NP-MRD: Showing NP-Card for 13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol (NP0305992)

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Record Information

Version

2.0

Created at

2022-09-10 22:12:16 UTC

Updated at

2022-09-10 22:12:16 UTC

NP-MRD ID

NP0305992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol

Description

13-Chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]Pentacosa-2,4,6,9(14),10,12-hexaene-3,4,5,11,21,22-hexol belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. 13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol is found in Curculigo sinensis. Based on a literature review very few articles have been published on 13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]Pentacosa-2,4,6,9(14),10,12-hexaene-3,4,5,11,21,22-hexol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112200122D          

 34 39  0  0  0  0            999 V2000
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    4.4090   -2.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6821   -1.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9737   -2.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309112200122D          

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M  END
> <DATABASE_ID>
NP0305992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC2OC3CC4=C(Cl)C=C(O)C=C4C4C3C(OC2C(O)C1O)C1=C(O)C(O)=C(O)C=C41

> <INCHI_IDENTIFIER>
InChI=1S/C23H23ClO10/c24-10-2-6(26)1-8-7(10)4-12-16-14(8)9-3-11(27)17(28)19(30)15(9)21(16)34-22-20(31)18(29)13(5-25)33-23(22)32-12/h1-3,12-14,16,18,20-23,25-31H,4-5H2

> <INCHI_KEY>
ARLTXIWVWNCPFP-UHFFFAOYSA-N

> <FORMULA>
C23H23ClO10

> <MOLECULAR_WEIGHT>
494.88

> <EXACT_MASS>
494.0979746

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
48.170200196349896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0^{2,7}.0^{8,25}.0^{9,14}.0^{18,23}]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol

> <JCHEM_LOGP>
1.0211011883333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.227604334768072

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.596075596047614

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810837551591494

> <JCHEM_POLAR_SURFACE_AREA>
169.29999999999998

> <JCHEM_REFRACTIVITY>
116.01119999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0^{2,7}.0^{8,25}.0^{9,14}.0^{18,23}]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0      14.790  -5.092   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      13.300  -5.481   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.218  -4.385   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.728  -4.775   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.646  -3.679   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.230  -4.286   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.873  -3.558   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.551  -4.497   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.134  -3.893   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.903  -4.818   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       3.089  -6.347   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       1.486  -4.215   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.301  -2.686   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.116  -2.082   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.532  -1.761   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.948  -2.364   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.180  -1.439   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.316   0.095   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.267   1.222   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.719   2.695   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.670   3.822   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.220   3.039   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.672   4.511   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.269   1.911   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.770   2.256   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.817   0.439   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.608  -0.882   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.147  -0.949   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.053  -2.194   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.543  -1.805   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.951  -0.320   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.625  -2.900   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      14.115  -2.511   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.596  -2.043   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16   18   34                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   18   27                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28    5   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3   33                                                  
CONECT   33   32                                                            
CONECT   34   27    7   17                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₃ClO₁₀

Average Mass

494.8800 Da

Monoisotopic Mass

494.09797 Da

IUPAC Name

13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0^{2,7}.0^{8,25}.0^{9,14}.0^{18,23}]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol

Traditional Name

13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0^{2,7}.0^{8,25}.0^{9,14}.0^{18,23}]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol

CAS Registry Number

Not Available

SMILES

OCC1OC2OC3CC4=C(Cl)C=C(O)C=C4C4C3C(OC2C(O)C1O)C1=C(O)C(O)=C(O)C=C41

InChI Identifier

InChI=1S/C23H23ClO10/c24-10-2-6(26)1-8-7(10)4-12-16-14(8)9-3-11(27)17(28)19(30)15(9)21(16)34-22-20(31)18(29)13(5-25)33-23(22)32-12/h1-3,12-14,16,18,20-23,25-31H,4-5H2

InChI Key

ARLTXIWVWNCPFP-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
Curculigo sinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Fluorenes

Sub Class

Not Available

Direct Parent

Fluorenes

Alternative Parents

Substituents

Fluorene
Tetralin
Indane
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
1,4-dioxepane
Dioxepane
Aryl chloride
Aryl halide
Oxane
Monosaccharide
Secondary alcohol
Acetal
Oxacycle
Dialkyl ether
Organoheterocyclic compound
Ether
Polyol
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Organooxygen compound
Organohalogen compound
Organochloride
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	1.02	ChemAxon
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	169.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	116.01 m³·mol⁻¹	ChemAxon
Polarizability	48.17 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

162848168

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol (NP0305992)

MOL for NP0305992 (13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol)

3D MOL for NP0305992 (13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol)

3D SDF for NP0305992 (13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol)

3D-SDF for NP0305992 (13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol)

PDB for NP0305992 (13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol)

3D PDB for NP0305992 (13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol)

SMILES for NP0305992 (13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol)

INCHI for NP0305992 (13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol)

Structure for NP0305992 (13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol)

3D Structure for NP0305992 (13-chloro-20-(hydroxymethyl)-17,19,24-trioxahexacyclo[14.8.1.0²,⁷.0⁸,²⁵.0⁹,¹⁴.0¹⁸,²³]pentacosa-2,4,6,9,11,13-hexaene-3,4,5,11,21,22-hexol)