NP-MRD: Showing NP-Card for (1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate (NP0287919)

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Record Information

Version

2.0

Created at

2022-09-09 17:24:29 UTC

Updated at

2022-09-09 17:24:29 UTC

NP-MRD ID

NP0287919

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate

Description

(1S,2S,3R,4R,7R,8S,10Z,12S,13S,17R)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]Heptadeca-10,14-dien-12-yl butanoate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate is found in Tritonia tetraquetra. Based on a literature review very few articles have been published on (1S,2S,3R,4R,7R,8S,10Z,12S,13S,17R)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]Heptadeca-10,14-dien-12-yl butanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092219242D          

 35 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309092219242D          

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 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 33 32  1  1  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0287919

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@H]1\C=C/C(=C)[C@H](Cl)[C@@H]2OC(=O)[C@H](C)[C@@]2(O)[C@@H](OC(C)=O)[C@H]2[C@@H](C)C(=O)C=C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C26H33ClO8/c1-7-8-19(30)34-18-10-9-13(2)21(27)23-26(32,15(4)24(31)35-23)22(33-16(5)28)20-14(3)17(29)11-12-25(18,20)6/h9-12,14-15,18,20-23,32H,2,7-8H2,1,3-6H3/b10-9-/t14-,15-,18-,20+,21-,22-,23-,25+,26+/m0/s1

> <INCHI_KEY>
PECVBLOYWOKDGU-XWMDCASLSA-N

> <FORMULA>
C26H33ClO8

> <MOLECULAR_WEIGHT>
508.99

> <EXACT_MASS>
508.1863957

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
51.20728381740146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,4R,7R,8S,10Z,12S,13S,17R)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadeca-10,14-dien-12-yl butanoate

> <JCHEM_LOGP>
3.4599246463333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.33845216285296

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.371354706751053

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9485689762225933

> <JCHEM_POLAR_SURFACE_AREA>
116.20000000000003

> <JCHEM_REFRACTIVITY>
127.95629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4R,7R,8S,10Z,12S,13S,17R)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadeca-10,14-dien-12-yl butanoate

> <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      -5.519   9.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.839   7.554   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.505   6.784   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.879   5.377   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.199   3.871   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.865   3.101   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.532   3.871   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.532   5.411   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.198   3.101   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.136   3.871   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.469   3.101   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.343   2.840   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.812   2.679   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.438   1.594   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.065   0.188   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.596   0.027   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.222  -1.380   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -7.501   1.273   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.033   1.112   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.875   2.679   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.209   3.449   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -9.353   2.419   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -10.818   2.895   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -11.962   1.864   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -11.138   4.401   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -8.835   4.856   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -9.605   3.523   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -10.367   4.695   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -11.873   5.015   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.993   6.102   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -12.499   6.422   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -9.848   7.133   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -8.515   6.363   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.370   7.393   0.000  0.00  0.00           C+0
HETATM   35 Cl   UNK     0      -7.997   8.800   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    5   13   14   20                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12   21                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   28   33                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   26   34                                                  
CONECT   34   33    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,3R,4R,7R,8S,10Z,12S,13S,17R)-2-(Acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0,]heptadeca-10,14-dien-12-yl butanoic acid	Generator

Chemical Formula

C₂₆H₃₃ClO₈

Average Mass

508.9900 Da

Monoisotopic Mass

508.18640 Da

IUPAC Name

(1S,2S,3R,4R,7R,8S,10Z,12S,13S,17R)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadeca-10,14-dien-12-yl butanoate

Traditional Name

(1S,2S,3R,4R,7R,8S,10Z,12S,13S,17R)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadeca-10,14-dien-12-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@H]1\C=C/C(=C)[C@H](Cl)[C@@H]2OC(=O)[C@H](C)[C@@]2(O)[C@@H](OC(C)=O)[C@H]2[C@@H](C)C(=O)C=C[C@]12C

InChI Identifier

InChI=1S/C26H33ClO8/c1-7-8-19(30)34-18-10-9-13(2)21(27)23-26(32,15(4)24(31)35-23)22(33-16(5)28)20-14(3)17(29)11-12-25(18,20)6/h9-12,14-15,18,20-23,32H,2,7-8H2,1,3-6H3/b10-9-/t14-,15-,18-,20+,21-,22-,23-,25+,26+/m0/s1

InChI Key

PECVBLOYWOKDGU-XWMDCASLSA-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
Tritonia tetraquetra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Tricarboxylic acid or derivatives
Cyclohexenone
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Cyclic ketone
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Alkyl halide
Organooxygen compound
Organochloride
Organohalogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.46	ChemAxon
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	127.96 m³·mol⁻¹	ChemAxon
Polarizability	51.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

13894909

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate (NP0287919)

MOL for NP0287919 ((1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate)

3D MOL for NP0287919 ((1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate)

3D SDF for NP0287919 ((1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate)

3D-SDF for NP0287919 ((1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate)

PDB for NP0287919 ((1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate)

3D PDB for NP0287919 ((1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate)

SMILES for NP0287919 ((1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate)

INCHI for NP0287919 ((1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate)

Structure for NP0287919 ((1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate)

3D Structure for NP0287919 ((1s,2s,3r,4r,7r,8s,10z,12s,13s,17r)-2-(acetyloxy)-8-chloro-3-hydroxy-4,13,17-trimethyl-9-methylidene-5,16-dioxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-10,14-dien-12-yl butanoate)