NP-MRD: Showing NP-Card for Bakuchiol (NP0070936)

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Record Information

Version

2.0

Created at

2022-04-28 16:20:58 UTC

Updated at

2022-04-28 16:20:58 UTC

NP-MRD ID

NP0070936

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bakuchiol

Description

Bakuchiol belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Bakuchiol is found in Psoralea corylifolia , Otholobium glandulosum, Otholobium pubescens, Psorallea corylifolia, Psorallea drupacea and Spiraea formosana . Bakuchiol was first documented in 2022 (PMID: 35427048). Based on a literature review a small amount of articles have been published on Bakuchiol (PMID: 35424800) (PMID: 35178925) (PMID: 35036111) (PMID: 35000392).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
   -1.4955   -0.1736    3.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4611   -0.5571    2.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342   -0.1127    1.0777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4062    1.3538    0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764   -0.5373    0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9573    0.1348   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3169   -0.2195   -0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0263    0.5819   -1.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3205    0.2722   -1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8827   -0.8794   -1.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1850   -1.2168   -1.4487 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2078   -1.6950   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9059   -1.3471    0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0981   -0.9504    0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5631   -0.8961    0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2257    0.3865    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1186    0.5248   -0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4237   -0.6542   -1.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7749    1.8154   -1.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5959   -0.5298    4.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2817    0.4854    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2572   -1.2316    2.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832    1.8516    1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228    1.6999    1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8471    1.7157    0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5170   -1.4418    1.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4755    1.0402   -0.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5454    1.4710   -1.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8883    0.9020   -2.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3154   -1.8052   -2.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6382   -2.5929    0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3768   -2.0009    0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637   -0.8082   -0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -2.0259    0.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821   -1.6334   -0.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9288   -1.3276    1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421    1.2544    0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8754   -1.4798   -1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5133   -1.0029   -2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1937   -0.3628   -2.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2365    2.4354   -1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8003    1.6856   -1.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8124    2.4531   -0.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 19  1  0
 17 16  2  3
 16 15  1  0
 15 14  1  0
  3 14  1  6
  3  4  1  0
  3  2  1  0
  2  1  2  3
  3  5  1  0
  5  6  2  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  2  0
 13  7  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 16 37  1  0
 15 35  1  0
 15 36  1  0
 14 33  1  0
 14 34  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  2 22  1  0
  1 20  1  0
  1 21  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
M  END


  Mrv1652304282218202D          

 19 19  0  0  1  0            999 V2000
    1.4289    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
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2539    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  9 18  1  6  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070936

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O/c1-5-18(4,13-6-7-15(2)3)14-12-16-8-10-17(19)11-9-16/h5,7-12,14,19H,1,6,13H2,2-4H3/b14-12+/t18-/m1/s1

> <INCHI_KEY>
LFYJSSARVMHQJB-QIXNEVBVSA-N

> <FORMULA>
C18H24O

> <MOLECULAR_WEIGHT>
256.389

> <EXACT_MASS>
256.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.198652598620004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dien-1-yl]phenol

> <ALOGPS_LOGP>
6.06

> <JCHEM_LOGP>
5.624947392

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.528192746886448

> <JCHEM_PKA_STRONGEST_BASIC>
-5.947957449317028

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
85.47109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bakuchiol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.207   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.977   7.494   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.127   6.160   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12   18                                             
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    9                                                            
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₄O

Average Mass

256.3890 Da

Monoisotopic Mass

256.18272 Da

IUPAC Name

4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dien-1-yl]phenol

Traditional Name

bakuchiol

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H24O/c1-5-18(4,13-6-7-15(2)3)14-12-16-8-10-17(19)11-9-16/h5,7-12,14,19H,1,6,13H2,2-4H3/b14-12+/t18-/m1/s1

InChI Key

LFYJSSARVMHQJB-QIXNEVBVSA-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
Cullen corylifolium	Plant	KNApSAcK
Otholobium glandulosum	LOTUS Database	35616633
Otholobium pubescens	LOTUS Database	35616633
Psorallea corylifolia	-	KNApSAcK
Psorallea drupacea	-	KNApSAcK
Spiraea formosana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Aromatic monoterpenoid
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	6.06	ALOGPS
logP	5.62	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.53	ChemAxon
pKa (Strongest Basic)	-5.9	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	6	ChemAxon
Refractivity	85.47 m³·mol⁻¹	ChemAxon
Polarizability	31.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00029787

Chemspider ID

4579217

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bakuchiol

METLIN ID

Not Available

PubChem Compound

5468522

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Krishna TPA, Edachery B, Athalathil S: Correction: Bakuchiol - a natural meroterpenoid: structure, isolation, synthesis and functionalization approaches. RSC Adv. 2022 Apr 7;12(17):10862. doi: 10.1039/d2ra90033e. eCollection 2022 Mar 31. [PubMed:35427048 ]
Adarsh Krishna TP, Edachery B, Athalathil S: Bakuchiol - a natural meroterpenoid: structure, isolation, synthesis and functionalization approaches. RSC Adv. 2022 Mar 21;12(14):8815-8832. doi: 10.1039/d1ra08771a. eCollection 2022 Mar 15. [PubMed:35424800 ]
Wu YL, Wang XY, Zhang H, Chen YL, Zhang ML, Chen XF, Niu L, Li WX, Tang JF: [Study on alleviating effect of Glycyrrhizae Radix et Rhizoma on Psoraleae Fructus-induced liver injury based on network pharmacology and cell experiments]. Zhongguo Zhong Yao Za Zhi. 2022 Jan;47(1):176-187. doi: 10.19540/j.cnki.cjcmm.20211025.401. [PubMed:35178925 ]
Fahim A, Himratul-Aznita WH, Abdul-Rahman PS, Alam MK: Efficacy of bakuchiol-garlic combination against virulent genes of Candida albicans. PeerJ. 2022 Jan 3;9:e12251. doi: 10.7717/peerj.12251. eCollection 2022. [PubMed:35036111 ]
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Showing NP-Card for Bakuchiol (NP0070936)

MOL for NP0070936 (Bakuchiol)

3D MOL for NP0070936 (Bakuchiol)

3D SDF for NP0070936 (Bakuchiol)

3D-SDF for NP0070936 (Bakuchiol)

PDB for NP0070936 (Bakuchiol)

3D PDB for NP0070936 (Bakuchiol)

SMILES for NP0070936 (Bakuchiol)

INCHI for NP0070936 (Bakuchiol)

Structure for NP0070936 (Bakuchiol)

3D Structure for NP0070936 (Bakuchiol)