NP-MRD: Showing NP-Card for (1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione (NP0216401)

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Record Information

Version

2.0

Created at

2022-09-05 16:20:40 UTC

Updated at

2022-09-05 16:20:40 UTC

NP-MRD ID

NP0216401

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione

Description

Cycloatalantin belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. (1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione is found in Atalantia ceylanica. Based on a literature review very few articles have been published on Cycloatalantin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052218202D          

 34 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309052218202D          

 34 40  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0216401

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC[C@]23C=CC(=O)C12C(=O)[C@H](O)[C@]1(C)[C@@H]3CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O8/c1-21(2)25-15(27)6-9-24(25,12-32-21)14-5-8-22(3)18(13-7-10-31-11-13)33-20(30)19-26(22,34-19)23(14,4)16(28)17(25)29/h6-7,9-11,14,16,18-19,28H,5,8,12H2,1-4H3/t14-,16-,18-,19+,22-,23-,24-,25?,26+/m0/s1

> <INCHI_KEY>
IUXAGRKMQRVAMG-CLRAGQPTSA-N

> <FORMULA>
C26H28O8

> <MOLECULAR_WEIGHT>
468.502

> <EXACT_MASS>
468.178417862

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.50628480187911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,6R,9S,11R,12S,13R)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0^{1,15}.0^{2,12}.0^{5,11}.0^{9,11}]henicos-19-ene-8,14,21-trione

> <JCHEM_LOGP>
2.2729533383333322

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.831961016658965

> <JCHEM_PKA_STRONGEST_BASIC>
-2.851145569130609

> <JCHEM_POLAR_SURFACE_AREA>
115.57000000000002

> <JCHEM_REFRACTIVITY>
116.3041

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,6R,9S,11R,12S,13R)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0^{1,15}.0^{2,12}.0^{5,11}.0^{9,11}]henicos-19-ene-8,14,21-trione

> <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      10.564   1.726   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.887   1.009   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.511   2.812   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.423   0.821   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.132  -0.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.866   0.300   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.064  -0.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.355   0.171   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.955   1.659   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.989   3.081   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.417   1.738   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.447   2.934   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.661   4.556   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.926   2.692   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.822   4.219   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.375   1.254   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.775   1.870   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.345   0.058   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.795  -1.380   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.274  -1.622   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.304  -0.426   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.904  -1.969   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.783  -0.668   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.232  -2.106   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.072  -3.397   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.103  -4.595   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.335  -4.044   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.255  -2.506   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.187   0.528   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.364   1.966   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.772   3.102   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.884   2.208   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.405   2.450   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.855   1.012   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   11                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11   18                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    2    6   12                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   34                                             
CONECT   17   16                                                            
CONECT   18   16    6   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   34                                             
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   23   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32   34                                                       
CONECT   34   33   32   21   16                                             
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₈

Average Mass

468.5020 Da

Monoisotopic Mass

468.17842 Da

IUPAC Name

(1S,2R,5S,6R,9S,11R,12S,13R)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0^{1,15}.0^{2,12}.0^{5,11}.0^{9,11}]henicos-19-ene-8,14,21-trione

Traditional Name

(1S,2R,5S,6R,9S,11R,12S,13R)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0^{1,15}.0^{2,12}.0^{5,11}.0^{9,11}]henicos-19-ene-8,14,21-trione

CAS Registry Number

Not Available

SMILES

CC1(C)OC[C@]23C=CC(=O)C12C(=O)[C@H](O)[C@]1(C)[C@@H]3CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1

InChI Identifier

InChI=1S/C26H28O8/c1-21(2)25-15(27)6-9-24(25,12-32-21)14-5-8-22(3)18(13-7-10-31-11-13)33-20(30)19-26(22,34-19)23(14,4)16(28)17(25)29/h6-7,9-11,14,16,18-19,28H,5,8,12H2,1-4H3/t14-,16-,18-,19+,22-,23-,24-,25?,26+/m0/s1

InChI Key

IUXAGRKMQRVAMG-CLRAGQPTSA-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
Atalantia ceylanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Steroid lactone
18-oxosteroid
2-oxosteroid
Oxosteroid
12-oxosteroid
Steroid
Naphthopyran
Naphthalene
Delta_valerolactone
Dioxepane
Delta valerolactone
1,4-dioxepane
Pyran
Oxane
Heteroaromatic compound
Tetrahydrofuran
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.27	ChemAxon
pKa (Strongest Acidic)	12.83	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	115.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	116.3 m³·mol⁻¹	ChemAxon
Polarizability	46.51 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

101664422

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione (NP0216401)

MOL for NP0216401 ((1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione)

3D MOL for NP0216401 ((1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione)

3D SDF for NP0216401 ((1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione)

3D-SDF for NP0216401 ((1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione)

PDB for NP0216401 ((1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione)

3D PDB for NP0216401 ((1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione)

SMILES for NP0216401 ((1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione)

INCHI for NP0216401 ((1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione)

Structure for NP0216401 ((1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione)

3D Structure for NP0216401 ((1s,2r,5s,6s,9s,11r,12s,13r)-6-(furan-3-yl)-13-hydroxy-5,12,16,16-tetramethyl-7,10,17-trioxahexacyclo[13.3.3.0¹,¹⁵.0²,¹².0⁵,¹¹.0⁹,¹¹]henicos-19-ene-8,14,21-trione)