NP-MRD: Showing NP-Card for CCB (NP0332905)

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Record Information

Version

2.0

Created at

2024-05-02 00:22:30 UTC

Updated at

2024-09-03 04:20:38 UTC

NP-MRD ID

NP0332905

Natural Product DOI

https://doi.org/10.57994/2186

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CCB

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01142302592D          

 27 30  0  0  1  0            999 V2000
   -0.6788   -0.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1406   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0931   -0.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965    0.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    1.2580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2322    2.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721    1.0682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1189    1.8788    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092    0.2780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3340    0.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8720   -0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5994   -1.1448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6827   -0.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9553    0.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7660    0.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3040    0.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1146    0.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6526   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4633   -0.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4173    1.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6067    1.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9504    1.5379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8276   -0.4831    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435   -0.3224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7748   -1.1300    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171    0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7590    0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  7  5  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  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
 14 20  2  0  0  0  0
 10 21  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
  9 23  1  6  0  0  0
  9 24  1  0  0  0  0
 24  2  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
M  END


  Mrv2104 01142302592D          

 27 30  0  0  1  0            999 V2000
   -0.6788   -0.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1406   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0931   -0.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0965    0.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    1.2580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2322    2.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721    1.0682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1189    1.8788    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092    0.2780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3340    0.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8720   -0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5994   -1.1448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6827   -0.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9553    0.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7660    0.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3040    0.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1146    0.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6526   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4633   -0.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4173    1.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6067    1.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9504    1.5379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8276   -0.4831    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435   -0.3224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7748   -1.1300    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171    0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7590    0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  7  5  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  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
 14 20  2  0  0  0  0
 10 21  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
  9 23  1  6  0  0  0
  9 24  1  0  0  0  0
 24  2  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332905

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12OC3=C(C(O)=CC(CCCCC)=C3)[C@@]1([H])[C@@]1([H])CC[C@]2(C)OC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O3/c1-5-6-7-8-13-11-15(22)18-16(12-13)23-19-17(18)14-9-10-21(19,4)24-20(14,2)3/h11-12,14,17,19,22H,5-10H2,1-4H3/t14-,17-,19+,21+/m1/s1

> <INCHI_KEY>
RFLHMZVKMQKUEC-DYZHCLJRSA-N

> <FORMULA>
C21H30O3

> <MOLECULAR_WEIGHT>
330.468

> <EXACT_MASS>
330.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.00244493851312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,10S,11S)-11,13,13-trimethyl-6-pentyl-9,12-dioxatetracyclo[9.2.2.0^{2,10}.0^{3,8}]pentadeca-3(8),4,6-trien-4-ol

> <JCHEM_LOGP>
5.121329329

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.897989753309023

> <JCHEM_PKA_STRONGEST_BASIC>
-4.13932586165713

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
95.417

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,10S,11S)-11,13,13-trimethyl-6-pentyl-9,12-dioxatetracyclo[9.2.2.0^{2,10}.0^{3,8}]pentadeca-3(8),4,6-trien-4-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  C   UNK     0      -1.267  -0.427   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.262  -0.248   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.174  -1.785   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.180   1.227   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.876   2.348   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.433   3.823   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.375   1.994   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0       2.089   3.507   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0       2.817   0.519   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.357   0.484   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.361  -0.683   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.852  -2.137   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.874  -0.398   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.383   1.056   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.896   1.342   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.901   0.174   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.414   0.460   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.418  -0.707   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.931  -0.421   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.379   2.223   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.866   1.938   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.641   2.871   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       3.412  -0.902   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       1.761  -0.602   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       1.446  -2.109   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       1.712   0.455   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.417   1.439   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   24                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   27                                             
CONECT    6    5                                                            
CONECT    7    5    8    9   22                                             
CONECT    8    7                                                            
CONECT    9    7   10   23   24                                             
CONECT   10    9   11   21                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   14   21                                                       
CONECT   21   10   20   22                                                  
CONECT   22   21    7                                                       
CONECT   23    9                                                            
CONECT   24    9    2   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26    5                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₃

Average Mass

330.4680 Da

Monoisotopic Mass

330.21949 Da

IUPAC Name

(1R,2R,10S,11S)-11,13,13-trimethyl-6-pentyl-9,12-dioxatetracyclo[9.2.2.0^{2,10}.0^{3,8}]pentadeca-3(8),4,6-trien-4-ol

Traditional Name

(1R,2R,10S,11S)-11,13,13-trimethyl-6-pentyl-9,12-dioxatetracyclo[9.2.2.0^{2,10}.0^{3,8}]pentadeca-3(8),4,6-trien-4-ol

CAS Registry Number

Not Available

SMILES

[H][C@]12OC3=C(C(O)=CC(CCCCC)=C3)[C@@]1([H])[C@@]1([H])CC[C@]2(C)OC1(C)C

InChI Identifier

InChI=1S/C21H30O3/c1-5-6-7-8-13-11-15(22)18-16(12-13)23-19-17(18)14-9-10-21(19,4)24-20(14,2)3/h11-12,14,17,19,22H,5-10H2,1-4H3/t14-,17-,19+,21+/m1/s1

InChI Key

RFLHMZVKMQKUEC-DYZHCLJRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3CN, experimental)	alessio.porta@unipv.it	University of Pavia	Alessio Porta	2024-05-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3CN, experimental)	alessio.porta@unipv.it	University of Pavia	Alessio Porta	2024-05-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3CN, experimental)	alessio.porta@unipv.it	University of Pavia	Alessio Porta	2024-05-02	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3CN, experimental)	alessio.porta@unipv.it	University of Pavia	Alessio Porta	2024-05-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3CN, experimental)	alessio.porta@unipv.it	University of Pavia	Alessio Porta	2024-05-02	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
sp.		Not Available

Chemical Taxonomy

Classification

Not classified

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	5.12	ChemAxon
pKa (Strongest Acidic)	9.9	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.42 m³·mol⁻¹	ChemAxon
Polarizability	39 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

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 ]

Showing NP-Card for CCB (NP0332905)

MOL for NP0332905 (CCB)

3D MOL for NP0332905 (CCB)

3D SDF for NP0332905 (CCB)

3D-SDF for NP0332905 (CCB)

PDB for NP0332905 (CCB)

3D PDB for NP0332905 (CCB)

SMILES for NP0332905 (CCB)

INCHI for NP0332905 (CCB)

Structure for NP0332905 (CCB)

3D Structure for NP0332905 (CCB)