NP-MRD: Showing NP-Card for (1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid (NP0220037)

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Record Information

Version

1.0

Created at

2022-09-05 21:14:00 UTC

Updated at

2022-09-05 21:14:00 UTC

NP-MRD ID

NP0220037

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid

Description

Sarcopetaloic acid, also known as sarcopetaloate, belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. (1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid is found in Croton sarcopetalus. It was first documented in 2022 (PMID: 36075445). Based on a literature review a significant number of articles have been published on Sarcopetaloic acid (PMID: 36075423) (PMID: 36075416) (PMID: 36075366) (PMID: 36075339).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223142D          

 23 25  0  0  1  0            999 V2000
    4.9901   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225    0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267   -0.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8901    0.2369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1926    1.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0161    0.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6696   -0.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8708   -0.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2926   -0.1760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4939   -0.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359   -1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1861   -0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8830   -0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1363    1.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351    1.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132    0.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7338    1.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120    0.8254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5326    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9544    2.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1556    2.0024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750    3.0038    0.0000 O   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  1  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 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
 16 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220037

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@]2(CC[C@@H]3C(C)(C)C(=O)CC[C@@]3(C)[C@@H]2CC(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-13-5-9-20(12-13)10-6-14-18(2,3)16(21)7-8-19(14,4)15(20)11-17(22)23/h5,9,12,14-15H,6-8,10-11H2,1-4H3,(H,22,23)/t14-,15+,19-,20-/m1/s1

> <INCHI_KEY>
PTNYLVIHHOOWHT-HRYATBACSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.617821534325174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,1'S,4'aS,8'aS)-3,5',5',8'a-tetramethyl-6'-oxo-3',4',4'a,5',6',7',8',8'a-octahydro-1'H-spiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-yl]acetic acid

> <JCHEM_LOGP>
3.8300331833333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.95867330267067

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.778957117708255

> <JCHEM_PKA_STRONGEST_BASIC>
-7.470885163760265

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
92.0487

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,1'S,4'aS,8'aS)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       9.315  -0.275   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.882   0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.583  -0.538   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.395   0.442   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.960   1.875   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.497   1.781   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.983  -1.042   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.492  -1.427   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.413  -0.329   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.922  -0.714   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.560  -2.115   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.347  -1.586   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.157   0.385   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.648  -0.001   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.254   1.869   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.745   2.254   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.825   1.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.236   2.639   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.316   1.541   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.727   3.025   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.648   4.123   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.157   3.738   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.060   5.607   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   19                                             
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    4   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
Sarcopetaloate	Generator

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4410 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

2-[(1S,1'S,4'aS,8'aS)-3,5',5',8'a-tetramethyl-6'-oxo-3',4',4'a,5',6',7',8',8'a-octahydro-1'H-spiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-yl]acetic acid

Traditional Name

(1S,1'S,4'aS,8'aS)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid

CAS Registry Number

Not Available

SMILES

CC1=C[C@]2(CC[C@@H]3C(C)(C)C(=O)CC[C@@]3(C)[C@@H]2CC(O)=O)C=C1

InChI Identifier

InChI=1S/C20H28O3/c1-13-5-9-20(12-13)10-6-14-18(2,3)16(21)7-8-19(14,4)15(20)11-17(22)23/h5,9,12,14-15H,6-8,10-11H2,1-4H3,(H,22,23)/t14-,15+,19-,20-/m1/s1

InChI Key

PTNYLVIHHOOWHT-HRYATBACSA-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
Croton sarcopetalus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	3.83	ChemAxon
pKa (Strongest Acidic)	4.78	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.05 m³·mol⁻¹	ChemAxon
Polarizability	35.62 Å³	ChemAxon
Number of Rings	3	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

C00046900

Chemspider ID

8980684

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10805379

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Duan SF, Zhang MM, Zhang X, Liu W, Zhang SH, Yang B, Dong Q, Han JG, Yu HL, Li T, Ji XY, Wu DD, Zhang XJ: HA-ADT suppresses esophageal squamous cell carcinoma progression via apoptosis promotion and autophagy inhibition. Exp Cell Res. 2022 Sep 6;420(1):113341. doi: 10.1016/j.yexcr.2022.113341. [PubMed:36075445 ]
Zhu Y, Xu T, Zhao D: Metal-doped carbon-supported/modified titanate nanotubes for perfluorooctane sulfonate degradation in water: Effects of preparation conditions, mechanisms, and parameter optimization. Sci Total Environ. 2022 Sep 5:158573. doi: 10.1016/j.scitotenv.2022.158573. [PubMed:36075423 ]
Ju YR, Chen CF, Lim YC, Tsai CY, Chen CW, Dong CD: Developing ecological risk assessment of metals released from sediment based on sediment quality guidelines linking with the properties: A case study for Kaohsiung Harbor. Sci Total Environ. 2022 Sep 6;852:158407. doi: 10.1016/j.scitotenv.2022.158407. [PubMed:36075416 ]
Lasters R, Groffen T, Eens M, Coertjens D, Gebbink WA, Hofman J, Bervoets L: Home-produced eggs: An important human exposure pathway of perfluoroalkylated substances (PFAS). Chemosphere. 2022 Sep 5;308(Pt 1):136283. doi: 10.1016/j.chemosphere.2022.136283. [PubMed:36075366 ]
Zou M, Tian W, Chu M, Gao H, Zhang D: Biochar composite derived from cellulase hydrolysis apple branch for quinolone antibiotics enhanced removal: Precursor pyrolysis performance, functional group introduction and adsorption mechanisms. Environ Pollut. 2022 Sep 5;313:120104. doi: 10.1016/j.envpol.2022.120104. [PubMed:36075339 ]
LOTUS database [Link]

Showing NP-Card for (1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid (NP0220037)

MOL for NP0220037 ((1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid)

3D MOL for NP0220037 ((1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid)

3D SDF for NP0220037 ((1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid)

3D-SDF for NP0220037 ((1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid)

PDB for NP0220037 ((1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid)

3D PDB for NP0220037 ((1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid)

SMILES for NP0220037 ((1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid)

INCHI for NP0220037 ((1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid)

Structure for NP0220037 ((1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid)

3D Structure for NP0220037 ((1s,1's,4'as,8'as)-3,5',5',8'a-tetramethyl-6'-oxo-1',3',4',4'a,7',8'-hexahydrospiro[cyclopentane-1,2'-naphthalene]-2,4-dien-1'-ylacetic acid)