NP-MRD: Showing NP-Card for Cycloartolakoochol (NP0085437)

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Record Information

Version

2.0

Created at

2022-04-29 05:57:55 UTC

Updated at

2022-04-29 05:57:56 UTC

NP-MRD ID

NP0085437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cycloartolakoochol

Description

2-[(1S,4R,13S)-1,5,5-trimethyl-10-(3-methylbut-2-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]Pentadeca-7(12),8,10-trien-9-yl]-1-benzofuran-6-ol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Cycloartolakoochol is found in Artocarpus lakoocha . Based on a literature review very few articles have been published on 2-[(1S,4R,13S)-1,5,5-trimethyl-10-(3-methylbut-2-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]Pentadeca-7(12),8,10-trien-9-yl]-1-benzofuran-6-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207572D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292207572D          

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M  END
> <DATABASE_ID>
NP0085437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@]3(C)CC[C@@]1([H])C(C)(C)OC1=CC(C4=CC5=CC=C(O)C=C5O4)=C(CC=C(C)C)C(O3)=C21

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O4/c1-16(2)6-9-19-20(24-12-17-7-8-18(30)13-23(17)31-24)14-25-26-21-15-29(5,33-27(19)26)11-10-22(21)28(3,4)32-25/h6-8,12-14,21-22,30H,9-11,15H2,1-5H3/t21-,22+,29-/m0/s1

> <INCHI_KEY>
MGQFZUKDGZUBJQ-KERYWQKISA-N

> <FORMULA>
C29H32O4

> <MOLECULAR_WEIGHT>
444.571

> <EXACT_MASS>
444.23005951

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
51.13613112072674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1S,4R,13S)-1,5,5-trimethyl-10-(3-methylbut-2-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7,9,11-trien-9-yl]-1-benzofuran-6-ol

> <ALOGPS_LOGP>
7.70

> <JCHEM_LOGP>
6.480702272999999

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.124755227673983

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8602905052229057

> <JCHEM_POLAR_SURFACE_AREA>
51.83

> <JCHEM_REFRACTIVITY>
130.4969

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S,4R,13S)-1,5,5-trimethyl-10-(3-methylbut-2-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7,9,11-trien-9-yl]-1-benzofuran-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      12.577  -0.157   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.122  -0.660   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.830  -2.172   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.374  -2.676   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.211  -1.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.683  -1.856   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.030  -0.461   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.518  -0.169   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.469  -1.346   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.038  -2.777   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.084  -3.986   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.654  -5.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.178  -5.639   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.700  -6.625   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.873  -1.211   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.473  -2.211   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.176  -1.698   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.921  -3.045   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.473  -0.587   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.297   1.075   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.616  -0.708   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.527   0.318   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.083   0.620   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       0.898   1.927   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0      -0.821   1.779   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      -1.792   2.975   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       0.176   3.086   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.213   3.752   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.546   4.581   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.764   3.025   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.454   1.600   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.991   1.290   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.155   0.590   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.503  -0.155   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.958   0.349   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   33                                                  
CONECT    8    7    9   32                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   21                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   25                                                       
CONECT   21   17   23                                                       
CONECT   22   15   23   31                                                  
CONECT   23   22   21   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   20   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   22   30   32                                                  
CONECT   32   31    8                                                       
CONECT   33    7   34                                                       
CONECT   34    5   33   35                                                  
CONECT   35   34    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₂O₄

Average Mass

444.5710 Da

Monoisotopic Mass

444.23006 Da

IUPAC Name

2-[(1S,4R,13S)-1,5,5-trimethyl-10-(3-methylbut-2-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7,9,11-trien-9-yl]-1-benzofuran-6-ol

Traditional Name

2-[(1S,4R,13S)-1,5,5-trimethyl-10-(3-methylbut-2-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7,9,11-trien-9-yl]-1-benzofuran-6-ol

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@]3(C)CC[C@@]1([H])C(C)(C)OC1=CC(C4=CC5=CC=C(O)C=C5O4)=C(CC=C(C)C)C(O3)=C21

InChI Identifier

InChI=1S/C29H32O4/c1-16(2)6-9-19-20(24-12-17-7-8-18(30)13-23(17)31-24)14-25-26-21-15-29(5,33-27(19)26)11-10-22(21)28(3,4)32-25/h6-8,12-14,21-22,30H,9-11,15H2,1-5H3/t21-,22+,29-/m0/s1

InChI Key

MGQFZUKDGZUBJQ-KERYWQKISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Artocarpus lacucha	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
4'-prenylated 2-arybenzofuran
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Furan
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
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	7.7	ALOGPS
logP	6.48	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	130.5 m³·mol⁻¹	ChemAxon
Polarizability	51.14 Å³	ChemAxon
Number of Rings	6	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

C00055297

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

162973439

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cycloartolakoochol (NP0085437)

MOL for NP0085437 (Cycloartolakoochol)

3D MOL for NP0085437 (Cycloartolakoochol)

3D SDF for NP0085437 (Cycloartolakoochol)

3D-SDF for NP0085437 (Cycloartolakoochol)

PDB for NP0085437 (Cycloartolakoochol)

3D PDB for NP0085437 (Cycloartolakoochol)

SMILES for NP0085437 (Cycloartolakoochol)

INCHI for NP0085437 (Cycloartolakoochol)

Structure for NP0085437 (Cycloartolakoochol)

3D Structure for NP0085437 (Cycloartolakoochol)