NP-MRD: Showing NP-Card for Crispane (NP0049201)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 21:08:42 UTC

Updated at

2022-03-17 21:08:42 UTC

NP-MRD ID

NP0049201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Crispane

Description

Crispane, also known as lasidiol angelate, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Crispane is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Crispane has been detected, but not quantified in, herbs and spices and parsley. Crispane is found in Heliopsis helianthoides. Crispane was first documented in 1998 (PMID: 11711088). This could make crispane a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222502D          

 24 25  0  0  1  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  1  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  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
    1.4289    0.8250    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
    2.8579   -1.6500    0.0000 O   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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171   -2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 11 19  1  0  0  0  0
  1 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  1 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0049201

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-7-14(4)18(21)23-17-12-15(5)19(6)11-9-8-10-16(19)20(17,22)13(2)3/h7,12-13,16-17,22H,8-11H2,1-6H3/b14-7-/t16-,17-,19+,20-/m0/s1

> <INCHI_KEY>
NXPBEWQMSGGADR-XUDYDAPFSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.4663

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.59034538597753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4aS,8aS)-1-hydroxy-4,4a-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
5.001596525333334

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.35537522569549

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5181588762807925

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
94.2403

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4aS,8aS)-1-hydroxy-1-isopropyl-4,4a-dimethyl-2,5,6,7,8,8a-hexahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         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       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.390  -4.440   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.405  -4.493   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       1.334  -3.850   0.000  0.00  0.00           H+0
CONECT    1    2    6   19   24                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   11    1   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    1                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
Lasidiol angelate	HMDB
(1S,2S,4AS,8as)-1-hydroxy-4,4a-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₃₂O₃

Average Mass

320.4663 Da

Monoisotopic Mass

320.23514 Da

IUPAC Name

(1S,2S,4aS,8aS)-1-hydroxy-4,4a-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(1S,2S,4aS,8aS)-1-hydroxy-1-isopropyl-4,4a-dimethyl-2,5,6,7,8,8a-hexahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

79803-28-4

SMILES

C\C=C(\C)C(=O)O[C@H]1C=C(C)[C@@]2(C)CCCC[C@]2([H])[C@@]1(O)C(C)C

InChI Identifier

InChI=1S/C20H32O3/c1-7-14(4)18(21)23-17-12-15(5)19(6)11-9-8-10-16(19)20(17,22)13(2)3/h7,12-13,16-17,22H,8-11H2,1-6H3/b14-7-/t16-,17-,19+,20-/m0/s1

InChI Key

NXPBEWQMSGGADR-XUDYDAPFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Heliopsis helianthoides	LOTUS Database	35616633
Petroselinum crispum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
P-menthane monoterpenoid
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
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
logP	5.11	ALOGPS
logP	5	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.36	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.24 m³·mol⁻¹	ChemAxon
Polarizability	37.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038694

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018099

KNApSAcK ID

Not Available

Chemspider ID

30777287

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752434

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Appendino G, Jakupovic J, Bossio E: Structural revision of the parsley sesquiterpenes crispanone and crispane. Phytochemistry. 1998 Nov 20;49(6):1719-1722. doi: 10.1016/s0031-9422(98)00296-9. [PubMed:11711088 ]

Showing NP-Card for Crispane (NP0049201)

MOL for NP0049201 (Crispane)

3D MOL for NP0049201 (Crispane)

3D SDF for NP0049201 (Crispane)

3D-SDF for NP0049201 (Crispane)

PDB for NP0049201 (Crispane)

3D PDB for NP0049201 (Crispane)

SMILES for NP0049201 (Crispane)

INCHI for NP0049201 (Crispane)

Structure for NP0049201 (Crispane)

3D Structure for NP0049201 (Crispane)