NP-MRD: Showing NP-Card for Myltaylorione B (NP0075595)

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Record Information

Version

2.0

Created at

2022-04-28 20:51:33 UTC

Updated at

2022-04-28 20:51:34 UTC

NP-MRD ID

NP0075595

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Myltaylorione B

Description

(1S,1'S,2S,2'S,4S,4'R,7'R,8'R)-6-[(1R,3R)-2,2-dimethyl-3-(3-oxobutyl)cyclopropyl]-3',3',5,7'-tetramethylspiro[bicyclo[2.2.1]Heptane-2,11'-tetracyclo[5.4.0.0¹,⁸.0²,⁴]Undecan]-5-en-10'-one belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Myltaylorione B is found in Mylia taylorii. Based on a literature review very few articles have been published on (1S,1'S,2S,2'S,4S,4'R,7'R,8'R)-6-[(1R,3R)-2,2-dimethyl-3-(3-oxobutyl)cyclopropyl]-3',3',5,7'-tetramethylspiro[bicyclo[2.2.1]Heptane-2,11'-tetracyclo[5.4.0.0¹,⁸.0²,⁴]Undecan]-5-en-10'-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222512D          

 32 38  0  0  1  0            999 V2000
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  4 32  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282222512D          

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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 23 30  1  0  0  0  0
 23 31  1  0  0  0  0
  4 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0075595

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CC[C@@H]1[C@@H](C2=C(C)[C@H]3C[C@@H]2[C@]2(C3)C(=O)C[C@@H]3[C@@]4(C)CC[C@@H]5[C@@H](C5(C)C)[C@@]234)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O2/c1-15(31)8-9-18-24(26(18,3)4)23-16(2)17-12-20(23)29(14-17)22(32)13-21-28(7)11-10-19-25(27(19,5)6)30(21,28)29/h17-21,24-25H,8-14H2,1-7H3/t17-,18+,19+,20-,21+,24-,25-,28+,29+,30-/m0/s1

> <INCHI_KEY>
XCZLPIZRULKIIM-KYEXHSOWSA-N

> <FORMULA>
C30H42O2

> <MOLECULAR_WEIGHT>
434.664

> <EXACT_MASS>
434.318480592

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.88764050396243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,1'S,2S,2'S,4S,4'R,7'R,8'R)-6-[(1R,3R)-2,2-dimethyl-3-(3-oxobutyl)cyclopropyl]-3',3',5,7'-tetramethylspiro[bicyclo[2.2.1]heptane-2,11'-tetracyclo[5.4.0.0^{1,8}.0^{2,4}]undecan]-5-en-10'-one

> <ALOGPS_LOGP>
4.66

> <JCHEM_LOGP>
5.074697273

> <ALOGPS_LOGS>
-5.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.864136936677383

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.245636296611945

> <JCHEM_PKA_STRONGEST_BASIC>
-7.070970671856535

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
127.74579999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,1'S,2S,2'S,4S,4'R,7'R,8'R)-6-[(1R,3R)-2,2-dimethyl-3-(3-oxobutyl)cyclopropyl]-3',3',5,7'-tetramethylspiro[bicyclo[2.2.1]heptane-2,11'-tetracyclo[5.4.0.0^{1,8}.0^{2,4}]undecan]-5-en-10'-one

> <JCHEM_VEBER_RULE>
1

$$$$

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       2.111   3.509   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.642   3.970   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.492   2.928   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.157   1.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.312   0.964   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.229   2.015   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.580   3.047   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.004   2.460   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.619   4.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.178  -0.078   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.819  -1.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.349  -1.302   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.391  -2.437   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.654   0.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.892  -0.709   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.304  -0.094   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.478   1.436   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.240   2.352   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.828   1.737   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.683   0.865   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.890   2.051   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.542  -1.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.072  -1.184   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.157  -2.422   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.983  -3.952   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.221  -4.868   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.047  -6.398   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.286  -7.313   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.635  -7.012   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.877   0.130   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.582  -1.490   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.660   1.089   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10   32                                             
CONECT    5    4    6   10   14                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    1    8    9                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15   19                                             
CONECT   15   14   16   20                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   15                                                       
CONECT   21   17                                                            
CONECT   22   16   23   24                                                  
CONECT   23   22   24   30   31                                             
CONECT   24   23   22   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   23                                                            
CONECT   31   23                                                            
CONECT   32    4                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₂

Average Mass

434.6640 Da

Monoisotopic Mass

434.31848 Da

IUPAC Name

(1S,1'S,2S,2'S,4S,4'R,7'R,8'R)-6-[(1R,3R)-2,2-dimethyl-3-(3-oxobutyl)cyclopropyl]-3',3',5,7'-tetramethylspiro[bicyclo[2.2.1]heptane-2,11'-tetracyclo[5.4.0.0^{1,8}.0^{2,4}]undecan]-5-en-10'-one

Traditional Name

(1S,1'S,2S,2'S,4S,4'R,7'R,8'R)-6-[(1R,3R)-2,2-dimethyl-3-(3-oxobutyl)cyclopropyl]-3',3',5,7'-tetramethylspiro[bicyclo[2.2.1]heptane-2,11'-tetracyclo[5.4.0.0^{1,8}.0^{2,4}]undecan]-5-en-10'-one

CAS Registry Number

Not Available

SMILES

CC(=O)CC[C@@H]1[C@@H](C2=C(C)[C@H]3C[C@@H]2[C@]2(C3)C(=O)C[C@@H]3[C@@]4(C)CC[C@@H]5[C@@H](C5(C)C)[C@@]234)C1(C)C

InChI Identifier

InChI=1S/C30H42O2/c1-15(31)8-9-18-24(26(18,3)4)23-16(2)17-12-20(23)29(14-17)22(32)13-21-28(7)11-10-19-25(27(19,5)6)30(21,28)29/h17-21,24-25H,8-14H2,1-7H3/t17-,18+,19+,20-,21+,24-,25-,28+,29+,30-/m0/s1

InChI Key

XCZLPIZRULKIIM-KYEXHSOWSA-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
Mylia taylori	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

5,10-cycloaromadendrane sesquiterpenoids

Alternative Parents

Substituents

5,10-cycloaromadendrane sesquiterpenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.66	ALOGPS
logP	5.07	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	19.25	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.75 m³·mol⁻¹	ChemAxon
Polarizability	51.89 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

163106534

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Myltaylorione B (NP0075595)

MOL for NP0075595 (Myltaylorione B)

3D MOL for NP0075595 (Myltaylorione B)

3D SDF for NP0075595 (Myltaylorione B)

3D-SDF for NP0075595 (Myltaylorione B)

PDB for NP0075595 (Myltaylorione B)

3D PDB for NP0075595 (Myltaylorione B)

SMILES for NP0075595 (Myltaylorione B)

INCHI for NP0075595 (Myltaylorione B)

Structure for NP0075595 (Myltaylorione B)

3D Structure for NP0075595 (Myltaylorione B)