doi: 10.3390/molecules21010082. [PubMed:26784155 ]
Cassiano C, Margarucci L, Esposito R, Riccio R, Tosco A, Casapullo A, Monti MC: In cell scalaradial interactome profiling using a bio-orthogonal clickable probe. Chem Commun (Camb). 2014 Jun 7;50(45):6043-5. doi: 10.1039/c4cc00989d. Epub 2014 Apr 28. [PubMed:24769547 ]
LOTUS database [Link]

Showing NP-Card for scalaradial (NP0288272)

MOL for NP0288272 (scalaradial)

3D MOL for NP0288272 (scalaradial)

3D SDF for NP0288272 (scalaradial)

3D-SDF for NP0288272 (scalaradial)

PDB for NP0288272 (scalaradial)

3D PDB for NP0288272 (scalaradial)

SMILES for NP0288272 (scalaradial)

INCHI for NP0288272 (scalaradial)

Structure for NP0288272 (scalaradial)

3D Structure for NP0288272 (scalaradial)