NP-MRD: Showing NP-Card for Rubianol a (NP0071759)

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Record Information

Version

2.0

Created at

2022-04-28 17:06:10 UTC

Updated at

2022-04-28 17:06:10 UTC

NP-MRD ID

NP0071759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rubianol a

Description

(1S,2S,5R,6S,8R,9R,10R,14S,16R,19S,21S)-8,16,21-trihydroxy-5-(hydroxymethyl)-2,10,14,18,18-pentamethyl-6-(propan-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicos-12-en-17-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Rubianol a is found in Rubia yunnanensis. Based on a literature review very few articles have been published on (1S,2S,5R,6S,8R,9R,10R,14S,16R,19S,21S)-8,16,21-trihydroxy-5-(hydroxymethyl)-2,10,14,18,18-pentamethyl-6-(propan-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicos-12-en-17-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219062D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282219062D          

 35 39  0  0  1  0            999 V2000
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    5.1979   -1.0759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6880    1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288    2.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4687    1.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7573    1.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4333    2.4766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  1  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  9 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  2  0  0  0  0
 17 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
 16 22  1  1  0  0  0
 14 23  1  6  0  0  0
 11 24  1  6  0  0  0
  6 25  1  6  0  0  0
  5 26  1  1  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 29  1  0  0  0  0
 29 30  1  1  0  0  0
 27 31  1  6  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  2 34  1  6  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1C[C@@H](O)[C@H]2[C@@]1(CO)CC[C@@]1(C)[C@@H]3[C@@H](O)C[C@@H]4C(C)(C)C(=O)[C@H](O)C[C@]4(C)C3=CC[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O5/c1-16(2)18-12-20(33)24-29(7)9-8-17-23(28(29,6)10-11-30(18,24)15-31)19(32)13-22-26(3,4)25(35)21(34)14-27(17,22)5/h8,16,18-24,31-34H,9-15H2,1-7H3/t18-,19-,20+,21+,22+,23-,24+,27+,28-,29+,30+/m0/s1

> <INCHI_KEY>
ZAGSMKWHSPITNU-NMDBISJHSA-N

> <FORMULA>
C30H48O5

> <MOLECULAR_WEIGHT>
488.709

> <EXACT_MASS>
488.350174646

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
56.62996921364682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R,6S,8R,9R,10R,14S,16R,19S,21S)-8,16,21-trihydroxy-5-(hydroxymethyl)-2,10,14,18,18-pentamethyl-6-(propan-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-12-en-17-one

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
3.184273844999999

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.697986346249806

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.344339658045765

> <JCHEM_PKA_STRONGEST_BASIC>
-0.423600267211948

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
137.61039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,6S,8R,9R,10R,14S,16R,19S,21S)-8,16,21-trihydroxy-5-(hydroxymethyl)-6-isopropyl-2,10,14,18,18-pentamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-12-en-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.033   0.653   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.823   1.975   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.073   3.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.534   3.343   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.743   2.022   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.493   0.676   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.703  -0.645   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.163  -0.622   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.413   0.723   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.204   2.045   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.454   3.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.914   3.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.124   2.092   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874   0.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.083  -0.575   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.543  -0.552   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.206   0.793   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.746   0.817   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.584   2.115   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.709   2.951   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.554   3.655   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.247  -1.874   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.623  -0.599   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.244   4.712   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.243  -0.669   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.994   3.367   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.324   1.632   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.462   0.098   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.046  -0.507   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.703  -2.008   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.484   2.645   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.187   4.156   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.941   2.146   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.747   3.207   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.142   4.623   0.000  0.00  0.00           O+0
CONECT    1    2    6   29                                                  
CONECT    2    1    3   27   34                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10   26                                             
CONECT    6    5    1    7   25                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13    9   15   23                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16                                                            
CONECT   23   14                                                            
CONECT   24   11                                                            
CONECT   25    6                                                            
CONECT   26    5                                                            
CONECT   27    2   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28    1   30                                                  
CONECT   30   29                                                            
CONECT   31   27   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    2   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₅

Average Mass

488.7090 Da

Monoisotopic Mass

488.35017 Da

IUPAC Name

(1S,2S,5R,6S,8R,9R,10R,14S,16R,19S,21S)-8,16,21-trihydroxy-5-(hydroxymethyl)-2,10,14,18,18-pentamethyl-6-(propan-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-12-en-17-one

Traditional Name

(1S,2S,5R,6S,8R,9R,10R,14S,16R,19S,21S)-8,16,21-trihydroxy-5-(hydroxymethyl)-6-isopropyl-2,10,14,18,18-pentamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-12-en-17-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1C[C@@H](O)[C@H]2[C@@]1(CO)CC[C@@]1(C)[C@@H]3[C@@H](O)C[C@@H]4C(C)(C)C(=O)[C@H](O)C[C@]4(C)C3=CC[C@]21C

InChI Identifier

InChI=1S/C30H48O5/c1-16(2)18-12-20(33)24-29(7)9-8-17-23(28(29,6)10-11-30(18,24)15-31)19(32)13-22-26(3,4)25(35)21(34)14-27(17,22)5/h8,16,18-24,31-34H,9-15H2,1-7H3/t18-,19-,20+,21+,22+,23-,24+,27+,28-,29+,30+/m0/s1

InChI Key

ZAGSMKWHSPITNU-NMDBISJHSA-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
Rubia yunnanensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
18-hydroxysteroid
1-hydroxysteroid
Hydroxysteroid
15-hydroxysteroid
Steroid
Delta-5-steroid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	3.65	ALOGPS
logP	3.18	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	13.34	ChemAxon
pKa (Strongest Basic)	-0.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	137.61 m³·mol⁻¹	ChemAxon
Polarizability	56.63 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

162878627

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Rubianol a (NP0071759)

MOL for NP0071759 (Rubianol a)

3D MOL for NP0071759 (Rubianol a)

3D SDF for NP0071759 (Rubianol a)

3D-SDF for NP0071759 (Rubianol a)

PDB for NP0071759 (Rubianol a)

3D PDB for NP0071759 (Rubianol a)

SMILES for NP0071759 (Rubianol a)

INCHI for NP0071759 (Rubianol a)

Structure for NP0071759 (Rubianol a)

3D Structure for NP0071759 (Rubianol a)