NP-MRD: Showing NP-Card for (1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione (NP0261923)

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Record Information

Version

2.0

Created at

2022-09-08 04:30:42 UTC

Updated at

2022-09-08 04:30:42 UTC

NP-MRD ID

NP0261923

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione

Description

Subtrifloralactone E 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. (1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione is found in Deprea subtriflora. Based on a literature review very few articles have been published on Subtrifloralactone E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082206302D          

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M  END

     RDKit          3D

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  Mrv1652309082206302D          

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M  END
> <DATABASE_ID>
NP0261923

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC(OC(=O)[C@@H]1C)[C@](C)(O)[C@H]1[C@@H](O)C[C@@H]2[C@@H]1C(=O)C[C@H]1[C@H]2CC=C2C=CCC(=O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O6/c1-13-10-22(33-25(31)14(13)2)27(4,32)24-20(29)11-17-16-9-8-15-6-5-7-21(30)26(15,3)18(16)12-19(28)23(17)24/h5-6,8,13-14,16-18,20,22-24,29,32H,7,9-12H2,1-4H3/t13-,14+,16-,17-,18-,20-,22?,23+,24-,26-,27-/m0/s1

> <INCHI_KEY>
NVKJYOVOBGGULO-RYRMUPRVSA-N

> <FORMULA>
C27H36O6

> <MOLECULAR_WEIGHT>
456.579

> <EXACT_MASS>
456.251188879

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.11805297693037

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,13S,14R,15S)-14-[(1R)-1-[(4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-13-hydroxy-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,7-diene-3,16-dione

> <JCHEM_LOGP>
2.399047882333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.808143694061922

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.660349945891149

> <JCHEM_PKA_STRONGEST_BASIC>
-2.877526243655133

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
124.31099999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11S,13S,14R,15S)-14-[(1R)-1-[(4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-13-hydroxy-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,7-diene-3,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.366  -8.084   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.837  -7.079   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.566  -4.918   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.998  -6.808   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.284  -6.510   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.417  -8.505   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.472  -9.721   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.053 -11.147   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.947  -9.510   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.001 -10.726   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9   28                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   16   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   13   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   12    8                                                  
CONECT   29    4   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    2   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₆

Average Mass

456.5790 Da

Monoisotopic Mass

456.25119 Da

IUPAC Name

(1S,2R,10S,11S,13S,14R,15S)-14-[(1R)-1-[(4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-13-hydroxy-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,7-diene-3,16-dione

Traditional Name

(1S,2R,10S,11S,13S,14R,15S)-14-[(1R)-1-[(4S,5R)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-13-hydroxy-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,7-diene-3,16-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1CC(OC(=O)[C@@H]1C)[C@](C)(O)[C@H]1[C@@H](O)C[C@@H]2[C@@H]1C(=O)C[C@H]1[C@H]2CC=C2C=CCC(=O)[C@]12C

InChI Identifier

InChI=1S/C27H36O6/c1-13-10-22(33-25(31)14(13)2)27(4,32)24-20(29)11-17-16-9-8-15-6-5-7-21(30)26(15,3)18(16)12-19(28)23(17)24/h5-6,8,13-14,16-18,20,22-24,29,32H,7,9-12H2,1-4H3/t13-,14+,16-,17-,18-,20-,22?,23+,24-,26-,27-/m0/s1

InChI Key

NVKJYOVOBGGULO-RYRMUPRVSA-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
Deprea subtriflora	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
20-hydroxysteroid
16-hydroxysteroid
16-beta-hydroxysteroid
Oxosteroid
12-oxosteroid
1-oxosteroid
Hydroxysteroid
Steroid
Cyclohexenone
Delta_valerolactone
Delta valerolactone
Oxane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.4	ChemAxon
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	124.31 m³·mol⁻¹	ChemAxon
Polarizability	51.12 Å³	ChemAxon
Number of Rings	5	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

9234679

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11059522

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione (NP0261923)

MOL for NP0261923 ((1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione)

3D MOL for NP0261923 ((1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione)

3D SDF for NP0261923 ((1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione)

3D-SDF for NP0261923 ((1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione)

PDB for NP0261923 ((1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione)

3D PDB for NP0261923 ((1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione)

SMILES for NP0261923 ((1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione)

INCHI for NP0261923 ((1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione)

Structure for NP0261923 ((1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione)

3D Structure for NP0261923 ((1r,2s,3as,3bs,9ar,9bs,11as)-1-[(1r)-1-[(4s,5r)-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-2-hydroxy-9a-methyl-1h,2h,3h,3ah,3bh,4h,8h,9bh,10h,11ah-cyclopenta[a]phenanthrene-9,11-dione)