NP-MRD: Showing NP-Card for (2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate (NP0322898)

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Record Information

Version

2.0

Created at

2022-09-12 01:57:52 UTC

Updated at

2022-09-12 01:57:52 UTC

NP-MRD ID

NP0322898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate

Description

Salpichrolide E belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. (2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate is found in Salpichroa origanifolia. It was first documented in 2021 (PMID: 33535944). Based on a literature review very few articles have been published on Salpichrolide E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203572D          

 33 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309122203572D          

 33 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0322898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](C[C@H](OC=O)[C@@H](C)C1=CC=C2[C@@H]3C[C@@H]4O[C@@]44CC=CC(=O)[C@]4(C)[C@H]3CCC2=C1)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O5/c1-16(18(3)30)12-24(32-15-29)17(2)19-7-9-21-20(13-19)8-10-23-22(21)14-26-28(33-26)11-5-6-25(31)27(23,28)4/h5-7,9,13,15-17,22-24,26H,8,10-12,14H2,1-4H3/t16-,17-,22-,23-,24-,26-,27-,28-/m0/s1

> <INCHI_KEY>
QOJVHSLLYFXPDM-SHUNRACASA-N

> <FORMULA>
C28H34O5

> <MOLECULAR_WEIGHT>
450.575

> <EXACT_MASS>
450.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.32756642870385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,5S)-5-methyl-2-[(1S,2R,7R,9S,11R)-2-methyl-3-oxo-8-oxapentacyclo[9.8.0.0^{2,7}.0^{7,9}.0^{12,17}]nonadeca-4,12,14,16-tetraen-15-yl]-6-oxoheptan-3-yl formate

> <JCHEM_LOGP>
5.197233797666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.229839299517632

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.629036360009287

> <JCHEM_PKA_STRONGEST_BASIC>
-4.18267780698016

> <JCHEM_POLAR_SURFACE_AREA>
72.97

> <JCHEM_REFRACTIVITY>
126.21359999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,5S)-5-methyl-2-[(1S,2R,7R,9S,11R)-2-methyl-3-oxo-8-oxapentacyclo[9.8.0.0^{2,7}.0^{7,9}.0^{12,17}]nonadeca-4,12,14,16-tetraen-15-yl]-6-oxoheptan-3-yl formate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.978  -8.264   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.208  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -8.978  -5.596   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.898  -8.264   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.898  -5.596   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.358  -5.596   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.588  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.048  -6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.278  -8.264   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.588  -4.263   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.358  -2.929   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.048  -4.263   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.278  -2.929   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.262  -2.929   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.032  -4.263   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.262  -5.596   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.278  -5.596   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.032  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.572  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.342  -5.596   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.572  -4.263   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.342  -2.929   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.882  -2.929   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.422  -2.929   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.652  -4.263   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.192  -4.263   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.962  -5.596   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.192  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.652  -6.930   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.882  -8.264   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.882  -5.596   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.112  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   32                                                  
CONECT   22   21   16   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   26                                                       
CONECT   26   25   24   27   32                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   21   26   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

C₂₈H₃₄O₅

Average Mass

450.5750 Da

Monoisotopic Mass

450.24062 Da

IUPAC Name

(2S,3S,5S)-5-methyl-2-[(1S,2R,7R,9S,11R)-2-methyl-3-oxo-8-oxapentacyclo[9.8.0.0^{2,7}.0^{7,9}.0^{12,17}]nonadeca-4,12,14,16-tetraen-15-yl]-6-oxoheptan-3-yl formate

Traditional Name

(2S,3S,5S)-5-methyl-2-[(1S,2R,7R,9S,11R)-2-methyl-3-oxo-8-oxapentacyclo[9.8.0.0^{2,7}.0^{7,9}.0^{12,17}]nonadeca-4,12,14,16-tetraen-15-yl]-6-oxoheptan-3-yl formate

CAS Registry Number

Not Available

SMILES

C[C@@H](C[C@H](OC=O)[C@@H](C)C1=CC=C2[C@@H]3C[C@@H]4O[C@@]44CC=CC(=O)[C@]4(C)[C@H]3CCC2=C1)C(C)=O

InChI Identifier

InChI=1S/C28H34O5/c1-16(18(3)30)12-24(32-15-29)17(2)19-7-9-21-20(13-19)8-10-23-22(21)14-26-28(33-26)11-5-6-25(31)27(23,28)4/h5-7,9,13,15-17,22-24,26H,8,10-12,14H2,1-4H3/t16-,17-,22-,23-,24-,26-,27-,28-/m0/s1

InChI Key

QOJVHSLLYFXPDM-SHUNRACASA-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
Salpichroa origanifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Tetralin
Cyclohexenone
Oxepane
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	5.2	ChemAxon
pKa (Strongest Acidic)	14.63	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.97 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.21 m³·mol⁻¹	ChemAxon
Polarizability	50.33 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

101999889

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Monadi T, Azadbakht M, Ahmadi A, Chabra A: A Comprehensive Review on the Ethnopharmacology, Phytochemistry, Pharmacology, and Toxicology of the Mandragora Genus; from Folk Medicine to Modern Medicine. Curr Pharm Des. 2021;27(34):3609-3637. doi: 10.2174/1381612827666210203143445. [PubMed:33535944 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate (NP0322898)

MOL for NP0322898 ((2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate)

3D MOL for NP0322898 ((2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate)

3D SDF for NP0322898 ((2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate)

3D-SDF for NP0322898 ((2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate)

PDB for NP0322898 ((2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate)

3D PDB for NP0322898 ((2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate)

SMILES for NP0322898 ((2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate)

INCHI for NP0322898 ((2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate)

Structure for NP0322898 ((2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate)

3D Structure for NP0322898 ((2s,3s,5s)-2-[(4ar,5as,6ar,12as,12br)-12b-methyl-1-oxo-4h,5ah,6h,6ah,11h,12h,12ah-chryseno[6,6a-b]oxiren-9-yl]-5-methyl-6-oxoheptan-3-yl formate)