NP-MRD: Showing NP-Card for 1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid (NP0083701)

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Record Information

Version

2.0

Created at

2022-04-29 04:39:24 UTC

Updated at

2022-04-29 04:39:24 UTC

NP-MRD ID

NP0083701

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid

Description

1Beta,2alpha,3alpha,24-Tetrahydroxyurs-12,20(30)-diene-28-oic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid is found in Gentiana dahurica and Gentiana straminea . Based on a literature review very few articles have been published on 1beta,2alpha,3alpha,24-Tetrahydroxyurs-12,20(30)-diene-28-oic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206392D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292206392D          

 39 43  0  0  1  0            999 V2000
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   10.3638   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7763   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1263   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4763   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 19 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 15 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 13 37  1  0  0  0  0
  3 37  1  0  0  0  0
  2 38  1  0  0  0  0
  7 38  1  0  0  0  0
 38 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0083701

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)C(=C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)[C@H](O)[C@@H](O)[C@@H](O)[C@]2(C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O6/c1-16-9-12-30(25(35)36)14-13-27(4)18(21(30)17(16)2)7-8-20-28(27,5)11-10-19-26(3,15-31)23(33)22(32)24(34)29(19,20)6/h7,17,19-24,31-34H,1,8-15H2,2-6H3,(H,35,36)/t17-,19-,20-,21-,22-,23+,24+,26+,27+,28+,29-,30-/m0/s1

> <INCHI_KEY>
BGGVRHKDEJGDIK-YERDUVNTSA-N

> <FORMULA>
C30H46O6

> <MOLECULAR_WEIGHT>
502.692

> <EXACT_MASS>
502.329439201

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
56.82539352407381

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4aS,6aS,6bR,8aR,9S,10S,11R,12S,12aR,12bS,14bS)-10,11,12-trihydroxy-9-(hydroxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
2.9594886880000013

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.958443747187093

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.580572080064237

> <JCHEM_PKA_STRONGEST_BASIC>
-2.787602198055474

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
137.8192

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aS,6aS,6bR,8aR,9S,10S,11R,12S,12aR,12bS,14bS)-10,11,12-trihydroxy-9-(hydroxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-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      10.876  -6.517   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.106  -5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      11.646  -5.184   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      10.106  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.566  -2.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.796  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -1.183   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.106   0.151   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       7.796  -1.183   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.876  -1.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.416  -1.183   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.186  -2.516   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.956  -1.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.726  -2.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.887  -0.985   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.496  -1.183   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.036  -1.183   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.806  -2.516   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      18.576  -3.850   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      19.346  -2.516   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.078  -1.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.793  -1.990   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      21.060  -0.473   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      20.116  -3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      21.656  -3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      19.346  -5.184   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      20.116  -6.517   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.806  -5.184   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.036  -6.517   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      17.036  -3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.266  -5.184   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.496  -3.850   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0      13.956  -3.850   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0      14.726  -5.184   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.186  -5.184   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.416  -3.850   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.566  -5.184   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.796  -6.517   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4    5   37                                             
CONECT    4    3                                                            
CONECT    5    3    6    8   11                                             
CONECT    6    5    7                                                       
CONECT    7    6   38                                                       
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   37                                             
CONECT   14   13                                                            
CONECT   15   13   16   17   33                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   31                                             
CONECT   20   19                                                            
CONECT   21   19   22   23   25                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   21   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   19   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   15   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   13    3                                                  
CONECT   38    2    7   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
1b,2a,3a,24-Tetrahydroxyurs-12,20(30)-diene-28-Oate	Generator
1b,2a,3a,24-Tetrahydroxyurs-12,20(30)-diene-28-Oic acid	Generator
1beta,2alpha,3alpha,24-Tetrahydroxyurs-12,20(30)-diene-28-Oate	Generator
1Β,2α,3α,24-tetrahydroxyurs-12,20(30)-diene-28-Oate	Generator
1Β,2α,3α,24-tetrahydroxyurs-12,20(30)-diene-28-Oic acid	Generator

Chemical Formula

C₃₀H₄₆O₆

Average Mass

502.6920 Da

Monoisotopic Mass

502.32944 Da

IUPAC Name

(1R,4aS,6aS,6bR,8aR,9S,10S,11R,12S,12aR,12bS,14bS)-10,11,12-trihydroxy-9-(hydroxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

(1R,4aS,6aS,6bR,8aR,9S,10S,11R,12S,12aR,12bS,14bS)-10,11,12-trihydroxy-9-(hydroxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)C(=C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)[C@H](O)[C@@H](O)[C@@H](O)[C@]2(C)CO

InChI Identifier

InChI=1S/C30H46O6/c1-16-9-12-30(25(35)36)14-13-27(4)18(21(30)17(16)2)7-8-20-28(27,5)11-10-19-26(3,15-31)23(33)22(32)24(34)29(19,20)6/h7,17,19-24,31-34H,1,8-15H2,2-6H3,(H,35,36)/t17-,19-,20-,21-,22-,23+,24+,26+,27+,28+,29-,30-/m0/s1

InChI Key

BGGVRHKDEJGDIK-YERDUVNTSA-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
Gentiana dahurica	LOTUS Database	35616633
Gentiana straminea	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
12-hydroxysteroid
12-beta-hydroxysteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
Hydroxysteroid
Steroid
Cyclitol or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Organic oxygen compound
Organooxygen compound
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	3.47	ALOGPS
logP	2.96	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	137.82 m³·mol⁻¹	ChemAxon
Polarizability	56.83 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00052568

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

50917866

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid (NP0083701)

MOL for NP0083701 (1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid)

3D MOL for NP0083701 (1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid)

3D SDF for NP0083701 (1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid)

3D-SDF for NP0083701 (1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid)

PDB for NP0083701 (1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid)

3D PDB for NP0083701 (1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid)

SMILES for NP0083701 (1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid)

INCHI for NP0083701 (1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid)

Structure for NP0083701 (1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid)

3D Structure for NP0083701 (1beta,2alpha,3alpha,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid)