NP-MRD: Showing NP-Card for Homalomenol A (NP0139958)

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Record Information

Version

2.0

Created at

2022-06-29 20:18:25 UTC

Updated at

2022-06-29 20:18:25 UTC

NP-MRD ID

NP0139958

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Homalomenol A

Description

(+)-Homalomenol A belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Homalomenol A is found in Chimonanthus praecox, Homalomena aromatica and Magnolia biondii. Homalomenol A was first documented in 1992 (PMID: 1368861). Based on a literature review a small amount of articles have been published on (+)-homalomenol A (PMID: 18975180).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
    3.2219   -0.2500   -0.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8684    0.8939    0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8149    2.0731    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716    0.9293    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8392   -0.2041    0.7472 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5643   -0.7405    2.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793   -1.1958    2.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720   -1.1365    0.6967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6618   -2.3568    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457   -1.0384    0.4852 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2546   -2.1035   -0.2630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0605    0.2890   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2415    0.5495   -1.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7400    0.5388   -1.0939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2778    1.9948   -1.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1037   -0.2149   -2.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5440    0.1459    0.3072 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3125   -0.1581   -1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6145   -0.3196   -1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1805   -1.2308   -0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6276    2.7400   -0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8486    1.7061    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7281    2.6126    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843    1.8077    1.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2124   -0.9915    0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6866    0.0972    2.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -1.5984    2.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5276   -0.4196    2.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0195   -2.1904    2.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5018   -2.2747   -1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2511   -2.7150    0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4045   -3.1905    0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481   -1.0715    1.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1348   -1.9730   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095    1.0736    0.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1241    0.2767   -0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5799    1.5164   -1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926   -0.2168   -2.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9470    2.5466   -1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434    2.0259   -1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895    2.5212   -0.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    0.3104   -2.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9149    0.9417    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 17  1  0
 17 14  1  0
 14 15  1  0
 14 16  1  6
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  1  0
 17  5  1  0
 10  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  6
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 17 43  1  1
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 13 37  1  0
 13 38  1  0
 12 35  1  0
 12 36  1  0
 10 33  1  1
 11 34  1  0
M  END


  Mrv1652306292222182D          

 17 18  0  0  1  0            999 V2000
   -1.4604    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9683    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7429    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -1.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  1  0  0  0
  9 14  1  6  0  0  0
  9 15  1  1  0  0  0
  7 16  1  1  0  0  0
  2 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139958

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C[C@H]1CC[C@]2(C)[C@@H]1[C@@](C)(O)CC[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O2/c1-10(2)9-11-5-7-14(3)12(16)6-8-15(4,17)13(11)14/h9,11-13,16-17H,5-8H2,1-4H3/t11-,12-,13-,14+,15+/m1/s1

> <INCHI_KEY>
FKMCEEHVCIIPLE-ZSAUSMIDSA-N

> <FORMULA>
C15H26O2

> <MOLECULAR_WEIGHT>
238.371

> <EXACT_MASS>
238.193280077

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
28.548698446524345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3aR,4R,7S,7aR)-3a,7-dimethyl-1-(2-methylprop-1-en-1-yl)-octahydro-1H-indene-4,7-diol

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.320936910666666

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.033169589759218

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.417277964292328

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9100342391626652

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
70.8725

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3aR,4R,7S,7aR)-3a,7-dimethyl-1-(2-methylprop-1-en-1-yl)-hexahydro-1H-indene-4,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -2.726   3.192   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.807   1.597   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.253   1.597   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.036  -3.604   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.281   0.583   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12   16                                             
CONECT    8    7    4    9                                                  
CONECT    9    8   10   14   15                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
CONECT   14    9                                                            
CONECT   15    9                                                            
CONECT   16    7                                                            
CONECT   17    2                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Homalomenol a	ChEBI

Chemical Formula

C₁₅H₂₆O₂

Average Mass

238.3710 Da

Monoisotopic Mass

238.19328 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=C[C@H]1CC[C@]2(C)[C@@H]1[C@@](C)(O)CC[C@H]2O

InChI Identifier

InChI=1S/C15H26O2/c1-10(2)9-11-5-7-14(3)12(16)6-8-15(4,17)13(11)14/h9,11-13,16-17H,5-8H2,1-4H3/t11-,12-,13-,14+,15+/m1/s1

InChI Key

FKMCEEHVCIIPLE-ZSAUSMIDSA-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
Chimonanthus praecox	LOTUS Database	35616633
Homalomena aromatica	LOTUS Database	35616633
Magnolia biondii	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

Sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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

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

28424465

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91884956

PDB ID

Not Available

ChEBI ID

132900

Good Scents ID

Not Available

References

General References

Jung KY, Kim DS, Oh SR, Lee IS, Lee JJ, Lee HK, Shin DH, Kim EH, Cheong CJ: Sesquiterpene components from the flower buds ofMagnolia fargesii. Arch Pharm Res. 1997 Aug;20(4):363-7. doi: 10.1007/BF02976201. [PubMed:18975180 ]
Sung TV, Steffan B, Steglich W, Klebe G, Adam G: Sesquiterpenoids from the roots of Homalomena aromatica. Phytochemistry. 1992 Oct;31(10):3515-20. doi: 10.1016/0031-9422(92)83719-f. [PubMed:1368861 ]

Showing NP-Card for Homalomenol A (NP0139958)

MOL for NP0139958 (Homalomenol A)

3D MOL for NP0139958 (Homalomenol A)

3D SDF for NP0139958 (Homalomenol A)

3D-SDF for NP0139958 (Homalomenol A)

PDB for NP0139958 (Homalomenol A)

3D PDB for NP0139958 (Homalomenol A)

SMILES for NP0139958 (Homalomenol A)

INCHI for NP0139958 (Homalomenol A)

Structure for NP0139958 (Homalomenol A)

3D Structure for NP0139958 (Homalomenol A)