NP-MRD: Showing NP-Card for Sterpuric acid (NP0064479)

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Record Information

Version

1.0

Created at

2022-04-28 08:42:29 UTC

Updated at

2024-04-19 09:38:58 UTC

NP-MRD ID

NP0064479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sterpuric acid

Description

Sterpuric acid, also known as sterpate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sterpuric acid is found in Stereum purpureum and Flammulina velutipes. It was first documented in 2005 (PMID: 15719637). Based on a literature review a small amount of articles have been published on sterpuric acid (PMID: 22746380) (PMID: 29243621).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -0.7595    0.7947   -2.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7695    0.3147   -1.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3778    0.0587   -0.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7998    0.1511   -1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6451    0.0543    0.0356 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1564   -1.3527    0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7873    0.9906    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9624    1.8841    0.8556 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7210    0.8703   -1.0081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6842    0.3534    1.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4782   -0.4231    0.6809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7175   -0.2999    1.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9905    0.1030    0.8941 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6509    1.2686    1.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247   -1.0342    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -1.2391   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0338    0.1411   -0.5828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0093    1.0750   -1.0055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119    0.1789   -3.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2026    0.6634   -3.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0318    1.8642   -2.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9402   -0.7379   -1.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9729    1.1081   -1.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7592   -1.8269    1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8710   -1.9800   -0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2748   -1.3490    0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1359   -0.0229   -1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188    1.4408    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0663   -0.0274    2.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8280   -1.4922    0.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5097    0.3773    2.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890   -1.2987    2.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    0.8328    2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3355    1.8185    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8875    1.9322    2.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7518   -1.8563    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0594   -0.7209    0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5294   -1.3289   -1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8963   -2.0220   -0.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9250    0.7363   -0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
  5  7  1  0
  7  9  1  0
  7  8  2  0
 17  2  1  0
 11  3  1  0
 17 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  6
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  0
  9 27  1  0
M  END


  Mrv1652304282210422D          

 18 20  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650    1.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7751    1.5080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736    2.7529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650    1.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1773    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1773    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    0.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    2.7323    0.0000 O   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  6  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  6  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  1  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
  1 16  1  0  0  0  0
  2 17  1  6  0  0  0
  1 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0064479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C[C@](C)(C[C@H]2C[C@]2(C)CC[C@]12O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-9-11-8-13(2,12(16)17)6-10(11)7-14(3)4-5-15(9,14)18/h10,18H,4-8H2,1-3H3,(H,16,17)/t10-,13-,14-,15-/m0/s1

> <INCHI_KEY>
PQUVTIVCCBHWFH-HJPIBITLSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.338

> <EXACT_MASS>
250.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.690827437576978

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2aS,3aR,5S,7aR)-7a-hydroxy-2a,5,7-trimethyl-1H,2H,2aH,3H,3aH,4H,5H,6H,7aH-cyclobuta[f]indene-5-carboxylic acid

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.2458006556666668

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.707037580074118

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.61524009927939

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7399438863152138

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
68.51910000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2aR,5S,6aR,7aS)-2a-hydroxy-3,5,7a-trimethyl-1H,2H,4H,6H,6aH,7H-cyclobuta[f]indene-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       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.121   3.599   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.447   2.815   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.137   5.139   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.121   2.087   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.798   2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.798   3.613   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.656   0.585   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.656   5.100   0.000  0.00  0.00           O+0
CONECT    1    2    6   16   18                                             
CONECT    2    1    3   15   17                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11   14                                             
CONECT   10    9    4                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9                                                            
CONECT   15    2   16                                                       
CONECT   16   15    1                                                       
CONECT   17    2                                                            
CONECT   18    1                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
Sterpate	Generator
Sterpic acid	Generator

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3380 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

(2aS,3aR,5S,7aR)-7a-hydroxy-2a,5,7-trimethyl-1H,2H,2aH,3H,3aH,4H,5H,6H,7aH-cyclobuta[f]indene-5-carboxylic acid

Traditional Name

(2aR,5S,6aR,7aS)-2a-hydroxy-3,5,7a-trimethyl-1H,2H,4H,6H,6aH,7H-cyclobuta[f]indene-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=C2C[C@](C)(C[C@H]2C[C@]2(C)CC[C@]12O)C(O)=O

InChI Identifier

InChI=1S/C15H22O3/c1-9-11-8-13(2,12(16)17)6-10(11)7-14(3)4-5-15(9,14)18/h10,18H,4-8H2,1-3H3,(H,16,17)/t10-,13-,14-,15-/m0/s1

InChI Key

PQUVTIVCCBHWFH-HJPIBITLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	phamthihuong@sookmyung.ac.kr	Not Available	Not Available	2022-12-23	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	phamthihuong@sookmyung.ac.kr	Not Available	Not Available	2022-12-23	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	phamthihuong@sookmyung.ac.kr	Not Available	Not Available	2022-12-23	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	phamthihuong@sookmyung.ac.kr	Not Available	Not Available	2022-12-23	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, CD3OD, experimental)	phamthihuong@sookmyung.ac.kr	Not Available	Not Available	2022-12-23	View Spectrum

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
Chondrostereum purpureum	Fungi	KNApSAcK
Flammulina velutipes	LOTUS Database	35616633

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

Sterpuran sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Cyclobutanol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.06	ALOGPS
logP	2.25	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-0.74	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.52 m³·mol⁻¹	ChemAxon
Polarizability	27.69 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

C00021475

Chemspider ID

22899163

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sterpuric acid

METLIN ID

Not Available

PubChem Compound

14108443

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Schuffler A, Wollinsky B, Anke T, Liermann JC, Opatz T: Isolactarane and sterpurane sesquiterpenoids from the basidiomycete Phlebia uda. J Nat Prod. 2012 Jul 27;75(7):1405-8. doi: 10.1021/np3000552. Epub 2012 Jun 29. [PubMed:22746380 ]
Wang Y, Bao L, Yang X, Li L, Li S, Gao H, Yao XS, Wen H, Liu HW: Bioactive sesquiterpenoids from the solid culture of the edible mushroom Flammulina velutipes growing on cooked rice. Food Chem. 2012 Jun 1;132(3):1346-1353. doi: 10.1016/j.foodchem.2011.11.117. Epub 2011 Dec 6. [PubMed:29243621 ]
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Showing NP-Card for Sterpuric acid (NP0064479)

MOL for NP0064479 (Sterpuric acid)

3D MOL for NP0064479 (Sterpuric acid)

3D SDF for NP0064479 (Sterpuric acid)

3D-SDF for NP0064479 (Sterpuric acid)

PDB for NP0064479 (Sterpuric acid)

3D PDB for NP0064479 (Sterpuric acid)

SMILES for NP0064479 (Sterpuric acid)

INCHI for NP0064479 (Sterpuric acid)

Structure for NP0064479 (Sterpuric acid)

3D Structure for NP0064479 (Sterpuric acid)