NP-MRD: Showing NP-Card for Acrostalidic acid (NP0066055)

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Record Information

Version

2.0

Created at

2022-04-28 10:13:31 UTC

Updated at

2022-04-28 10:13:31 UTC

NP-MRD ID

NP0066055

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acrostalidic acid

Description

Acrostalidic acid, also known as acrostalidate, 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. Acrostalidic acid is found in Acrostalagmus spp. and Oidiodendron truncatum. Acrostalidic acid was first documented in 1999 (PMID: 10605057). Based on a literature review very few articles have been published on Acrostalidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.9994    0.8938    1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0949    0.3714   -0.0887 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4402    1.2582   -1.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6463    1.9749   -1.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7849    1.2659   -1.6167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4864   -1.0259   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6971   -2.1183    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2838   -1.8529    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471   -0.5510   -0.1245 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4499   -0.6062   -1.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5891   -0.2968    0.5394 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6302   -1.3180    0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785   -0.6628    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -1.0957   -0.7802 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2687    0.4045    0.9244 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2433    1.3354    1.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1155    1.0622    0.2378 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1203    2.1308    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1636    1.8812    0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6860    0.5238    0.3802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0356    0.6435    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9242    2.0090    1.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6445    0.5655    2.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0116    1.1313   -2.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5537   -1.1522   -0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5881   -1.1313   -1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7266   -2.9935   -0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919   -2.5306    1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4254   -2.6554    0.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1260   -1.7869    1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7838   -1.6589   -1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4034   -0.4240   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    0.0336   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829   -0.3351    1.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653   -2.0474    1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4189   -1.9329   -0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8781    1.0942    2.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5797    2.3755    1.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.0134   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878    3.1690    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8532    2.7076    0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191    0.3313    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  6
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  2  1  0
  2  1  1  1
  2 20  1  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  2  0
 13 12  1  0
 12 11  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
 20  9  1  0
 11 17  1  0
 11  9  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
  8 29  1  0
  8 30  1  0
  7 27  1  0
  7 28  1  0
  6 25  1  0
  6 26  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 20 42  1  1
 19 41  1  0
 18 40  1  0
 17 39  1  6
 16 37  1  0
 16 38  1  0
 12 35  1  0
 12 36  1  0
 11 34  1  1
  5 24  1  0
M  END


  Mrv1652304282212132D          

 20 22  0  0  1  0            999 V2000
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3016   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300   -0.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2728   -1.5637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308   -1.1265    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
  4 10  1  6  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 15  1  6  0  0  0
  5 16  1  6  0  0  0
  3 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  3 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0066055

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC[C@@](C)([C@@H]1C=C[C@H]1COC(=O)C[C@H]21)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O4/c1-15-6-3-7-16(2,14(18)19)12(15)5-4-10-9-20-13(17)8-11(10)15/h4-5,10-12H,3,6-9H2,1-2H3,(H,18,19)/t10-,11-,12+,15+,16-/m0/s1

> <INCHI_KEY>
QZDLOWBWMWAWPV-KSMPYDNASA-N

> <FORMULA>
C16H22O4

> <MOLECULAR_WEIGHT>
278.348

> <EXACT_MASS>
278.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.545020434861016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,6aR,7S,10aR,10bS)-7,10a-dimethyl-2-oxo-1H,2H,4H,4aH,6aH,7H,8H,9H,10H,10aH,10bH-naphtho[2,1-c]pyran-7-carboxylic acid

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
2.387857219333333

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.414751104764854

> <JCHEM_PKA_STRONGEST_BASIC>
-7.037568379175426

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
74.1587

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,6aR,7S,10aR,10bS)-7,10a-dimethyl-2-oxo-1H,4H,4aH,6aH,8H,9H,10H,10bH-naphtho[2,1-c]pyran-7-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       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.206   0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.030  -1.380   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.389  -0.657   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.976  -2.919   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.777  -2.103   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17   20                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   16                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   15                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7                                                       
CONECT   16    5                                                            
CONECT   17    3   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    3                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
Acrostalidate	Generator

Chemical Formula

C₁₆H₂₂O₄

Average Mass

278.3480 Da

Monoisotopic Mass

278.15181 Da

IUPAC Name

(4aR,6aR,7S,10aR,10bS)-7,10a-dimethyl-2-oxo-1H,2H,4H,4aH,6aH,7H,8H,9H,10H,10aH,10bH-naphtho[2,1-c]pyran-7-carboxylic acid

Traditional Name

(4aR,6aR,7S,10aR,10bS)-7,10a-dimethyl-2-oxo-1H,4H,4aH,6aH,8H,9H,10H,10bH-naphtho[2,1-c]pyran-7-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@]12CCC[C@@](C)([C@@H]1C=C[C@H]1COC(=O)C[C@H]21)C(O)=O

InChI Identifier

InChI=1S/C16H22O4/c1-15-6-3-7-16(2,14(18)19)12(15)5-4-10-9-20-13(17)8-11(10)15/h4-5,10-12H,3,6-9H2,1-2H3,(H,18,19)/t10-,11-,12+,15+,16-/m0/s1

InChI Key

QZDLOWBWMWAWPV-KSMPYDNASA-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
Acrostalagmus spp.	Fungi	KNApSAcK
Oidiodendron truncatum	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
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Pyran
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	2.33	ALOGPS
logP	2.39	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.41	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.16 m³·mol⁻¹	ChemAxon
Polarizability	29.55 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

C00023378

Chemspider ID

10366471

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23252180

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hosoe T, Nozawa K, Lumley TC, Currah RS, Fukushima K, Takizawa K, Miyaji M, Kawai K: Tetranorditerpene lactones, potent antifungal antibiotics for human pathogenic yeasts, from a unique species of Oidiodendron. Chem Pharm Bull (Tokyo). 1999 Nov;47(11):1591-7. doi: 10.1248/cpb.47.1591. [PubMed:10605057 ]

Showing NP-Card for Acrostalidic acid (NP0066055)

MOL for NP0066055 (Acrostalidic acid)

3D MOL for NP0066055 (Acrostalidic acid)

3D SDF for NP0066055 (Acrostalidic acid)

3D-SDF for NP0066055 (Acrostalidic acid)

PDB for NP0066055 (Acrostalidic acid)

3D PDB for NP0066055 (Acrostalidic acid)

SMILES for NP0066055 (Acrostalidic acid)

INCHI for NP0066055 (Acrostalidic acid)

Structure for NP0066055 (Acrostalidic acid)

3D Structure for NP0066055 (Acrostalidic acid)