NP-MRD: Showing NP-Card for 1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one (NP0221095)

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Record Information

Version

1.0

Created at

2022-09-05 22:34:53 UTC

Updated at

2022-09-05 22:34:53 UTC

NP-MRD ID

NP0221095

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one

Description

1-[9-Hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]Pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. 1-[9-Hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]Pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171512452D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171512452D          

 34 38  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0221095

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC1(C)OC2=C3C4CC(C)(CCC14)OC3=CC(O)=C2C(=O)C=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O4/c1-19(2)9-8-15-30(4)22-14-16-29(3)18-21(22)26-25(33-29)17-24(32)27(28(26)34-30)23(31)13-12-20-10-6-5-7-11-20/h5-7,9-13,17,21-22,32H,8,14-16,18H2,1-4H3

> <INCHI_KEY>
KBIUSJRYMLTVOW-UHFFFAOYSA-N

> <FORMULA>
C30H34O4

> <MOLECULAR_WEIGHT>
458.598

> <EXACT_MASS>
458.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.27780458555796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-8-yl]-3-phenylprop-2-en-1-one

> <ALOGPS_LOGP>
6.75

> <JCHEM_LOGP>
7.330532885333334

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.96366260658283

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.524514681905009

> <JCHEM_PKA_STRONGEST_BASIC>
-4.623359166925517

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
136.9439

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.47e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-8-yl]-3-phenylprop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.195  -7.972   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.825  -6.477   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.934  -5.409   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.564  -3.914   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.085  -3.487   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.714  -1.993   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.674  -2.658   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.303  -1.931   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.992  -0.506   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.066   0.776   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.622   0.474   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.077   1.802   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.637   2.791   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.382   4.139   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.934   1.681   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.759   0.019   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.282  -0.686   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.012   3.305   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.412   2.304   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.007   2.440   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.057   1.263   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.569   1.555   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.530  -0.196   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.536  -1.362   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.049  -1.074   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.029  -2.816   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.035  -3.983   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.528  -5.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.534  -6.603   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.026  -8.057   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.514  -8.345   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.508  -7.179   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.015  -5.725   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.345  -6.050   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   17                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   18                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    6   11                                                  
CONECT   18   13   19                                                       
CONECT   19   18   10   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    9   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34    2                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄O₄

Average Mass

458.5980 Da

Monoisotopic Mass

458.24571 Da

IUPAC Name

1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-8-yl]-3-phenylprop-2-en-1-one

Traditional Name

1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-8-yl]-3-phenylprop-2-en-1-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC1(C)OC2=C3C4CC(C)(CCC14)OC3=CC(O)=C2C(=O)C=CC1=CC=CC=C1

InChI Identifier

InChI=1S/C30H34O4/c1-19(2)9-8-15-30(4)22-14-16-29(3)18-21(22)26-25(33-29)17-24(32)27(28(26)34-30)23(31)13-12-20-10-6-5-7-11-20/h5-7,9-13,17,21-22,32H,8,14-16,18H2,1-4H3

InChI Key

KBIUSJRYMLTVOW-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Chromane
Benzopyran
1-benzopyran
Styrene
Aryl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	6.75	ALOGPS
logP	7.33	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	7.52	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.94 m³·mol⁻¹	ChemAxon
Polarizability	52.28 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one (NP0221095)

MOL for NP0221095 (1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one)

3D MOL for NP0221095 (1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one)

3D SDF for NP0221095 (1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one)

3D-SDF for NP0221095 (1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one)

PDB for NP0221095 (1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one)

3D PDB for NP0221095 (1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one)

SMILES for NP0221095 (1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one)

INCHI for NP0221095 (1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one)

Structure for NP0221095 (1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one)

3D Structure for NP0221095 (1-[9-hydroxy-1,5-dimethyl-5-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one)