NP-MRD: Showing NP-Card for (1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one (NP0219060)

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Record Information

Version

2.0

Created at

2022-09-05 19:56:01 UTC

Updated at

2022-09-05 19:56:01 UTC

NP-MRD ID

NP0219060

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one

Description

Plecmillin A 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. Based on a literature review very few articles have been published on Plecmillin A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052221562D          

 26 31  0  0  1  0            999 V2000
    3.7761   -0.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0958    0.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515   -0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6712    0.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7352    1.1185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9578    0.8424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550    1.4965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9217    2.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7129    1.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109    2.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1176    3.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3264    3.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619    4.3557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5659    2.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566    2.9852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6124    3.7295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7233    2.3049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1900    1.6246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3675    1.5606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4796    1.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436    2.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2879    2.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9682    2.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042    1.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5845    0.8966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1598    1.0075    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  1  0  0  0
 17 19  1  0  0  0  0
  7 19  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 20 26  1  0  0  0  0
  2 26  1  0  0  0  0
M  END


  Mrv1652309052221562D          

 26 31  0  0  1  0            999 V2000
    3.7761   -0.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0958    0.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515   -0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6712    0.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7352    1.1185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9578    0.8424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550    1.4965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9217    2.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7129    1.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109    2.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1176    3.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3264    3.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619    4.3557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5659    2.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566    2.9852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6124    3.7295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7233    2.3049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1900    1.6246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3675    1.5606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4796    1.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436    2.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2879    2.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9682    2.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042    1.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5845    0.8966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1598    1.0075    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  1  0  0  0
 17 19  1  0  0  0  0
  7 19  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 20 26  1  0  0  0  0
  2 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219060

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H]2O[C@@H]2[C@@H]2O[C@]3(C=CC(=O)C4=C(O)C=CC=C34)C3=C2C1=C(O)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C20H14O6/c21-10-3-1-2-8-13(10)12(23)6-7-20(8)9-4-5-11(22)15-14(9)17(26-20)19-18(25-19)16(15)24/h1-7,16-19,21-22,24H/t16-,17+,18-,19+,20-/m0/s1

> <INCHI_KEY>
KLUZLYJDODRQCZ-YHDCXSKOSA-N

> <FORMULA>
C20H14O6

> <MOLECULAR_WEIGHT>
350.326

> <EXACT_MASS>
350.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.32296640266662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,1'R,9'S,10'S,12'R)-5,7',9'-trihydroxy-4H-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0^{4,13}.0^{10,12}]tridecane]-4'(13'),5',7'-trien-4-one

> <JCHEM_LOGP>
2.232483056

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.648618612787434

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.583774743148759

> <JCHEM_PKA_STRONGEST_BASIC>
-3.65329993127959

> <JCHEM_POLAR_SURFACE_AREA>
99.52000000000001

> <JCHEM_REFRACTIVITY>
91.3545

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,1'R,9'S,10'S,12'R)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0^{4,13}.0^{10,12}]tridecane]-4'(13'),5',7'-trien-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       7.049  -0.526   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.779   0.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.389  -0.319   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.120   0.552   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.239   2.088   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.788   1.573   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.849   2.794   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.721   4.063   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.197   3.627   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.314   4.688   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.953   6.185   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.476   6.622   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.169   8.131   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.056   5.453   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.479   5.572   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.143   6.962   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.350   4.302   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.221   3.033   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.686   2.913   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.628   2.752   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.748   4.287   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.137   4.951   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.407   4.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.288   2.545   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.558   1.674   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.898   1.881   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9   20                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17   19                                                       
CONECT   19   18   17    7                                                  
CONECT   20    5   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20    2                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₄O₆

Average Mass

350.3260 Da

Monoisotopic Mass

350.07904 Da

IUPAC Name

(1R,1'R,9'S,10'S,12'R)-5,7',9'-trihydroxy-4H-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0^{4,13}.0^{10,12}]tridecane]-4'(13'),5',7'-trien-4-one

Traditional Name

(1R,1'R,9'S,10'S,12'R)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0^{4,13}.0^{10,12}]tridecane]-4'(13'),5',7'-trien-4-one

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H]2O[C@@H]2[C@@H]2O[C@]3(C=CC(=O)C4=C(O)C=CC=C34)C3=C2C1=C(O)C=C3

InChI Identifier

InChI=1S/C20H14O6/c21-10-3-1-2-8-13(10)12(23)6-7-20(8)9-4-5-11(22)15-14(9)17(26-20)19-18(25-19)16(15)24/h1-7,16-19,21-22,24H/t16-,17+,18-,19+,20-/m0/s1

InChI Key

KLUZLYJDODRQCZ-YHDCXSKOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Naphthalene
Isocoumaran
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.23	ChemAxon
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.35 m³·mol⁻¹	ChemAxon
Polarizability	34.32 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

132548501

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one (NP0219060)

MOL for NP0219060 ((1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one)

3D MOL for NP0219060 ((1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one)

3D SDF for NP0219060 ((1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one)

3D-SDF for NP0219060 ((1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one)

PDB for NP0219060 ((1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one)

3D PDB for NP0219060 ((1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one)

SMILES for NP0219060 ((1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one)

INCHI for NP0219060 ((1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one)

Structure for NP0219060 ((1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one)

3D Structure for NP0219060 ((1r,1'r,9's,10's,12'r)-5,7',9'-trihydroxy-2',11'-dioxaspiro[naphthalene-1,3'-tetracyclo[6.4.1.0⁴,¹³.0¹⁰,¹²]tridecane]-4'(13'),5',7'-trien-4-one)