NP-MRD: Showing NP-Card for Ligudentatol (NP0078580)

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Record Information

Version

2.0

Created at

2022-04-28 23:38:07 UTC

Updated at

2022-04-28 23:38:07 UTC

NP-MRD ID

NP0078580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ligudentatol

Description

Ligudentatol 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. Ligudentatol is found in Ligularia dentata and Sorbus cuspidata. Ligudentatol was first documented in 2007 (PMID: 17672339). Based on a literature review a small amount of articles have been published on Ligudentatol (PMID: 24769287) (PMID: 24700669).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.4377   -0.5145    1.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7754   -0.3023    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4403   -0.6101   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4062    0.2302    0.5659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2778    1.5700   -0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0158    2.2197    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1122    1.3009    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3624    1.8698   -0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586    1.1144   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2825   -0.2293   -0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900   -1.0003   -1.0085 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296   -0.7908   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9114   -2.2556   -0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9067   -0.0522   -0.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3962   -0.7175   -0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9915   -0.3045    2.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4425   -0.9035    1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4726   -0.9608   -0.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5207    0.2920   -1.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199   -1.3672   -1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0604    0.3883    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518    1.3917   -1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1194    2.2281    0.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0725    2.2532    1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1029    3.1875   -0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    2.9383    0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4335    1.5846   -0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2612   -1.9895   -1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4592   -2.8026    0.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8640   -2.5985   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3761   -2.5184   -1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2646   -1.5974    0.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -1.0536   -1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15  4  1  0
 14  7  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  1 16  1  0
  1 17  1  0
  4 21  1  1
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
M  END


  Mrv1652304292201382D          

 15 16  0  0  1  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    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  2  0  0  0  0
  1  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  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  3 14  1  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CCC2=CC=C(O)C(C)=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O/c1-9(2)12-5-4-11-6-7-14(15)10(3)13(11)8-12/h6-7,12,15H,1,4-5,8H2,2-3H3/t12-/m1/s1

> <INCHI_KEY>
BVEBOMULMBWPIS-GFCCVEGCSA-N

> <FORMULA>
C14H18O

> <MOLECULAR_WEIGHT>
202.297

> <EXACT_MASS>
202.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.20593213979453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7R)-1-methyl-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

> <ALOGPS_LOGP>
4.48

> <JCHEM_LOGP>
4.306317136333334

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.72789716717295

> <JCHEM_PKA_STRONGEST_BASIC>
-5.428413383320664

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
64.038

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7R)-1-methyl-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    1                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3                                                            
CONECT   15    2                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₈O

Average Mass

202.2970 Da

Monoisotopic Mass

202.13577 Da

IUPAC Name

(7R)-1-methyl-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

Traditional Name

(7R)-1-methyl-7-(prop-1-en-2-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CCC2=CC=C(O)C(C)=C2C1

InChI Identifier

InChI=1S/C14H18O/c1-9(2)12-5-4-11-6-7-14(15)10(3)13(11)8-12/h6-7,12,15H,1,4-5,8H2,2-3H3/t12-/m1/s1

InChI Key

BVEBOMULMBWPIS-GFCCVEGCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ligularia dentata	Plant	KNApSAcK
Sorbus cuspidata	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
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.48	ALOGPS
logP	4.31	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	10.73	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.04 m³·mol⁻¹	ChemAxon
Polarizability	24.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00042699

Chemspider ID

9184187

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11009001

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang CY, Geng CA, Huang XY, Wang H, Xu HB, Liang WJ, Ma YB, Zhang XM, Zhou J, Chen JJ: Noreudesmane sesquiterpenoids from the leaves of Nicotiana tabacum. Fitoterapia. 2014 Jul;96:81-7. doi: 10.1016/j.fitote.2014.04.010. Epub 2014 Apr 24. [PubMed:24769287 ]
Moustafa GA, Suizu H, Aoyama H, Arai M, Akai S, Yoshimitsu T: Enantiospecific synthesis and cytotoxicity evaluation of ligudentatol: a programmed aromatization approach to the 2,3,4-trisubstituted phenolic motif via visible-light-mediated group transfer radical cyclization. Chem Asian J. 2014 Jun;9(6):1506-10. doi: 10.1002/asia.201400110. Epub 2014 Apr 2. [PubMed:24700669 ]
Xue HQ, Ma XM, Wei XN, Wu SX, Wang HQ: [Study on chemical constiuents from Ligularia intermedia of shanxi]. Zhongguo Zhong Yao Za Zhi. 2007 Jun;32(11):1044-7. [PubMed:17672339 ]

Showing NP-Card for Ligudentatol (NP0078580)

MOL for NP0078580 (Ligudentatol)

3D MOL for NP0078580 (Ligudentatol)

3D SDF for NP0078580 (Ligudentatol)

3D-SDF for NP0078580 (Ligudentatol)

PDB for NP0078580 (Ligudentatol)

3D PDB for NP0078580 (Ligudentatol)

SMILES for NP0078580 (Ligudentatol)

INCHI for NP0078580 (Ligudentatol)

Structure for NP0078580 (Ligudentatol)

3D Structure for NP0078580 (Ligudentatol)