NP-MRD: Showing NP-Card for Aridacin A (NP0331920)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2023-10-05 16:03:32 UTC

Updated at

2024-05-11 00:26:22 UTC

NP-MRD ID

NP0331920

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aridacin A

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 10052316032D          

 28 30  0  0  1  0            999 V2000
    1.0373   -0.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3571   -0.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299    0.4713    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6012    1.2280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1055    0.5035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5433   -0.1957    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -0.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295    0.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4690    1.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170    1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5882    2.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685    1.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    1.1681    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4275    1.3202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2033    1.0771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5344    0.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456   -0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -0.2521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2632   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277   -0.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014   -1.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -1.0744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104   -2.2255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7520   -1.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4208   -2.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6921    1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9816    2.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  5  3  1  0  0  0  0
  5  6  1  6  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 27  1  6  0  0  0
 10 28  1  0  0  0  0
M  END


  Mrv2104 10052316032D          

 28 30  0  0  1  0            999 V2000
    1.0373   -0.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3571   -0.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299    0.4713    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6012    1.2280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1055    0.5035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5433   -0.1957    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -0.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295    0.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4690    1.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3170    1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5882    2.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685    1.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    1.1681    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4275    1.3202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2033    1.0771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5344    0.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456   -0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -0.2521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2632   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277   -0.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014   -1.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -1.0744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104   -2.2255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7520   -1.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4208   -2.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6921    1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9816    2.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  5  3  1  0  0  0  0
  5  6  1  6  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 27  1  6  0  0  0
 10 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331920

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C(=C)CCC1=C(C)CC[C@]1([H])[C@@H](C)CC[C@]([H])([C@]21[H])C(O)(CO)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-11-4-7-15-12(2)6-9-16(20(24,10-21)19(22)23)18(15)17-13(3)5-8-14(11)17/h12,15-18,21,24H,3-10H2,1-2H3,(H,22,23)/t12-,15+,16+,17-,18+,20?/m0/s1

> <INCHI_KEY>
QGHUXFLPLLLSNP-YYERRBGRSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.247888253508506

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(6aR,7S,10R,10aS,10bS)-4,7-dimethyl-1-methylidene-1H,2H,3H,5H,6H,6aH,7H,8H,9H,10H,10aH,10bH-cyclohexa[e]azulen-10-yl]-2,3-dihydroxypropanoic acid

> <JCHEM_LOGP>
2.7345751269999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.94150904660745

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.205577916151434

> <JCHEM_PKA_STRONGEST_BASIC>
-3.180741581267608

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
93.09389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(6aR,7S,10R,10aS,10bS)-4,7-dimethyl-1-methylidene-2H,3H,5H,6H,6aH,7H,8H,9H,10H,10aH,10bH-cyclohexa[e]azulen-10-yl]-2,3-dihydroxypropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-23         0                                  
HETATM    1  C   UNK     0       1.936  -1.857   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.533  -0.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.736   0.880   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       1.122   2.292   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       0.197   0.940   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       1.014  -0.365   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       4.033  -0.086   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.162   1.448   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.742   2.045   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.458   3.559   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.098   4.281   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.315   3.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.716   2.180   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       0.798   2.464   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      -2.246   2.011   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.864   0.600   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.952  -0.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.421  -0.471   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       0.491  -1.711   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.732  -0.799   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.749  -2.624   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.160  -2.005   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.579  -4.154   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.404  -2.952   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.786  -4.362   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.159   3.251   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.699   4.472   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5    9                                             
CONECT    4    3                                                            
CONECT    5    3    6   13   18                                             
CONECT    6    5                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    5   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   22   25                                             
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26                                                       
CONECT   26   25                                                            
CONECT   27   15                                                            
CONECT   28   10                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

2-[(6aR,7S,10R,10aS,10bS)-4,7-dimethyl-1-methylidene-1H,2H,3H,5H,6H,6aH,7H,8H,9H,10H,10aH,10bH-cyclohexa[e]azulen-10-yl]-2,3-dihydroxypropanoic acid

Traditional Name

2-[(6aR,7S,10R,10aS,10bS)-4,7-dimethyl-1-methylidene-2H,3H,5H,6H,6aH,7H,8H,9H,10H,10aH,10bH-cyclohexa[e]azulen-10-yl]-2,3-dihydroxypropanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@]12C(=C)CCC1=C(C)CC[C@]1([H])[C@@H](C)CC[C@]([H])([C@]21[H])C(O)(CO)C(O)=O

InChI Identifier

InChI=1S/C20H30O4/c1-11-4-7-15-12(2)6-9-16(20(24,10-21)19(22)23)18(15)17-13(3)5-8-14(11)17/h12,15-18,21,24H,3-10H2,1-2H3,(H,22,23)/t12-,15+,16+,17-,18+,20?/m0/s1

InChI Key

QGHUXFLPLLLSNP-YYERRBGRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2024-05-09	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2024-05-09	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2024-05-09	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2023-10-05	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2023-10-05	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 101 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2023-10-05	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2023-10-05	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2023-10-05	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2023-10-05	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2023-10-05	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	Not Available	China Pharmaceutical University	Zengyuan Wang	2023-10-05	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.132470802, CD₃OD, simulated)	wzengyuan@hotmail.com	China Pharmaceutical University	zengyuan	2024-05-09	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
arida		Not Available

Chemical Taxonomy

Classification

Not classified

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	2.73	ChemAxon
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.09 m³·mol⁻¹	ChemAxon
Polarizability	37.25 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

Not Available

References

General References

Wang Z, Yang Q, He J, Li H, Pan X, Li Z, Xu HM, Rudolf JD, Tantillo DJ, Dong LB: Cytochrome P450 Mediated Cyclization in Eunicellane Derived Diterpenoid Biosynthesis. Angew Chem Int Ed Engl. 2023 Nov 6;62(45):e202312490. doi: 10.1002/anie.202312490. Epub 2023 Oct 6. [PubMed:37735947 ]

Showing NP-Card for Aridacin A (NP0331920)

MOL for NP0331920 (Aridacin A)

3D MOL for NP0331920 (Aridacin A)

3D SDF for NP0331920 (Aridacin A)

3D-SDF for NP0331920 (Aridacin A)

PDB for NP0331920 (Aridacin A)

3D PDB for NP0331920 (Aridacin A)

SMILES for NP0331920 (Aridacin A)

INCHI for NP0331920 (Aridacin A)

Structure for NP0331920 (Aridacin A)

3D Structure for NP0331920 (Aridacin A)