NP-MRD: Showing NP-Card for Scutalsin (NP0081179)

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Record Information

Version

2.0

Created at

2022-04-29 02:08:48 UTC

Updated at

2022-04-29 02:08:48 UTC

NP-MRD ID

NP0081179

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Scutalsin

Description

(2R,15S,18R)-14,15-Dihydro-2alpha,18-epoxy-15-hydroxy-18-O-(2-methylpropanoyl)-18-O-deacetyl-3-deoxycaryoptinol belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Scutalsin is found in Scutellaria polyodon. Based on a literature review very few articles have been published on (2R,15S,18R)-14,15-Dihydro-2alpha,18-epoxy-15-hydroxy-18-O-(2-methylpropanoyl)-18-O-deacetyl-3-deoxycaryoptinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204082D          

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M  END

     RDKit          3D

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M  END


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 18 23  1  0  0  0  0
 22 24  1  1  0  0  0
  7 25  1  6  0  0  0
  4 26  1  0  0  0  0
 26 27  1  0  0  0  0
  1 27  1  6  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081179

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@H]1O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4C[C@H]5C[C@@H](O)O[C@H]5O4)[C@H](C)C[C@H](OC(C)=O)[C@]13[C@@]1(CO1)C2

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O9/c1-12(2)21(29)35-23-26-17(9-16(32-23)10-25(26)11-30-25)24(5,13(3)6-19(26)31-14(4)27)18-7-15-8-20(28)34-22(15)33-18/h12-13,15-20,22-23,28H,6-11H2,1-5H3/t13-,15+,16-,17-,18+,19+,20+,22-,23-,24+,25+,26+/m1/s1

> <INCHI_KEY>
BKNXMAVBDJZREO-MSBZVKQZSA-N

> <FORMULA>
C26H38O9

> <MOLECULAR_WEIGHT>
494.581

> <EXACT_MASS>
494.251582804

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.03010004622307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,2'S,4'R,5'S,6'R,8'R,11'R)-5'-[(2S,3aS,5S,6aR)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-2'-(acetyloxy)-4',5'-dimethyl-12'-oxaspiro[oxirane-2,10'-tricyclo[6.2.2.0^{1,6}]dodecane]-11'-yl 2-methylpropanoate

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
2.248697317999998

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.39171063174857

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7386005606606676

> <JCHEM_POLAR_SURFACE_AREA>
113.05000000000001

> <JCHEM_REFRACTIVITY>
119.73169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'S,4'R,5'S,6'R,8'R,11'R)-5'-[(2S,3aS,5S,6aR)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-2'-(acetyloxy)-4',5'-dimethyl-12'-oxaspiro[oxirane-2,10'-tricyclo[6.2.2.0^{1,6}]dodecane]-11'-yl 2-methylpropanoate

> <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       6.261  -3.872   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.309  -2.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.971  -0.797   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.245  -0.344   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.158  -1.688   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.584  -3.361   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.588  -1.424   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.861  -0.013   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.815   1.251   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.341   0.986   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.175   2.280   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.472   3.650   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.934   3.726   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.307   4.944   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.327   0.119   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.211  -2.114   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.961  -3.634   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.562  -3.865   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.252  -2.489   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.157  -1.407   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.775  -2.720   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.025  -4.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.658  -4.947   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.402  -4.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.348  -2.945   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.109  -1.466   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.604  -2.720   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       7.635  -1.256   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.579  -2.473   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.998  -3.899   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.105  -2.263   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.686  -0.836   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.049  -3.479   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.455   0.665   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.479  -0.484   0.000  0.00  0.00           O+0
CONECT    1    2    6   27                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   34   35                                             
CONECT    4    3    5   10   26                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   16   25                                             
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8                                                            
CONECT   16    7   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   16                                                       
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22                                                            
CONECT   25    7                                                            
CONECT   26    4   27   28                                                  
CONECT   27   26    1                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    3   35                                                       
CONECT   35   34    3                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
(2R,15S,18R)-14,15-Dihydro-2a,18-epoxy-15-hydroxy-18-O-(2-methylpropanoyl)-18-O-deacetyl-3-deoxycaryoptinol	Generator
(2R,15S,18R)-14,15-Dihydro-2α,18-epoxy-15-hydroxy-18-O-(2-methylpropanoyl)-18-O-deacetyl-3-deoxycaryoptinol	Generator

Chemical Formula

C₂₆H₃₈O₉

Average Mass

494.5810 Da

Monoisotopic Mass

494.25158 Da

IUPAC Name

(1'R,2R,2'S,4'R,5'S,6'R,8'R,11'R)-5'-[(2S,3aS,5S,6aR)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-2'-(acetyloxy)-4',5'-dimethyl-12'-oxaspiro[oxirane-2,10'-tricyclo[6.2.2.0^{1,6}]dodecane]-11'-yl 2-methylpropanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@H]1O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4C[C@H]5C[C@@H](O)O[C@H]5O4)[C@H](C)C[C@H](OC(C)=O)[C@]13[C@@]1(CO1)C2

InChI Identifier

InChI=1S/C26H38O9/c1-12(2)21(29)35-23-26-17(9-16(32-23)10-25(26)11-30-25)24(5,13(3)6-19(26)31-14(4)27)18-7-15-8-20(28)34-22(15)33-18/h12-13,15-20,22-23,28H,6-11H2,1-5H3/t13-,15+,16-,17-,18+,19+,20+,22-,23-,24+,25+,26+/m1/s1

InChI Key

BKNXMAVBDJZREO-MSBZVKQZSA-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
Scutellaria polyodon	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
Oxane
Dicarboxylic acid or derivatives
Tetrahydrofuran
Hemiacetal
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
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	1.81	ALOGPS
logP	2.25	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.39	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	113.05 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.73 m³·mol⁻¹	ChemAxon
Polarizability	52.03 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101992372

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Scutalsin (NP0081179)

MOL for NP0081179 (Scutalsin)

3D MOL for NP0081179 (Scutalsin)

3D SDF for NP0081179 (Scutalsin)

3D-SDF for NP0081179 (Scutalsin)

PDB for NP0081179 (Scutalsin)

3D PDB for NP0081179 (Scutalsin)

SMILES for NP0081179 (Scutalsin)

INCHI for NP0081179 (Scutalsin)

Structure for NP0081179 (Scutalsin)

3D Structure for NP0081179 (Scutalsin)