NP-MRD: Showing NP-Card for Aplysin 20 (NP0050544)

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Record Information

Version

2.0

Created at

2022-04-27 21:56:25 UTC

Updated at

2022-04-27 21:56:25 UTC

NP-MRD ID

NP0050544

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aplysin 20

Description

(1S,2R,4aS,6S,8aS)-6-bromo-1-[(3E)-5-hydroxy-3-methylpent-3-en-1-yl]-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Aplysin 20 is found in Aplysia kurodai and Marginosporum aberrans. Based on a literature review very few articles have been published on (1S,2R,4aS,6S,8aS)-6-bromo-1-[(3E)-5-hydroxy-3-methylpent-3-en-1-yl]-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223562D          

 23 24  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -0.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 Br  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  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
  8 11  1  1  0  0  0
  8 12  1  6  0  0  0
  7 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 15 19  1  0  0  0  0
  5 20  1  1  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  2 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050544

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CC[C@@H]1[C@](C)(O)CC[C@@H]2C(C)(C)[C@@H](Br)CC[C@]12C)=C/CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H35BrO2/c1-14(10-13-22)6-7-16-19(4)11-9-17(21)18(2,3)15(19)8-12-20(16,5)23/h10,15-17,22-23H,6-9,11-13H2,1-5H3/b14-10+/t15-,16+,17+,19+,20-/m1/s1

> <INCHI_KEY>
VUFPGDSZNJURQC-ZDDZEKOJSA-N

> <FORMULA>
C20H35BrO2

> <MOLECULAR_WEIGHT>
387.402

> <EXACT_MASS>
386.182043

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.678910203063346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4aS,6S,8aS)-6-bromo-1-[(3E)-5-hydroxy-3-methylpent-3-en-1-yl]-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

> <ALOGPS_LOGP>
5.50

> <JCHEM_LOGP>
4.501025084

> <ALOGPS_LOGS>
-5.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.33003040577717

> <JCHEM_PKA_STRONGEST_BASIC>
-0.43544902440311806

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
101.5084

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4aS,6S,8aS)-6-bromo-1-[(3E)-5-hydroxy-3-methylpent-3-en-1-yl]-2,5,5,8a-tetramethyl-hexahydro-1H-naphthalen-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.817   0.536   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.540  -0.716   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.723  -4.440   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.723  -4.440   0.000  0.00  0.00           C+0
HETATM   23 Br   UNK     0      -2.667  -3.080   0.000  0.00  0.00          Br+0
CONECT    1    2    6                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4   21   22                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   20                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   13                                                  
CONECT    8    7    9   11   12                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    7   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   15                                                            
CONECT   20    5                                                            
CONECT   21    3                                                            
CONECT   22    3                                                            
CONECT   23    2                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₅BrO₂

Average Mass

387.4020 Da

Monoisotopic Mass

386.18204 Da

IUPAC Name

(1S,2R,4aS,6S,8aS)-6-bromo-1-[(3E)-5-hydroxy-3-methylpent-3-en-1-yl]-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

Traditional Name

(1S,2R,4aS,6S,8aS)-6-bromo-1-[(3E)-5-hydroxy-3-methylpent-3-en-1-yl]-2,5,5,8a-tetramethyl-hexahydro-1H-naphthalen-2-ol

CAS Registry Number

Not Available

SMILES

C\C(CC[C@@H]1[C@](C)(O)CC[C@@H]2C(C)(C)[C@@H](Br)CC[C@]12C)=C/CO

InChI Identifier

InChI=1S/C20H35BrO2/c1-14(10-13-22)6-7-16-19(4)11-9-17(21)18(2,3)15(19)8-12-20(16,5)23/h10,15-17,22-23H,6-9,11-13H2,1-5H3/b14-10+/t15-,16+,17+,19+,20-/m1/s1

InChI Key

VUFPGDSZNJURQC-ZDDZEKOJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aplysia kurodai	Animalia	KNApSAcK
Marginosporum aberrans	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Labdane diterpenoid
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organobromide
Organohalogen compound
Alkyl halide
Alkyl bromide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.5	ALOGPS
logP	4.5	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	16.33	ChemAxon
pKa (Strongest Basic)	-0.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.51 m³·mol⁻¹	ChemAxon
Polarizability	40.68 Å³	ChemAxon
Number of Rings	2	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

162908153

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Aplysin 20 (NP0050544)

MOL for NP0050544 (Aplysin 20)

3D MOL for NP0050544 (Aplysin 20)

3D SDF for NP0050544 (Aplysin 20)

3D-SDF for NP0050544 (Aplysin 20)

PDB for NP0050544 (Aplysin 20)

3D PDB for NP0050544 (Aplysin 20)

SMILES for NP0050544 (Aplysin 20)

INCHI for NP0050544 (Aplysin 20)

Structure for NP0050544 (Aplysin 20)

3D Structure for NP0050544 (Aplysin 20)