NP-MRD: Showing NP-Card for 6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one (NP0261674)

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Record Information

Version

2.0

Created at

2022-09-08 04:11:17 UTC

Updated at

2022-09-08 04:11:17 UTC

NP-MRD ID

NP0261674

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one

Description

CHEMBL2235444 belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one is found in Broussonetia papyrifera. CHEMBL2235444 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191514222D          

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M  END


  Mrv1533004191514222D          

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 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
  6 25  2  0  0  0  0
 18 25  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 11 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  2  0  0  0  0
  2 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261674

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCOC1=C2OC(C)(C)C=CC2=C2OC3=C(OC4=C(C(O)=CC(O)=C4C(C)(C)C=C)C3=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O7/c1-8-29(4,5)22-19(32)14-18(31)21-23(33)28-26(36-27(21)22)17-13-20(34-12-10-15(2)3)25-16(24(17)35-28)9-11-30(6,7)37-25/h8-11,13-14,31-32H,1,12H2,2-7H3

> <INCHI_KEY>
TVLDODQYCCAAQZ-UHFFFAOYSA-N

> <FORMULA>
C30H30O7

> <MOLECULAR_WEIGHT>
502.563

> <EXACT_MASS>
502.199153306

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
55.59962490758852

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(21),2(11),4(9),5,7,13,15,19-octaen-10-one

> <ALOGPS_LOGP>
5.63

> <JCHEM_LOGP>
6.871469276666668

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.906178397163488

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.155160878529591

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9029914609922174

> <JCHEM_POLAR_SURFACE_AREA>
98.36000000000001

> <JCHEM_REFRACTIVITY>
142.7825

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(21),2(11),4(9),5,7,13,15,19-octaen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.362   8.861   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.036   7.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.174   6.200   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.848   4.815   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.384   4.707   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.058   3.322   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.594   3.213   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.268   1.829   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.748   1.403   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.055   2.218   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.414   1.494   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.467  -0.045   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.160  -0.860   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.212  -2.399   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.801  -0.136   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.353  -0.662   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.406   0.553   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.870   0.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.008  -0.615   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.472  -0.506   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.202   0.879   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.449  -0.026   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.309   1.949   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.660   2.155   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.196   2.046   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.826  -0.769   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.878  -2.308   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.132   0.046   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.080   1.585   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.386   2.400   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.721   2.309   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.668   3.848   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.207   3.901   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.129   3.796   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.616   5.387   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.256   6.111   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.572   7.367   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   31                                                  
CONECT   12   11   13   26                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25                                                       
CONECT   25   24    6   18                                                  
CONECT   26   12   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   11   32                                                  
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32   36                                                       
CONECT   36   35                                                            
CONECT   37    2                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₀O₇

Average Mass

502.5630 Da

Monoisotopic Mass

502.19915 Da

IUPAC Name

6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(21),2(11),4(9),5,7,13,15,19-octaen-10-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCOC1=C2OC(C)(C)C=CC2=C2OC3=C(OC4=C(C(O)=CC(O)=C4C(C)(C)C=C)C3=O)C2=C1

InChI Identifier

InChI=1S/C30H30O7/c1-8-29(4,5)22-19(32)14-18(31)21-23(33)28-26(36-27(21)22)17-13-20(34-12-10-15(2)3)25-16(24(17)35-28)9-11-30(6,7)37-25/h8-11,13-14,31-32H,1,12H2,2-7H3

InChI Key

TVLDODQYCCAAQZ-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

Species Name	Source	Reference
Broussonetia papyrifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Chromone
Benzofuran
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Benzenoid
Pyran
Furan
Heteroaromatic compound
Vinylogous acid
Ether
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	5.63	ALOGPS
logP	6.87	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.16	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	142.78 m³·mol⁻¹	ChemAxon
Polarizability	55.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

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

44612850

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one (NP0261674)

MOL for NP0261674 (6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one)

3D MOL for NP0261674 (6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one)

3D SDF for NP0261674 (6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one)

3D-SDF for NP0261674 (6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one)

PDB for NP0261674 (6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one)

3D PDB for NP0261674 (6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one)

SMILES for NP0261674 (6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one)

INCHI for NP0261674 (6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one)

Structure for NP0261674 (6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one)

3D Structure for NP0261674 (6,8-dihydroxy-17,17-dimethyl-20-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylbut-3-en-2-yl)-3,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2(11),4,6,8,14(19),15,20-octaen-10-one)