NP-MRD: Showing NP-Card for Coriaceumin A (NP0332087)

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Record Information

Version

1.0

Created at

2023-11-02 04:00:56 UTC

Updated at

2024-05-04 05:44:26 UTC

NP-MRD ID

NP0332087

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Coriaceumin A

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 11022304002D          

 26 28  0  0  1  0            999 V2000
    3.3311    0.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6171    0.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4113   -0.0253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4441   -0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591   -0.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702   -1.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5737   -1.9550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2937   -2.3577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0025   -1.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3050   -3.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250   -3.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0362   -4.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7563   -4.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4650   -4.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7675   -5.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8537   -1.5522    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9261   -2.4661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1505   -3.2600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068   -2.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5957   -1.7219    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8017   -1.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6922   -0.9026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8673   -0.9138    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3398   -0.3915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5424    0.4082    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5734   -0.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  7 16  1  1  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 20 19  1  0  0  0  0
 20 21  1  1  0  0  0
 22 20  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24  5  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 22 26  1  0  0  0  0
M  END


  Mrv2104 11022304002D          

 26 28  0  0  1  0            999 V2000
    3.3311    0.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6171    0.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4113   -0.0253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4441   -0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591   -0.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702   -1.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5737   -1.9550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2937   -2.3577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0025   -1.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3050   -3.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250   -3.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0362   -4.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7563   -4.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4650   -4.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7675   -5.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8537   -1.5522    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9261   -2.4661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1505   -3.2600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068   -2.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5957   -1.7219    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8017   -1.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6922   -0.9026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8673   -0.9138    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3398   -0.3915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5424    0.4082    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5734   -0.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  7 16  1  1  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 20 19  1  0  0  0  0
 20 21  1  1  0  0  0
 22 20  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24  5  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 22 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332087

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@]1([H])C1=C(CNC1=O)[C@]([H])([C@H](C)CCC=C(C)C)[C@H](O)C[C@H]2C

> <INCHI_IDENTIFIER>
InChI=1S/C20H31NO2/c1-11(2)6-5-7-12(3)18-16-10-21-20(23)19(16)15-9-14(15)13(4)8-17(18)22/h6,12-15,17-18,22H,5,7-10H2,1-4H3,(H,21,23)/t12-,13-,14+,15+,17-,18+/m1/s1

> <INCHI_KEY>
QJIMPZHIIVLGTD-ZTNNJZCJSA-N

> <FORMULA>
C20H31NO2

> <MOLECULAR_WEIGHT>
317.473

> <EXACT_MASS>
317.235479242

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.525054261109474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4S,5R,7R,8S)-7-hydroxy-5-methyl-8-[(2R)-6-methylhept-5-en-2-yl]-11-azatricyclo[7.3.0.0^{2,4}]dodec-1(9)-en-12-one

> <JCHEM_LOGP>
2.8499012266666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.898856152815288

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.060622481071235

> <JCHEM_PKA_STRONGEST_BASIC>
-0.008297646872634774

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
94.77399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,5R,7R,8S)-7-hydroxy-5-methyl-8-[(2R)-6-methylhept-5-en-2-yl]-11-azatricyclo[7.3.0.0^{2,4}]dodec-1(9)-en-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-NOV-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-NOV-23         0                                  
HETATM    1  O   UNK     0       6.218   1.814   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.752   0.370   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       8.234  -0.047   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.296  -1.586   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.897  -0.911   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.851  -2.120   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.671  -3.649   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.015  -4.401   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.338  -3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.036  -5.941   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.380  -6.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.401  -8.232   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.745  -8.984   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.068  -8.196   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.766 -10.524   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       5.327  -2.897   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       5.462  -4.603   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.881  -6.085   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.933  -4.423   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.979  -3.214   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.497  -3.633   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.159  -1.685   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       1.619  -1.706   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       4.368  -0.731   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       4.746   0.762   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       2.937  -0.161   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3    6                                                       
CONECT    5    2    6   24                                                  
CONECT    6    5    4    7                                                  
CONECT    7    6    8   16   17                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    7                                                            
CONECT   17    7   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   26                                             
CONECT   23   22                                                            
CONECT   24   22    5   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   22                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₁NO₂

Average Mass

317.4730 Da

Monoisotopic Mass

317.23548 Da

IUPAC Name

(2S,4S,5R,7R,8S)-7-hydroxy-5-methyl-8-[(2R)-6-methylhept-5-en-2-yl]-11-azatricyclo[7.3.0.0^{2,4}]dodec-1(9)-en-12-one

Traditional Name

(2S,4S,5R,7R,8S)-7-hydroxy-5-methyl-8-[(2R)-6-methylhept-5-en-2-yl]-11-azatricyclo[7.3.0.0^{2,4}]dodec-1(9)-en-12-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@]1([H])C1=C(CNC1=O)[C@]([H])([C@H](C)CCC=C(C)C)[C@H](O)C[C@H]2C

InChI Identifier

InChI=1S/C20H31NO2/c1-11(2)6-5-7-12(3)18-16-10-21-20(23)19(16)15-9-14(15)13(4)8-17(18)22/h6,12-15,17-18,22H,5,7-10H2,1-4H3,(H,21,23)/t12-,13-,14+,15+,17-,18+/m1/s1

InChI Key

QJIMPZHIIVLGTD-ZTNNJZCJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	mscjx2013@126.com	Not Available	Not Available	2024-05-04	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 601 MHz, CDCl3, experimental)	mscjx2013@126.com	Not Available	Not Available	2023-11-02	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 601 MHz, CDCl3, experimental)	mscjx2013@126.com	Not Available	Not Available	2023-11-02	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 601 MHz, CDCl3, experimental)	mscjx2013@126.com	Not Available	Not Available	2023-11-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 601 MHz, CDCl3, experimental)	mscjx2013@126.com	Not Available	Not Available	2023-11-02	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 601 MHz, CDCl3, experimental)	mscjx2013@126.com	Not Available	Not Available	2023-11-02	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CDCl3, experimental)	mscjx2013@126.com	Not Available	Not Available	2023-11-02	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, 600, CDCl₃, simulated)	mscjx2013@126.com	Nanchang University	Shui-Chun Mao	2024-05-04	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
coriacea		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	2.85	ChemAxon
pKa (Strongest Acidic)	13.06	ChemAxon
pKa (Strongest Basic)	-0.0083	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.77 m³·mol⁻¹	ChemAxon
Polarizability	37.53 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 K, Xu CH, Tong L, Wang B, Liu AH, Li SW, Mao SC: Coriaceumins A-D, the First Nitrogen-Containing Crenulide Diterpenoids from the Brown Alga Dictyota coriacea Collected in the East China Sea. J Nat Prod. 2024 Jan 26;87(1):121-131. doi: 10.1021/acs.jnatprod.3c00898. Epub 2023 Dec 27. [PubMed:38151459 ]

Showing NP-Card for Coriaceumin A (NP0332087)

MOL for NP0332087 (Coriaceumin A)

3D MOL for NP0332087 (Coriaceumin A)

3D SDF for NP0332087 (Coriaceumin A)

3D-SDF for NP0332087 (Coriaceumin A)

PDB for NP0332087 (Coriaceumin A)

3D PDB for NP0332087 (Coriaceumin A)

SMILES for NP0332087 (Coriaceumin A)

INCHI for NP0332087 (Coriaceumin A)

Structure for NP0332087 (Coriaceumin A)

3D Structure for NP0332087 (Coriaceumin A)