NP-MRD: Showing NP-Card for (+)-Ulosin B (NP0080931)

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Record Information

Version

2.0

Created at

2022-04-29 01:54:13 UTC

Updated at

2022-04-29 01:54:13 UTC

NP-MRD ID

NP0080931

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Ulosin B

Description

1-Chloro-N-[(1E,6S,10R)-6,10-dihydroxy-11-methyl-3,7-dimethylidenedodeca-1,11-dien-1-yl]methanecarbonimidoyl chloride belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (+)-Ulosin B is found in Ulosa spongia. Based on a literature review very few articles have been published on 1-chloro-N-[(1E,6S,10R)-6,10-dihydroxy-11-methyl-3,7-dimethylidenedodeca-1,11-dien-1-yl]methanecarbonimidoyl chloride.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 43  0  0  0  0  0  0  0  0999 V2000
    2.9203   -1.9841   -0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2473   -1.2325    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8174   -1.8770    1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748   -1.1751    2.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6964   -1.7133    3.9551 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1852   -2.1424    4.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -3.8544    5.3687 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1360   -1.1648    6.0858 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0310    0.2171    0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842    0.7096   -0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    0.2837   -0.1593 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4539   -1.0432    0.0663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2166    0.7662   -1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1996    1.4613   -2.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    0.4208   -1.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535    0.9719   -2.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8857    0.6137   -2.1957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0910   -0.7663   -2.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5891    1.0910   -1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4758    2.0704   -1.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4150    0.5920    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0876   -3.0627   -0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5260   -1.6433   -1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9496   -2.9598    1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0103   -0.0961    2.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6141    0.5334    1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.7738    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0753    1.8349   -0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4401    0.3471   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236    0.8443    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4969   -1.2493    1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4538    1.8247   -3.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2643    1.7211   -2.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -0.6693   -1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0499    0.8944   -0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137    0.5446   -3.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236    2.0859   -2.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3851    1.0751   -3.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6565   -1.3240   -1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6634    2.4868   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0022    2.4378   -0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4639    0.4284    0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9749    1.3557    1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8811   -0.3471    0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  1  0
 19 20  2  3
 19 17  1  0
 17 18  1  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  2  3
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10  9  1  0
  9  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 20 40  1  0
 20 41  1  0
 17 38  1  6
 18 39  1  0
 16 36  1  0
 16 37  1  0
 15 34  1  0
 15 35  1  0
 14 32  1  0
 14 33  1  0
 11 30  1  1
 12 31  1  0
 10 28  1  0
 10 29  1  0
  9 26  1  0
  9 27  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
M  END


  Mrv1652304292203542D          

 21 20  0  0  1  0            999 V2000
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    3.2704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    3.2704    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    2.0329    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 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
 12 14  1  0  0  0  0
 14 15  2  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
 17 19  1  0  0  0  0
  9 20  1  1  0  0  0
  4 21  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0080931

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H](O)CCC(=C)[C@@H](O)CCC(=C)\C=C\N=C(Cl)Cl

> <INCHI_IDENTIFIER>
InChI=1S/C16H23Cl2NO2/c1-11(2)14(20)8-6-13(4)15(21)7-5-12(3)9-10-19-16(17)18/h9-10,14-15,20-21H,1,3-8H2,2H3/b10-9+/t14-,15+/m1/s1

> <INCHI_KEY>
ZSIZXRJEOIETMM-SPZIKGKASA-N

> <FORMULA>
C16H23Cl2NO2

> <MOLECULAR_WEIGHT>
332.27

> <EXACT_MASS>
331.1105844

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.33416083330731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-chloro-N-[(1E,6S,10R)-6,10-dihydroxy-11-methyl-3,7-dimethylidenedodeca-1,11-dien-1-yl]methanecarbonimidoyl chloride

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
3.801973336333332

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.426134857252904

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.098877223876173

> <JCHEM_PKA_STRONGEST_BASIC>
1.9599988702528668

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
90.95300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-chloro-N-[(1E,6S,10R)-6,10-dihydroxy-11-methyl-3,7-dimethylidenedodeca-1,11-dien-1-yl]methanecarbonimidoyl chloride

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.240   3.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.575   3.795   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.909   3.795   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.577   5.335   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      23.910   6.105   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      25.244   5.335   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      26.578   6.105   0.000  0.00  0.00          Cl+0
HETATM   19 Cl   UNK     0      25.244   3.795   0.000  0.00  0.00          Cl+0
HETATM   20  O   UNK     0      15.908   7.645   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.574   7.645   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    9                                                            
CONECT   21    4                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₃Cl₂NO₂

Average Mass

332.2700 Da

Monoisotopic Mass

331.11058 Da

IUPAC Name

1-chloro-N-[(1E,6S,10R)-6,10-dihydroxy-11-methyl-3,7-dimethylidenedodeca-1,11-dien-1-yl]methanecarbonimidoyl chloride

Traditional Name

1-chloro-N-[(1E,6S,10R)-6,10-dihydroxy-11-methyl-3,7-dimethylidenedodeca-1,11-dien-1-yl]methanecarbonimidoyl chloride

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H](O)CCC(=C)[C@@H](O)CCC(=C)\C=C\N=C(Cl)Cl

InChI Identifier

InChI=1S/C16H23Cl2NO2/c1-11(2)14(20)8-6-13(4)15(21)7-5-12(3)9-10-19-16(17)18/h9-10,14-15,20-21H,1,3-8H2,2H3/b10-9+/t14-,15+/m1/s1

InChI Key

ZSIZXRJEOIETMM-SPZIKGKASA-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
Ulosa spongia	-	KNApSAcK

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

Farsesane sesquiterpenoid
Sesquiterpenoid
Isocyanide dichloride
Secondary alcohol
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	3.26	ALOGPS
logP	3.8	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.1	ChemAxon
pKa (Strongest Basic)	1.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	90.95 m³·mol⁻¹	ChemAxon
Polarizability	35.33 Å³	ChemAxon
Number of Rings	0	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162945665

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Ulosin B (NP0080931)

MOL for NP0080931 ((+)-Ulosin B)

3D MOL for NP0080931 ((+)-Ulosin B)

3D SDF for NP0080931 ((+)-Ulosin B)

3D-SDF for NP0080931 ((+)-Ulosin B)

PDB for NP0080931 ((+)-Ulosin B)

3D PDB for NP0080931 ((+)-Ulosin B)

SMILES for NP0080931 ((+)-Ulosin B)

INCHI for NP0080931 ((+)-Ulosin B)

Structure for NP0080931 ((+)-Ulosin B)

3D Structure for NP0080931 ((+)-Ulosin B)