NP-MRD: Showing NP-Card for 9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen (NP0338340)

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Record Information

Version

2.0

Created at

2024-09-11 14:58:58 UTC

Updated at

2024-09-11 14:58:58 UTC

NP-MRD ID

NP0338340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen

Description

9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen, also known as protorifamycin I, belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group. 9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen has been detected, but not quantified in, citrus. This could make 9-hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310492D          

 27 29  0  0  0  0            999 V2000
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  6  2  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  2  0  0  0  0
 16  8  1  0  0  0  0
 17 11  1  0  0  0  0
 18  9  1  0  0  0  0
 19 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 17  2  0  0  0  0
 21 16  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  2  0  0  0  0
 23 18  2  0  0  0  0
 24  4  1  0  0  0  0
 24 22  1  0  0  0  0
 25 12  1  0  0  0  0
 25 19  1  0  0  0  0
 26 13  1  0  0  0  0
 26 20  1  0  0  0  0
 27 18  1  0  0  0  0
 27 21  1  0  0  0  0
M  END


  Mrv0541 05061310492D          

 27 29  0  0  0  0            999 V2000
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  6  2  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  2  0  0  0  0
 16  8  1  0  0  0  0
 17 11  1  0  0  0  0
 18  9  1  0  0  0  0
 19 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 17  2  0  0  0  0
 21 16  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  2  0  0  0  0
 23 18  2  0  0  0  0
 24  4  1  0  0  0  0
 24 22  1  0  0  0  0
 25 12  1  0  0  0  0
 25 19  1  0  0  0  0
 26 13  1  0  0  0  0
 26 20  1  0  0  0  0
 27 18  1  0  0  0  0
 27 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC(=O)C=CC2=C(OC\C=C(/C)CCC=C(C)C)C2=C1OC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O5/c1-14(2)6-5-7-15(3)10-12-25-19-16-8-9-18(23)27-21(16)22(24-4)20-17(19)11-13-26-20/h6,8-11,13H,5,7,12H2,1-4H3/b15-10+

> <INCHI_KEY>
OQHQALGVQDTJDN-XNTDXEJSSA-N

> <FORMULA>
C22H24O5

> <MOLECULAR_WEIGHT>
368.423

> <EXACT_MASS>
368.162373878

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
40.676478105220255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-9-methoxy-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
4.94

> <JCHEM_LOGP>
4.648100849333334

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0782471427066302

> <JCHEM_POLAR_SURFACE_AREA>
57.900000000000006

> <JCHEM_REFRACTIVITY>
106.23689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-9-methoxyfuro[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.132   2.016   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   24                                                            
CONECT    5    6    7                                                       
CONECT    6    5   14                                                       
CONECT    7    5   15                                                       
CONECT    8    9   16                                                       
CONECT    9    8   18                                                       
CONECT   10   12   15                                                       
CONECT   11   13   17                                                       
CONECT   12   10   25                                                       
CONECT   13   11   26                                                       
CONECT   14    1    2    6                                                  
CONECT   15    3    7   10                                                  
CONECT   16    8   19   21                                                  
CONECT   17   11   19   20                                                  
CONECT   18    9   23   27                                                  
CONECT   19   16   17   25                                                  
CONECT   20   17   22   26                                                  
CONECT   21   16   22   27                                                  
CONECT   22   20   21   24                                                  
CONECT   23   18                                                            
CONECT   24    4   22                                                       
CONECT   25   12   19                                                       
CONECT   26   13   20                                                       
CONECT   27   18   21                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
Protorifamycin I	HMDB

Chemical Formula

C₂₂H₂₄O₅

Average Mass

368.4230 Da

Monoisotopic Mass

368.16237 Da

IUPAC Name

4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-9-methoxy-7H-furo[3,2-g]chromen-7-one

Traditional Name

4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-9-methoxyfuro[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

COC1=C2OC(=O)C=CC2=C(OC\C=C(/C)CCC=C(C)C)C2=C1OC=C2

InChI Identifier

InChI=1S/C22H24O5/c1-14(2)6-5-7-15(3)10-12-25-19-16-8-9-18(23)27-21(16)22(24-4)20-17(19)11-13-26-20/h6,8-11,13H,5,7,12H2,1-4H3/b15-10+

InChI Key

OQHQALGVQDTJDN-XNTDXEJSSA-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 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

8-methoxypsoralens

Alternative Parents

Substituents

8-methoxypsoralen
Terpene lactone
Aromatic monoterpenoid
Benzopyran
Monoterpenoid
1-benzopyran
Benzofuran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Furan
Heteroaromatic compound
Lactone
Ether
Organoheterocyclic compound
Oxacycle
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	4.94	ALOGPS
logP	4.65	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	106.24 m³·mol⁻¹	ChemAxon
Polarizability	40.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0039057

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018555

KNApSAcK ID

Not Available

Chemspider ID

4944685

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440422

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen (NP0338340)

MOL for NP0338340 (9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen)

3D MOL for NP0338340 (9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen)

3D SDF for NP0338340 (9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen)

3D-SDF for NP0338340 (9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen)

PDB for NP0338340 (9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen)

3D PDB for NP0338340 (9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen)

SMILES for NP0338340 (9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen)

INCHI for NP0338340 (9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen)

Structure for NP0338340 (9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen)

3D Structure for NP0338340 (9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen)