NP-MRD: Showing NP-Card for (+)-4-epi-cryptomeridiol (NP0170041)

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Record Information

Version

2.0

Created at

2022-09-03 06:06:28 UTC

Updated at

2022-09-03 06:06:28 UTC

NP-MRD ID

NP0170041

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-4-epi-cryptomeridiol

Description

(+)-4-Epi-cryptomeridiol, also known as cryptomeridiol, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. (+)-4-epi-cryptomeridiol is found in Artemisia argyi, Artemisia campestris, Carissa spinarum, Chamaecyparis formosensis, Chamaecyparis obtusa, Cryptomeria japonica, Cymbopogon parkeri, Dysphania graveolens, Juniperus thurifera, Laggera crispata, Magnolia obovata, Neolitsea hiiranensis, Ratibida mexicana, Santolina rosmarinifolia and Sphaeranthus indicus. (+)-4-epi-cryptomeridiol was first documented in 2002 (PMID: 12141862). Based on a literature review very few articles have been published on (+)-4-epi-cryptomeridiol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
    4.0099   -0.2909    0.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9004   -0.5874   -0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1536    0.1432   -1.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -1.9585   -0.5666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5949   -0.2682    0.3717 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4896    1.1839    0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638    1.4896    1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986    1.0070    0.5287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0206    1.7541   -0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2768    1.2186    1.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4238    0.8075    0.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2009   -0.3766   -0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0199   -1.2129   -0.0641 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7006   -2.0622   -1.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4433   -2.1656    0.8949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8126   -0.4819    0.3722 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4068   -0.7048   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059    0.6171    0.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7386   -1.1454    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6573   -0.1320    1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -0.2429   -2.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1897   -0.0903   -1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0846    1.2373   -1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8431   -2.2402   -0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -0.8652    1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6650    1.8780   -0.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2658    1.3503    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0767    0.9301    2.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1090    2.5908    1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9069    2.4535   -0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1373    2.4538   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1219    1.1547   -1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3725    2.3057    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2397    0.6106    2.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3181    0.6907    1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7147    1.6681   -0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1489   -0.1196   -1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1195   -1.0304   -0.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7040   -2.4735   -1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1195   -2.9246   -0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2134   -1.4783   -2.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.9430    1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5446   -0.8527    1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5709   -1.7668   -0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4400   -0.1307   -1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 13 16  1  0
 16 17  1  0
 17  5  1  0
 16  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  1
  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
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  1
 17 44  1  0
 17 45  1  0
M  END


  Mrv1652309032208062D          

 17 18  0  0  1  0            999 V2000
   -0.7145   -2.0625    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
    0.4125   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  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  2  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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3882   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -2.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  2  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 13 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  1  0  0  0
  5 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0170041

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@H]1CC[C@]2(C)CCC[C@](C)(O)[C@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H28O2/c1-13(2,16)11-6-9-14(3)7-5-8-15(4,17)12(14)10-11/h11-12,16-17H,5-10H2,1-4H3/t11-,12-,14-,15-/m0/s1

> <INCHI_KEY>
LKKDASYGWYYFIK-JURCDPSOSA-N

> <FORMULA>
C15H28O2

> <MOLECULAR_WEIGHT>
240.387

> <EXACT_MASS>
240.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
28.999761650073154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aS,7S,8aS)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-decahydronaphthalen-1-ol

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
2.564166504

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.247839291212376

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3584089913637104

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
70.2661

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,7S,8aS)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-octahydronaphthalen-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -3.850   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       0.770  -4.414   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.770  -1.746   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   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   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   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  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.325  -4.260   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.345  -4.260   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13    8   17                                                  
CONECT   17   16    5                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Cryptomeridiol	MeSH

Chemical Formula

C₁₅H₂₈O₂

Average Mass

240.3870 Da

Monoisotopic Mass

240.20893 Da

IUPAC Name

(1S,4aS,7S,8aS)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-decahydronaphthalen-1-ol

Traditional Name

(1S,4aS,7S,8aS)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-octahydronaphthalen-1-ol

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@H]1CC[C@]2(C)CCC[C@](C)(O)[C@H]2C1

InChI Identifier

InChI=1S/C15H28O2/c1-13(2,16)11-6-9-14(3)7-5-8-15(4,17)12(14)10-11/h11-12,16-17H,5-10H2,1-4H3/t11-,12-,14-,15-/m0/s1

InChI Key

LKKDASYGWYYFIK-JURCDPSOSA-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
Artemisia argyi	LOTUS Database	35616633
Artemisia campestris	LOTUS Database	35616633
Carissa spinarum	LOTUS Database	35616633
Chamaecyparis formosensis	LOTUS Database	35616633
Chamaecyparis obtusa	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cymbopogon parkeri	LOTUS Database	35616633
Dysphania graveolens	LOTUS Database	35616633
Juniperus thurifera	LOTUS Database	35616633
Laggera crispata	LOTUS Database	35616633
Magnolia obovata	LOTUS Database	35616633
Neolitsea hiiranensis	LOTUS Database	35616633
Ratibida mexicana	LOTUS Database	35616633
Santolina rosmarinifolia	LOTUS Database	35616633
Sphaeranthus indicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

eudesmane sesquiterpenoid (CHEBI:70477 )

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	3.26	ALOGPS
logP	2.56	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	19.25	ChemAxon
pKa (Strongest Basic)	-0.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.27 m³·mol⁻¹	ChemAxon
Polarizability	29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

Not Available

Chemspider ID

28945141

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70698175

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Garcia-Granados A, Gutierrez MC, Parra A, Rivas F: Chemical-microbiological synthesis of cryptomeridiol derivatives by Gliocladium roseum: semisynthesis of 11-hydroxyeudesmanolides. J Nat Prod. 2002 Jul;65(7):1011-5. doi: 10.1021/np010631m. [PubMed:12141862 ]
LOTUS database [Link]

Showing NP-Card for (+)-4-epi-cryptomeridiol (NP0170041)

MOL for NP0170041 ((+)-4-epi-cryptomeridiol)

3D MOL for NP0170041 ((+)-4-epi-cryptomeridiol)

3D SDF for NP0170041 ((+)-4-epi-cryptomeridiol)

3D-SDF for NP0170041 ((+)-4-epi-cryptomeridiol)

PDB for NP0170041 ((+)-4-epi-cryptomeridiol)

3D PDB for NP0170041 ((+)-4-epi-cryptomeridiol)

SMILES for NP0170041 ((+)-4-epi-cryptomeridiol)

INCHI for NP0170041 ((+)-4-epi-cryptomeridiol)

Structure for NP0170041 ((+)-4-epi-cryptomeridiol)

3D Structure for NP0170041 ((+)-4-epi-cryptomeridiol)