NP-MRD: Showing NP-Card for 5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one (NP0323176)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 02:26:12 UTC

Updated at

2022-09-12 02:26:13 UTC

NP-MRD ID

NP0323176

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one

Description

5,18,19-Trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]Nonadeca-2(7),12(17),13,15-tetraen-3-one belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. 5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one is found in Streptomyces griseus. Based on a literature review very few articles have been published on 5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]Nonadeca-2(7),12(17),13,15-tetraen-3-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122204262D          

 26 30  0  0  0  0            999 V2000
    2.9857    1.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5715    1.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613    0.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653    0.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3551   -0.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9408   -1.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9470   -0.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7760    0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0259    0.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3654   -0.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1130   -0.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5132   -1.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2975   -1.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6525   -1.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0804   -0.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3092    0.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7371    0.7906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1100    0.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6821   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1681    0.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4230   -0.5629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4534   -0.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1694   -1.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3630   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8271   -2.1889    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 15 23  1  0  0  0  0
 16 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
M  END


  Mrv1652309122204262D          

 26 30  0  0  0  0            999 V2000
    2.9857    1.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5715    1.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613    0.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653    0.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3551   -0.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9408   -1.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9470   -0.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7760    0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0259    0.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3654   -0.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1130   -0.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5132   -1.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2975   -1.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6525   -1.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0804   -0.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3092    0.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7371    0.7906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1100    0.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6821   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1681    0.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4230   -0.5629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4534   -0.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1694   -1.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3630   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8271   -2.1889    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 15 23  1  0  0  0  0
 16 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC2=C1C(O)C1(O)C3CC4=C(C1C2O3)C(=O)CC(C)(O)C4

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O6/c1-19(23)7-9-6-13-20(24)16(14(9)11(21)8-19)17(26-13)10-4-3-5-12(25-2)15(10)18(20)22/h3-5,13,16-18,22-24H,6-8H2,1-2H3

> <INCHI_KEY>
OYXKPETZJCTWDM-UHFFFAOYSA-N

> <FORMULA>
C20H22O6

> <MOLECULAR_WEIGHT>
358.39

> <EXACT_MASS>
358.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.070555004716994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0^{2,7}.0^{9,19}.0^{12,17}]nonadeca-2(7),12(17),13,15-tetraen-3-one

> <JCHEM_LOGP>
-0.05873108633333274

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.777357117751546

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.284136566747655

> <JCHEM_PKA_STRONGEST_BASIC>
-2.890971617659144

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
92.5084

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0^{2,7}.0^{9,19}.0^{12,17}]nonadeca-2(7),12(17),13,15-tetraen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       5.573   3.319   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.667   2.235   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.274   0.746   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.789   0.341   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.396  -1.148   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.490  -2.233   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.975  -1.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.368  -0.339   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.915   0.002   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.382   1.469   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.015  -1.206   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.411  -0.555   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.291  -3.250   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.755  -3.629   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.418  -2.223   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.350  -1.113   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.777   0.366   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.709   1.476   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.272   0.736   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.340  -0.373   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.247   0.871   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      15.723  -1.051   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.913  -1.853   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.649  -2.051   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.144  -2.854   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.011  -4.086   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   24                                             
CONECT   12   11                                                            
CONECT   13   11   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   15                                                       
CONECT   24   16   11   25                                                  
CONECT   25   24    7   26                                                  
CONECT   26   25   13                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₆

Average Mass

358.3900 Da

Monoisotopic Mass

358.14164 Da

IUPAC Name

5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0^{2,7}.0^{9,19}.0^{12,17}]nonadeca-2(7),12(17),13,15-tetraen-3-one

Traditional Name

5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0^{2,7}.0^{9,19}.0^{12,17}]nonadeca-2(7),12(17),13,15-tetraen-3-one

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C1C(O)C1(O)C3CC4=C(C1C2O3)C(=O)CC(C)(O)C4

InChI Identifier

InChI=1S/C20H22O6/c1-19(23)7-9-6-13-20(24)16(14(9)11(21)8-19)17(26-13)10-4-3-5-12(25-2)15(10)18(20)22/h3-5,13,16-18,22-24H,6-8H2,1-2H3

InChI Key

OYXKPETZJCTWDM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces griseus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Anisole
Cyclohexenone
Alkyl aryl ether
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	-0.059	ChemAxon
pKa (Strongest Acidic)	12.28	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.51 m³·mol⁻¹	ChemAxon
Polarizability	37.07 Å³	ChemAxon
Number of Rings	5	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

162814821

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one (NP0323176)

MOL for NP0323176 (5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one)

3D MOL for NP0323176 (5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one)

3D SDF for NP0323176 (5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one)

3D-SDF for NP0323176 (5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one)

PDB for NP0323176 (5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one)

3D PDB for NP0323176 (5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one)

SMILES for NP0323176 (5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one)

INCHI for NP0323176 (5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one)

Structure for NP0323176 (5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one)

3D Structure for NP0323176 (5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0²,⁷.0⁹,¹⁹.0¹²,¹⁷]nonadeca-2(7),12(17),13,15-tetraen-3-one)