NP-MRD: Showing NP-Card for Caulophyllogenin (NP0085767)

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Record Information

Version

2.0

Created at

2022-04-29 06:14:29 UTC

Updated at

2022-04-29 06:14:29 UTC

NP-MRD ID

NP0085767

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Caulophyllogenin

Description

Caulophyllogenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Caulophyllogenin is found in Medicago arabica, Medicago arborea, Medicago hybrida, Medicago polymorpha , Medicago sativa and Medicago truncatula. Caulophyllogenin was first documented in 2010 (PMID: 19720119). Based on a literature review a significant number of articles have been published on Caulophyllogenin (PMID: 34201300) (PMID: 23444041) (PMID: 22465503) (PMID: 31981958) (PMID: 27283034) (PMID: 23576356).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208142D          

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M  END

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M  END


  Mrv1652304292208142D          

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    1.1270    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6907    1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337   -1.1144    0.0000 C   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
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  5 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  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  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 25 28  1  6  0  0  0
 20 29  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 18 33  1  0  0  0  0
  9 33  1  0  0  0  0
 33 34  1  6  0  0  0
 20 35  1  6  0  0  0
 14 36  1  6  0  0  0
 14 37  1  0  0  0  0
  2 37  1  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085767

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC(C)(C)CC[C@@]1([C@H](O)C[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)[C@@](C)(CO)[C@]3([H])CC[C@@]12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O5/c1-25(2)13-14-30(24(34)35)19(15-25)18-7-8-21-26(3)11-10-22(32)27(4,17-31)20(26)9-12-28(21,5)29(18,6)16-23(30)33/h7,19-23,31-33H,8-17H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,23+,26-,27-,28+,29+,30+/m0/s1

> <INCHI_KEY>
FABOBEOYNMHSHB-UAWZMHPWSA-N

> <FORMULA>
C30H48O5

> <MOLECULAR_WEIGHT>
488.709

> <EXACT_MASS>
488.350174646

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
56.765393540607256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aR,5R,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-5,10-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-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>
4.77

> <JCHEM_LOGP>
4.083251209666667

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.267507962644647

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.608656387053311

> <JCHEM_PKA_STRONGEST_BASIC>
-2.78544259344066

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
136.91469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,5R,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-5,10-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-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      12.791  -1.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.804   4.771   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.574   3.437   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.735   4.969   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       3.644   2.104   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.883   2.630   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.151   4.147   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.831   3.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       1.334   3.437   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.023   3.635   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0       8.264  -0.564   0.000  0.00  0.00           H+0
HETATM   37  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.076  -2.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37   38                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11   14                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   15   33                                             
CONECT   10    9                                                            
CONECT   11    5   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    5   15   36   37                                             
CONECT   15   14    9   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   33                                             
CONECT   19   18                                                            
CONECT   20   18   21   29   35                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   28   29                                             
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29   20   25   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   18    9   34                                             
CONECT   34   33                                                            
CONECT   35   20                                                            
CONECT   36   14                                                            
CONECT   37   14    2                                                       
CONECT   38    2                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(3beta,16alpha)-3,16,23-Trihydroxyolean-12-en-28-Oic acid	MeSH

Chemical Formula

C₃₀H₄₈O₅

Average Mass

488.7090 Da

Monoisotopic Mass

488.35017 Da

IUPAC Name

(4aR,5R,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-5,10-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-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

(4aR,5R,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-5,10-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-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)(C)CC[C@@]1([C@H](O)C[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)[C@@](C)(CO)[C@]3([H])CC[C@@]12C)C(O)=O

InChI Identifier

InChI=1S/C30H48O5/c1-25(2)13-14-30(24(34)35)19(15-25)18-7-8-21-26(3)11-10-22(32)27(4,17-31)20(26)9-12-28(21,5)29(18,6)16-23(30)33/h7,19-23,31-33H,8-17H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,23+,26-,27-,28+,29+,30+/m0/s1

InChI Key

FABOBEOYNMHSHB-UAWZMHPWSA-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
Medicago arabica	Plant	KNApSAcK
Medicago arborea	Plant	KNApSAcK
Medicago hybrida	Plant	KNApSAcK
Medicago polymorpha	Plant	KNApSAcK
Medicago sativa	Plant	KNApSAcK
Medicago truncatula	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
Steroid
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary 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	4.77	ALOGPS
logP	4.08	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.61	ChemAxon
pKa (Strongest Basic)	-2.8	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	2	ChemAxon
Refractivity	136.91 m³·mol⁻¹	ChemAxon
Polarizability	56.77 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

C00055758

Chemspider ID

94216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

104361

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lourenco A, Marques AV, Gominho J: The Identification of New Triterpenoids in Eucalyptus globulus Wood. Molecules. 2021 Jun 8;26(12). pii: molecules26123495. doi: 10.3390/molecules26123495. [PubMed:34201300 ]
Quang TH, Ngan NT, Van Minh C, Van Kiem P, Nhiem NX, Tai BH, Thao NP, Chae D, Mathema VB, Koh YS, Lee JH, Yang SY, Kim YH: Inhibitory effects of oleanane-type triterpenes and saponins from the stem bark of Kalopanax pictus on LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells. Arch Pharm Res. 2013 Mar;36(3):327-34. doi: 10.1007/s12272-013-0031-8. Epub 2013 Feb 27. [PubMed:23444041 ]
Zhang Y, Ma Z, Hu C, Wang L, Li L, Song S: Cytotoxic triterpene saponins from the leaves of Aralia elata. Fitoterapia. 2012 Jun;83(4):806-11. doi: 10.1016/j.fitote.2012.03.015. Epub 2012 Mar 20. [PubMed:22465503 ]
Bechkri S, Alabdul Magid A, Sayagh C, Berrehal D, Harakat D, Voutquenne-Nazabadioko L, Kabouche Z, Kabouche A: Triterpene saponins from Silene gallica collected in North-Eastern Algeria. Phytochemistry. 2020 Apr;172:112274. doi: 10.1016/j.phytochem.2020.112274. Epub 2020 Jan 23. [PubMed:31981958 ]
Montanari R, Capelli D, Tava A, Galli A, Laghezza A, Tortorella P, Loiodice F, Pochetti G: Screening of saponins and sapogenins from Medicago species as potential PPARgamma agonists and X-ray structure of the complex PPARgamma/caulophyllogenin. Sci Rep. 2016 Jun 10;6:27658. doi: 10.1038/srep27658. [PubMed:27283034 ]
Kuang HX, Wang ZB, Wang QH, Yang BY, Xiao HB, Okada Y, Okuyama T: Triterpene glucosides from the leaves of Aralia elata and their cytotoxic activities. Chem Biodivers. 2013 Apr;10(4):703-10. doi: 10.1002/cbdv.201200087. [PubMed:23576356 ]
Zhang Y, Peng Y, Li L, Zhao L, Hu Y, Hu C, Song S: Studies on cytotoxic triterpene saponins from the leaves of Aralia elata. Food Chem. 2013 May 1;138(1):208-13. doi: 10.1016/j.foodchem.2012.10.041. Epub 2012 Nov 8. [PubMed:23265478 ]
Tava A, Pecetti L, Romani M, Mella M, Avato P: Triterpenoid glycosides from the leaves of two cultivars of Medicago polymorpha L. J Agric Food Chem. 2011 Jun 8;59(11):6142-9. doi: 10.1021/jf2005854. Epub 2011 May 13. [PubMed:21526796 ]
Li G, Zhang Y, Yang B, Xia Y, Zhang Y, Lu S, Kuang H: Leiyemudanosides A-C, three new bidesmosidic triterpenoid saponins from the roots of Caulophyllum robustum. Fitoterapia. 2010 Apr;81(3):200-4. doi: 10.1016/j.fitote.2009.08.025. Epub 2009 Aug 29. [PubMed:19720119 ]

Showing NP-Card for Caulophyllogenin (NP0085767)

MOL for NP0085767 (Caulophyllogenin)

3D MOL for NP0085767 (Caulophyllogenin)

3D SDF for NP0085767 (Caulophyllogenin)

3D-SDF for NP0085767 (Caulophyllogenin)

PDB for NP0085767 (Caulophyllogenin)

3D PDB for NP0085767 (Caulophyllogenin)

SMILES for NP0085767 (Caulophyllogenin)

INCHI for NP0085767 (Caulophyllogenin)

Structure for NP0085767 (Caulophyllogenin)

3D Structure for NP0085767 (Caulophyllogenin)