NP-MRD: Showing NP-Card for Thorectidol Acetate (NP0331488)

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Record Information

Version

2.0

Created at

2023-02-02 00:01:45 UTC

Updated at

2024-09-03 04:15:53 UTC

NP-MRD ID

NP0331488

Natural Product DOI

https://doi.org/10.57994/0442

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thorectidol Acetate

Description

Thorectidol Acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thorectidol Acetate was first documented in 2023 (PMID: 36657039). Based on a literature review very few articles have been published on Thorectidol Acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652302022301012D          

 28 30  0  0  0  0            999 V2000
   -2.8697   -0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519   -0.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6216   -1.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037   -2.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913   -2.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037   -3.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7162   -2.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2465   -1.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9643   -0.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 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
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  2  0  0  0  0
 11 22  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
M  END


  Mrv1652302022301012D          

 28 30  0  0  0  0            999 V2000
   -2.8697   -0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519   -0.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6216   -1.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037   -2.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913   -2.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037   -3.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7162   -2.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2465   -1.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9643   -0.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 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
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  2  0  0  0  0
 11 22  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331488

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC(C)=O)=CC2=C1OC(C)(CCC1=C(C)CCCC1(C)C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O4/c1-16-8-7-11-23(3,4)20(16)10-13-24(5)12-9-18-14-19(27-17(2)25)15-21(26-6)22(18)28-24/h9,12,14-15H,7-8,10-11,13H2,1-6H3

> <INCHI_KEY>
VCENDWPOQZUYQM-UHFFFAOYSA-N

> <FORMULA>
C24H32O4

> <MOLECULAR_WEIGHT>
384.516

> <EXACT_MASS>
384.23005951

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.72119579631385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-methoxy-2-methyl-2-[2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethyl]-2H-chromen-6-yl acetate

> <JCHEM_LOGP>
5.3169658470000005

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6343432846233785

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
112.47810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
8-methoxy-2-methyl-2-[2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethyl]chromen-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-FEB-23         0                                  
HETATM    1  C   UNK     0      -5.357  -0.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.883  -1.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.894  -2.752   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.377  -2.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.850  -1.037   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.860   0.677   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.420  -4.199   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.904  -4.467   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.420  -5.739   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.937  -4.467   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.927  -3.287   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.400  -1.840   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6   12                                                       
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   11                                                       
CONECT   23    3   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    2                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
Thorectidol acetic acid	Generator

Chemical Formula

C₂₄H₃₂O₄

Average Mass

384.5160 Da

Monoisotopic Mass

384.23006 Da

IUPAC Name

8-methoxy-2-methyl-2-[2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethyl]-2H-chromen-6-yl acetate

Traditional Name

8-methoxy-2-methyl-2-[2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethyl]chromen-6-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(OC(C)=O)=CC2=C1OC(C)(CCC1=C(C)CCCC1(C)C)C=C2

InChI Identifier

InChI=1S/C24H32O4/c1-16-8-7-11-23(3,4)20(16)10-13-24(5)12-9-18-14-19(27-17(2)25)15-21(26-6)22(18)28-24/h9,12,14-15H,7-8,10-11,13H2,1-6H3

InChI Key

VCENDWPOQZUYQM-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C6D6, experimental)	davewill@chem.ubc.ca	Not Available	Not Available	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C6D6, experimental)	davewill@chem.ubc.ca	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C6D6, experimental)	davewill@chem.ubc.ca	Not Available	Not Available	2024-05-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C6D6, experimental)	davewill@chem.ubc.ca	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C6D6, experimental)	davewill@chem.ubc.ca	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C6D6, experimental)	davewill@chem.ubc.ca	Not Available	Not Available	2024-05-11	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C6D6, experimental)	davewill@chem.ubc.ca	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dactylospongia elegans		Not Available

Chemical Taxonomy

Description

This compound 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

Farsesane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Sesquiterpenoid
1-benzopyran
Benzopyran
Anisole
Alkyl aryl ether
Benzenoid
Pyran
Enol ester
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	5.32	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.48 m³·mol⁻¹	ChemAxon
Polarizability	43.72 Å³	ChemAxon
Number of Rings	3	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

171354790

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Williams DE, Cassel J, Zhu JL, Yang JX, de Voogd NJ, Matainaho T, Salvino JM, Wang YA, Montaner LJ, Tietjen I, Andersen RJ: Thorectidiol A Isolated from the Marine Sponge Dactylospongia elegans Disrupts Interactions of the SARS-CoV-2 Spike Receptor Binding Domain with the Host ACE2 Receptor. J Nat Prod. 2023 Mar 24;86(3):582-588. doi: 10.1021/acs.jnatprod.2c01030. Epub 2023 Jan 19. [PubMed:36657039 ]
DOI: 10.1021/acs.jnatprod.2c01030
PMID: 36657039

Showing NP-Card for Thorectidol Acetate (NP0331488)

MOL for NP0331488 (Thorectidol Acetate)

3D MOL for NP0331488 (Thorectidol Acetate)

3D SDF for NP0331488 (Thorectidol Acetate)

3D-SDF for NP0331488 (Thorectidol Acetate)

PDB for NP0331488 (Thorectidol Acetate)

3D PDB for NP0331488 (Thorectidol Acetate)

SMILES for NP0331488 (Thorectidol Acetate)

INCHI for NP0331488 (Thorectidol Acetate)

Structure for NP0331488 (Thorectidol Acetate)

3D Structure for NP0331488 (Thorectidol Acetate)