NP-MRD: Showing NP-Card for (2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione (NP0215655)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 15:20:28 UTC

Updated at

2022-09-05 15:20:28 UTC

NP-MRD ID

NP0215655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione

Description

Rabdoumbrosanin belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). (2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione is found in Isodon umbrosus and Lepidolaena taylorii. Based on a literature review very few articles have been published on Rabdoumbrosanin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052217202D          

 23 25  0  0  1  0            999 V2000
    5.0900    0.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3775    1.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3101    2.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356    2.6650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5072    2.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785    1.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4746    0.8885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0458    0.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2210    0.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5832    1.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466    0.4568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2537    1.6311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3212    0.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250    0.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0002    0.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042    1.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0329    2.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2643    2.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1947    3.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8577    2.3548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2864    3.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1112    3.0408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5399    3.7457    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  6  0  0  0
  2  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
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0215655

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]2(C)[C@@H]1C[C@@H](O)C1=C[C@@H](CCC2=O)C(=C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-12-13-6-7-17(22)20(4)9-5-8-19(2,3)16(20)11-15(21)14(10-13)18(12)23/h10,13,15-16,21H,1,5-9,11H2,2-4H3/t13-,15-,16-,20-/m1/s1

> <INCHI_KEY>
HPCCGLBGTJGBJM-KHTYJDQRSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.28568836913419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4R,9R,13R)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0^{4,9}]hexadec-1(16)-ene-10,15-dione

> <JCHEM_LOGP>
3.9229122746666674

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.611100632660765

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.395038969963164

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0634087905924083

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
91.43059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4R,9R,13R)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0^{4,9}]hexadec-1(16)-ene-10,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       9.501   1.659   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.171   2.436   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.045   3.971   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.213   4.975   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.547   4.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747   3.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.486   1.659   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.686   0.343   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.146   0.378   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.955   2.202   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.140   0.853   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.207   3.045   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.333   1.510   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.407   1.729   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.867   1.764   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.128   3.115   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.928   4.431   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.493   4.991   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.230   5.941   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.468   4.396   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.268   5.711   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.808   5.676   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.608   6.992   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   20                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   12   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    5   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4410 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

(2R,4R,9R,13R)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0^{4,9}]hexadec-1(16)-ene-10,15-dione

Traditional Name

(2R,4R,9R,13R)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0^{4,9}]hexadec-1(16)-ene-10,15-dione

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@@H]1C[C@@H](O)C1=C[C@@H](CCC2=O)C(=C)C1=O

InChI Identifier

InChI=1S/C20H28O3/c1-12-13-6-7-17(22)20(4)9-5-8-19(2,3)16(20)11-15(21)14(10-13)18(12)23/h10,13,15-16,21H,1,5-9,11H2,2-4H3/t13-,15-,16-,20-/m1/s1

InChI Key

HPCCGLBGTJGBJM-KHTYJDQRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isodon umbrosus	LOTUS Database	35616633
Lepidolaena taylorii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Secondary alcohols

Alternative Parents

Substituents

Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	3.92	ChemAxon
pKa (Strongest Acidic)	14.4	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.43 m³·mol⁻¹	ChemAxon
Polarizability	35.29 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10270560

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14378403

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione (NP0215655)

MOL for NP0215655 ((2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione)

3D MOL for NP0215655 ((2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione)

3D SDF for NP0215655 ((2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione)

3D-SDF for NP0215655 ((2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione)

PDB for NP0215655 ((2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione)

3D PDB for NP0215655 ((2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione)

SMILES for NP0215655 ((2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione)

INCHI for NP0215655 ((2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione)

Structure for NP0215655 ((2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione)

3D Structure for NP0215655 ((2r,4r,9r,13r)-2-hydroxy-5,5,9-trimethyl-14-methylidenetricyclo[11.2.1.0⁴,⁹]hexadec-1(16)-ene-10,15-dione)