NP-MRD: Showing NP-Card for dorsilurin i (NP0238605)

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Record Information

Version

2.0

Created at

2022-09-06 22:01:42 UTC

Updated at

2022-09-06 22:01:42 UTC

NP-MRD ID

NP0238605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dorsilurin i

Description

5,8-Dihydroxy-4-[3-hydroxy-4-(2-hydroxy-3-methylbut-3-en-1-yl)phenyl]-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0²,⁷]Tetradeca-1(10),2(7),4,8-tetraen-6-one belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position. dorsilurin i is found in Dorstenia psilurus. 5,8-Dihydroxy-4-[3-hydroxy-4-(2-hydroxy-3-methylbut-3-en-1-yl)phenyl]-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-3,11-dioxatricyclo[8.4.0.0²,⁷]Tetradeca-1(10),2(7),4,8-tetraen-6-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151514282D          

 37 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004151514282D          

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 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 15 22  2  0  0  0  0
 12 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 23 35  1  0  0  0  0
 11 36  1  0  0  0  0
  2 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238605

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC=C(CC(O)C(C)=C)C(O)=C2)C2=C1OC(C)(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O7/c1-15(2)7-10-19-24(33)23-25(34)26(35)27(36-29(23)20-11-12-30(5,6)37-28(19)20)18-9-8-17(22(32)14-18)13-21(31)16(3)4/h7-9,14,21,31-33,35H,3,10-13H2,1-2,4-6H3

> <INCHI_KEY>
LGOMXMSCNFANHV-UHFFFAOYSA-N

> <FORMULA>
C30H34O7

> <MOLECULAR_WEIGHT>
506.595

> <EXACT_MASS>
506.230453435

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
57.02545442851863

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5-dihydroxy-2-[3-hydroxy-4-(2-hydroxy-3-methylbut-3-en-1-yl)phenyl]-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H,9H,10H-pyrano[2,3-h]chromen-4-one

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
6.071624308

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.052208500913551

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.392527150407581

> <JCHEM_PKA_STRONGEST_BASIC>
-3.036810011436253

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
145.2598

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dorsilurin I

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      -1.746   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.206   6.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.184  -0.564   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.386  -0.220   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.386   1.760   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.564   2.104   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.804  -3.231   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.034  -4.565   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.804  -5.898   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.344  -5.898   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.114  -4.565   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.114  -7.232   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.654  -7.232   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.344  -8.566   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.494  -4.565   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.724  -5.898   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.564   7.438   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   22                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   36                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21    5   15                                                  
CONECT   23   12   24   35                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   26   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   23                                                       
CONECT   36   11                                                            
CONECT   37    2                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄O₇

Average Mass

506.5950 Da

Monoisotopic Mass

506.23045 Da

IUPAC Name

3,5-dihydroxy-2-[3-hydroxy-4-(2-hydroxy-3-methylbut-3-en-1-yl)phenyl]-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H,9H,10H-pyrano[2,3-h]chromen-4-one

Traditional Name

dorsilurin I

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC=C(CC(O)C(C)=C)C(O)=C2)C2=C1OC(C)(C)CC2

InChI Identifier

InChI=1S/C30H34O7/c1-15(2)7-10-19-24(33)23-25(34)26(35)27(36-29(23)20-11-12-30(5,6)37-28(19)20)18-9-8-17(22(32)14-18)13-21(31)16(3)4/h7-9,14,21,31-33,35H,3,10-13H2,1-2,4-6H3

InChI Key

LGOMXMSCNFANHV-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
Dorstenia psilurus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

8-prenylated flavones

Alternative Parents

Substituents

6-prenylated flavone
8-prenylated flavone
Pyranoflavonoid
3-hydroxyflavone
Hydroxyflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
5-hydroxyflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
Chromane
1-benzopyran
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	4.51	ALOGPS
logP	6.07	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	7.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	145.26 m³·mol⁻¹	ChemAxon
Polarizability	57.03 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

74399253

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for dorsilurin i (NP0238605)

MOL for NP0238605 (dorsilurin i)

3D MOL for NP0238605 (dorsilurin i)

3D SDF for NP0238605 (dorsilurin i)

3D-SDF for NP0238605 (dorsilurin i)

PDB for NP0238605 (dorsilurin i)

3D PDB for NP0238605 (dorsilurin i)

SMILES for NP0238605 (dorsilurin i)

INCHI for NP0238605 (dorsilurin i)

Structure for NP0238605 (dorsilurin i)

3D Structure for NP0238605 (dorsilurin i)