NP-MRD: Showing NP-Card for (3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate (NP0197000)

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Record Information

Version

2.0

Created at

2022-09-04 15:11:06 UTC

Updated at

2022-09-04 15:11:07 UTC

NP-MRD ID

NP0197000

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate

Description

CHEMBL3581568 belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. (3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate is found in Veratrum nigrum. Based on a literature review very few articles have been published on CHEMBL3581568.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217112D          

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M  END


  Mrv1652309042217112D          

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 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 14 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 31  1  6  0  0  0
 13 32  1  0  0  0  0
  8 32  1  0  0  0  0
 10 33  1  0  0  0  0
  5 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197000

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]([C@@H]1NC[C@@H](C)C[C@H]1O)C1=CC=C2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC2=C1C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H41NO3/c1-16-12-27(32)28(30-15-16)18(3)22-8-9-23-24-7-6-20-13-21(33-19(4)31)10-11-29(20,5)26(24)14-25(23)17(22)2/h6,8-9,16,18,21,24,26-28,30,32H,7,10-15H2,1-5H3/t16-,18-,21-,24-,26-,27+,28-,29-/m0/s1

> <INCHI_KEY>
JYLXRDJEJNXLAL-NADQLLQKSA-N

> <FORMULA>
C29H41NO3

> <MOLECULAR_WEIGHT>
451.651

> <EXACT_MASS>
451.308644184

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.66169656592412

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6aR,11aS,11bR)-9-[(1S)-1-[(2S,3R,5S)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1H,2H,3H,4H,6H,6aH,11H,11aH,11bH-cyclohexa[a]fluoren-3-yl acetate

> <JCHEM_LOGP>
4.854311790333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.57388006587032

> <JCHEM_PKA_STRONGEST_BASIC>
9.91318775167225

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
133.24039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6aR,11aS,11bR)-9-[(1S)-1-[(2S,3R,5S)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1H,2H,3H,4H,6H,6aH,11H,11aH-cyclohexa[a]fluoren-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      13.413  -0.870   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.875  -0.782   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.030  -2.069   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.183   0.594   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.645   0.682   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.953   2.057   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.415   2.146   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.570   0.858   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.878   2.234   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.263  -0.517   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.418  -1.805   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.881  -1.717   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.188  -0.341   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.702   0.064   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.407  -0.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.038  -0.063   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.035   1.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.404   2.181   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.699   1.349   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.477   3.720   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -0.181   4.552   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -0.255   6.091   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.623   6.796   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.697   8.335   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.919   5.964   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.846   4.426   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.141   3.593   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.260   2.308   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.187   3.847   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.629   1.603   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.070   2.147   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.033   0.946   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.800  -0.606   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   32                                             
CONECT    9    8                                                            
CONECT   10    8   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13   15   30                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20   27                                                  
CONECT   27   26                                                            
CONECT   28   17   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   14   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   13    8                                                  
CONECT   33   10    5                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₁NO₃

Average Mass

451.6510 Da

Monoisotopic Mass

451.30864 Da

IUPAC Name

(3S,6aR,11aS,11bR)-9-[(1S)-1-[(2S,3R,5S)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1H,2H,3H,4H,6H,6aH,11H,11aH,11bH-cyclohexa[a]fluoren-3-yl acetate

Traditional Name

(3S,6aR,11aS,11bR)-9-[(1S)-1-[(2S,3R,5S)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1H,2H,3H,4H,6H,6aH,11H,11aH-cyclohexa[a]fluoren-3-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]([C@@H]1NC[C@@H](C)C[C@H]1O)C1=CC=C2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC2=C1C)OC(C)=O

InChI Identifier

InChI=1S/C29H41NO3/c1-16-12-27(32)28(30-15-16)18(3)22-8-9-23-24-7-6-20-13-21(33-19(4)31)10-11-29(20,5)26(24)14-25(23)17(22)2/h6,8-9,16,18,21,24,26-28,30,32H,7,10-15H2,1-5H3/t16-,18-,21-,24-,26-,27+,28-,29-/m0/s1

InChI Key

JYLXRDJEJNXLAL-NADQLLQKSA-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
Veratrum nigrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Fluorenes

Sub Class

Not Available

Direct Parent

Fluorenes

Alternative Parents

Substituents

Fluorene
Indane
Aralkylamine
Piperidine
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Organic nitrogen compound
Amine
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	4.85	ChemAxon
pKa (Strongest Acidic)	14.57	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.24 m³·mol⁻¹	ChemAxon
Polarizability	54.66 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

59007063

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122178950

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate (NP0197000)

MOL for NP0197000 ((3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate)

3D MOL for NP0197000 ((3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate)

3D SDF for NP0197000 ((3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate)

3D-SDF for NP0197000 ((3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate)

PDB for NP0197000 ((3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate)

3D PDB for NP0197000 ((3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate)

SMILES for NP0197000 ((3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate)

INCHI for NP0197000 ((3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate)

Structure for NP0197000 ((3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate)

3D Structure for NP0197000 ((3s,6ar,11as,11br)-9-[(1s)-1-[(2s,3r,5s)-3-hydroxy-5-methylpiperidin-2-yl]ethyl]-10,11b-dimethyl-1h,2h,3h,4h,6h,6ah,11h,11ah-cyclohexa[a]fluoren-3-yl acetate)