NP-MRD: Showing NP-Card for (1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate (NP0255499)

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Record Information

Version

1.0

Created at

2022-09-07 20:01:21 UTC

Updated at

2022-09-07 20:01:21 UTC

NP-MRD ID

NP0255499

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate

Description

(1R,2R,3S,7S,8R,9R,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]Octadec-4-en-9-yl acetate belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate is found in Briareum excavatum and Briareum stechei. It was first documented in 2002 (PMID: 35412727). Based on a literature review a significant number of articles have been published on (1R,2R,3S,7S,8R,9R,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]Octadec-4-en-9-yl acetate (PMID: 36099392) (PMID: 31661213) (PMID: 31593386) (PMID: 29589881).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222012D          

 33 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072222012D          

 33 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0255499

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@@H]3C[C@@H](OC(C)=O)[C@@]4(C)[C@H](CC=C(C)[C@@H]4[C@@H](O)[C@]12O3)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H31ClO8/c1-10-7-8-16(30-13(4)26)23(6)17(31-14(5)27)9-15-11(2)19(25)21-24(33-15,20(28)18(10)23)12(3)22(29)32-21/h7,12,15-21,28H,2,8-9H2,1,3-6H3/t12-,15-,16-,17+,18+,19-,20+,21-,23+,24+/m0/s1

> <INCHI_KEY>
KCKRPJJFBBQDGW-DOODRCPXSA-N

> <FORMULA>
C24H31ClO8

> <MOLECULAR_WEIGHT>
482.95

> <EXACT_MASS>
482.1707457

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.74911906074885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,7S,8R,9R,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadec-4-en-9-yl acetate

> <JCHEM_LOGP>
1.6679693356666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.575745921432969

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4217687339652185

> <JCHEM_POLAR_SURFACE_AREA>
108.36

> <JCHEM_REFRACTIVITY>
116.33249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,7S,8R,9R,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadec-4-en-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       1.856   8.366   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.232   6.873   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.783   6.468   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.356   6.779   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.688   5.932   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.954   6.809   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.827   8.344   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.093   9.221   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.435   9.002   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.010   4.396   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.030   5.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.545   4.267   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.423   5.532   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.958   5.403   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.837   6.667   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.614   4.009   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.200   2.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.321   1.609   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.787   1.738   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.908   0.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.131   3.132   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.538   2.869   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.272   1.352   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.077   3.685   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.516   5.021   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.732   2.111   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.810   1.011   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.206   1.806   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.562   0.408   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.456   3.149   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.536   4.263   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.078   5.800   0.000  0.00  0.00           C+0
HETATM   33 Cl   UNK     0      -0.408   6.206   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12   21                                             
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   10   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   31                                             
CONECT   25   24    3                                                       
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   24   32                                                  
CONECT   32   31    2   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,3S,7S,8R,9R,11S,13S,14R,17R)-7-(Acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0,.0,]octadec-4-en-9-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₁ClO₈

Average Mass

482.9500 Da

Monoisotopic Mass

482.17075 Da

IUPAC Name

(1R,2R,3S,7S,8R,9R,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadec-4-en-9-yl acetate

Traditional Name

(1R,2R,3S,7S,8R,9R,11S,13S,14R,17R)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadec-4-en-9-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@@H]3C[C@@H](OC(C)=O)[C@@]4(C)[C@H](CC=C(C)[C@@H]4[C@@H](O)[C@]12O3)OC(C)=O

InChI Identifier

InChI=1S/C24H31ClO8/c1-10-7-8-16(30-13(4)26)23(6)17(31-14(5)27)9-15-11(2)19(25)21-24(33-15,20(28)18(10)23)12(3)22(29)32-21/h7,12,15-21,28H,2,8-9H2,1,3-6H3/t12-,15-,16-,17+,18+,19-,20+,21-,23+,24+/m0/s1

InChI Key

KCKRPJJFBBQDGW-DOODRCPXSA-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
Briareum excavatum	LOTUS Database	35616633
Briareum stechei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Tricarboxylic acid or derivatives
Gamma butyrolactone
Oxane
Pyran
Furan
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Alkyl halide
Organooxygen compound
Alkyl chloride
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	1.67	ChemAxon
pKa (Strongest Acidic)	13.58	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.33 m³·mol⁻¹	ChemAxon
Polarizability	47.75 Å³	ChemAxon
Number of Rings	4	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

10477127

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10743422

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Freebody J: "The Root of All Evil is Inactivity": The Response of French Psychiatrists to New Approaches to Patient Work and Occupation, 1918-1939. 2021. [PubMed:36099392 ]
Authors unspecified: Childhood Pulmonary Inflammatory Myofibroblastic Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:35412727 ]
Authors unspecified: Childhood Adrenocortical Carcinoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31661213 ]
Authors unspecified: Childhood Breast Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593386 ]
Authors unspecified: Cognitive Impairment in Adults with Non-Central Nervous System Cancers (PDQ(R)): Patient Version. 2002. [PubMed:29589881 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate (NP0255499)

MOL for NP0255499 ((1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate)

3D MOL for NP0255499 ((1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate)

3D SDF for NP0255499 ((1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate)

3D-SDF for NP0255499 ((1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate)

PDB for NP0255499 ((1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate)

3D PDB for NP0255499 ((1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate)

SMILES for NP0255499 ((1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate)

INCHI for NP0255499 ((1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate)

Structure for NP0255499 ((1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate)

3D Structure for NP0255499 ((1r,2r,3s,7s,8r,9r,11s,13s,14r,17r)-7-(acetyloxy)-13-chloro-2-hydroxy-4,8,17-trimethyl-12-methylidene-16-oxo-15,18-dioxatetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadec-4-en-9-yl acetate)