NP-MRD: Showing NP-Card for (16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione (NP0217545)

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Record Information

Version

2.0

Created at

2022-09-05 17:55:34 UTC

Updated at

2022-09-05 17:55:34 UTC

NP-MRD ID

NP0217545

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione

Description

(16R,17S)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-7,7-dimethyl-13-(propan-2-yl)-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]Nonadeca-1(11),2,4,8,12,14(19)-hexaene-6,10-dione belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review very few articles have been published on (16R,17S)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-7,7-dimethyl-13-(propan-2-yl)-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]Nonadeca-1(11),2,4,8,12,14(19)-hexaene-6,10-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052219552D          

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M  END

     RDKit          3D

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  Mrv1652309052219552D          

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 14 21  1  0  0  0  0
 21 22  2  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  5 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217545

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@H]1OC2=C(C=C3C(C=C4C=CC(=O)C(C)(C)C4=CC3=O)=C2O[C@H]1CO)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O7/c1-15(2)18-12-19-20(10-16-7-9-26(34)30(3,4)21(16)13-23(19)33)29-28(18)37-27(25(14-31)36-29)17-6-8-22(32)24(11-17)35-5/h6-13,15,25,27,31-32H,14H2,1-5H3/t25-,27+/m0/s1

> <INCHI_KEY>
STCQKVIMCUPRKK-AHKZPQOWSA-N

> <FORMULA>
C30H30O7

> <MOLECULAR_WEIGHT>
502.563

> <EXACT_MASS>
502.199153306

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
54.54085619660742

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(16R,17S)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-7,7-dimethyl-13-(propan-2-yl)-15,18-dioxatetracyclo[9.8.0.0^{3,8}.0^{14,19}]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione

> <JCHEM_LOGP>
4.724845815666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.530628472062766

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908129650217061

> <JCHEM_PKA_STRONGEST_BASIC>
2.902019747127733

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
141.74919999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(16R,17S)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0^{3,8}.0^{14,19}]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.342  -3.210   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.908  -2.646   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.704  -3.606   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.729  -3.042   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.934  -4.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.367  -3.439   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.596  -1.916   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.029  -1.352   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.258   0.171   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.053   1.130   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.282   2.653   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.620   0.567   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.691   0.734   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.896  -0.226   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.229   0.545   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.113   2.081   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.663  -0.017   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.117  -1.488   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.251  -2.761   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.715  -2.877   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.667  -1.749   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.234  -2.312   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.005  -3.835   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.572  -4.398   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.343  -5.921   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.910  -6.485   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.919  -4.148   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.455  -4.262   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.322  -2.990   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.858  -3.104   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.653  -1.602   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.016  -0.886   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.821  -0.072   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.705  -5.525   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.272  -6.088   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.933  -5.129   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.366  -5.692   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   14   22                                                  
CONECT   22   21    8   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    6   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   19   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   18   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    5   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₀O₇

Average Mass

502.5630 Da

Monoisotopic Mass

502.19915 Da

IUPAC Name

(16R,17S)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-7,7-dimethyl-13-(propan-2-yl)-15,18-dioxatetracyclo[9.8.0.0^{3,8}.0^{14,19}]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione

Traditional Name

(16R,17S)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0^{3,8}.0^{14,19}]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@H]1OC2=C(C=C3C(C=C4C=CC(=O)C(C)(C)C4=CC3=O)=C2O[C@H]1CO)C(C)C

InChI Identifier

InChI=1S/C30H30O7/c1-15(2)18-12-19-20(10-16-7-9-26(34)30(3,4)21(16)13-23(19)33)29-28(18)37-27(25(14-31)36-29)17-6-8-22(32)24(11-17)35-5/h6-13,15,25,27,31-32H,14H2,1-5H3/t25-,27+/m0/s1

InChI Key

STCQKVIMCUPRKK-AHKZPQOWSA-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

Not Available

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

Abeoabietane diterpenoid
Diterpenoid
Phenylbenzodioxane
2-phenylbenzo-1,4-dioxane
Benzo-1,4-dioxane
Benzodioxane
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Tropone
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Para-dioxin
Cyclic ketone
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.72	ChemAxon
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	141.75 m³·mol⁻¹	ChemAxon
Polarizability	54.54 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	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

162892286

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione (NP0217545)

MOL for NP0217545 ((16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione)

3D MOL for NP0217545 ((16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione)

3D SDF for NP0217545 ((16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione)

3D-SDF for NP0217545 ((16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione)

PDB for NP0217545 ((16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione)

3D PDB for NP0217545 ((16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione)

SMILES for NP0217545 ((16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione)

INCHI for NP0217545 ((16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione)

Structure for NP0217545 ((16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione)

3D Structure for NP0217545 ((16r,17s)-16-(4-hydroxy-3-methoxyphenyl)-17-(hydroxymethyl)-13-isopropyl-7,7-dimethyl-15,18-dioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),2,4,8,11,13-hexaene-6,10-dione)