NP-MRD: Showing NP-Card for (+)-Rosamultic acid (NP0079611)

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Record Information

Version

2.0

Created at

2022-04-29 00:37:26 UTC

Updated at

2022-04-29 00:37:26 UTC

NP-MRD ID

NP0079611

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Rosamultic acid

Description

(1S,2R,5R,6R,9R,10S,14S,15R,16R,19S)-15-hydroxy-6,8-bis(hydroxymethyl)-1,2,6,9,15,16-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosa-7,12-diene-19-carboxylic acid belongs to the class of organic compounds known as hydroxysteroids. Hydroxysteroids are compounds containing an steroid backbone, with at least one hydrogen substituted by a hydroxyl group. (+)-Rosamultic acid is found in Rosa multiflora . Based on a literature review very few articles have been published on (1S,2R,5R,6R,9R,10S,14S,15R,16R,19S)-15-hydroxy-6,8-bis(hydroxymethyl)-1,2,6,9,15,16-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosa-7,12-diene-19-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202372D          

 35 39  0  0  1  0            999 V2000
    6.1403    0.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816   -0.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 33  1  1  0  0  0
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 34 35  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292202372D          

 35 39  0  0  1  0            999 V2000
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    3.7112    1.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -0.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -1.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8025   -1.6372    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  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  1  0  0  0
  4  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 15  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 22 25  1  6  0  0  0
 21 26  1  1  0  0  0
 21 27  1  6  0  0  0
 19 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 16 31  1  6  0  0  0
 11 32  1  1  0  0  0
  3 33  1  1  0  0  0
  2 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079611

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@]5(C)[C@@H](CC[C@@]34C)[C@](C)(CO)C=C5CO)[C@@H]2[C@]1(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O5/c1-18-9-12-30(24(33)34)14-13-26(3)20(23(30)29(18,6)35)7-8-22-27(26,4)11-10-21-25(2,17-32)15-19(16-31)28(21,22)5/h7,15,18,21-23,31-32,35H,8-14,16-17H2,1-6H3,(H,33,34)/t18-,21+,22+,23-,25+,26-,27-,28+,29-,30+/m1/s1

> <INCHI_KEY>
KQDIKHGGEUXUOH-HYUJUATISA-N

> <FORMULA>
C30H46O5

> <MOLECULAR_WEIGHT>
486.693

> <EXACT_MASS>
486.334524581

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.03620602277903

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5R,6R,9R,10S,14S,15R,16R,19S)-15-hydroxy-6,8-bis(hydroxymethyl)-1,2,6,9,15,16-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-7,12-diene-19-carboxylic acid

> <ALOGPS_LOGP>
4.25

> <JCHEM_LOGP>
3.450691618333333

> <ALOGPS_LOGS>
-4.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.48554983624447

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.570991152529081

> <JCHEM_PKA_STRONGEST_BASIC>
-1.155582974206594

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
138.1346

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,6R,9R,10S,14S,15R,16R,19S)-15-hydroxy-6,8-bis(hydroxymethyl)-1,2,6,9,15,16-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-7,12-diene-19-carboxylic acid

> <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      11.462   0.098   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.046  -0.507   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.033   0.653   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.823   1.975   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.324   1.632   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.832   1.945   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.857   0.795   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.838   3.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.073   3.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.534   3.343   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.743   2.022   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.493   0.676   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.703  -0.645   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.163  -0.622   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.413   0.723   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.204   2.045   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.454   3.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.914   3.414   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.124   2.092   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874   0.747   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.083  -0.575   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.543  -0.552   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.206   0.793   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.584   2.115   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.247  -1.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.377  -1.411   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.114  -2.115   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.374   3.437   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.166   3.460   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.164   4.759   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.994   3.367   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.928   3.550   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.385  -0.744   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.703  -2.008   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.831  -3.056   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3   34                                                  
CONECT    3    2    4   12   33                                             
CONECT    4    3    5    9                                                  
CONECT    5    4    1    6    8                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16   32                                             
CONECT   12   11    3   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   11   17   31                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24   28                                             
CONECT   20   19   15   21                                                  
CONECT   21   20   22   26   27                                             
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   22                                                            
CONECT   26   21                                                            
CONECT   27   21                                                            
CONECT   28   19   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   16                                                            
CONECT   32   11                                                            
CONECT   33    3                                                            
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

Value	Source
(1S,2R,5R,6R,9R,10S,14S,15R,16R,19S)-15-Hydroxy-6,8-bis(hydroxymethyl)-1,2,6,9,15,16-hexamethylpentacyclo[11.8.0.0,.0,.0,]henicosa-7,12-diene-19-carboxylate	Generator

Chemical Formula

C₃₀H₄₆O₅

Average Mass

486.6930 Da

Monoisotopic Mass

486.33452 Da

IUPAC Name

(1S,2R,5R,6R,9R,10S,14S,15R,16R,19S)-15-hydroxy-6,8-bis(hydroxymethyl)-1,2,6,9,15,16-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-7,12-diene-19-carboxylic acid

Traditional Name

(1S,2R,5R,6R,9R,10S,14S,15R,16R,19S)-15-hydroxy-6,8-bis(hydroxymethyl)-1,2,6,9,15,16-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosa-7,12-diene-19-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@]5(C)[C@@H](CC[C@@]34C)[C@](C)(CO)C=C5CO)[C@@H]2[C@]1(C)O)C(O)=O

InChI Identifier

InChI=1S/C30H46O5/c1-18-9-12-30(24(33)34)14-13-26(3)20(23(30)29(18,6)35)7-8-22-27(26,4)11-10-21-25(2,17-32)15-19(16-31)28(21,22)5/h7,15,18,21-23,31-32,35H,8-14,16-17H2,1-6H3,(H,33,34)/t18-,21+,22+,23-,25+,26-,27-,28+,29-,30+/m1/s1

InChI Key

KQDIKHGGEUXUOH-HYUJUATISA-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
Rosa multiflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxysteroids. Hydroxysteroids are compounds containing an steroid backbone, with at least one hydrogen substituted by a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

Hydroxysteroids

Alternative Parents

Substituents

20-hydroxysteroid
3-carboxy steroid
Steroid acid
Hydroxysteroid
Delta-5-steroid
Tertiary alcohol
Cyclic alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
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	4.25	ALOGPS
logP	3.45	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	138.13 m³·mol⁻¹	ChemAxon
Polarizability	56.04 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

154497372

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Rosamultic acid (NP0079611)

MOL for NP0079611 ((+)-Rosamultic acid)

3D MOL for NP0079611 ((+)-Rosamultic acid)

3D SDF for NP0079611 ((+)-Rosamultic acid)

3D-SDF for NP0079611 ((+)-Rosamultic acid)

PDB for NP0079611 ((+)-Rosamultic acid)

3D PDB for NP0079611 ((+)-Rosamultic acid)

SMILES for NP0079611 ((+)-Rosamultic acid)

INCHI for NP0079611 ((+)-Rosamultic acid)

Structure for NP0079611 ((+)-Rosamultic acid)

3D Structure for NP0079611 ((+)-Rosamultic acid)