NP-MRD: Showing NP-Card for 2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate (NP0286952)

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Record Information

Version

2.0

Created at

2022-09-09 15:46:34 UTC

Updated at

2022-09-09 15:46:35 UTC

NP-MRD ID

NP0286952

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate

Description

2-[6-(Acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-4b,5,6,7,8,10-hexahydrophenanthren-2-yl]-3-hydroxypropyl acetate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate is found in Plectranthus scutellarioides. Based on a literature review very few articles have been published on 2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-4b,5,6,7,8,10-hexahydrophenanthren-2-yl]-3-hydroxypropyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092217462D          

 34 36  0  0  0  0            999 V2000
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    6.2388   -2.9980    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


  Mrv1652309092217462D          

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M  END
> <DATABASE_ID>
NP0286952

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC(CO)C1=C(O)C(O)=C2C(=C1O)C(=O)C(O)=C1C(C)(C)CC(CC21C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O10/c1-10(26)33-9-12(8-25)14-17(28)15-16(20(31)18(14)29)24(5)7-13(34-11(2)27)6-23(3,4)22(24)21(32)19(15)30/h12-13,25,28-29,31-32H,6-9H2,1-5H3

> <INCHI_KEY>
BLLJRCSMXYBSCC-UHFFFAOYSA-N

> <FORMULA>
C24H30O10

> <MOLECULAR_WEIGHT>
478.494

> <EXACT_MASS>
478.183897166

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.70804775082752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-4b,5,6,7,8,10-hexahydrophenanthren-2-yl]-3-hydroxypropyl acetate

> <JCHEM_LOGP>
1.3291943113333338

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.98511569390062

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.571958123408324

> <JCHEM_PKA_STRONGEST_BASIC>
-2.732394946271408

> <JCHEM_POLAR_SURFACE_AREA>
170.82

> <JCHEM_REFRACTIVITY>
120.90419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5H-phenanthren-2-yl]-3-hydroxypropyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       8.566  -8.264   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.566  -5.596   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.876  -6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.646  -5.596   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.186  -5.596   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.956  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.186  -8.264   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.956  -4.263   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.496  -4.263   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      16.266  -5.596   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      16.266  -2.929   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      17.806  -2.929   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      15.496  -1.595   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.956  -1.595   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.186  -2.929   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.646  -2.929   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.186  -0.262   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.646  -0.262   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.956   1.072   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.186   2.406   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      15.496   1.072   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.266   2.406   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.819   2.932   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.533   3.922   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.806   2.406   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.576   1.072   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      20.116   1.072   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      20.886  -0.262   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      22.426  -0.262   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      20.116  -1.595   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      17.806  -0.262   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.266  -0.262   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.036  -1.595   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   33                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15    9   17                                                  
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   33                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   33                                                       
CONECT   33   32   22   14   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
2-[6-(Acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-4b,5,6,7,8,10-hexahydrophenanthren-2-yl]-3-hydroxypropyl acetic acid	Generator

Chemical Formula

C₂₄H₃₀O₁₀

Average Mass

478.4940 Da

Monoisotopic Mass

478.18390 Da

IUPAC Name

2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-4b,5,6,7,8,10-hexahydrophenanthren-2-yl]-3-hydroxypropyl acetate

Traditional Name

2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5H-phenanthren-2-yl]-3-hydroxypropyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC(CO)C1=C(O)C(O)=C2C(=C1O)C(=O)C(O)=C1C(C)(C)CC(CC21C)OC(C)=O

InChI Identifier

InChI=1S/C24H30O10/c1-10(26)33-9-12(8-25)14-17(28)15-16(20(31)18(14)29)24(5)7-13(34-11(2)27)6-23(3,4)22(24)21(32)19(15)30/h12-13,25,28-29,31-32H,6-9H2,1-5H3

InChI Key

BLLJRCSMXYBSCC-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
Coleus blumei	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

Abietane diterpenoid
Diterpenoid
Hydrophenanthrene
Phenanthrene
Naphthalene
Aryl ketone
Dicarboxylic acid or derivatives
Benzenoid
Vinylogous acid
Ketone
Carboxylic acid ester
Enol
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Primary alcohol
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	1.33	ChemAxon
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	120.9 m³·mol⁻¹	ChemAxon
Polarizability	48.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

85089588

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate (NP0286952)

MOL for NP0286952 (2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate)

3D MOL for NP0286952 (2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate)

3D SDF for NP0286952 (2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate)

3D-SDF for NP0286952 (2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate)

PDB for NP0286952 (2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate)

3D PDB for NP0286952 (2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate)

SMILES for NP0286952 (2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate)

INCHI for NP0286952 (2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate)

Structure for NP0286952 (2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate)

3D Structure for NP0286952 (2-[6-(acetyloxy)-1,3,4,9-tetrahydroxy-4b,8,8-trimethyl-10-oxo-6,7-dihydro-5h-phenanthren-2-yl]-3-hydroxypropyl acetate)