NP-MRD: Showing NP-Card for (+)-Hardwickiic acid (NP0046990)

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Record Information

Version

1.0

Created at

2022-03-17 20:32:49 UTC

Updated at

2022-03-17 20:32:49 UTC

NP-MRD ID

NP0046990

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Hardwickiic acid

Description

(+)-Hardwickiic acid belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. (+)-Hardwickiic acid is found in Chrozophora oblongifolia, Copaifera duckei, Copaifera guianensis , Croton lechleri, Croton lechleri Mull.Arg. , Croton megistocarpus, Diplostephium meyenii, Duranta erecta, Echinodorus grandiflorus, Pulicaria salviifolia, Salvia divinorum, Salvia regla, Salvia wagneriana, Solidago rugosa and Tinospora crispa. Clerodanes arise from labdanes by two methyl migrations (+)-Hardwickiic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223322D          

 23 25  0  0  0  0            999 V2000
    2.6328    0.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4721    0.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5481   -0.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8614   -0.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274   -0.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4881   -0.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533    0.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1140    0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433   -0.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6480   -0.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6480   -1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3354   -1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981   -1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981   -0.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374    0.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5481   -0.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427    0.8010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8007    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1140    0.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720    1.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2587    0.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114    0.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9453    0.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 19  1  0  0  0  0
 10 11  1  0  0  0  0
 10 22  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 22  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046990

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(C)C(CCC=C2C(O)=O)C1(C)CCC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-14-7-10-20(3)16(18(21)22)5-4-6-17(20)19(14,2)11-8-15-9-12-23-13-15/h5,9,12-14,17H,4,6-8,10-11H2,1-3H3,(H,21,22)

> <INCHI_KEY>
HHWOKJDCJVESIF-UHFFFAOYSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.25763062609803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
5.077313079666666

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4560168800551585

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4717746532202276

> <JCHEM_POLAR_SURFACE_AREA>
50.440000000000005

> <JCHEM_REFRACTIVITY>
91.0766

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

> <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       4.915   1.067   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.481   0.925   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.623  -0.783   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.341  -1.495   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.344  -0.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.778  -0.498   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.779   0.497   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.213   0.212   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.641  -1.210   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.210  -0.355   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.210  -1.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.493  -2.777   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.916  -1.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.916  -0.498   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.483   0.071   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.623  -0.925   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -6.053   1.495   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.495   2.777   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.213   1.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.068   2.634   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.350   1.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.635   0.355   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.631   1.495   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   19                                             
CONECT    9    8                                                            
CONECT   10    8   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   19                                                            
CONECT   19    8   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   10   14   21   23                                             
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
(+)-Hardwickiate	Generator
Hardwickic acid, (-)-isomer	MeSH
Hardwickic acid	MeSH

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4345 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

Traditional Name

5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1CCC2(C)C(CCC=C2C(O)=O)C1(C)CCC1=COC=C1

InChI Identifier

InChI=1S/C20H28O3/c1-14-7-10-20(3)16(18(21)22)5-4-6-17(20)19(14,2)11-8-15-9-12-23-13-15/h5,9,12-14,17H,4,6-8,10-11H2,1-3H3,(H,21,22)

InChI Key

HHWOKJDCJVESIF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chrozophora oblongifolia	LOTUS Database	35616633
Copaifera duckei	Plant	KNApSAcK
Copaifera guianensis	Plant	KNApSAcK
Croton lechleri	LOTUS Database	35616633
Croton lechleri Mull.Arg.	Plant	KNApSAcK
Croton megistocarpus	LOTUS Database	35616633
Diplostephium meyenii	LOTUS Database	35616633
Duranta erecta	LOTUS Database	35616633
Echinodorus grandiflorus	LOTUS Database	35616633
Pulicaria salviifolia	LOTUS Database	35616633
Ribes nigrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia divinorum	LOTUS Database	35616633
Salvia regla	LOTUS Database	35616633
Salvia wagneriana	LOTUS Database	35616633
Solidago rugosa	LOTUS Database	35616633
Tinospora crispa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	5.33	ALOGPS
logP	5.08	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.08 m³·mol⁻¹	ChemAxon
Polarizability	36.26 Å³	ChemAxon
Number of Rings	3	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB006871

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15559627

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Hardwickiic acid (NP0046990)

MOL for NP0046990 ((+)-Hardwickiic acid)

3D MOL for NP0046990 ((+)-Hardwickiic acid)

3D SDF for NP0046990 ((+)-Hardwickiic acid)

3D-SDF for NP0046990 ((+)-Hardwickiic acid)

PDB for NP0046990 ((+)-Hardwickiic acid)

3D PDB for NP0046990 ((+)-Hardwickiic acid)

SMILES for NP0046990 ((+)-Hardwickiic acid)

INCHI for NP0046990 ((+)-Hardwickiic acid)

Structure for NP0046990 ((+)-Hardwickiic acid)

3D Structure for NP0046990 ((+)-Hardwickiic acid)