NP-MRD: Showing NP-Card for 11-Deoxo-6-oxo-5alpha,6-dihydrojervine (NP0069410)

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Record Information

Version

2.0

Created at

2022-04-28 14:45:29 UTC

Updated at

2022-04-28 14:45:29 UTC

NP-MRD ID

NP0069410

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Deoxo-6-oxo-5alpha,6-dihydrojervine

Description

Peimisine belongs to the class of organic compounds known as jerveratrum-type alkaloids. These are steroidal alkaloids with a structure that is based on the jervane ring system. Jerveratrum alkaloids have alkamines with 1-3 oxygen atoms, and occur as such or as monoglycosides. 11-Deoxo-6-oxo-5alpha,6-dihydrojervine is found in Fritillaria anhuiensis, Fritillaria cirrhosa, Fritillaria ebeiensis var. purpurea, Fritillaria hupehensis , Fritillaria monantha, Fritillaria ningguoensis, Fritillaria pallidiflora , Fritillaria roylei , Fritillaria siechuanica, Fritillaria taipaiensis, Fritillaria thunbergii , Fritillaria unibracteata, Fritillaria ussuriensis , Fritillaria wabuensia and Fritillaria walujewii . 11-Deoxo-6-oxo-5alpha,6-dihydrojervine was first documented in 2021 (PMID: 34650616). Based on a literature review a small amount of articles have been published on Peimisine (PMID: 35011398) (PMID: 34939324) (PMID: 34205249) (PMID: 34136153).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216452D          

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    6.6729    1.1806    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.4594   -0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3425    0.6590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  7 29  1  1  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282216452D          

 31 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0069410

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2NC[C@@H](C)C[C@H]2O[C@]11CC[C@H]2[C@@H]3CC(=O)[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC2=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C27H41NO3/c1-14-9-24-25(28-13-14)16(3)27(31-24)8-6-18-19(15(27)2)11-21-20(18)12-23(30)22-10-17(29)5-7-26(21,22)4/h14,16-18,20-22,24-25,28-29H,5-13H2,1-4H3/t14-,16+,17-,18+,20-,21-,22+,24+,25-,26+,27-/m0/s1

> <INCHI_KEY>
KYELXPJVGNZIGC-GKFGJCLESA-N

> <FORMULA>
C27H41NO3

> <MOLECULAR_WEIGHT>
427.629

> <EXACT_MASS>
427.308644184

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.51682949285041

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3'R,3'aS,4aS,6'S,6aR,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',4a,5,5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-icosahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-5-one

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
3.2787955483333335

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.418424241734304

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.234279099870616

> <JCHEM_PKA_STRONGEST_BASIC>
9.934024597163146

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
121.98639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3'R,3'aS,4aS,6'S,6aR,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',4a,5',6,6',6a,6b,7,7',7'a,8,11,11a-octadecahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      13.580  -0.664   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.541   0.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.979   1.974   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.456   2.204   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.495   1.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.058  -0.434   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.973   1.230   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.411   2.664   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.371   3.868   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.894   3.637   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.855   4.841   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.873   2.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.485   1.082   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.001   0.673   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.904   1.754   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.292   3.244   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.777   3.653   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.700   2.715   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.415   1.867   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.824   0.382   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.362   0.312   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.210  -0.973   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       1.743  -0.715   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       0.253  -0.327   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.157   1.158   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.925   2.255   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.647   1.546   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.092  -0.864   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.783   0.252   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.535  -0.204   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      16.064   0.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   30                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   29                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14   29                                                  
CONECT   14   13   15   28                                                  
CONECT   15   14   16   18   21                                             
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   15   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   19                                                       
CONECT   27   25                                                            
CONECT   28   14                                                            
CONECT   29   13    7                                                       
CONECT   30    5                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Value	Source
Peimissine	MeSH

Chemical Formula

C₂₇H₄₁NO₃

Average Mass

427.6290 Da

Monoisotopic Mass

427.30864 Da

IUPAC Name

(3S,3'R,3'aS,4aS,6'S,6aR,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',4a,5,5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-icosahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-5-one

Traditional Name

(3S,3'R,3'aS,4aS,6'S,6aR,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',4a,5',6,6',6a,6b,7,7',7'a,8,11,11a-octadecahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-5-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2NC[C@@H](C)C[C@H]2O[C@]11CC[C@H]2[C@@H]3CC(=O)[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC2=C1C

InChI Identifier

InChI=1S/C27H41NO3/c1-14-9-24-25(28-13-14)16(3)27(31-24)8-6-18-19(15(27)2)11-21-20(18)12-23(30)22-10-17(29)5-7-26(21,22)4/h14,16-18,20-22,24-25,28-29H,5-13H2,1-4H3/t14-,16+,17-,18+,20-,21-,22+,24+,25-,26+,27-/m0/s1

InChI Key

KYELXPJVGNZIGC-GKFGJCLESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Fritillaria anhuiensis	Plant	KNApSAcK
Fritillaria cirrhosa	LOTUS Database	35616633
Fritillaria ebeiensis var. purpurea	Plant	KNApSAcK
Fritillaria hupehensis	Plant	KNApSAcK
Fritillaria monantha	Plant	KNApSAcK
Fritillaria ningguoensis	Plant	KNApSAcK
Fritillaria pallidiflora	Plant	KNApSAcK
Fritillaria roylei	Plant	KNApSAcK
Fritillaria siechuanica	Plant	KNApSAcK
Fritillaria taipaiensis	Plant	KNApSAcK
Fritillaria thunbergii	Plant	KNApSAcK
Fritillaria unibracteata	LOTUS Database	35616633
Fritillaria ussuriensis	Plant	KNApSAcK
Fritillaria wabuensia	Plant	KNApSAcK
Fritillaria walujewii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jerveratrum-type alkaloids. These are steroidal alkaloids with a structure that is based on the jervane ring system. Jerveratrum alkaloids have alkamines with 1-3 oxygen atoms, and occur as such or as monoglycosides.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Jerveratrum-type alkaloids

Alternative Parents

Substituents

Jerveratrum-type alkaloid
Azasteroid
Alkaloid or derivatives
Piperidine
Cyclic alcohol
Tetrahydrofuran
Ketone
Secondary alcohol
Dialkyl ether
Secondary aliphatic amine
Ether
Oxacycle
Secondary amine
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
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	3.28	ALOGPS
logP	3.28	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	15.23	ChemAxon
pKa (Strongest Basic)	9.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	121.99 m³·mol⁻¹	ChemAxon
Polarizability	51.52 Å³	ChemAxon
Number of Rings	6	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

141684

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161294

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu W, Wei L, Kanai Y, He X: Studies on the Incompatibility between Bulbus fritillariae and Radix aconiti praeparata Based on the P-gp. Evid Based Complement Alternat Med. 2021 Oct 5;2021:8351717. doi: 10.1155/2021/8351717. eCollection 2021. [PubMed:34650616 ]
Shim KS, Gu DR, Hwang YH, Yang H, Ryuk JA, Ha H: Water Extract of Fritillariae thunbergii Bulbus Inhibits RANKL-Mediated Osteoclastogenesis and Ovariectomy-Induced Trabecular Bone Loss. Molecules. 2021 Dec 28;27(1). pii: molecules27010169. doi: 10.3390/molecules27010169. [PubMed:35011398 ]
Jin X, Gao X, Lan M, Li CN, Sun JM, Zhang H: Study the mechanism of peimisine derivatives on NF-kappaB inflammation pathway on mice with acute lung injury induced by lipopolysaccharide. Chem Biol Drug Des. 2022 May;99(5):717-726. doi: 10.1111/cbdd.14013. Epub 2022 Jan 1. [PubMed:34939324 ]
Ghanem SS, Fayed HS, Zhu Q, Lu JH, Vaikath NN, Ponraj J, Mansour S, El-Agnaf OMA: Natural Alkaloid Compounds as Inhibitors for Alpha-Synuclein Seeded Fibril Formation and Toxicity. Molecules. 2021 Jun 19;26(12). pii: molecules26123736. doi: 10.3390/molecules26123736. [PubMed:34205249 ]
Ma B, Ma J, Li B, Tao Q, Gan J, Yan Z: Effects of different harvesting times and processing methods on the quality of cultivated Fritillaria cirrhosa D. Don. Food Sci Nutr. 2021 Mar 15;9(6):2853-2861. doi: 10.1002/fsn3.2241. eCollection 2021 Jun. [PubMed:34136153 ]

Showing NP-Card for 11-Deoxo-6-oxo-5alpha,6-dihydrojervine (NP0069410)

MOL for NP0069410 (11-Deoxo-6-oxo-5alpha,6-dihydrojervine)

3D MOL for NP0069410 (11-Deoxo-6-oxo-5alpha,6-dihydrojervine)

3D SDF for NP0069410 (11-Deoxo-6-oxo-5alpha,6-dihydrojervine)

3D-SDF for NP0069410 (11-Deoxo-6-oxo-5alpha,6-dihydrojervine)

PDB for NP0069410 (11-Deoxo-6-oxo-5alpha,6-dihydrojervine)

3D PDB for NP0069410 (11-Deoxo-6-oxo-5alpha,6-dihydrojervine)

SMILES for NP0069410 (11-Deoxo-6-oxo-5alpha,6-dihydrojervine)

INCHI for NP0069410 (11-Deoxo-6-oxo-5alpha,6-dihydrojervine)

Structure for NP0069410 (11-Deoxo-6-oxo-5alpha,6-dihydrojervine)

3D Structure for NP0069410 (11-Deoxo-6-oxo-5alpha,6-dihydrojervine)