NP-MRD: Showing NP-Card for (-)-Orthosiphol G (NP0073114)

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Record Information

Version

2.0

Created at

2022-04-28 18:22:35 UTC

Updated at

2022-04-28 18:22:35 UTC

NP-MRD ID

NP0073114

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Orthosiphol G

Description

CHEMBL448947 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (-)-Orthosiphol G is found in Orthosiphon stamineus . Based on a literature review very few articles have been published on CHEMBL448947.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220222D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282220222D          

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   -1.5386    0.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3016   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 16  5  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  6  0  0  0
 18 20  1  1  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 23 27  1  6  0  0  0
 23 28  1  1  0  0  0
 28 29  2  0  0  0  0
 17 30  1  6  0  0  0
  5 31  1  6  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  2 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  1 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073114

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@@H](OC(C)=O)C(C)(C)[C@@H]2C[C@@H](O)[C@]3(O)[C@H]([C@H](O)C[C@](C)(C=C)C3=O)[C@@]2(C)[C@H]1OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O10/c1-8-29(6)15-19(34)23-30(7)20(14-21(35)31(23,38)27(29)37)28(4,5)24(40-17(3)33)22(39-16(2)32)25(30)41-26(36)18-12-10-9-11-13-18/h8-13,19-25,34-35,38H,1,14-15H2,2-7H3/t19-,20+,21-,22+,23-,24-,25+,29+,30+,31+/m1/s1

> <INCHI_KEY>
HVCLVVFTATWQBZ-SRHIYTGZSA-N

> <FORMULA>
C31H40O10

> <MOLECULAR_WEIGHT>
572.651

> <EXACT_MASS>
572.262147488

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
59.228872172933606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,4aS,4bS,5R,7R,8aR,9R,10aS)-2,3-bis(acetyloxy)-7-ethenyl-5,8a,9-trihydroxy-1,1,4a,7-tetramethyl-8-oxo-tetradecahydrophenanthren-4-yl benzoate

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.7771508703333323

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.411282059483998

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.847611056095747

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8989298714482805

> <JCHEM_POLAR_SURFACE_AREA>
156.66

> <JCHEM_REFRACTIVITY>
145.10539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,4aS,4bS,5R,7R,8aR,9R,10aS)-2,3-bis(acetyloxy)-7-ethenyl-5,8a,9-trihydroxy-1,1,4a,7-tetramethyl-8-oxo-octahydro-2H-phenanthren-4-yl benzoate

> <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       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.184   4.771   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.724   4.771   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.414   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.874   6.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104   7.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874   8.772   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   8.772   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.184   7.438   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.566   0.047   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.566   1.493   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.872   0.677   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334  -1.897   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.030  -1.380   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.777  -2.103   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.344  -0.564   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       9.804   4.771   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
CONECT    1    2    6   38                                                  
CONECT    2    1    3   34                                                  
CONECT    3    2    4   32   33                                             
CONECT    4    3    5   19                                                  
CONECT    5    4    6   16   31                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    5   17   25                                                  
CONECT   17   16   18   21   30                                             
CONECT   18   17   19   20                                                  
CONECT   19   18    4                                                       
CONECT   20   18                                                            
CONECT   21   17   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   27   28                                             
CONECT   24   23   25                                                       
CONECT   25   24   16   26                                                  
CONECT   26   25                                                            
CONECT   27   23                                                            
CONECT   28   23   29                                                       
CONECT   29   28                                                            
CONECT   30   17                                                            
CONECT   31    5                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    2   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    1   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₀O₁₀

Average Mass

572.6510 Da

Monoisotopic Mass

572.26215 Da

IUPAC Name

(2S,3S,4R,4aS,4bS,5R,7R,8aR,9R,10aS)-2,3-bis(acetyloxy)-7-ethenyl-5,8a,9-trihydroxy-1,1,4a,7-tetramethyl-8-oxo-tetradecahydrophenanthren-4-yl benzoate

Traditional Name

(2S,3S,4R,4aS,4bS,5R,7R,8aR,9R,10aS)-2,3-bis(acetyloxy)-7-ethenyl-5,8a,9-trihydroxy-1,1,4a,7-tetramethyl-8-oxo-octahydro-2H-phenanthren-4-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@@H](OC(C)=O)C(C)(C)[C@@H]2C[C@@H](O)[C@]3(O)[C@H]([C@H](O)C[C@](C)(C=C)C3=O)[C@@]2(C)[C@H]1OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C31H40O10/c1-8-29(6)15-19(34)23-30(7)20(14-21(35)31(23,38)27(29)37)28(4,5)24(40-17(3)33)22(39-16(2)32)25(30)41-26(36)18-12-10-9-11-13-18/h8-13,19-25,34-35,38H,1,14-15H2,2-7H3/t19-,20+,21-,22+,23-,24-,25+,29+,30+,31+/m1/s1

InChI Key

HVCLVVFTATWQBZ-SRHIYTGZSA-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
Orthosiphon stamineus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Pimarane diterpenoid
Hydrophenanthrene
Phenanthrene
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Cyclitol or derivatives
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.34	ALOGPS
logP	2.78	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.85	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	156.66 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	145.11 m³·mol⁻¹	ChemAxon
Polarizability	59.23 Å³	ChemAxon
Number of Rings	4	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

8252323

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10076785

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Orthosiphol G (NP0073114)

MOL for NP0073114 ((-)-Orthosiphol G)

3D MOL for NP0073114 ((-)-Orthosiphol G)

3D SDF for NP0073114 ((-)-Orthosiphol G)

3D-SDF for NP0073114 ((-)-Orthosiphol G)

PDB for NP0073114 ((-)-Orthosiphol G)

3D PDB for NP0073114 ((-)-Orthosiphol G)

SMILES for NP0073114 ((-)-Orthosiphol G)

INCHI for NP0073114 ((-)-Orthosiphol G)

Structure for NP0073114 ((-)-Orthosiphol G)

3D Structure for NP0073114 ((-)-Orthosiphol G)