NP-MRD: Showing NP-Card for 16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate (NP0170559)

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Record Information

Version

2.0

Created at

2022-09-03 06:45:20 UTC

Updated at

2022-09-03 06:45:20 UTC

NP-MRD ID

NP0170559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate

Description

Jolkinol A belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate is found in Euphorbia micractina. Jolkinol A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191514252D          

 35 39  0  0  0  0            999 V2000
    8.0744    1.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2563    0.9661    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


  Mrv1533004191514252D          

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 28 31  1  0  0  0  0
  4 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 33  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0170559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2(OC(=O)C=CC3=CC=CC=C3)C(C3OC3(C)CCC3C(C=C(CO)C2=O)C3(C)C)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O6/c1-17-15-29(34-22(31)11-10-18-8-6-5-7-9-18)23(24(17)32)26-28(4,35-26)13-12-20-21(27(20,2)3)14-19(16-30)25(29)33/h5-11,14,17,20-21,23-24,26,30,32H,12-13,15-16H2,1-4H3

> <INCHI_KEY>
ZLHWPIKKGZWBKR-UHFFFAOYSA-N

> <FORMULA>
C29H36O6

> <MOLECULAR_WEIGHT>
480.601

> <EXACT_MASS>
480.251188879

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.90209710677958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
4.357358539333333

> <ALOGPS_LOGS>
-5.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.087493760210545

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.370970842408116

> <JCHEM_PKA_STRONGEST_BASIC>
-2.817584830646936

> <JCHEM_POLAR_SURFACE_AREA>
96.36000000000001

> <JCHEM_REFRACTIVITY>
133.00239999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      15.072   2.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.545   1.803   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.486   2.922   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.096   2.261   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.421   3.766   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.888   4.236   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.213   5.742   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.028   3.202   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.495   3.672   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.635   2.638   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.102   3.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.242   2.074   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.917   0.569   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.450   0.098   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.310   1.133   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.295   0.733   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.809   0.451   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.470  -0.940   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.637  -0.659   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.690  -2.198   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.330  -1.474   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.948  -2.966   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.791  -1.454   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.506  -0.605   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.885   0.804   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.124   2.326   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.147   3.476   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.631   3.891   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.651   5.431   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.994   6.183   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.102   3.437   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.952   4.722   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.687   1.772   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.578   2.841   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.303   1.095   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16   31                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    4   17   19                                                  
CONECT   17   16    2   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19   21                                                       
CONECT   21   20   19   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28    4   32                                                  
CONECT   32   31                                                            
CONECT   33   26   25   34   35                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
1a,1b,2,3,4,5,7a,8,8a,9,10,10a-Dodecahydro-2-hydroxy-6-(hydroxymethyl)-3,8,8,10a-tetramethyl-5-oxo-4ah-cyclopenta(3,4)cyclopropa(8,9)cycloundec(1,2-b)oxiren-4a-yl ester	MeSH

Chemical Formula

C₂₉H₃₆O₆

Average Mass

480.6010 Da

Monoisotopic Mass

480.25119 Da

IUPAC Name

16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate

Traditional Name

16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC1CC2(OC(=O)C=CC3=CC=CC=C3)C(C3OC3(C)CCC3C(C=C(CO)C2=O)C3(C)C)C1O

InChI Identifier

InChI=1S/C29H36O6/c1-17-15-29(34-22(31)11-10-18-8-6-5-7-9-18)23(24(17)32)26-28(4,35-26)13-12-20-21(27(20,2)3)14-19(16-30)25(29)33/h5-11,14,17,20-21,23-24,26,30,32H,12-13,15-16H2,1-4H3

InChI Key

ZLHWPIKKGZWBKR-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
Euphorbia micractina	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
Lathyrane diterpenoid
Cinnamic acid or derivatives
Cinnamic acid ester
Styrene
Fatty acid ester
Alpha-acyloxy ketone
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Oxirane
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
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	3.38	ALOGPS
logP	4.36	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	14.37	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133 m³·mol⁻¹	ChemAxon
Polarizability	52.9 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

3081534

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate (NP0170559)

MOL for NP0170559 (16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate)

3D MOL for NP0170559 (16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate)

3D SDF for NP0170559 (16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate)

3D-SDF for NP0170559 (16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate)

PDB for NP0170559 (16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate)

3D PDB for NP0170559 (16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate)

SMILES for NP0170559 (16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate)

INCHI for NP0170559 (16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate)

Structure for NP0170559 (16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate)

3D Structure for NP0170559 (16-hydroxy-11-(hydroxymethyl)-4,8,8,15-tetramethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-13-yl 3-phenylprop-2-enoate)