NP-MRD: Showing NP-Card for (1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one (NP0245401)

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Record Information

Version

2.0

Created at

2022-09-07 06:28:23 UTC

Updated at

2022-09-07 06:28:23 UTC

NP-MRD ID

NP0245401

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one

Description

Perovskone belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. (1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one is found in Salvia bucharica. (1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one was first documented in 2011 (PMID: 21967089). Based on a literature review a small amount of articles have been published on Perovskone (PMID: 30565934) (PMID: 33886312).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208282D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072208282D          

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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 16  1  1  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 32  1  0  0  0  0
 20 32  1  0  0  0  0
 17 32  1  0  0  0  0
 32 33  1  1  0  0  0
 15 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245401

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2OC(C)(C)[C@H]3CC4C(C)=CC[C@@]5(CCC6[C@@]7(C[C@]45[C@@]23O7)CCCC6(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O3/c1-17(2)22-23(31)27-13-9-18(3)19-15-21-26(6,7)32-24(22)30(21)29(19,27)16-28(33-30)12-8-11-25(4,5)20(28)10-14-27/h9,17,19-21H,8,10-16H2,1-7H3/t19?,20?,21-,27-,28+,29+,30+/m1/s1

> <INCHI_KEY>
DVCBBGWACDEUAQ-IXQQZYDCSA-N

> <FORMULA>
C30H42O3

> <MOLECULAR_WEIGHT>
450.663

> <EXACT_MASS>
450.313395212

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.18319126527371

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9S,11S,12R,16R)-5,5,15,15,19-pentamethyl-23-(propan-2-yl)-14,24-dioxaheptacyclo[11.8.2.1^{9,12}.0^{1,11}.0^{4,9}.0^{11,18}.0^{12,16}]tetracosa-13(23),19-dien-22-one

> <JCHEM_LOGP>
5.721500023666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.172909885513776

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
131.77129999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S,11S,12R,16R)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1^{9,12}.0^{1,11}.0^{4,9}.0^{11,18}.0^{12,16}]tetracosa-13(23),19-dien-22-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.085  -3.025   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.968  -4.085   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.405  -5.424   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.225  -6.203   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.263  -6.008   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.054  -7.030   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.494  -6.360   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.981  -4.582   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.542  -4.580   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.288  -6.099   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.998  -5.083   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.266  -3.253   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.476  -1.922   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.914  -1.922   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.796  -3.122   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.261  -2.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.406  -4.409   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.481  -3.526   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.284  -1.777   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.847  -2.233   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.429  -2.108   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.121  -0.599   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.889  -1.617   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.101  -3.509   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.974  -4.574   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.952  -6.156   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.264  -6.963   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.619  -6.229   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.222  -8.502   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.585  -6.873   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.510  -8.411   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.599  -3.727   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.310  -2.663   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17   30                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    8   16   33                                             
CONECT   16   15   17                                                       
CONECT   17   16    5   18   32                                             
CONECT   18   17    2   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26    5   31                                                  
CONECT   31   30                                                            
CONECT   32   25   20   17   33                                             
CONECT   33   32   15                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₃

Average Mass

450.6630 Da

Monoisotopic Mass

450.31340 Da

IUPAC Name

(1R,9S,11S,12R,16R)-5,5,15,15,19-pentamethyl-23-(propan-2-yl)-14,24-dioxaheptacyclo[11.8.2.1^{9,12}.0^{1,11}.0^{4,9}.0^{11,18}.0^{12,16}]tetracosa-13(23),19-dien-22-one

Traditional Name

(1R,9S,11S,12R,16R)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1^{9,12}.0^{1,11}.0^{4,9}.0^{11,18}.0^{12,16}]tetracosa-13(23),19-dien-22-one

CAS Registry Number

Not Available

SMILES

CC(C)C1=C2OC(C)(C)[C@H]3CC4C(C)=CC[C@@]5(CCC6[C@@]7(C[C@]45[C@@]23O7)CCCC6(C)C)C1=O

InChI Identifier

InChI=1S/C30H42O3/c1-17(2)22-23(31)27-13-9-18(3)19-15-21-26(6,7)32-24(22)30(21)29(19,27)16-28(33-30)12-8-11-25(4,5)20(28)10-14-27/h9,17,19-21H,8,10-16H2,1-7H3/t19?,20?,21-,27-,28+,29+,30+/m1/s1

InChI Key

DVCBBGWACDEUAQ-IXQQZYDCSA-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
Salvia bucharica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Naphthofuran
Cyclohexenone
Oxolane
Vinylogous ester
Ketone
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	5.72	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	131.77 m³·mol⁻¹	ChemAxon
Polarizability	52.18 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

C00000501

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

101629488

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Moridi Farimani M, Bahadori MB, Taheri S, Ebrahimi SN, Zimmermann S, Brun R, Amin G, Hamburger M: Triterpenoids with rare carbon skeletons from Salvia hydrangea: antiprotozoal activity and absolute configurations. J Nat Prod. 2011 Oct 28;74(10):2200-5. doi: 10.1021/np200559c. Epub 2011 Oct 3. [PubMed:21967089 ]
Tabefam M, Moridi Farimani M, Danton O, Ramseyer J, Nejad Ebrahimi S, Neuburger M, Kaiser M, Salehi P, Potterat O, Hamburger M: Antiprotozoal Isoprenoids from Salvia hydrangea. J Nat Prod. 2018 Dec 28;81(12):2682-2691. doi: 10.1021/acs.jnatprod.8b00498. Epub 2018 Dec 19. [PubMed:30565934 ]
Yang B, Wen G, Zhang Q, Hou M, He H, Gao S: Asymmetric Total Synthesis and Biosynthetic Implications of Perovskones, Hydrangenone, and Hydrangenone B. J Am Chem Soc. 2021 May 5;143(17):6370-6375. doi: 10.1021/jacs.1c02674. Epub 2021 Apr 22. [PubMed:33886312 ]
LOTUS database [Link]

Showing NP-Card for (1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one (NP0245401)

MOL for NP0245401 ((1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one)

3D MOL for NP0245401 ((1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one)

3D SDF for NP0245401 ((1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one)

3D-SDF for NP0245401 ((1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one)

PDB for NP0245401 ((1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one)

3D PDB for NP0245401 ((1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one)

SMILES for NP0245401 ((1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one)

INCHI for NP0245401 ((1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one)

Structure for NP0245401 ((1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one)

3D Structure for NP0245401 ((1r,9s,11s,12r,16r)-23-isopropyl-5,5,15,15,19-pentamethyl-14,24-dioxaheptacyclo[11.8.2.1⁹,¹².0¹,¹¹.0⁴,⁹.0¹¹,¹⁸.0¹²,¹⁶]tetracosa-13(23),19-dien-22-one)