NP-MRD: Showing NP-Card for (5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one (NP0249820)

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Record Information

Version

2.0

Created at

2022-09-07 12:29:34 UTC

Updated at

2022-09-07 12:29:34 UTC

NP-MRD ID

NP0249820

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one

Description

(5S)-5-[(E)-2-[(3S,4aR,6aR,8R,10aS,10bR)-8-hydroxy-3,4a,7,7,10a-pentamethyl-dodecahydro-1H-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methyl-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one is found in Salvia aethiopis. Based on a literature review very few articles have been published on (5S)-5-[(E)-2-[(3S,4aR,6aR,8R,10aS,10bR)-8-hydroxy-3,4a,7,7,10a-pentamethyl-dodecahydro-1H-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methyl-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072214292D          

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M  END

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  Mrv1652309072214292D          

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M  END
> <DATABASE_ID>
NP0249820

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]1(OC(=O)C=C1C)\C=C\[C@]1(C)CC[C@H]2[C@@](C)(CC[C@H]3C(C)(C)[C@H](O)CC[C@]23C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C26H40O5/c1-17-16-21(28)30-26(17,29-7)15-14-23(4)11-8-19-24(5)12-10-20(27)22(2,3)18(24)9-13-25(19,6)31-23/h14-16,18-20,27H,8-13H2,1-7H3/b15-14+/t18-,19+,20+,23-,24-,25+,26-/m0/s1

> <INCHI_KEY>
KOQSFTNOGWIFJZ-KUAYCZFLSA-N

> <FORMULA>
C26H40O5

> <MOLECULAR_WEIGHT>
432.601

> <EXACT_MASS>
432.287574388

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.19292989880178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-5-[(E)-2-[(3S,4aR,6aR,8R,10aS,10bR)-8-hydroxy-3,4a,7,7,10a-pentamethyl-dodecahydro-1H-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
5.185377993333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.489432219616308

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8348204594203245

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
121.59329999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-[(E)-2-[(3S,4aR,6aR,8R,10aS,10bR)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1H-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.696  -1.523   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.159  -1.630   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.298  -0.354   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.119  -1.344   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.386  -2.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.386  -4.840   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.644  -2.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.034  -3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.171  -5.710   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.456  -6.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -6.517   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.564  -5.184   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.658   0.369   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.391   1.886   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.460   2.994   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.866   2.100   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.191   0.716   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.326   0.449   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26   30                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   25                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12   13   20                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   10   24   25                                             
CONECT   24   23                                                            
CONECT   25   23    6                                                       
CONECT   26    3   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29    3   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₀O₅

Average Mass

432.6010 Da

Monoisotopic Mass

432.28757 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@]1(OC(=O)C=C1C)\C=C\[C@]1(C)CC[C@H]2[C@@](C)(CC[C@H]3C(C)(C)[C@H](O)CC[C@]23C)O1

InChI Identifier

InChI=1S/C26H40O5/c1-17-16-21(28)30-26(17,29-7)15-14-23(4)11-8-19-24(5)12-10-20(27)22(2,3)18(24)9-13-25(19,6)31-23/h14-16,18-20,27H,8-13H2,1-7H3/b15-14+/t18-,19+,20+,23-,24-,25+,26-/m0/s1

InChI Key

KOQSFTNOGWIFJZ-KUAYCZFLSA-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
Salvia aethiopis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Naphthopyran
Naphthofuran
Naphthalene
Ketal
2-furanone
Oxane
Pyran
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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

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

162870503

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one (NP0249820)

MOL for NP0249820 ((5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one)

3D MOL for NP0249820 ((5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one)

3D SDF for NP0249820 ((5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one)

3D-SDF for NP0249820 ((5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one)

PDB for NP0249820 ((5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one)

3D PDB for NP0249820 ((5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one)

SMILES for NP0249820 ((5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one)

INCHI for NP0249820 ((5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one)

Structure for NP0249820 ((5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one)

3D Structure for NP0249820 ((5s)-5-[(1e)-2-[(3s,4ar,6ar,8r,10as,10br)-8-hydroxy-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran-3-yl]ethenyl]-5-methoxy-4-methylfuran-2-one)