NP-MRD: Showing NP-Card for (-)-Scutebarbatine C (NP0071822)

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Record Information

Version

2.0

Created at

2022-04-28 17:10:15 UTC

Updated at

2022-04-28 17:10:15 UTC

NP-MRD ID

NP0071822

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Scutebarbatine C

Description

(1R,2S,3R,4S,4aR,8S,8aS)-2-(benzoyloxy)-3,8-dihydroxy-3,4,8,8a-tetramethyl-4-[(E)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethenyl]-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl pyridine-3-carboxylate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (-)-Scutebarbatine C is found in Scutellaria barbata and Scutellaria barbata D.DON. . Based on a literature review very few articles have been published on (1R,2S,3R,4S,4aR,8S,8aS)-2-(benzoyloxy)-3,8-dihydroxy-3,4,8,8a-tetramethyl-4-[(E)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethenyl]-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl pyridine-3-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219102D          

 42 46  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652304282219102D          

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    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806    0.2871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3791    1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7664    2.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4047    2.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9982    3.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8834    4.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266    3.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834    2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  9 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
  8 29  1  1  0  0  0
  8 30  1  6  0  0  0
  7 31  1  1  0  0  0
  7 32  1  6  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 39  1  0  0  0  0
  4 40  1  6  0  0  0
  3 41  1  1  0  0  0
  3 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0071822

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(O)C=CC[C@@H]2[C@](C)(\C=C\C3=CC(=O)OC3)[C@@](C)(O)[C@@H](OC(=O)C3=CC=CC=C3)[C@H](OC(=O)C3=CN=CC=C3)[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C33H35NO8/c1-30(16-14-21-18-25(35)40-20-21)24-13-8-15-31(2,38)32(24,3)26(41-29(37)23-12-9-17-34-19-23)27(33(30,4)39)42-28(36)22-10-6-5-7-11-22/h5-12,14-19,24,26-27,38-39H,13,20H2,1-4H3/b16-14+/t24-,26+,27+,30+,31+,32+,33+/m1/s1

> <INCHI_KEY>
XOXFENMJJYQPJP-MATCGBRLSA-N

> <FORMULA>
C33H35NO8

> <MOLECULAR_WEIGHT>
573.642

> <EXACT_MASS>
573.236267091

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
58.895236109805424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3R,4S,4aR,8S,8aS)-2-(benzoyloxy)-3,8-dihydroxy-3,4,8,8a-tetramethyl-4-[(E)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethenyl]-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl pyridine-3-carboxylate

> <ALOGPS_LOGP>
3.87

> <JCHEM_LOGP>
4.1808487696666665

> <ALOGPS_LOGS>
-5.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.384245240653836

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.596087580226962

> <JCHEM_PKA_STRONGEST_BASIC>
3.2398316694561293

> <JCHEM_POLAR_SURFACE_AREA>
132.25000000000003

> <JCHEM_REFRACTIVITY>
155.77170000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,4S,4aR,8S,8aS)-2-(benzoyloxy)-3,8-dihydroxy-3,4,8,8a-tetramethyl-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-1,2,4a,5-tetrahydronaphthalen-1-yl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.335  -9.240   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.817   0.536   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.540  -0.716   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.944   1.360   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.390   1.360   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.574   2.666   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.297   4.025   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.622   5.410   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.730   6.479   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.516   8.004   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       5.090   5.756   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.822   4.240   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -0.723  -4.440   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       0.723  -4.440   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   41   42                                             
CONECT    4    3    5   10   40                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   31   32                                             
CONECT    8    7    9   29   30                                             
CONECT    9    8   10   20                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    9   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29    8                                                            
CONECT   30    8                                                            
CONECT   31    7                                                            
CONECT   32    7   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   34                                                       
CONECT   40    4                                                            
CONECT   41    3                                                            
CONECT   42    3                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3R,4S,4AR,8S,8as)-2-(benzoyloxy)-3,8-dihydroxy-3,4,8,8a-tetramethyl-4-[(e)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethenyl]-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₃₃H₃₅NO₈

Average Mass

573.6420 Da

Monoisotopic Mass

573.23627 Da

IUPAC Name

(1R,2S,3R,4S,4aR,8S,8aS)-2-(benzoyloxy)-3,8-dihydroxy-3,4,8,8a-tetramethyl-4-[(E)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethenyl]-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl pyridine-3-carboxylate

Traditional Name

(1R,2S,3R,4S,4aR,8S,8aS)-2-(benzoyloxy)-3,8-dihydroxy-3,4,8,8a-tetramethyl-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-1,2,4a,5-tetrahydronaphthalen-1-yl pyridine-3-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@]1(O)C=CC[C@@H]2[C@](C)(\C=C\C3=CC(=O)OC3)[C@@](C)(O)[C@@H](OC(=O)C3=CC=CC=C3)[C@H](OC(=O)C3=CN=CC=C3)[C@@]12C

InChI Identifier

InChI=1S/C33H35NO8/c1-30(16-14-21-18-25(35)40-20-21)24-13-8-15-31(2,38)32(24,3)26(41-29(37)23-12-9-17-34-19-23)27(33(30,4)39)42-28(36)22-10-6-5-7-11-22/h5-12,14-19,24,26-27,38-39H,13,20H2,1-4H3/b16-14+/t24-,26+,27+,30+,31+,32+,33+/m1/s1

InChI Key

XOXFENMJJYQPJP-MATCGBRLSA-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 barbata	LOTUS Database	35616633
Scutellaria barbata D.DON.	Plant	KNApSAcK

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

Clerodane diterpenoid
Diterpenoid
Diterpene lactone
Benzoate ester
Tricarboxylic acid or derivatives
Pyridine carboxylic acid or derivatives
Pyridine carboxylic acid
Benzoic acid or derivatives
Benzoyl
Benzenoid
Pyridine
2-furanone
Monocyclic benzene moiety
Cyclitol or derivatives
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Dihydrofuran
Cyclic alcohol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	3.87	ALOGPS
logP	4.18	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	7.6	ChemAxon
pKa (Strongest Basic)	3.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	132.25 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	155.77 m³·mol⁻¹	ChemAxon
Polarizability	58.9 Å³	ChemAxon
Number of Rings	5	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

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

162918107

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Scutebarbatine C (NP0071822)

MOL for NP0071822 ((-)-Scutebarbatine C)

3D MOL for NP0071822 ((-)-Scutebarbatine C)

3D SDF for NP0071822 ((-)-Scutebarbatine C)

3D-SDF for NP0071822 ((-)-Scutebarbatine C)

PDB for NP0071822 ((-)-Scutebarbatine C)

3D PDB for NP0071822 ((-)-Scutebarbatine C)

SMILES for NP0071822 ((-)-Scutebarbatine C)

INCHI for NP0071822 ((-)-Scutebarbatine C)

Structure for NP0071822 ((-)-Scutebarbatine C)

3D Structure for NP0071822 ((-)-Scutebarbatine C)