NP-MRD: Showing NP-Card for Officinalic acid (NP0063486)

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Record Information

Version

2.0

Created at

2022-04-28 07:53:32 UTC

Updated at

2022-04-28 07:53:32 UTC

NP-MRD ID

NP0063486

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Officinalic acid

Description

(1S,3S,8R,9S,10S,13S,16S,21S,22R)-4,4,8,17,17,21-hexamethyl-14,23-dioxo-24,25-dioxahexacyclo[11.11.1.0¹,¹⁰.0³,⁸.0¹³,²².0¹⁶,²¹]Pentacosane-9-carboxylic acid belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Officinalic acid is found in Fomes officinalis and Fomitopsis officinalis. Based on a literature review very few articles have been published on (1S,3S,8R,9S,10S,13S,16S,21S,22R)-4,4,8,17,17,21-hexamethyl-14,23-dioxo-24,25-dioxahexacyclo[11.11.1.0¹,¹⁰.0³,⁸.0¹³,²².0¹⁶,²¹]Pentacosane-9-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209532D          

 36 41  0  0  1  0            999 V2000
    7.5624    2.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 18 35  1  1  0  0  0
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  4 36  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282209532D          

 36 41  0  0  1  0            999 V2000
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    1.9455    2.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269    4.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1302    3.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    2.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142    3.7615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8166    4.4346    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 11 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
 28 32  1  0  0  0  0
 28 33  1  0  0  0  0
 23 34  1  6  0  0  0
 18 35  1  1  0  0  0
 10 35  1  1  0  0  0
  4 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0063486

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@@]2(C)[C@H]1CC(=O)[C@]13CC[C@H]4[C@H](C(O)=O)[C@]5(C)CCCC(C)(C)[C@@H]5C[C@@]4(OC(=O)[C@H]21)O3

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O6/c1-25(2)10-8-13-28(6)18(25)15-20(31)29-14-9-17-21(23(32)33)27(5)12-7-11-26(3,4)19(27)16-30(17,36-29)35-24(34)22(28)29/h17-19,21-22H,7-16H2,1-6H3,(H,32,33)/t17-,18-,19-,21+,22+,27+,28-,29+,30+/m0/s1

> <INCHI_KEY>
ODGNNLIOBJLXBP-XEARGBAXSA-N

> <FORMULA>
C30H44O6

> <MOLECULAR_WEIGHT>
500.676

> <EXACT_MASS>
500.313789137

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.20350145387316

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,8R,9S,10S,13S,16S,21S,22R)-4,4,8,17,17,21-hexamethyl-14,23-dioxo-24,25-dioxahexacyclo[11.11.1.0^{1,10}.0^{3,8}.0^{13,22}.0^{16,21}]pentacosane-9-carboxylic acid

> <ALOGPS_LOGP>
5.10

> <JCHEM_LOGP>
5.977749202333332

> <ALOGPS_LOGS>
-5.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.582419762538997

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.269487858397743

> <JCHEM_PKA_STRONGEST_BASIC>
-4.44261180390682

> <JCHEM_POLAR_SURFACE_AREA>
89.89999999999999

> <JCHEM_REFRACTIVITY>
133.26879999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.24e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,8R,9S,10S,13S,16S,21S,22R)-4,4,8,17,17,21-hexamethyl-14,23-dioxo-24,25-dioxahexacyclo[11.11.1.0^{1,10}.0^{3,8}.0^{13,22}.0^{16,21}]pentacosane-9-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      14.117   4.456   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.663   5.896   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.688   7.089   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.168   6.842   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.622   5.402   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.597   4.209   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.438   3.194   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.790   2.681   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.083   5.187   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.957   6.344   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.669   7.815   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.210   8.049   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.773   9.483   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.296   9.712   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.813  10.687   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.877   9.192   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.282   9.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.401   7.687   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.706   6.191   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.501   4.800   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.789   3.435   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.087   4.942   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.168   5.907   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.186   7.093   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.702   8.542   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.232   8.806   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.681  10.279   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.667   6.835   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.131   5.391   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.113   4.205   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.632   4.463   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.357   8.344   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.243   7.421   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.159   4.728   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.680   7.021   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      12.724   8.278   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12   36                                             
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   22   35                                             
CONECT   11   10   12   16                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   26   35                                             
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   10                                                       
CONECT   23   19   24   31   34                                             
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   18   27                                                  
CONECT   27   26                                                            
CONECT   28   24   29   32   33                                             
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   23                                                       
CONECT   32   28                                                            
CONECT   33   28                                                            
CONECT   34   23                                                            
CONECT   35   18   10                                                       
CONECT   36    4                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Value	Source
(1S,3S,8R,9S,10S,13S,16S,21S,22R)-4,4,8,17,17,21-Hexamethyl-14,23-dioxo-24,25-dioxahexacyclo[11.11.1.0,.0,.0,.0,]pentacosane-9-carboxylate	Generator

Chemical Formula

C₃₀H₄₄O₆

Average Mass

500.6760 Da

Monoisotopic Mass

500.31379 Da

IUPAC Name

(1S,3S,8R,9S,10S,13S,16S,21S,22R)-4,4,8,17,17,21-hexamethyl-14,23-dioxo-24,25-dioxahexacyclo[11.11.1.0^{1,10}.0^{3,8}.0^{13,22}.0^{16,21}]pentacosane-9-carboxylic acid

Traditional Name

(1S,3S,8R,9S,10S,13S,16S,21S,22R)-4,4,8,17,17,21-hexamethyl-14,23-dioxo-24,25-dioxahexacyclo[11.11.1.0^{1,10}.0^{3,8}.0^{13,22}.0^{16,21}]pentacosane-9-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@@]2(C)[C@H]1CC(=O)[C@]13CC[C@H]4[C@H](C(O)=O)[C@]5(C)CCCC(C)(C)[C@@H]5C[C@@]4(OC(=O)[C@H]21)O3

InChI Identifier

InChI=1S/C30H44O6/c1-25(2)10-8-13-28(6)18(25)15-20(31)29-14-9-17-21(23(32)33)27(5)12-7-11-26(3,4)19(27)16-30(17,36-29)35-24(34)22(28)29/h17-19,21-22H,7-16H2,1-6H3,(H,32,33)/t17-,18-,19-,21+,22+,27+,28-,29+,30+/m0/s1

InChI Key

ODGNNLIOBJLXBP-XEARGBAXSA-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
Fomes officinalis	Fungi	KNApSAcK
Fomitopsis officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Ketal
Pyran
Oxane
Dicarboxylic acid or derivatives
Meta-dioxane
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.1	ALOGPS
logP	5.98	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.27 m³·mol⁻¹	ChemAxon
Polarizability	56.2 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	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

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

162860105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Officinalic acid (NP0063486)

MOL for NP0063486 (Officinalic acid)

3D MOL for NP0063486 (Officinalic acid)

3D SDF for NP0063486 (Officinalic acid)

3D-SDF for NP0063486 (Officinalic acid)

PDB for NP0063486 (Officinalic acid)

3D PDB for NP0063486 (Officinalic acid)

SMILES for NP0063486 (Officinalic acid)

INCHI for NP0063486 (Officinalic acid)

Structure for NP0063486 (Officinalic acid)

3D Structure for NP0063486 (Officinalic acid)