NP-MRD: Showing NP-Card for (1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione (NP0256080)

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Record Information

Version

1.0

Created at

2022-09-07 20:47:46 UTC

Updated at

2022-09-07 20:47:46 UTC

NP-MRD ID

NP0256080

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione

Description

Sarocladione belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione is found in Sarocladium kiliense. It was first documented in 2019 (PMID: 31165123). Based on a literature review very few articles have been published on Sarocladione (PMID: 33682234).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222472D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072222472D          

 31 33  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0256080

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2C(=O)[C@@H]3CC(=O)C[C@@H](CC\C(C)=C\CC[C@]12C)O3

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O3/c1-18(2)20(4)10-11-21(5)24-13-14-25-27(30)26-17-22(29)16-23(31-26)12-9-19(3)8-7-15-28(24,25)6/h8,10-11,18,20-21,23-26H,7,9,12-17H2,1-6H3/b11-10+,19-8+/t20-,21+,23+,24+,25-,26-,28+/m0/s1

> <INCHI_KEY>
RGPQXGREEVWBLC-NZQVDVCMSA-N

> <FORMULA>
C28H44O3

> <MOLECULAR_WEIGHT>
428.657

> <EXACT_MASS>
428.329045277

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
50.94906732031749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,6R,7R,10E,14R)-6-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0^{3,7}]octadec-10-ene-2,16-dione

> <JCHEM_LOGP>
7.082592829666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.742365287552573

> <JCHEM_PKA_STRONGEST_BASIC>
-4.224630885533402

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
129.15199999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,6R,7R,10E,14R)-6-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0^{3,7}]octadec-10-ene-2,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.613   0.210   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.842  -1.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.800  -2.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.706  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.800  -0.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.276   1.171   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.596   2.677   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.783   1.491   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.813   0.346   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.319   0.666   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.795   2.131   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.350  -0.478   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.856  -0.158   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.874  -1.943   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   11                                             
CONECT    7    6                                                            
CONECT    8    6    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    8   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29    2                                                       
CONECT   31   28   23                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₄O₃

Average Mass

428.6570 Da

Monoisotopic Mass

428.32905 Da

IUPAC Name

(1S,3R,6R,7R,10E,14R)-6-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0^{3,7}]octadec-10-ene-2,16-dione

Traditional Name

(1S,3R,6R,7R,10E,14R)-6-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0^{3,7}]octadec-10-ene-2,16-dione

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2C(=O)[C@@H]3CC(=O)C[C@@H](CC\C(C)=C\CC[C@]12C)O3

InChI Identifier

InChI=1S/C28H44O3/c1-18(2)20(4)10-11-21(5)24-13-14-25-27(30)26-17-22(29)16-23(31-26)12-9-19(3)8-7-15-28(24,25)6/h8,10-11,18,20-21,23-26H,7,9,12-17H2,1-6H3/b11-10+,19-8+/t20-,21+,23+,24+,25-,26-,28+/m0/s1

InChI Key

RGPQXGREEVWBLC-NZQVDVCMSA-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
Sarocladium kiliense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oxane
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	7.08	ChemAxon
pKa (Strongest Acidic)	15.74	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	129.15 m³·mol⁻¹	ChemAxon
Polarizability	50.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

74786518

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146682276

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fan SQ, Xie CL, Xia JM, Xing CP, Luo ZH, Shao Z, Yan XJ, He S, Yang XW: Sarocladione, a unique 5,10:8,9-diseco-steroid from the deep-sea-derived fungus Sarocladium kiliense. Org Biomol Chem. 2019 Jun 18;17(24):5925-5928. doi: 10.1039/c9ob01159e. [PubMed:31165123 ]
Ning Y, Tian H, Gui J: Biogenesis-Guided Synthesis and Structural Revision of Sarocladione Enabled by Ruthenium-Catalyzed Endoperoxide Fragmentation. Angew Chem Int Ed Engl. 2021 May 10;60(20):11222-11226. doi: 10.1002/anie.202101451. Epub 2021 Apr 12. [PubMed:33682234 ]
LOTUS database [Link]

Showing NP-Card for (1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione (NP0256080)

MOL for NP0256080 ((1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione)

3D MOL for NP0256080 ((1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione)

3D SDF for NP0256080 ((1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione)

3D-SDF for NP0256080 ((1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione)

PDB for NP0256080 ((1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione)

3D PDB for NP0256080 ((1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione)

SMILES for NP0256080 ((1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione)

INCHI for NP0256080 ((1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione)

Structure for NP0256080 ((1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione)

3D Structure for NP0256080 ((1s,3r,6r,7r,10e,14r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-7,11-dimethyl-18-oxatricyclo[12.3.1.0³,⁷]octadec-10-ene-2,16-dione)