NP-MRD: Showing NP-Card for (+)-Rhodomollein XIX (NP0079274)

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Record Information

Version

2.0

Created at

2022-04-29 00:18:41 UTC

Updated at

2022-04-29 00:18:41 UTC

NP-MRD ID

NP0079274

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Rhodomollein XIX

Description

(1R,3R,4R,6R,7R,8R,10S,13S,16S)-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]Hexadec-14-ene-3,4,6,7,16-pentol belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). (+)-Rhodomollein XIX is found in Rhododendron molle . Based on a literature review very few articles have been published on (1R,3R,4R,6R,7R,8R,10S,13S,16S)-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]Hexadec-14-ene-3,4,6,7,16-pentol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292202182D          

 25 28  0  0  1  0            999 V2000
    0.9575    1.4908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5864    0.6866    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0945    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762    0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287    1.3192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4019    2.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527    2.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0328    1.0451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3260    1.7879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6113    0.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0083   -0.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8114   -0.2207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4469    0.3060    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4404    1.1310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7868    1.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9831    2.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    1.3921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7132    0.7286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2335    0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8452   -0.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769   -0.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5381    0.7351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717    2.1788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6051   -0.5037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058   -1.0225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  3  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  1  0  0  0
  5  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
  1 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  6  0  0  0
 17 23  1  1  0  0  0
 13 24  1  6  0  0  0
 12 25  1  6  0  0  0
M  END


  Mrv1652304292202182D          

 25 28  0  0  1  0            999 V2000
    0.9575    1.4908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5864    0.6866    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0945    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762    0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287    1.3192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4019    2.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527    2.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0328    1.0451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3260    1.7879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6113    0.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0083   -0.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8114   -0.2207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4469    0.3060    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4404    1.1310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7868    1.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9831    2.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    1.3921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7132    0.7286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2335    0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8452   -0.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769   -0.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5381    0.7351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717    2.1788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6051   -0.5037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058   -1.0225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  3  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  1  0  0  0
  5  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
  1 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  6  0  0  0
 17 23  1  1  0  0  0
 13 24  1  6  0  0  0
 12 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0079274

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@]23C[C@@H](O)[C@@]4(O)[C@@H]([C@@H](O)[C@H](O)C4(C)C)C(=C)[C@@H]2CC[C@@H]1[C@@H]3O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-9-7-19-8-13(21)20(25)14(15(22)17(24)18(20,3)4)10(2)12(19)6-5-11(9)16(19)23/h7,11-17,21-25H,2,5-6,8H2,1,3-4H3/t11-,12-,13+,14+,15+,16-,17-,19-,20+/m0/s1

> <INCHI_KEY>
OIFHQQMEVVIQFJ-RZYCJEPQSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.455

> <EXACT_MASS>
350.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
45.057802222617326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,4R,6R,7R,8R,10S,13S,16S)-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadec-14-ene-3,4,6,7,16-pentol

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
-0.37573426566666573

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.56353224723502

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.868470997869956

> <JCHEM_PKA_STRONGEST_BASIC>
-3.088680543831434

> <JCHEM_POLAR_SURFACE_AREA>
101.15

> <JCHEM_REFRACTIVITY>
93.59919999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4R,6R,7R,8R,10S,13S,16S)-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadec-14-ene-3,4,6,7,16-pentol

> <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       1.787   2.783   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.095   1.282   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.176   0.169   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.635   0.884   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.360   2.462   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.750   3.936   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.845   4.144   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.061   1.951   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.609   3.337   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.008   0.185   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.882  -0.082   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.381  -0.412   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.568   0.571   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.555   2.111   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.335   3.089   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.702   4.585   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.016   2.599   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.931   1.360   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.036   0.107   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.178  -0.926   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.743  -1.405   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.471   1.372   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.480   4.067   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.863  -0.940   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.744  -1.909   0.000  0.00  0.00           O+0
CONECT    1    2    7   15                                                  
CONECT    2    1    3    8   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1                                                       
CONECT    8    5    2    9                                                  
CONECT    9    8                                                            
CONECT   10    4                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14   19   24                                             
CONECT   14   13   15   17                                                  
CONECT   15   14    1   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18   23                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   13   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18                                                            
CONECT   23   17                                                            
CONECT   24   13                                                            
CONECT   25   12                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₅

Average Mass

350.4550 Da

Monoisotopic Mass

350.20932 Da

IUPAC Name

(1R,3R,4R,6R,7R,8R,10S,13S,16S)-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadec-14-ene-3,4,6,7,16-pentol

Traditional Name

(1R,3R,4R,6R,7R,8R,10S,13S,16S)-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadec-14-ene-3,4,6,7,16-pentol

CAS Registry Number

Not Available

SMILES

CC1=C[C@]23C[C@@H](O)[C@@]4(O)[C@@H]([C@@H](O)[C@H](O)C4(C)C)C(=C)[C@@H]2CC[C@@H]1[C@@H]3O

InChI Identifier

InChI=1S/C20H30O5/c1-9-7-19-8-13(21)20(25)14(15(22)17(24)18(20,3)4)10(2)12(19)6-5-11(9)16(19)23/h7,11-17,21-25H,2,5-6,8H2,1,3-4H3/t11-,12-,13+,14+,15+,16-,17-,19-,20+/m0/s1

InChI Key

OIFHQQMEVVIQFJ-RZYCJEPQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rhododendron molle	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Hydrocarbon derivative
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	0.4	ALOGPS
logP	-0.38	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	93.6 m³·mol⁻¹	ChemAxon
Polarizability	45.06 Å³	ChemAxon
Number of Rings	4	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

163105365

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Rhodomollein XIX (NP0079274)

MOL for NP0079274 ((+)-Rhodomollein XIX)

3D MOL for NP0079274 ((+)-Rhodomollein XIX)

3D SDF for NP0079274 ((+)-Rhodomollein XIX)

3D-SDF for NP0079274 ((+)-Rhodomollein XIX)

PDB for NP0079274 ((+)-Rhodomollein XIX)

3D PDB for NP0079274 ((+)-Rhodomollein XIX)

SMILES for NP0079274 ((+)-Rhodomollein XIX)

INCHI for NP0079274 ((+)-Rhodomollein XIX)

Structure for NP0079274 ((+)-Rhodomollein XIX)

3D Structure for NP0079274 ((+)-Rhodomollein XIX)