NP-MRD: Showing NP-Card for (2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate (NP0325160)

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Record Information

Version

1.0

Created at

2022-09-12 05:42:07 UTC

Updated at

2022-09-12 05:42:07 UTC

NP-MRD ID

NP0325160

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate

Description

Orthosiphol D belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate is found in Orthosiphon aristatus. It was first documented in 2002 (PMID: 11914974). Based on a literature review very few articles have been published on orthosiphol D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207422D          

 40 43  0  0  1  0            999 V2000
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  1  2  2  0  0  0  0
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  3 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309122207422D          

 40 43  0  0  1  0            999 V2000
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    2.7770   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  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  6  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
 16 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
  3 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0325160

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C(OC(C)=O)=C[C@]2(C)[C@H]2[C@@H](C[C@](C)(C=C)C(=O)[C@]12O)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H36O9/c1-8-29(6)15-20(40-26(35)19-12-10-9-11-13-19)24-30(7)16-21(38-17(2)32)25(34)28(4,5)22(30)14-23(39-18(3)33)31(24,37)27(29)36/h8-13,16,20,22-24,37H,1,14-15H2,2-7H3/t20-,22+,23-,24-,29+,30+,31+/m1/s1

> <INCHI_KEY>
LSZJDNYREMWISO-FHGPSSOVSA-N

> <FORMULA>
C31H36O9

> <MOLECULAR_WEIGHT>
552.62

> <EXACT_MASS>
552.235932739

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.87962058963696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4R,4aS,4bR,8aR,10R,10aR)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-1,2,3,4,4a,4b,7,8,8a,9,10,10a-dodecahydrophenanthren-4-yl benzoate

> <JCHEM_LOGP>
4.283445024

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.812141613758627

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1931692581419755

> <JCHEM_POLAR_SURFACE_AREA>
133.27

> <JCHEM_REFRACTIVITY>
144.77480000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4R,4aS,4bR,8aR,10R,10aR)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate

> <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      -1.119  -1.344   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.386  -2.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.386  -4.840   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.874  -1.183   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.104   0.151   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.564   0.151   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.874   1.485   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.104   2.818   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874   4.152   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   4.152   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184   2.818   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   1.485   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.644  -2.516   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.494  -1.183   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.034  -1.183   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.804   0.151   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.804  -2.516   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.034  -3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.171  -5.710   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.456  -6.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.104  -7.851   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.874  -9.185   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.414  -9.185   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.104 -10.518   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.334  -6.517   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.206  -6.517   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   39                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   16                                                  
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    6   17   37                                                  
CONECT   17   16   18   19   30                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   17   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32   16   38   39                                             
CONECT   38   37                                                            
CONECT   39   37    3   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₆O₉

Average Mass

552.6200 Da

Monoisotopic Mass

552.23593 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C(OC(C)=O)=C[C@]2(C)[C@H]2[C@@H](C[C@](C)(C=C)C(=O)[C@]12O)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C31H36O9/c1-8-29(6)15-20(40-26(35)19-12-10-9-11-13-19)24-30(7)16-21(38-17(2)32)25(34)28(4,5)22(30)14-23(39-18(3)33)31(24,37)27(29)36/h8-13,16,20,22-24,37H,1,14-15H2,2-7H3/t20-,22+,23-,24-,29+,30+,31+/m1/s1

InChI Key

LSZJDNYREMWISO-FHGPSSOVSA-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
Orthosiphon aristatus	LOTUS Database	35616633

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
Phenanthrene
Hydrophenanthrene
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Cyclohexenone
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Tertiary alcohol
Enol ester
Carboxylic acid ester
Cyclic ketone
Ketone
Carboxylic acid derivative
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00044974

Chemspider ID

24686524

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44583689

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Awale S, Tezuka Y, Banskota AH, Kouda K, Tun KM, Kadota S: Four highly oxygenated isopimarane-type diterpenes of Orthosiphon stamineus. Planta Med. 2002 Mar;68(3):286-8. doi: 10.1055/s-2002-23137. [PubMed:11914974 ]
LOTUS database [Link]

Showing NP-Card for (2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate (NP0325160)

MOL for NP0325160 ((2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate)

3D MOL for NP0325160 ((2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate)

3D SDF for NP0325160 ((2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate)

3D-SDF for NP0325160 ((2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate)

PDB for NP0325160 ((2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate)

3D PDB for NP0325160 ((2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate)

SMILES for NP0325160 ((2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate)

INCHI for NP0325160 ((2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate)

Structure for NP0325160 ((2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate)

3D Structure for NP0325160 ((2r,4r,4as,4br,8ar,10r,10ar)-6,10-bis(acetyloxy)-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl benzoate)