NP-MRD: Showing NP-Card for (1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate (NP0323183)

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Record Information

Version

2.0

Created at

2022-09-12 02:26:49 UTC

Updated at

2022-09-12 02:26:50 UTC

NP-MRD ID

NP0323183

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate

Description

(1S,2R,3S,4R,4aR,8aS)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2S)-6-oxo-2H,3H,4H,6H-furo[2,3-c]furan-2-yl]-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl pyridine-3-carboxylate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate is found in Scutellaria barbata. Based on a literature review very few articles have been published on (1S,2R,3S,4R,4aR,8aS)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2S)-6-oxo-2H,3H,4H,6H-furo[2,3-c]furan-2-yl]-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl pyridine-3-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122204262D          

 34 38  0  0  1  0            999 V2000
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   -0.0748   -3.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0460   -2.5066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309122204262D          

 34 38  0  0  1  0            999 V2000
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 26 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 28 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323183

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC[C@H]2[C@](C)([C@@H]3CC4=C(O3)C(=O)OC4)[C@](C)(O)[C@H](O)[C@@H](OC(=O)C3=CC=CN=C3)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C26H31NO7/c1-14-7-5-9-17-24(14,2)21(34-22(29)15-8-6-10-27-12-15)20(28)26(4,31)25(17,3)18-11-16-13-32-23(30)19(16)33-18/h6-8,10,12,17-18,20-21,28,31H,5,9,11,13H2,1-4H3/t17-,18+,20-,21-,24-,25-,26-/m1/s1

> <INCHI_KEY>
ADBRHQRSKHISPR-ACXBYKOSSA-N

> <FORMULA>
C26H31NO7

> <MOLECULAR_WEIGHT>
469.534

> <EXACT_MASS>
469.210052342

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
49.394976528746284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,3S,4R,4aR,8aS)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2S)-6-oxo-2H,3H,4H,6H-furo[2,3-c]furan-2-yl]-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl pyridine-3-carboxylate

> <JCHEM_LOGP>
1.9670944976666656

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.394926476379407

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.734717906436025

> <JCHEM_PKA_STRONGEST_BASIC>
3.2397729186984097

> <JCHEM_POLAR_SURFACE_AREA>
115.18000000000002

> <JCHEM_REFRACTIVITY>
123.0882

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S,4R,4aR,8aS)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2S)-6-oxo-2H,3H,4H-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.499  -6.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.140  -6.218   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.166  -7.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.526  -6.311   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.580  -4.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.274  -3.956   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.086  -4.679   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.446  -5.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.392  -3.863   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.752  -4.586   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.058  -3.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.004  -2.231   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.417  -4.493   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.471  -6.032   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.831  -6.755   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.137  -5.939   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -8.083  -4.400   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -6.723  -3.677   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.338  -2.324   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.644  -1.508   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.022  -1.601   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.926  -0.387   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.052  -0.456   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.328  -2.417   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.189  -1.140   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.868  -2.417   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.773  -3.663   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.237  -3.187   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.237  -1.647   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.773  -1.171   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.702  -1.171   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.178   0.294   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       7.607  -2.417   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.702  -3.663   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    9   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21    6   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   26                                                       
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   28                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,3S,4R,4AR,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2S)-6-oxo-2H,3H,4H,6H-furo[2,3-c]furan-2-yl]-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₁NO₇

Average Mass

469.5340 Da

Monoisotopic Mass

469.21005 Da

IUPAC Name

(1S,2R,3S,4R,4aR,8aS)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2S)-6-oxo-2H,3H,4H,6H-furo[2,3-c]furan-2-yl]-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl pyridine-3-carboxylate

Traditional Name

(1S,2R,3S,4R,4aR,8aS)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2S)-6-oxo-2H,3H,4H-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl pyridine-3-carboxylate

CAS Registry Number

Not Available

SMILES

CC1=CCC[C@H]2[C@](C)([C@@H]3CC4=C(O3)C(=O)OC4)[C@](C)(O)[C@H](O)[C@@H](OC(=O)C3=CC=CN=C3)[C@]12C

InChI Identifier

InChI=1S/C26H31NO7/c1-14-7-5-9-17-24(14,2)21(34-22(29)15-8-6-10-27-12-15)20(28)26(4,31)25(17,3)18-11-16-13-32-23(30)19(16)33-18/h6-8,10,12,17-18,20-21,28,31H,5,9,11,13H2,1-4H3/t17-,18+,20-,21-,24-,25-,26-/m1/s1

InChI Key

ADBRHQRSKHISPR-ACXBYKOSSA-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
Scutellaria barbata	LOTUS Database	35616633

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
Clerodane diterpenoid
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Cyclitol or derivatives
2-furanone
Dicarboxylic acid or derivatives
Pyridine
Cyclic alcohol
Dihydrofuran
Heteroaromatic compound
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
1,2-diol
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Oxacycle
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.97	ChemAxon
pKa (Strongest Acidic)	12.73	ChemAxon
pKa (Strongest Basic)	3.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	115.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	123.09 m³·mol⁻¹	ChemAxon
Polarizability	49.39 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

162911852

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate (NP0323183)

MOL for NP0323183 ((1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate)

3D MOL for NP0323183 ((1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate)

3D SDF for NP0323183 ((1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate)

3D-SDF for NP0323183 ((1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate)

PDB for NP0323183 ((1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate)

3D PDB for NP0323183 ((1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate)

SMILES for NP0323183 ((1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate)

INCHI for NP0323183 ((1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate)

Structure for NP0323183 ((1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate)

3D Structure for NP0323183 ((1s,2r,3s,4r,4ar,8as)-2,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(2s)-6-oxo-2h,3h,4h-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1h-naphthalen-1-yl pyridine-3-carboxylate)