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Showing NP-Card for Tuberosin (NP0047072)

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Record Information
Version2.0
Created at2022-03-17 20:34:09 UTC
Updated at2022-03-17 20:34:09 UTC
NP-MRD IDNP0047072
Secondary Accession NumbersNone
Natural Product Identification
Common NameTuberosin
Description Tuberosin is found in Calopogonium mucunoides, Pueraria candollei, Pueraria montana, Pueraria tuberosa and Sophora chrysophylla.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047072 (Tuberosin)


  Mrv0541 02241221422D          

 25 29  0  0  1  0            999 V2000
    6.8079   -0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4995    0.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4713    0.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7432    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0432    0.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3151    1.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6432   -0.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3714   -0.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0713   -0.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7995   -0.4120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8678   -0.3544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3604    0.2961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8222    0.9797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4612    1.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6382    1.7797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1763    1.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5374    0.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0755   -0.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2526   -0.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1085    0.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534    1.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9314    0.5289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3530    1.6113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3066    0.1955    0.0000 C   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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
  8 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
  7 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
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 24  1  1  0  0  0
  2 25  1  0  0  0  0
M  END
Download

3D MOL for NP0047072 (Tuberosin)

Download
3D SDF for NP0047072 (Tuberosin)

  Mrv0541 02241221422D          

 25 29  0  0  1  0            999 V2000
    6.8079   -0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4995    0.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4713    0.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7432    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0432    0.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3151    1.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151    0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6432   -0.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3714   -0.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0713   -0.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7995   -0.4120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8678   -0.3544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3604    0.2961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8222    0.9797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4612    1.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6382    1.7797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1763    1.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5374    0.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0755   -0.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2526   -0.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1085    0.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534    1.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9314    0.5289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3530    1.6113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3066    0.1955    0.0000 C   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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
  8 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
  7 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
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 24  1  1  0  0  0
  2 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047072

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=CC3=C(C=C2C=C1)[C@@]1(O)COC2=C(C=CC(O)=C2)[C@H]1O3

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O5/c1-19(2)6-5-11-7-14-17(9-15(11)25-19)24-18-13-4-3-12(21)8-16(13)23-10-20(14,18)22/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m1/s1

> <INCHI_KEY>
ZBTYHECJEINCMD-QUCCMNQESA-N

> <FORMULA>
C20H18O5

> <MOLECULAR_WEIGHT>
338.3539

> <EXACT_MASS>
338.115423686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.43088113196191

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,13R)-7,7-dimethyl-8,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-2(11),3,5,9,14(19),15,17-heptaene-1,17-diol

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
2.9123376819999995

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.055970665520434

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.413429647094496

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1009289875580235

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
92.07920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,13R)-7,7-dimethyl-8,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-2(11),3,5,9,14(19),15,17-heptaene-1,17-diol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047072 (Tuberosin)
Download
PDB for NP0047072 (Tuberosin)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      12.708  -1.382   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.132   0.046   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.080   1.585   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.721   2.309   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.414   1.494   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.055   2.218   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.748   1.403   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.801  -0.136   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.160  -0.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.466  -0.045   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.826  -0.769   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.353  -0.662   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.406   0.553   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.268   1.829   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.594   3.213   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.058   3.322   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.196   2.046   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.870   0.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.008  -0.615   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.472  -0.506   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.203   0.879   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.660   2.155   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.739   0.987   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.259   3.008   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.639   0.365   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11   25                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10    2                                                       
CONECT   12    8   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13    7   15   24                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   17                                                       
CONECT   23   21                                                            
CONECT   24   14                                                            
CONECT   25    2                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

Download
3D PDB for NP0047072 (Tuberosin)
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SMILES for NP0047072 (Tuberosin)
CC1(C)OC2=CC3=C(C=C2C=C1)[C@@]1(O)COC2=C(C=CC(O)=C2)[C@H]1O3
Download
INCHI for NP0047072 (Tuberosin)
InChI=1S/C20H18O5/c1-19(2)6-5-11-7-14-17(9-15(11)25-19)24-18-13-4-3-12(21)8-16(13)23-10-20(14,18)22/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H18O5
Average Mass338.3539 Da
Monoisotopic Mass338.11542 Da
IUPAC Name(1R,13R)-7,7-dimethyl-8,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-2(11),3,5,9,14(19),15,17-heptaene-1,17-diol
Traditional Name(1R,13R)-7,7-dimethyl-8,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-2(11),3,5,9,14(19),15,17-heptaene-1,17-diol
CAS Registry NumberNot Available
SMILES
CC1(C)OC2=CC3=C(C=C2C=C1)[C@@]1(O)COC2=C(C=CC(O)=C2)[C@H]1O3
InChI Identifier
InChI=1S/C20H18O5/c1-19(2)6-5-11-7-14-17(9-15(11)25-19)24-18-13-4-3-12(21)8-16(13)23-10-20(14,18)22/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m1/s1
InChI KeyZBTYHECJEINCMD-QUCCMNQESA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Calopogonium mucunoidesLOTUS Database
Pueraria candollei var. mirificaLOTUS Database
Pueraria montanaLOTUS Database
Pueraria tuberosaLOTUS Database
Solanum tuberosumFooDB
Sophora chrysophyllaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the  6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassIsoflavonoids  
Sub ClassFuranoisoflavonoids  
Direct ParentPterocarpans  
Alternative Parents
Substituents
  • Isoflavanol
    • 

  • Pterocarpan
    • 

  • Isoflavan
    • 

  • 2,2-dimethyl-1-benzopyran
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Coumaran
    • 

  • Benzofuran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Tertiary alcohol
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.25ALOGPS
logP2.91ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity92.08 m³·mol⁻¹ChemAxon
Polarizability35.43 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007156  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5318770  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available