NP-MRD: Showing NP-Card for Isocaulamidine B (NP0332187)

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Record Information

Version

1.0

Created at

2023-12-01 20:02:02 UTC

Updated at

2024-05-09 20:02:53 UTC

NP-MRD ID

NP0332187

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isocaulamidine B

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 12012320022D          

 30 35  0  0  1  0            999 V2000
    5.9415    3.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8926    2.1983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6150    1.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4243    1.9087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8269    1.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3586    0.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5106   -0.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3151   -0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8755    0.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6801    0.0353    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.6314    1.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5109    0.8740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1683    0.3754    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9287    0.6954    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0652   -0.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3048   -0.7631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6474   -0.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870   -0.5846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7839   -1.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297   -0.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328    0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9150    0.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119    0.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0515   -0.2275    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4693   -0.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1853    1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7505    0.5540    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9303    0.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0804    1.8174    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  5 11  1  0  0  0  0
 12  6  1  6  0  0  0
 12  3  1  0  0  0  0
 12 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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 20 26  1  0  0  0  0
 21 27  1  0  0  0  0
 28 17  1  1  0  0  0
 12 28  1  0  0  0  0
 28 27  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
M  END


  Mrv2104 12012320022D          

 30 35  0  0  1  0            999 V2000
    5.9415    3.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8926    2.1983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6150    1.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4243    1.9087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8269    1.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3586    0.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5106   -0.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3151   -0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8755    0.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6801    0.0353    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.6314    1.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5109    0.8740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1683    0.3754    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9287    0.6954    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0652   -0.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3048   -0.7631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6474   -0.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870   -0.5846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7839   -1.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297   -0.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328    0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9150    0.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119    0.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0515   -0.2275    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4693   -0.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1853    1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7505    0.5540    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9303    0.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0804    1.8174    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  5 11  1  0  0  0  0
 12  6  1  6  0  0  0
 12  3  1  0  0  0  0
 12 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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 20 26  1  0  0  0  0
 21 27  1  0  0  0  0
 28 17  1  1  0  0  0
 12 28  1  0  0  0  0
 28 27  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332187

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC[C@@]23CC4=C(C=C(Br)C=C4)N(C)C2=NC[C@@H](Cl)[C@]32C1=NC1=C2C=CC(Br)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H21Br2ClN4/c1-29-8-7-22-11-13-3-4-15(25)10-18(13)30(2)20(22)27-12-19(26)23(22)16-6-5-14(24)9-17(16)28-21(23)29/h3-6,9-10,19H,7-8,11-12H2,1-2H3/t19-,22-,23-/m1/s1

> <INCHI_KEY>
NBPHOTMKDYSRKJ-UEVCKROQSA-N

> <FORMULA>
C23H21Br2ClN4

> <MOLECULAR_WEIGHT>
548.71

> <EXACT_MASS>
545.98215

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
49.91182141736125

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,13S,14S)-6,18-dibromo-13-chloro-9,23-dimethyl-9,11,21,23-tetraazahexacyclo[12.11.0.0^{1,10}.0^{3,8}.0^{14,22}.0^{15,20}]pentacosa-3(8),4,6,10,15(20),16,18,21-octaene

> <JCHEM_LOGP>
5.284378663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.4634811250131445

> <JCHEM_POLAR_SURFACE_AREA>
31.200000000000003

> <JCHEM_REFRACTIVITY>
130.629

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,13S,14S)-6,18-dibromo-13-chloro-9,23-dimethyl-9,11,21,23-tetraazahexacyclo[12.11.0.0^{1,10}.0^{3,8}.0^{14,22}.0^{15,20}]pentacosa-3(8),4,6,10,15(20),16,18,21-octaene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 01-DEC-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-DEC-23         0                                  
HETATM    1  C   UNK     0      11.091   5.641   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      11.000   4.103   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      12.348   3.264   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      13.859   3.563   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      14.610   2.219   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.736   1.222   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.020  -0.382   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.522  -0.723   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.568   0.407   0.000  0.00  0.00           C+0
HETATM   10 Br   UNK     0      18.069   0.066   0.000  0.00  0.00          Br+0
HETATM   11  C   UNK     0      16.112   1.878   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.154   1.631   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.381   0.701   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      14.800   1.298   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0      13.188  -0.827   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      11.769  -1.424   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      10.542  -0.494   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       9.122  -1.091   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       8.930  -2.619   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.895  -0.161   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.088   1.367   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.861   2.298   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.441   1.701   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.249   0.173   0.000  0.00  0.00           C+0
HETATM   25 Br   UNK     0       3.830  -0.425   0.000  0.00  0.00          Br+0
HETATM   26  C   UNK     0       6.476  -0.758   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.679   2.098   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.734   1.034   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.203   1.648   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.483   3.393   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5                                                       
CONECT   12    6    3   13   28                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20                                                       
CONECT   27   21   28                                                       
CONECT   28   17   12   27   29                                             
CONECT   29   28   30                                                       
CONECT   30   29    2                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₁Br₂ClN₄

Average Mass

548.7100 Da

Monoisotopic Mass

545.98215 Da

IUPAC Name

(1R,13S,14S)-6,18-dibromo-13-chloro-9,23-dimethyl-9,11,21,23-tetraazahexacyclo[12.11.0.0^{1,10}.0^{3,8}.0^{14,22}.0^{15,20}]pentacosa-3(8),4,6,10,15(20),16,18,21-octaene

Traditional Name

(1R,13S,14S)-6,18-dibromo-13-chloro-9,23-dimethyl-9,11,21,23-tetraazahexacyclo[12.11.0.0^{1,10}.0^{3,8}.0^{14,22}.0^{15,20}]pentacosa-3(8),4,6,10,15(20),16,18,21-octaene

CAS Registry Number

Not Available

SMILES

CN1CC[C@@]23CC4=C(C=C(Br)C=C4)N(C)C2=NC[C@@H](Cl)[C@]32C1=NC1=C2C=CC(Br)=C1

InChI Identifier

InChI=1S/C23H21Br2ClN4/c1-29-8-7-22-11-13-3-4-15(25)10-18(13)30(2)20(22)27-12-19(26)23(22)16-6-5-14(24)9-17(16)28-21(23)29/h3-6,9-10,19H,7-8,11-12H2,1-2H3/t19-,22-,23-/m1/s1

InChI Key

NBPHOTMKDYSRKJ-UEVCKROQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-09	View Spectrum
HMBC NMR	[¹H, ¹⁵N] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-09	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-09	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-09	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-09	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-09	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
sp.		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	5.28	ChemAxon
pKa (Strongest Basic)	5.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	31.2 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	130.63 m³·mol⁻¹	ChemAxon
Polarizability	49.91 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Tian X, Wang D, Jiang W, Bokesch HR, Wilson BAP, O'Keefe BR, Gustafson KR: Rare Caulamidine Hexacyclic Alkaloids from the Marine Ascidian Polyandrocarpa sp. J Nat Prod. 2023 Jul 28;86(7):1855-1861. doi: 10.1021/acs.jnatprod.3c00393. Epub 2023 Jun 27. [PubMed:37368408 ]

Showing NP-Card for Isocaulamidine B (NP0332187)

MOL for NP0332187 (Isocaulamidine B)

3D MOL for NP0332187 (Isocaulamidine B)

3D SDF for NP0332187 (Isocaulamidine B)

3D-SDF for NP0332187 (Isocaulamidine B)

PDB for NP0332187 (Isocaulamidine B)

3D PDB for NP0332187 (Isocaulamidine B)

SMILES for NP0332187 (Isocaulamidine B)

INCHI for NP0332187 (Isocaulamidine B)

Structure for NP0332187 (Isocaulamidine B)

3D Structure for NP0332187 (Isocaulamidine B)