NP-MRD: Showing NP-Card for Delta-8-iso-THC (NP0332901)

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Record Information

Version

2.0

Created at

2024-05-01 23:53:22 UTC

Updated at

2024-09-03 04:20:38 UTC

NP-MRD ID

NP0332901

Natural Product DOI

https://doi.org/10.57994/2182

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Delta-8-iso-THC

Description

SCHEMBL13214159 belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Delta-8-iso-THC was first documented in 2024 (PMID: 38427968). Based on a literature review very few articles have been published on SCHEMBL13214159.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01142302302D          

 23 25  0  0  1  0            999 V2000
   -3.5809   -4.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5809   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2953   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2953   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8787   -2.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7037   -2.0208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0194   -1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7037   -4.0126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0194   -4.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8374   -4.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5172   -5.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8787   -4.0126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0422   -2.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5809   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8664   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1519   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7230   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0085   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7059   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8664   -3.4292    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
  6  5  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 10 14  1  0  0  0  0
 14  3  1  0  0  0  0
 14 15  1  6  0  0  0
  6 15  1  0  0  0  0
  4 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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 23  2  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1=CC(O)=C2[C@@H]3C[C@@](C)(CC[C@H]3C(C)=C)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O2/c1-5-6-7-8-15-11-18(22)20-17-13-21(4,23-19(20)12-15)10-9-16(17)14(2)3/h11-12,16-17,22H,2,5-10,13H2,1,3-4H3/t16-,17+,21+/m0/s1

> <INCHI_KEY>
NUXUDGMVYZUFNQ-CSODHUTKSA-N

> <FORMULA>
C21H30O2

> <MOLECULAR_WEIGHT>
314.469

> <EXACT_MASS>
314.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.26712570483541

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9R,12R)-9-methyl-5-pentyl-12-(prop-1-en-2-yl)-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2,4,6-trien-3-ol

> <JCHEM_LOGP>
6.002090777666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.029397650241572

> <JCHEM_PKA_STRONGEST_BASIC>
-4.882620578162212

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
95.661

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,12R)-9-methyl-5-pentyl-12-(prop-1-en-2-yl)-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2,4,6-trien-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 14-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JAN-23         0                                  
HETATM    1  O   UNK     0      -6.684  -8.711   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.684  -7.171   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.018  -6.401   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.018  -4.861   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -9.107  -3.772   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0     -10.647  -3.772   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.236  -2.349   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -11.736  -4.861   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -11.736  -6.401   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.647  -7.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -11.236  -8.913   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.763  -9.114   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.299 -10.135   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.107  -7.490   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.412  -5.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.684  -4.091   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.351  -4.861   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.017  -4.091   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.683  -4.861   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.350  -4.091   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.016  -4.861   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.318  -4.091   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.351  -6.401   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10    3   15                                                  
CONECT   15   14    6                                                       
CONECT   16    4   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   17    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₂

Average Mass

314.4690 Da

Monoisotopic Mass

314.22458 Da

IUPAC Name

(1R,9R,12R)-9-methyl-5-pentyl-12-(prop-1-en-2-yl)-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2,4,6-trien-3-ol

Traditional Name

(1R,9R,12R)-9-methyl-5-pentyl-12-(prop-1-en-2-yl)-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2,4,6-trien-3-ol

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC(O)=C2[C@@H]3C[C@@](C)(CC[C@H]3C(C)=C)OC2=C1

InChI Identifier

InChI=1S/C21H30O2/c1-5-6-7-8-15-11-18(22)20-17-13-21(4,23-19(20)12-15)10-9-16(17)14(2)3/h11-12,16-17,22H,2,5-10,13H2,1,3-4H3/t16-,17+,21+/m0/s1

InChI Key

NUXUDGMVYZUFNQ-CSODHUTKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C2D6OS, experimental)	[email protected]	University of Pavia	Alessio Porta	2024-05-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, CDCl3, experimental)	[email protected]	University of Pavia	Alessio Porta	2024-05-01	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
Moorena sp.		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Organic oxygen compound
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	6	ChemAxon
pKa (Strongest Acidic)	10.03	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.66 m³·mol⁻¹	ChemAxon
Polarizability	38.27 Å³	ChemAxon
Number of Rings	3	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

58828779

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

59444412

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Capucciati A, Casali E, Bini A, Doria F, Merli D, Porta A: Easy and Accessible Synthesis of Cannabinoids from CBD. J Nat Prod. 2024 Apr 26;87(4):869-875. doi: 10.1021/acs.jnatprod.3c01117. Epub 2024 Mar 1. [PubMed:38427968 ]
DOI: 10.1021/acs.jnatprod.3c01117
PMID: 38427968

Showing NP-Card for Delta-8-iso-THC (NP0332901)

MOL for NP0332901 (Delta-8-iso-THC)

3D MOL for NP0332901 (Delta-8-iso-THC)

3D SDF for NP0332901 (Delta-8-iso-THC)

3D-SDF for NP0332901 (Delta-8-iso-THC)

PDB for NP0332901 (Delta-8-iso-THC)

3D PDB for NP0332901 (Delta-8-iso-THC)

SMILES for NP0332901 (Delta-8-iso-THC)

INCHI for NP0332901 (Delta-8-iso-THC)

Structure for NP0332901 (Delta-8-iso-THC)

3D Structure for NP0332901 (Delta-8-iso-THC)