NP-MRD: Showing NP-Card for Terrecyclic Acid (NP0139471)

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Record Information

Version

2.0

Created at

2022-06-29 19:55:57 UTC

Updated at

2022-06-29 19:55:57 UTC

NP-MRD ID

NP0139471

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Terrecyclic Acid

Description

Terrecyclic acid A, also known as terrecyclate a, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Terrecyclic Acid was first documented in 2003 (PMID: 14695798). Based on a literature review very few articles have been published on Terrecyclic acid A (PMID: 16227407).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    2.5872    1.5956    1.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7477    1.2523    0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7032    1.8284   -1.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6163    2.3978   -1.8469 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2767    1.5550   -1.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1330    0.1634   -1.1643 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2325   -0.3625   -0.9035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0612   -1.8199   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3038   -2.2090   -0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1373   -1.1421    0.5773 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5170   -1.3464    0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -0.4591   -0.5912 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2162   -2.5162    0.3370 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6949    0.2321    0.2404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4892    0.7103    1.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7389    0.4017    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6611   -0.4311    1.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5384    1.5918   -0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    1.1108    2.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459    2.3542    0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3048    2.3013   -1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1675    1.6881   -2.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7483   -0.5002   -1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9505   -0.2247   -1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643   -2.4561   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7717   -2.1253    0.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -2.6584   -0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2347   -3.0671    0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1860   -1.3281    1.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194   -2.5815    0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4662    0.1909    2.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4141    1.7952    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1311   -1.0105    1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2634    0.3231    1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4225   -0.9850    0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5976    1.6758   -1.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2274    2.5467    0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321    1.5088    0.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  1  0
 16 15  1  0
 15 14  1  0
 14  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
  7 16  1  0
 14  2  1  6
 10 14  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 15 31  1  0
 15 32  1  0
  6 23  1  6
  5 21  1  0
  5 22  1  0
  1 19  1  0
  1 20  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  1
 13 30  1  0
M  END


  Mrv1652306292221552D          

 18 20  0  0  1  0            999 V2000
   -0.5340   -0.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0051    0.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940   -0.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3183   -0.5362    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8575    0.0883    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9077    1.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766    1.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2199    0.9571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0053    0.2271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6345    0.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3364    0.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0997    0.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1410   -0.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6746   -1.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6540   -0.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897    0.2468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023   -0.8191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7236    0.5472    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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
  5 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139471

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C[C@@]23[C@H](CC(=O)C2=C)[C@H]1CC[C@H]3C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-12(16)6-11-9-4-5-10(13(17)18)15(8,11)7-14(9,2)3/h9-11H,1,4-7H2,2-3H3,(H,17,18)/t9-,10+,11-,15-/m1/s1

> <INCHI_KEY>
SMAWCSOVJJHIOI-JNIYBQFBSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.55549892149965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,6R,9R)-11,11-dimethyl-2-methylidene-3-oxotricyclo[4.3.2.0^{1,5}]undecane-9-carboxylic acid

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.4275339123333333

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.540519019083826

> <JCHEM_PKA_STRONGEST_BASIC>
-5.197687762764373

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
67.0064

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,6R,9R)-11,11-dimethyl-2-methylidene-3-oxotricyclo[4.3.2.0^{1,5}]undecane-9-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -0.997  -0.866   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.010   0.300   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.922  -0.941   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.461  -1.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.467   0.165   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.561   1.896   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.823   2.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.411   1.787   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.877   0.424   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.051   1.420   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.361   0.611   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.786   1.195   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.997  -0.885   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.993  -2.060   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.954  -0.236   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.327   0.461   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.791  -1.529   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.351   1.021   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   18                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    9   13                                             
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    4   14                                                  
CONECT   14   13                                                            
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    2                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
Terrecyclate a	Generator

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)C[C@@]23[C@H](CC(=O)C2=C)[C@H]1CC[C@H]3C(O)=O

InChI Identifier

InChI=1S/C15H20O3/c1-8-12(16)6-11-9-4-5-10(13(17)18)15(8,11)7-14(9,2)3/h9-11H,1,4-7H2,2-3H3,(H,17,18)/t9-,10+,11-,15-/m1/s1

InChI Key

SMAWCSOVJJHIOI-JNIYBQFBSA-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

Not Available

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
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018433

Chemspider ID

10284827

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14807158

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wijeratne EM, Turbyville TJ, Zhang Z, Bigelow D, Pierson LS 3rd, VanEtten HD, Whitesell L, Canfield LM, Gunatilaka AA: Cytotoxic constituents of Aspergillus terreus from the rhizosphere of Opuntia versicolor of the Sonoran Desert. J Nat Prod. 2003 Dec;66(12):1567-73. doi: 10.1021/np030266u. [PubMed:14695798 ]
Turbyville TJ, Wijeratne EM, Whitesell L, Gunatilaka AA: The anticancer activity of the fungal metabolite terrecyclic acid A is associated with modulation of multiple cellular stress response pathways. Mol Cancer Ther. 2005 Oct;4(10):1569-76. doi: 10.1158/1535-7163.MCT-05-0050. [PubMed:16227407 ]

Showing NP-Card for Terrecyclic Acid (NP0139471)

MOL for NP0139471 (Terrecyclic Acid)

3D MOL for NP0139471 (Terrecyclic Acid)

3D SDF for NP0139471 (Terrecyclic Acid)

3D-SDF for NP0139471 (Terrecyclic Acid)

PDB for NP0139471 (Terrecyclic Acid)

3D PDB for NP0139471 (Terrecyclic Acid)

SMILES for NP0139471 (Terrecyclic Acid)

INCHI for NP0139471 (Terrecyclic Acid)

Structure for NP0139471 (Terrecyclic Acid)

3D Structure for NP0139471 (Terrecyclic Acid)