NP-MRD: Showing NP-Card for 5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid (NP0224478)

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Record Information

Version

2.0

Created at

2022-09-06 02:50:30 UTC

Updated at

2022-09-06 02:50:30 UTC

NP-MRD ID

NP0224478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid

Description

5-[3-(Hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. 5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid is found in Celtis australis. 5-[3-(Hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171510282D          

 26 27  0  0  0  0            999 V2000
    2.5645    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5329   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8829   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    2.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   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  2  0  0  0  0
  5  4  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
  9 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
  3 26  1  0  0  0  0
 20 26  2  0  0  0  0
M  END


  Mrv1533004171510282D          

 26 27  0  0  0  0            999 V2000
    2.5645    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5329   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8829   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    2.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   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  2  0  0  0  0
  5  4  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
  9 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
  3 26  1  0  0  0  0
 20 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0224478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=CCO)C(C=CCC=CS(O)(=O)=O)=CC2=C1C(CO)CO2

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O7S/c1-24-18-15(7-5-8-19)13(6-3-2-4-9-26(21,22)23)10-16-17(18)14(11-20)12-25-16/h3-7,9-10,14,19-20H,2,8,11-12H2,1H3,(H,21,22,23)

> <INCHI_KEY>
FADQOBMTUJMAHP-UHFFFAOYSA-N

> <FORMULA>
C18H22O7S

> <MOLECULAR_WEIGHT>
382.43

> <EXACT_MASS>
382.108624222

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
39.34887063654449

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
-0.29843419405957416

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.038425361779822

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.1810941936577715

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5278625607859038

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
101.04859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid

> <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       4.787   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.122   6.160   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0       8.788  -6.930   0.000  0.00  0.00           S+0
HETATM   16  O   UNK     0       8.788  -8.470   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.328  -6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.248  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.340   3.801   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19    9   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23    3   20                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
5-[3-(Hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonate	Generator
5-[3-(Hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulphonate	Generator
5-[3-(Hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulphonic acid	Generator

Chemical Formula

C₁₈H₂₂O₇S

Average Mass

382.4300 Da

Monoisotopic Mass

382.10862 Da

IUPAC Name

5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid

Traditional Name

5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C=CCO)C(C=CCC=CS(O)(=O)=O)=CC2=C1C(CO)CO2

InChI Identifier

InChI=1S/C18H22O7S/c1-24-18-15(7-5-8-19)13(6-3-2-4-9-26(21,22)23)10-16-17(18)14(11-20)12-25-16/h3-7,9-10,14,19-20H,2,8,11-12H2,1H3,(H,21,22,23)

InChI Key

FADQOBMTUJMAHP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Celtis australis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Anisole
Styrene
Alkyl aryl ether
Benzenoid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Ether
Oxacycle
Alcohol
Hydrocarbon derivative
Primary alcohol
Organosulfur compound
Organooxygen compound
Organic oxygen 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	0.53	ALOGPS
logP	-0.3	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	-1.2	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	101.05 m³·mol⁻¹	ChemAxon
Polarizability	39.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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 5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid (NP0224478)

MOL for NP0224478 (5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid)

3D MOL for NP0224478 (5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid)

3D SDF for NP0224478 (5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid)

3D-SDF for NP0224478 (5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid)

PDB for NP0224478 (5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid)

3D PDB for NP0224478 (5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid)

SMILES for NP0224478 (5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid)

INCHI for NP0224478 (5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid)

Structure for NP0224478 (5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid)

3D Structure for NP0224478 (5-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-4-methoxy-2,3-dihydro-1-benzofuran-6-yl]penta-1,4-diene-1-sulfonic acid)