NP-MRD: Showing NP-Card for (4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione (NP0226073)

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Record Information

Version

2.0

Created at

2022-09-06 04:59:49 UTC

Updated at

2022-09-06 04:59:50 UTC

NP-MRD ID

NP0226073

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione

Description

30358-74-8, Also known as conocarpan, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. (4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione is found in Krameria cytisoides, Krameria erecta, Krameria grayi, Krameria lanceolata, Krameria paucifolia, Krameria tomentosa, Piper aequale and Piper regnellii. Based on a literature review very few articles have been published on 30358-74-8.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206592D          

 23 25  0  0  1  0            999 V2000
   -0.6674   -0.4849    0.0000 O   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
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0396    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7425    3.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5494    3.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8044    4.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8465    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2394    1.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2065   -0.4849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1203   -1.3054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -0.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0464    0.6711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4995   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0226073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H](O)[C@H]1OC(=O)C2(OC(=O)C[C@H]2C2=CC=C(O)C=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O8/c16-6-10(18)12-13(20)15(14(21)22-12)9(5-11(19)23-15)7-1-3-8(17)4-2-7/h1-4,9-10,12-13,16-18,20H,5-6H2/t9-,10-,12+,13+,15?/m0/s1

> <INCHI_KEY>
JVCLQSJXGOABTC-IPNWIPTBSA-N

> <FORMULA>
C15H16O8

> <MOLECULAR_WEIGHT>
324.285

> <EXACT_MASS>
324.084517475

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.823955610767257

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,8R,9R)-8-[(1S)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione

> <JCHEM_LOGP>
-0.8059754030000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.559356869183297

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.498359917191829

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9749460869137856

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
73.3378

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,8R,9R)-8-[(1S)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.246  -0.905   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.941   3.481   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.910   4.625   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.386   6.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.892   6.410   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.368   7.874   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.923   5.265   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.447   3.801   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.275   2.016   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.180   3.262   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.740   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.740  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.986  -0.905   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.825  -2.437   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.392  -0.279   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.553   1.253   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.275  -0.476   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.799  -1.941   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    4   13   14   22                                             
CONECT   13   12    2                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17   12   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
Conocarpan	MeSH

Chemical Formula

C₁₅H₁₆O₈

Average Mass

324.2850 Da

Monoisotopic Mass

324.08452 Da

IUPAC Name

(4S,8R,9R)-8-[(1S)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione

Traditional Name

(4S,8R,9R)-8-[(1S)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione

CAS Registry Number

Not Available

SMILES

OC[C@H](O)[C@H]1OC(=O)C2(OC(=O)C[C@H]2C2=CC=C(O)C=C2)[C@@H]1O

InChI Identifier

InChI=1S/C15H16O8/c16-6-10(18)12-13(20)15(14(21)22-12)9(5-11(19)23-15)7-1-3-8(17)4-2-7/h1-4,9-10,12-13,16-18,20H,5-6H2/t9-,10-,12+,13+,15?/m0/s1

InChI Key

JVCLQSJXGOABTC-IPNWIPTBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Krameria cytisoides	LOTUS Database	35616633
Krameria erecta	LOTUS Database	35616633
Krameria grayi	LOTUS Database	35616633
Krameria lanceolata	LOTUS Database	35616633
Krameria paucifolia	LOTUS Database	35616633
Krameria tomentosa	LOTUS Database	35616633
Piper aequale	LOTUS Database	35616633
Piper regnellii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	-0.81	ChemAxon
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.34 m³·mol⁻¹	ChemAxon
Polarizability	29.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

168066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193664

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione (NP0226073)

MOL for NP0226073 ((4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione)

3D MOL for NP0226073 ((4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione)

3D SDF for NP0226073 ((4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione)

3D-SDF for NP0226073 ((4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione)

PDB for NP0226073 ((4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione)

3D PDB for NP0226073 ((4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione)

SMILES for NP0226073 ((4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione)

INCHI for NP0226073 ((4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione)

Structure for NP0226073 ((4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione)

3D Structure for NP0226073 ((4s,8r,9r)-8-[(1s)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione)