NP-MRD: Showing NP-Card for (R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid (NP0350985)

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Record Information

Version

2.0

Created at

2025-04-29 21:05:45 UTC

Updated at

2025-05-13 21:51:27 UTC

NP-MRD ID

NP0350985

Natural Product DOI

https://doi.org/10.57994/3972

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid

Description

Based on a literature review very few articles have been published on (R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02092323322D          

 23 24  0  0  1  0            999 V2000
   -0.1712    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9962   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  6  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0350985

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2O[C@@H](CC2=CC(=C1)C(O)=O)[C@@](C)(O)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O5/c1-11(2)6-5-7-18(3,21)15-10-12-8-13(17(19)20)9-14(22-4)16(12)23-15/h6,8-9,15,21H,5,7,10H2,1-4H3,(H,19,20)/t15-,18-/m0/s1

> <INCHI_KEY>
ZRDAFYSRFXOWIH-YJBOKZPZSA-N

> <FORMULA>
C18H24O5

> <MOLECULAR_WEIGHT>
320.385

> <EXACT_MASS>
320.162373873

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.33556789755835

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-7-methoxy-2,3-dihydro-1-benzofuran-5-carboxylic acid

> <JCHEM_LOGP>
3.1598594549999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.017023422949693

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.120029745440383

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2287542262317923

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
88.29529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-7-methoxy-2,3-dihydro-1-benzofuran-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-FEB-23         0                                  
HETATM    1  C   UNK     0      -0.320   0.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.860  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.170   0.031   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.940  -1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.170  -2.637   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.480  -1.303   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.320  -2.843   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.925  -2.073   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2                                                            
CONECT   10    2   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   22                                                       
CONECT   22   21   12   23                                                  
CONECT   23   22   10                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
(R)-2,3-Dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5En-2-yl]-2H-1-benzofuran-5-carboxylate	Generator

Chemical Formula

C₁₈H₂₄O₅

Average Mass

320.3850 Da

Monoisotopic Mass

320.16237 Da

IUPAC Name

(2S)-2-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-7-methoxy-2,3-dihydro-1-benzofuran-5-carboxylic acid

Traditional Name

(2S)-2-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-7-methoxy-2,3-dihydro-1-benzofuran-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C2O[C@@H](CC2=CC(=C1)C(O)=O)[C@@](C)(O)CCC=C(C)C

InChI Identifier

InChI=1S/C18H24O5/c1-11(2)6-5-7-18(3,21)15-10-12-8-13(17(19)20)9-14(22-4)16(12)23-15/h6,8-9,15,21H,5,7,10H2,1-4H3,(H,19,20)/t15-,18-/m0/s1

InChI Key

ZRDAFYSRFXOWIH-YJBOKZPZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Piper holdridgeanum		Not Available

Chemical Taxonomy

Classification

Not classified

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	3.16	ChemAxon
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	88.3 m³·mol⁻¹	ChemAxon
Polarizability	35.34 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

DOI: 10.3390/molecules30092020

Showing NP-Card for (R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid (NP0350985)

MOL for NP0350985 ((R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid)

3D MOL for NP0350985 ((R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid)

3D SDF for NP0350985 ((R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid)

3D-SDF for NP0350985 ((R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid)

PDB for NP0350985 ((R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid)

3D PDB for NP0350985 ((R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid)

SMILES for NP0350985 ((R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid)

INCHI for NP0350985 ((R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid)

Structure for NP0350985 ((R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid)

3D Structure for NP0350985 ((R)-2,3-dihydro-7-hydroxy-2-[(S)-2-hydroxy-6-methylhept-5en-2-yl]-2H-1-benzofuran-5-carboxylic acid)