NP-MRD: Showing NP-Card for 1-{9-hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one (NP0256761)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 21:41:35 UTC

Updated at

2022-09-07 21:41:35 UTC

NP-MRD ID

NP0256761

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

1-{9-Hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]Pentadeca-7(12),8,10-trien-10-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-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]Pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251511422D          

 29 33  0  0  0  0            999 V2000
    3.8869    3.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5017    2.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2139    1.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1574    1.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3771    0.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691    1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310    1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0905    1.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6028    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0088   -0.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8604   -0.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8408   -0.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5254   -0.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746    0.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023    1.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064    1.8742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594    2.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7731    3.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0401    3.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3001    3.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0138    4.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408    5.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545    5.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7814    6.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    6.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809    5.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3540    5.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9027    2.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    2.7713    0.0000 O   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
  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
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 18  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 17 28  2  0  0  0  0
  8 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
M  END


  Mrv1533004251511422D          

 29 33  0  0  0  0            999 V2000
    3.8869    3.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5017    2.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2139    1.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1574    1.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3771    0.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691    1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310    1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0905    1.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6028    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0088   -0.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8604   -0.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8408   -0.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5254   -0.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746    0.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023    1.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064    1.8742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594    2.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7731    3.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0401    3.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3001    3.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0138    4.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408    5.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545    5.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7814    6.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    6.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809    5.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3540    5.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9027    2.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    2.7713    0.0000 O   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
  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
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 18  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 17 28  2  0  0  0  0
  8 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256761

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=C3C4CC(C)(CCC14)OC3=C(C(=O)C=CC1=CC=CC=C1)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O4/c1-24(2)17-11-12-25(3)14-16(17)21-20(28-24)13-19(27)22(23(21)29-25)18(26)10-9-15-7-5-4-6-8-15/h4-10,13,16-17,27H,11-12,14H2,1-3H3

> <INCHI_KEY>
WNLBTQUQQKWXAK-UHFFFAOYSA-N

> <FORMULA>
C25H26O4

> <MOLECULAR_WEIGHT>
390.479

> <EXACT_MASS>
390.183109317

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.80233953923918

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.50

> <JCHEM_LOGP>
5.592864880333334

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.964048390226296

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.524873871395434

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6226873100729975

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
113.2183

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       7.255   6.035   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.536   4.673   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.866   3.608   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.760   1.935   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.304   1.192   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.356   2.312   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.031   3.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.902   2.611   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.992   1.334   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.750  -0.093   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.339  -0.144   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.303  -1.684   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.581  -1.056   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.446   1.718   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.938   3.194   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.572   3.499   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.978   4.356   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.443   5.800   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.075   6.060   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.427   6.985   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.892   8.430   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.876   9.615   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.342  11.059   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.325  12.244   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.843  11.984   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.378  10.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.394   9.355   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.552   4.147   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.898   5.173   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   29                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   28                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   28                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   17    8   29                                                  
CONECT   29   28    2                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₄

Average Mass

390.4790 Da

Monoisotopic Mass

390.18311 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=C3C4CC(C)(CCC14)OC3=C(C(=O)C=CC1=CC=CC=C1)C(O)=C2

InChI Identifier

InChI=1S/C25H26O4/c1-24(2)17-11-12-25(3)14-16(17)21-20(28-24)13-19(27)22(23(21)29-25)18(26)10-9-15-7-5-4-6-8-15/h4-10,13,16-17,27H,11-12,14H2,1-3H3

InChI Key

WNLBTQUQQKWXAK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Styrene
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Ketone
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	5.5	ALOGPS
logP	5.59	ChemAxon
logS	-5.5	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	3	ChemAxon
Refractivity	113.22 m³·mol⁻¹	ChemAxon
Polarizability	43.8 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

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-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one (NP0256761)

MOL for NP0256761 (1-{9-hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one)

3D MOL for NP0256761 (1-{9-hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one)

3D SDF for NP0256761 (1-{9-hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one)

3D-SDF for NP0256761 (1-{9-hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one)

PDB for NP0256761 (1-{9-hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one)

3D PDB for NP0256761 (1-{9-hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one)

SMILES for NP0256761 (1-{9-hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one)

INCHI for NP0256761 (1-{9-hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one)

Structure for NP0256761 (1-{9-hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one)

3D Structure for NP0256761 (1-{9-hydroxy-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.0⁴,¹³.0⁷,¹²]pentadeca-7(12),8,10-trien-10-yl}-3-phenylprop-2-en-1-one)