NP-MRD: Showing NP-Card for 5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate (NP0214270)

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Record Information

Version

2.0

Created at

2022-09-05 13:31:36 UTC

Updated at

2022-09-05 13:31:36 UTC

NP-MRD ID

NP0214270

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate

Description

5-Hydroxy-1,1,4a-trimethyl-6-oxo-7-(propan-2-yl)-1,2,3,4,4a,6-hexahydrophenanthren-3-yl 3,4-dihydroxybenzoate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate is found in Plectranthus parviflorus and Plectranthus strigosus. 5-Hydroxy-1,1,4a-trimethyl-6-oxo-7-(propan-2-yl)-1,2,3,4,4a,6-hexahydrophenanthren-3-yl 3,4-dihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181501122D          

 33 36  0  0  0  0            999 V2000
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    1.2079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004181501122D          

 33 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0214270

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=CC=C3C(C)(C)CC(CC3(C)C2=C(O)C1=O)OC(=O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O6/c1-14(2)18-10-15-7-9-21-26(3,4)12-17(13-27(21,5)22(15)24(31)23(18)30)33-25(32)16-6-8-19(28)20(29)11-16/h6-11,14,17,28-29,31H,12-13H2,1-5H3

> <INCHI_KEY>
ODFVSDJLTCHLCV-UHFFFAOYSA-N

> <FORMULA>
C27H30O6

> <MOLECULAR_WEIGHT>
450.531

> <EXACT_MASS>
450.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
49.20313100133803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-1,1,4a-trimethyl-6-oxo-7-(propan-2-yl)-1,2,3,4,4a,6-hexahydrophenanthren-3-yl 3,4-dihydroxybenzoate

> <ALOGPS_LOGP>
5.03

> <JCHEM_LOGP>
4.624968280666668

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.329525759505227

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.477814122905466

> <JCHEM_PKA_STRONGEST_BASIC>
-3.68249939813695

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
129.28759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2H-phenanthren-3-yl 3,4-dihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.255  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.485  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.457   1.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.172   0.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.875  -4.207   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.035  -4.207   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.805  -2.874   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.805  -5.541   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.345  -5.541   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.115  -6.875   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.345  -8.208   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.115  -9.542   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.805  -8.208   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.035  -9.542   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.035  -6.875   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15    9   17   18                                             
CONECT   17   16                                                            
CONECT   18   16    6   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    4   22                                                  
CONECT   22   21                                                            
CONECT   23   14   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   26                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-1,1,4a-trimethyl-6-oxo-7-(propan-2-yl)-1,2,3,4,4a,6-hexahydrophenanthren-3-yl 3,4-dihydroxybenzoic acid	Generator

Chemical Formula

C₂₇H₃₀O₆

Average Mass

450.5310 Da

Monoisotopic Mass

450.20424 Da

IUPAC Name

5-hydroxy-1,1,4a-trimethyl-6-oxo-7-(propan-2-yl)-1,2,3,4,4a,6-hexahydrophenanthren-3-yl 3,4-dihydroxybenzoate

Traditional Name

5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2H-phenanthren-3-yl 3,4-dihydroxybenzoate

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2=CC=C3C(C)(C)CC(CC3(C)C2=C(O)C1=O)OC(=O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C27H30O6/c1-14(2)18-10-15-7-9-21-26(3,4)12-17(13-27(21,5)22(15)24(31)23(18)30)33-25(32)16-6-8-19(28)20(29)11-16/h6-11,14,17,28-29,31H,12-13H2,1-5H3

InChI Key

ODFVSDJLTCHLCV-UHFFFAOYSA-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
Plectranthus parviflorus	LOTUS Database	35616633
Plectranthus strigosus	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
Abietane diterpenoid
Hydrophenanthrene
Phenanthrene
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Cyclic ketone
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Enol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	5.03	ALOGPS
logP	4.62	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	8.48	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	129.29 m³·mol⁻¹	ChemAxon
Polarizability	49.2 Å³	ChemAxon
Number of Rings	4	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate (NP0214270)

MOL for NP0214270 (5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate)

3D MOL for NP0214270 (5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate)

3D SDF for NP0214270 (5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate)

3D-SDF for NP0214270 (5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate)

PDB for NP0214270 (5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate)

3D PDB for NP0214270 (5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate)

SMILES for NP0214270 (5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate)

INCHI for NP0214270 (5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate)

Structure for NP0214270 (5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate)

3D Structure for NP0214270 (5-hydroxy-7-isopropyl-1,1,4a-trimethyl-6-oxo-3,4-dihydro-2h-phenanthren-3-yl 3,4-dihydroxybenzoate)