NP-MRD: Showing NP-Card for Tumulosic acid (NP0066380)

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Record Information

Version

2.0

Created at

2022-04-28 10:39:15 UTC

Updated at

2022-04-28 10:39:15 UTC

NP-MRD ID

NP0066380

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tumulosic acid

Description

Tumulosic acid, also known as tumulosate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Tumulosic acid is found in Daedalea dickinsii, Daedalea dicknsii, Melanoporia cajanderi, Melanoporia juniperina, Melanoporia nigra, Melanoporia purpuracea, Melanoporia rosea, Polyporus australiensis, Polyporus betulinus, Polyporus tumulosus, Spongiporus appendiculatus, Trametes dicknsii, Trametes feel, Trametes lilacino-gilva and Poria cocos . Tumulosic acid was first documented in 2013 (PMID: 23893636). Based on a literature review a small amount of articles have been published on Tumulosic acid (PMID: 35401186) (PMID: 30172532) (PMID: 29077044) (PMID: 24956845).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212392D          

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M  END


  Mrv1652304282212392D          

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    4.6673    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4101    4.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2421    1.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9283    2.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3527    3.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2150    1.7053    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  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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
  8 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
  7 14  1  0  0  0  0
 12 15  1  6  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 17 19  1  1  0  0  0
 16 20  1  6  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 11 31  1  1  0  0  0
  5 32  1  6  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  2 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0066380

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=C)CC[C@H]([C@H]1[C@H](O)C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H50O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h18,20,23-26,32-33H,3,9-17H2,1-2,4-8H3,(H,34,35)/t20-,23-,24+,25+,26+,29-,30-,31+/m1/s1

> <INCHI_KEY>
XADJANKGURNTIA-YEXRKOARSA-N

> <FORMULA>
C31H50O4

> <MOLECULAR_WEIGHT>
486.737

> <EXACT_MASS>
486.37091009

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
58.352892799829874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(2S,5S,7R,11R,13R,14R,15R)-5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-6-methyl-5-methylideneheptanoic acid

> <ALOGPS_LOGP>
5.39

> <JCHEM_LOGP>
5.678585907666669

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.901633417331983

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.773537913062996

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8069747832914828

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
141.3046

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2S,5S,7R,11R,13R,14R,15R)-5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-6-methyl-5-methylideneheptanoic acid

> <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      -7.198   2.359   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.228   3.503   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.752   4.968   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.246   5.288   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.216   4.144   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.692   2.679   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.709   4.464   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.233   5.929   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.264   7.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.770   6.753   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.727   6.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.697   5.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.172   3.640   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.679   3.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.448   4.074   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.710   5.731   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.549   7.262   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.957   7.583   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.694   8.293   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.044   4.961   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.044   3.421   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.378   2.651   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.710   2.651   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.378   5.731   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.711   4.961   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.045   5.731   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.045   7.271   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.379   4.961   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.712   5.731   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.379   3.421   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.632   7.495   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.185   2.999   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.200   5.495   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.125   6.462   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -9.735   3.183   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   35                                                  
CONECT    3    2    4   33   34                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   32                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   18   31                                             
CONECT   12   11   13   15   16                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12                                                            
CONECT   16   12   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   11                                                       
CONECT   19   17                                                            
CONECT   20   16   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   11                                                            
CONECT   32    5                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    2                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Tumulosate	Generator

Chemical Formula

C₃₁H₅₀O₄

Average Mass

486.7370 Da

Monoisotopic Mass

486.37091 Da

IUPAC Name

(2R)-2-[(2S,5S,7R,11R,13R,14R,15R)-5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-6-methyl-5-methylideneheptanoic acid

Traditional Name

(2R)-2-[(2S,5S,7R,11R,13R,14R,15R)-5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-6-methyl-5-methylideneheptanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)C(=C)CC[C@H]([C@H]1[C@H](O)C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3)C(O)=O

InChI Identifier

InChI=1S/C31H50O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h18,20,23-26,32-33H,3,9-17H2,1-2,4-8H3,(H,34,35)/t20-,23-,24+,25+,26+,29-,30-,31+/m1/s1

InChI Key

XADJANKGURNTIA-YEXRKOARSA-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
Daedalea dickinsii	LOTUS Database	35616633
Daedalea dicknsii	Fungi	KNApSAcK
Melanoporia cajanderi	-	KNApSAcK
Melanoporia juniperina	-	KNApSAcK
Melanoporia nigra	-	KNApSAcK
Melanoporia purpuracea	-	KNApSAcK
Melanoporia rosea	-	KNApSAcK
Polyporus australiensis	Fungi	KNApSAcK
Polyporus betulinus	Fungi	KNApSAcK
Polyporus tumulosus	Fungi	KNApSAcK
Spongiporus appendiculatus	-	KNApSAcK
Trametes dicknsii	Fungi	KNApSAcK
Trametes feel	Fungi	KNApSAcK
Trametes lilacino-gilva	Fungi	KNApSAcK
Wolfiporia cocos	-	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
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid acid
Hydroxysteroid
3-hydroxysteroid
14-alpha-methylsteroid
16-alpha-hydroxysteroid
16-hydroxysteroid
3-beta-hydroxysteroid
Steroid
Medium-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
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	5.39	ALOGPS
logP	5.68	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	141.3 m³·mol⁻¹	ChemAxon
Polarizability	58.35 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023800

Chemspider ID

21468698

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12314446

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Peng X, Jia C, Chi H, Wang P, Fu H, Li Y, Wang Q: Efficacy and Pharmacological Mechanism of Poria cocos-Based Formulas Combined With Chemotherapy for Ovarian Cancer: A Integrated Systems Pharmacology Study. Front Pharmacol. 2022 Mar 21;13:788810. doi: 10.3389/fphar.2022.788810. eCollection 2022. [PubMed:35401186 ]
Ji B, Zhao Y, Yu P, Yang B, Zhou C, Yu Z: LC-ESI-MS/MS method for simultaneous determination of eleven bioactive compounds in rat plasma after oral administration of Ling-Gui-Zhu-Gan Decoction and its application to a pharmacokinetics study. Talanta. 2018 Dec 1;190:450-459. doi: 10.1016/j.talanta.2018.08.020. Epub 2018 Aug 6. [PubMed:30172532 ]
Matsubara Y, Matsumoto T, Koseki J, Kaneko A, Aiba S, Yamasaki K: Inhibition of Human Kallikrein 5 Protease by Triterpenoids from Natural Sources. Molecules. 2017 Oct 27;22(11). pii: molecules22111829. doi: 10.3390/molecules22111829. [PubMed:29077044 ]
Yang PF, Liu C, Wang HQ, Li JC, Wang ZZ, Xiao W, Chen RY: [Chemical constituents of Poria cocos]. Zhongguo Zhong Yao Za Zhi. 2014 Mar;39(6):1030-3. [PubMed:24956845 ]
Lv C, Li Q, Zhang Y, Sui Z, He B, Xu H, Yin Y, Chen X, Bi K: A UFLC-MS/MS method with a switching ionization mode for simultaneous quantitation of polygalaxanthone III, four ginsenosides and tumulosic acid in rat plasma: application to a comparative pharmacokinetic study in normal and Alzheimer's disease rats. J Mass Spectrom. 2013 Aug;48(8):904-13. doi: 10.1002/jms.3230. [PubMed:23893636 ]

Showing NP-Card for Tumulosic acid (NP0066380)

MOL for NP0066380 (Tumulosic acid)

3D MOL for NP0066380 (Tumulosic acid)

3D SDF for NP0066380 (Tumulosic acid)

3D-SDF for NP0066380 (Tumulosic acid)

PDB for NP0066380 (Tumulosic acid)

3D PDB for NP0066380 (Tumulosic acid)

SMILES for NP0066380 (Tumulosic acid)

INCHI for NP0066380 (Tumulosic acid)

Structure for NP0066380 (Tumulosic acid)

3D Structure for NP0066380 (Tumulosic acid)