NP-MRD: Showing NP-Card for 3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid (NP0194645)

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Record Information

Version

2.0

Created at

2022-09-04 12:20:42 UTC

Updated at

2022-09-04 12:20:42 UTC

NP-MRD ID

NP0194645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid

Description

Stypoquinonic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid is found in Stypopodium zonale. 3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid was first documented in 2002 (PMID: 12444716). Based on a literature review very few articles have been published on stypoquinonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214202D          

 31 33  0  0  1  0            999 V2000
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    2.2754   -3.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7451   -4.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042214202D          

 31 33  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0194645

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@]2(C)[C@H](CCC(O)=O)C(CC[C@@H]2[C@@]1(C)CC1=CC(=O)C=C(C)C1=O)=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O4/c1-16(2)21-7-9-23-26(5,22(21)8-10-24(29)30)12-11-18(4)27(23,6)15-19-14-20(28)13-17(3)25(19)31/h13-14,18,22-23H,7-12,15H2,1-6H3,(H,29,30)/t18-,22-,23+,26+,27+/m1/s1

> <INCHI_KEY>
UKTQYWBDQDXWDJ-NTNJQHIWSA-N

> <FORMULA>
C27H38O4

> <MOLECULAR_WEIGHT>
426.597

> <EXACT_MASS>
426.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.463935897492206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(1S,4aR,5S,6R,8aR)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-decahydronaphthalen-1-yl]propanoic acid

> <JCHEM_LOGP>
6.173198478000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.968789092274135

> <JCHEM_PKA_STRONGEST_BASIC>
-7.7133973574912655

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
125.18779999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1S,4aR,5S,6R,8aR)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1H-naphthalen-1-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       5.764  -7.689   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.247  -7.421   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.258  -8.601   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.741  -8.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.751  -9.513   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.214  -6.887   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.204  -5.707   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.721  -5.974   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.711  -4.795   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   29                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   29                                             
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    9   15                                                  
CONECT   30    7    2   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
Stypoquinonate	Generator

Chemical Formula

C₂₇H₃₈O₄

Average Mass

426.5970 Da

Monoisotopic Mass

426.27701 Da

IUPAC Name

3-[(1S,4aR,5S,6R,8aR)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-decahydronaphthalen-1-yl]propanoic acid

Traditional Name

3-[(1S,4aR,5S,6R,8aR)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1H-naphthalen-1-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@]2(C)[C@H](CCC(O)=O)C(CC[C@@H]2[C@@]1(C)CC1=CC(=O)C=C(C)C1=O)=C(C)C

InChI Identifier

InChI=1S/C27H38O4/c1-16(2)21-7-9-23-26(5,22(21)8-10-24(29)30)12-11-18(4)27(23,6)15-19-14-20(28)13-17(3)25(19)31/h13-14,18,22-23H,7-12,15H2,1-6H3,(H,29,30)/t18-,22-,23+,26+,27+/m1/s1

InChI Key

UKTQYWBDQDXWDJ-NTNJQHIWSA-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
Stypopodium zonale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Prenylbenzoquinone
Carbocyclic fatty acid
Quinone
P-benzoquinone
Fatty acyl
Ketone
Cyclic ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
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	6.17	ChemAxon
pKa (Strongest Acidic)	4.97	ChemAxon
pKa (Strongest Basic)	-7.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.19 m³·mol⁻¹	ChemAxon
Polarizability	49.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00049681

Chemspider ID

8773906

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10598533

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dorta E, Cueto M, Brito I, Darias J: New terpenoids from the brown alga Stypopodium zonale. J Nat Prod. 2002 Nov;65(11):1727-30. doi: 10.1021/np020090g. [PubMed:12444716 ]
LOTUS database [Link]

Showing NP-Card for 3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid (NP0194645)

MOL for NP0194645 (3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

3D MOL for NP0194645 (3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

3D SDF for NP0194645 (3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

3D-SDF for NP0194645 (3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

PDB for NP0194645 (3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

3D PDB for NP0194645 (3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

SMILES for NP0194645 (3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

INCHI for NP0194645 (3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

Structure for NP0194645 (3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

3D Structure for NP0194645 (3-[(1s,4ar,5s,6r,8ar)-5,6,8a-trimethyl-5-[(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)