NP-MRD: Showing NP-Card for 6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one (NP0224902)

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Record Information

Version

2.0

Created at

2022-09-06 03:27:59 UTC

Updated at

2022-09-06 03:27:59 UTC

NP-MRD ID

NP0224902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one

Description

6,9,11-Trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]Tetracosa-2(7),3,5,8,10,12(24),16,18,20-nonaen-13-one belongs to the class of organic compounds known as isoflavans. These are polycyclic compounds with a structure based on the 3-phenyl-3,4-dihydro-2H-1-benzopyran skeleton. 6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one is found in Polytrichastrum alpinum and Polytrichastrum ohioense. 6,9,11-Trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]Tetracosa-2(7),3,5,8,10,12(24),16,18,20-nonaen-13-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191515322D          

 28 33  0  0  0  0            999 V2000
    2.4922   -0.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -1.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -2.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -3.0175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -2.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -2.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -3.4853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -2.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -1.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7 27  1  0  0  0  0
 15 27  1  0  0  0  0
 25 28  1  0  0  0  0
  2 28  1  0  0  0  0
  6 28  2  0  0  0  0
M  END


  Mrv1533004191515322D          

 28 33  0  0  0  0            999 V2000
    2.4922   -0.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -1.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -2.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -3.0175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -2.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -2.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -3.4853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -2.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -1.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7 27  1  0  0  0  0
 15 27  1  0  0  0  0
 25 28  1  0  0  0  0
  2 28  1  0  0  0  0
  6 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0224902

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC2=C1C1=C3C4C(CC(=O)C3=C(O)C=C1O)C1=CC=CC=C1OC24

> <INCHI_IDENTIFIER>
InChI=1S/C23H16O5/c24-13-6-3-5-11-18(13)21-16(27)9-15(26)20-14(25)8-12-10-4-1-2-7-17(10)28-23(11)19(12)22(20)21/h1-7,9,12,19,23-24,26-27H,8H2

> <INCHI_KEY>
VYRXNKPPFHPOIN-UHFFFAOYSA-N

> <FORMULA>
C23H16O5

> <MOLECULAR_WEIGHT>
372.376

> <EXACT_MASS>
372.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
37.73881909663736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2(7),3,5,8(24),9,11,16,18,20-nonaen-13-one

> <ALOGPS_LOGP>
3.87

> <JCHEM_LOGP>
4.188671518333333

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.861326764136436

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2464846781342205

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890957114795767

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
102.87619999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2(7),3,5,8(24),9,11,16,18,20-nonaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0       4.652  -1.558   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.660  -0.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.156   1.061   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.164   2.225   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.677   1.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.181   0.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.693   0.188   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.701   1.352   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.213   1.061   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.221   2.225   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.734   1.934   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.238   0.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.230  -0.685   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.717  -0.394   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.709  -1.558   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.213  -3.013   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.205  -4.178   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.709  -5.633   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.693  -3.887   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.685  -5.051   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.189  -6.506   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.172  -4.760   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -3.304   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.156  -3.013   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.677  -2.140   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.189  -2.431   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.197  -1.267   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.172  -0.685   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   28                                                  
CONECT   26   25   19   27                                                  
CONECT   27   26    7   15                                                  
CONECT   28   25    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₁₆O₅

Average Mass

372.3760 Da

Monoisotopic Mass

372.09977 Da

IUPAC Name

6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2(7),3,5,8(24),9,11,16,18,20-nonaen-13-one

Traditional Name

6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2(7),3,5,8(24),9,11,16,18,20-nonaen-13-one

CAS Registry Number

Not Available

SMILES

OC1=CC=CC2=C1C1=C3C4C(CC(=O)C3=C(O)C=C1O)C1=CC=CC=C1OC24

InChI Identifier

InChI=1S/C23H16O5/c24-13-6-3-5-11-18(13)21-16(27)9-15(26)20-14(25)8-12-10-4-1-2-7-17(10)28-23(11)19(12)22(20)21/h1-7,9,12,19,23-24,26-27H,8H2

InChI Key

VYRXNKPPFHPOIN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Polytrichastrum alpinum	LOTUS Database	35616633
Polytrichastrum ohioense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavans. These are polycyclic compounds with a structure based on the 3-phenyl-3,4-dihydro-2H-1-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavans

Alternative Parents

Substituents

Isoflavan
Naphthopyran
Phenanthrene
Xanthene
Dibenzopyran
1-naphthol
Tetralin
Chromane
1-benzopyran
Naphthalene
Benzopyran
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Vinylogous acid
Ketone
Polyol
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	3.87	ALOGPS
logP	4.19	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.25	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	102.88 m³·mol⁻¹	ChemAxon
Polarizability	37.74 Å³	ChemAxon
Number of Rings	6	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

85080634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one (NP0224902)

MOL for NP0224902 (6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one)

3D MOL for NP0224902 (6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one)

3D SDF for NP0224902 (6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one)

3D-SDF for NP0224902 (6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one)

PDB for NP0224902 (6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one)

3D PDB for NP0224902 (6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one)

SMILES for NP0224902 (6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one)

INCHI for NP0224902 (6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one)

Structure for NP0224902 (6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one)

3D Structure for NP0224902 (6,9,11-trihydroxy-22-oxahexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁶,²¹]tetracosa-2,4,6,8,10,12(24),16,18,20-nonaen-13-one)