NP-MRD: Showing NP-Card for 2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol (NP0310591)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 06:00:54 UTC

Updated at

2022-09-11 06:00:54 UTC

NP-MRD ID

NP0310591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol

Description

Xanthorrhizol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol is found in Chrysactinia mexicana, Cinnamomum iners, Commiphora kua, Curcuma aromatica, Curcuma longa, Curcuma xanthorrhiza, Iostephane heterophylla, Valeriana jatamansi and Zingiber officinale. 2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol was first documented in 2021 (PMID: 34829954). Based on a literature review a small amount of articles have been published on Xanthorrhizol (PMID: 35992318) (PMID: 35933899) (PMID: 35932370) (PMID: 34664399).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 38  0  0  0  0  0  0  0  0999 V2000
   -2.2402    1.8173    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2567    0.7515    0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6811    1.0993    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8374   -0.4786    0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4057   -0.8126    0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535   -1.8587   -0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5132   -2.1531    0.1203 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9216   -3.1997   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3528   -0.9546    0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291   -0.5693    1.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9486    0.5605    1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852    1.3180   -0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596    2.5243   -0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2052    0.9408   -1.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659    1.7240   -2.3511 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4095   -0.1758   -1.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6787    2.7640   -0.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147    2.0617    1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179    1.4573   -0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9425    1.9544    0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3556    0.2668    0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8953    1.4402   -0.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5683   -1.2690    0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7511    0.0780    0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2552   -1.2045    1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5501   -2.7772    0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1634   -1.5234   -1.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386   -2.5999    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435   -4.0795   -0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8624   -2.7920   -1.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9515   -3.5796   -0.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403   -1.1287    1.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5515    0.8409    1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8862    2.1662   -0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8340    3.1039    0.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5112    3.1882   -0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7392    1.5372   -3.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8181   -0.4384   -1.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16  9  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  7 28  1  1
  6 26  1  0
  6 27  1  0
  5 24  1  0
  5 25  1  0
  4 23  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
M  END


  Mrv1652309112208002D          

 16 16  0  0  1  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   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
    0.7145    2.0625    0.0000 C   0  0  1  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
    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
    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
    0.7145   -1.2375    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 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0310591

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-11(2)6-5-7-12(3)14-9-8-13(4)15(16)10-14/h6,8-10,12,16H,5,7H2,1-4H3/t12-/m1/s1

> <INCHI_KEY>
FKWGCEDRLNNZOZ-GFCCVEGCSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.34

> <EXACT_MASS>
218.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.597216512438067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]phenol

> <JCHEM_LOGP>
5.0878253093333345

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.41717718532451

> <JCHEM_PKA_STRONGEST_BASIC>
-5.466329342299741

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
71.0735

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]phenol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
Xanthorrizol	MeSH

Chemical Formula

C₁₅H₂₂O

Average Mass

218.3400 Da

Monoisotopic Mass

218.16707 Da

IUPAC Name

2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]phenol

Traditional Name

2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]phenol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H22O/c1-11(2)6-5-7-12(3)14-9-8-13(4)15(16)10-14/h6,8-10,12,16H,5,7H2,1-4H3/t12-/m1/s1

InChI Key

FKWGCEDRLNNZOZ-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Chrysactinia mexicana	LOTUS Database	35616633
Cinnamomum iners	LOTUS Database	35616633
Commiphora kua	LOTUS Database	35616633
Curcuma aromatica	LOTUS Database	35616633
Curcuma longa	LOTUS Database	35616633
Curcuma xanthorrhiza	LOTUS Database	35616633
Iostephane heterophylla	LOTUS Database	35616633
Valeriana jatamansi	LOTUS Database	35616633
Zingiber officinale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Bisabolane sesquiterpenoid
Sesquiterpenoid
P-cymene
O-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
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	5.09	ChemAxon
pKa (Strongest Acidic)	10.42	ChemAxon
pKa (Strongest Basic)	-5.5	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	4	ChemAxon
Refractivity	71.07 m³·mol⁻¹	ChemAxon
Polarizability	26.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00011622

Chemspider ID

84081

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

93135

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kang J, Won J, Hwang JK, Kang W: Bioavailability of xanthorrhizol following oral administration of a supercritical extract of Java turmeric. Food Sci Biotechnol. 2022 Aug 6;31(10):1309-1313. doi: 10.1007/s10068-022-01124-w. eCollection 2022 Sep. [PubMed:35992318 ]
Simamora A, Timotius KH, Yerer MB, Setiawan H, Mun'im A: Xanthorrhizol, a potential anticancer agent, from Curcuma xanthorrhiza Roxb. Phytomedicine. 2022 Oct;105:154359. doi: 10.1016/j.phymed.2022.154359. Epub 2022 Jul 29. [PubMed:35933899 ]
Zhou M, Li Y, Hou H, Zou W, Hu L, Gong L, Fan W, Wang R, Ibrahim IAA, Fan S: Xanthorrhizol Ameliorates Oxidative Stress and Inflammation in Freund's Complete Adjuvant-Induced Rheumatoid Arthritis in Rats. Appl Biochem Biotechnol. 2022 Dec;194(12):6423-6437. doi: 10.1007/s12010-022-04091-4. Epub 2022 Aug 6. [PubMed:35932370 ]
Kim M, Cho H, Ahn DG, Jung HG, Seo HY, Kim JS, Lee YJ, Choi JY, Park IH, Shin JS, Kim SJ, Oh JW: In Vitro Replication Inhibitory Activity of Xanthorrhizol against Severe Acute Respiratory Syndrome Coronavirus 2. Biomedicines. 2021 Nov 19;9(11):1725. doi: 10.3390/biomedicines9111725. [PubMed:34829954 ]
Cai Y, Sheng Z, Wang J: Xanthorrhizol inhibits non-small cell carcinoma (A549) cell growth and promotes apoptosis through modulation of PI3K/AKT and NF-kappaB signaling pathway. Environ Toxicol. 2022 Jan;37(1):120-130. doi: 10.1002/tox.23383. Epub 2021 Oct 18. [PubMed:34664399 ]
LOTUS database [Link]

Showing NP-Card for 2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol (NP0310591)

MOL for NP0310591 (2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol)

3D MOL for NP0310591 (2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol)

3D SDF for NP0310591 (2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol)

3D-SDF for NP0310591 (2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol)

PDB for NP0310591 (2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol)

3D PDB for NP0310591 (2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol)

SMILES for NP0310591 (2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol)

INCHI for NP0310591 (2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol)

Structure for NP0310591 (2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol)

3D Structure for NP0310591 (2-methyl-5-[(2r)-6-methylhept-5-en-2-yl]phenol)