NP-MRD: Showing NP-Card for Complicatic acid (NP0064751)

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Record Information

Version

2.0

Created at

2022-04-28 09:01:12 UTC

Updated at

2022-04-28 09:01:12 UTC

NP-MRD ID

NP0064751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Complicatic acid

Description

Complicatic acid, also known as complicatate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Complicatic acid is found in Stereum complicatum. Complicatic acid was first documented in 2008 (PMID: 18533462). Based on a literature review very few articles have been published on Complicatic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -2.4862    1.9515    1.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083    0.6535    0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2924   -0.4009    1.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3279   -0.2142    2.0736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7261   -1.7028    0.8930 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9817   -1.7787   -0.5718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7749   -1.4549   -0.0257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5090   -2.1056   -0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6182   -1.3132    0.1381 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5750   -0.7666   -0.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0577    0.5096   -0.1914 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4718    1.5543   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2074    0.2688    0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182    0.4707    1.9357 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3940   -0.1854    0.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682    1.0643    0.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0385   -0.0929    0.7362 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3706    0.0224    0.0725 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3391    0.5613   -1.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2770    2.3197    1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7768    2.6561    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1100   -2.5742    1.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593   -3.1773   -0.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4488   -2.1167   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1729   -1.9132    0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -0.6116   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -1.4375   -0.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5642    1.5710   -1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8994    1.3329   -2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1729    2.5577   -0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3824   -0.8161   -0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2066    1.4055    1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112    1.9247    0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296   -0.3408    1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2082    1.2773   -1.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540   -0.2224   -2.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519    1.1236   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  6
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  6
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 18  1  0
 18 19  1  6
 18 17  1  0
 17 16  1  0
 11 13  1  0
 13 15  1  0
 13 14  2  0
 16 11  1  0
 17  9  1  0
  5  7  1  0
 18  7  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 10 26  1  0
 10 27  1  0
  9 25  1  1
  8 23  1  0
  8 24  1  0
  5 22  1  1
  1 20  1  0
  1 21  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 17 34  1  1
 16 32  1  0
 16 33  1  0
 15 31  1  0
M  END


  Mrv1652304282211012D          

 19 22  0  0  1  0            999 V2000
    2.3125    1.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7683    0.3824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2552   -0.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4822    0.0248    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5177    0.8490    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7447    1.1374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2316    0.4914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6874   -0.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414    0.7798    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5059    1.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1519    2.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2889    1.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5773    2.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047   -0.0338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5038    0.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5479    1.5799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1952    0.3060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4690   -0.0531    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  1  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  9 14  1  6  0  0  0
  7 14  1  6  0  0  0
  6 15  1  6  0  0  0
  2 16  1  1  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 19  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0064751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(C[C@@H]2C[C@@]34O[C@@H]3C(=O)C(=C)[C@@]4(C)[C@@H]2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-7-10(16)11-15(19-11)5-8-4-13(2,12(17)18)6-9(8)14(7,15)3/h8-9,11H,1,4-6H2,2-3H3,(H,17,18)/t8-,9-,11-,13+,14+,15-/m1/s1

> <INCHI_KEY>
AIGBRUUHKLIFND-PMKYJIPRSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.305

> <EXACT_MASS>
262.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.9002544981851

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,5S,7R,8R,11S)-5,8-dimethyl-9-methylidene-10-oxo-12-oxatetracyclo[6.4.0.0^{1,11}.0^{3,7}]dodecane-5-carboxylic acid

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
2.126653901

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.20370152453998

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.243611538801415

> <JCHEM_PKA_STRONGEST_BASIC>
-4.285359797560922

> <JCHEM_POLAR_SURFACE_AREA>
66.9

> <JCHEM_REFRACTIVITY>
66.23450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,5S,7R,8R,11S)-5,8-dimethyl-9-methylidene-10-oxo-12-oxatetracyclo[6.4.0.0^{1,11}.0^{3,7}]dodecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.317   1.997   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.168   0.714   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.210  -0.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.767   0.046   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.833   1.585   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.390   2.123   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.432   0.917   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.283  -0.366   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.011   1.456   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.944   2.994   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.150   3.952   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.539   3.407   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.078   4.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.755  -0.063   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.348   3.329   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.540   1.411   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.623   2.949   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.831   0.571   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.475  -0.099   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   16   19                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7   12   15                                             
CONECT    7    6    8    9   14                                             
CONECT    8    7    4                                                       
CONECT    9    7   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12                                                            
CONECT   14    9    7                                                       
CONECT   15    6                                                            
CONECT   16    2   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
Complicatate	Generator

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3050 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

(1S,3R,5S,7R,8R,11S)-5,8-dimethyl-9-methylidene-10-oxo-12-oxatetracyclo[6.4.0.0^{1,11}.0^{3,7}]dodecane-5-carboxylic acid

Traditional Name

(1S,3R,5S,7R,8R,11S)-5,8-dimethyl-9-methylidene-10-oxo-12-oxatetracyclo[6.4.0.0^{1,11}.0^{3,7}]dodecane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@]1(C[C@@H]2C[C@@]34O[C@@H]3C(=O)C(=C)[C@@]4(C)[C@@H]2C1)C(O)=O

InChI Identifier

InChI=1S/C15H18O4/c1-7-10(16)11-15(19-11)5-8-4-13(2,12(17)18)6-9(8)14(7,15)3/h8-9,11H,1,4-6H2,2-3H3,(H,17,18)/t8-,9-,11-,13+,14+,15-/m1/s1

InChI Key

AIGBRUUHKLIFND-PMKYJIPRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Stereum complicatum	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oxane
Ketone
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aldehyde
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.85	ALOGPS
logP	2.13	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.24	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.23 m³·mol⁻¹	ChemAxon
Polarizability	26.9 Å³	ChemAxon
Number of Rings	4	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

C00021793

Chemspider ID

10150474

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11977127

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Birnbacher J, Schuffler A, Deininger F, Opatz T, Anke T: Isolation and biological activity of new norhirsutanes from Creolophus cirrhatus. Z Naturforsch C J Biosci. 2008 Mar-Apr;63(3-4):203-6. doi: 10.1515/znc-2008-3-407. [PubMed:18533462 ]

Showing NP-Card for Complicatic acid (NP0064751)

MOL for NP0064751 (Complicatic acid)

3D MOL for NP0064751 (Complicatic acid)

3D SDF for NP0064751 (Complicatic acid)

3D-SDF for NP0064751 (Complicatic acid)

PDB for NP0064751 (Complicatic acid)

3D PDB for NP0064751 (Complicatic acid)

SMILES for NP0064751 (Complicatic acid)

INCHI for NP0064751 (Complicatic acid)

Structure for NP0064751 (Complicatic acid)

3D Structure for NP0064751 (Complicatic acid)