NP-MRD: Showing NP-Card for scutebarbatine e (NP0196901)

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Record Information

Version

2.0

Created at

2022-09-04 15:04:28 UTC

Updated at

2022-09-04 15:04:29 UTC

NP-MRD ID

NP0196901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

scutebarbatine e

Description

Scutebarbatine E belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. scutebarbatine e is found in Scutellaria barbata. Based on a literature review a small amount of articles have been published on scutebarbatine E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217042D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042217042D          

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    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -3.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2745   -3.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1313   -4.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102   -5.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8597   -5.1211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4532   -4.5480    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  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
 10 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  6  0  0  0
 30 33  1  0  0  0  0
  7 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  6  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 37 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(O)[C@@H](OC(=O)C2=CC=CC=C2)[C@H](OC(=O)C2=CC=CN=C2)[C@]2(C)[C@H](CCC(=O)C2=C)[C@@]1(C)\C=C\C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C33H33NO8/c1-20-24(35)12-13-25-31(2,15-14-21-17-26(36)40-19-21)33(4,39)28(42-29(37)22-9-6-5-7-10-22)27(32(20,25)3)41-30(38)23-11-8-16-34-18-23/h5-11,14-18,25,27-28,39H,1,12-13,19H2,2-4H3/b15-14+/t25-,27+,28+,31-,32+,33+/m1/s1

> <INCHI_KEY>
QIEGXQSSMCKBHF-OUMZYSQDSA-N

> <FORMULA>
C33H33NO8

> <MOLECULAR_WEIGHT>
571.626

> <EXACT_MASS>
571.220617027

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
58.526771571995766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3R,4R,4aS,8aR)-2-(benzoyloxy)-3-hydroxy-3,4,8a-trimethyl-8-methylidene-7-oxo-4-[(E)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethenyl]-decahydronaphthalen-1-yl pyridine-3-carboxylate

> <JCHEM_LOGP>
4.609187289000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.474767658629112

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.596093291318709

> <JCHEM_PKA_STRONGEST_BASIC>
3.239739476652223

> <JCHEM_POLAR_SURFACE_AREA>
129.09

> <JCHEM_REFRACTIVITY>
153.67470000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,4R,4aS,8aR)-2-(benzoyloxy)-3-hydroxy-3,4,8a-trimethyl-8-methylidene-7-oxo-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-tetrahydro-1H-naphthalen-1-yl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.335   6.160   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.518  -2.043   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.528  -3.757   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.037  -7.105   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.512  -7.320   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.245  -8.836   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.139  -9.511   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       1.605  -9.559   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.713  -8.490   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   33                                                  
CONECT    8    7    2    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11   20                                                  
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   10   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   20   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30    7   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   37                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₃NO₈

Average Mass

571.6260 Da

Monoisotopic Mass

571.22062 Da

IUPAC Name

(1R,2S,3R,4R,4aS,8aR)-2-(benzoyloxy)-3-hydroxy-3,4,8a-trimethyl-8-methylidene-7-oxo-4-[(E)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethenyl]-decahydronaphthalen-1-yl pyridine-3-carboxylate

Traditional Name

(1R,2S,3R,4R,4aS,8aR)-2-(benzoyloxy)-3-hydroxy-3,4,8a-trimethyl-8-methylidene-7-oxo-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-tetrahydro-1H-naphthalen-1-yl pyridine-3-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@]1(O)[C@@H](OC(=O)C2=CC=CC=C2)[C@H](OC(=O)C2=CC=CN=C2)[C@]2(C)[C@H](CCC(=O)C2=C)[C@@]1(C)\C=C\C1=CC(=O)OC1

InChI Identifier

InChI=1S/C33H33NO8/c1-20-24(35)12-13-25-31(2,15-14-21-17-26(36)40-19-21)33(4,39)28(42-29(37)22-9-6-5-7-10-22)27(32(20,25)3)41-30(38)23-11-8-16-34-18-23/h5-11,14-18,25,27-28,39H,1,12-13,19H2,2-4H3/b15-14+/t25-,27+,28+,31-,32+,33+/m1/s1

InChI Key

QIEGXQSSMCKBHF-OUMZYSQDSA-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
Benzoate ester
Benzoic acid or derivatives
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Cyclitol or derivatives
Monocyclic benzene moiety
2-furanone
Pyridine
Benzenoid
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Enoate ester
Dihydrofuran
Cyclic alcohol
Lactone
Ketone
Cyclic ketone
Carboxylic acid ester
Azacycle
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

butenolide (CHEBI:66445 )
benzoate ester (CHEBI:66445 )
diterpene alkaloid (CHEBI:66445 )
pyridine alkaloid (CHEBI:66445 )
diterpene lactone (CHEBI:66445 )

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	4.61	ChemAxon
pKa (Strongest Acidic)	7.6	ChemAxon
pKa (Strongest Basic)	3.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	129.09 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	153.67 m³·mol⁻¹	ChemAxon
Polarizability	58.53 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

C00031328

Chemspider ID

9895850

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11721134

PDB ID

Not Available

ChEBI ID

66445

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for scutebarbatine e (NP0196901)

MOL for NP0196901 (scutebarbatine e)

3D MOL for NP0196901 (scutebarbatine e)

3D SDF for NP0196901 (scutebarbatine e)

3D-SDF for NP0196901 (scutebarbatine e)

PDB for NP0196901 (scutebarbatine e)

3D PDB for NP0196901 (scutebarbatine e)

SMILES for NP0196901 (scutebarbatine e)

INCHI for NP0196901 (scutebarbatine e)

Structure for NP0196901 (scutebarbatine e)

3D Structure for NP0196901 (scutebarbatine e)