NP-MRD: Showing NP-Card for (1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one (NP0170280)

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Record Information

Version

2.0

Created at

2022-09-03 06:24:53 UTC

Updated at

2022-09-03 06:24:53 UTC

NP-MRD ID

NP0170280

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one

Description

Swinhosterol B belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. (1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one is found in Theonella swinhoei. (1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one was first documented in 2012 (PMID: 22285937). Based on a literature review very few articles have been published on Swinhosterol B (PMID: 27548191).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032208242D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032208242D          

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  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9  2  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0170280

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O3/c1-18(2)19(3)8-9-20(4)22-11-13-27(32)29(22,7)16-14-24-26(31)12-10-23-21(5)25(30)15-17-28(23,24)6/h18-20,22-25,30H,5,8-17H2,1-4,6-7H3/t19-,20-,22-,23+,24+,25+,28+,29-/m1/s1

> <INCHI_KEY>
OAXZFWYEXPJYGH-OSZKIZGISA-N

> <FORMULA>
C29H48O3

> <MOLECULAR_WEIGHT>
444.7

> <EXACT_MASS>
444.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.1273750031144

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4aR,6S,8aS)-1-{2-[(1R,2R)-2-[(2R,5R)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-decahydronaphthalen-2-one

> <ALOGPS_LOGP>
5.31

> <JCHEM_LOGP>
7.089059489

> <ALOGPS_LOGS>
-6.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.615228408593584

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.095852263050514

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4446733581341493

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
131.75469999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.09e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aR,6S,8aS)-1-{2-[(1R,2R)-2-[(2R,5R)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1H-naphthalen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.491 -11.556   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.245 -10.651   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.162 -11.277   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.323 -12.809   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.408 -10.372   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.247  -8.840   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.160  -8.214   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.086  -7.309   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.406  -9.119   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.813  -8.493   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.974  -6.961   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.728  -6.056   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.889  -4.524   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.321  -6.682   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.925  -5.777   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.332  -6.404   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.578  -5.498   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.348  -6.832   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.547  -4.354   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.016  -4.515   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.317  -3.020   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.824  -3.340   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.985  -4.872   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.318  -5.642   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.318  -7.182   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.652  -4.872   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.986  -5.642   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.319  -4.872   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.319  -3.332   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.653  -5.642   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.987  -4.872   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.653  -7.182   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   14                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₈O₃

Average Mass

444.7000 Da

Monoisotopic Mass

444.36035 Da

IUPAC Name

(1R,4aR,6S,8aS)-1-{2-[(1R,2R)-2-[(2R,5R)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-decahydronaphthalen-2-one

Traditional Name

(1R,4aR,6S,8aS)-1-{2-[(1R,2R)-2-[(2R,5R)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1H-naphthalen-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H48O3/c1-18(2)19(3)8-9-20(4)22-11-13-27(32)29(22,7)16-14-24-26(31)12-10-23-21(5)25(30)15-17-28(23,24)6/h18-20,22-25,30H,5,8-17H2,1-4,6-7H3/t19-,20-,22-,23+,24+,25+,28+,29-/m1/s1

InChI Key

OAXZFWYEXPJYGH-OSZKIZGISA-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
Theonella swinhoei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
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	5.31	ALOGPS
logP	7.09	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.1	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	131.75 m³·mol⁻¹	ChemAxon
Polarizability	54.13 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

C00050241

Chemspider ID

8869964

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10694619

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abou-Hussein DR, Youssef DT: Mirabolides A and B; New Cytotoxic Glycerides from the Red Sea Sponge Theonella mirabilis. Mar Drugs. 2016 Aug 18;14(8):155. doi: 10.3390/md14080155. [PubMed:27548191 ]
De Marino S, Ummarino R, D'Auria MV, Chini MG, Bifulco G, D'Amore C, Renga B, Mencarelli A, Petek S, Fiorucci S, Zampella A: 4-Methylenesterols from Theonella swinhoei sponge are natural pregnane-X-receptor agonists and farnesoid-X-receptor antagonists that modulate innate immunity. Steroids. 2012 Apr;77(5):484-95. doi: 10.1016/j.steroids.2012.01.006. Epub 2012 Jan 20. [PubMed:22285937 ]
LOTUS database [Link]

Showing NP-Card for (1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one (NP0170280)

MOL for NP0170280 ((1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one)

3D MOL for NP0170280 ((1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one)

3D SDF for NP0170280 ((1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one)

3D-SDF for NP0170280 ((1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one)

PDB for NP0170280 ((1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one)

3D PDB for NP0170280 ((1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one)

SMILES for NP0170280 ((1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one)

INCHI for NP0170280 ((1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one)

Structure for NP0170280 ((1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one)

3D Structure for NP0170280 ((1r,4ar,6s,8as)-1-{2-[(1r,2r)-2-[(2r,5r)-5,6-dimethylheptan-2-yl]-1-methyl-5-oxocyclopentyl]ethyl}-6-hydroxy-8a-methyl-5-methylidene-hexahydro-1h-naphthalen-2-one)