NP-MRD: Showing NP-Card for Ganoderol B (NP0336967)

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Record Information

Version

2.0

Created at

2024-09-11 08:38:45 UTC

Updated at

2024-09-11 08:38:45 UTC

NP-MRD ID

NP0336967

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ganoderol B

Description

Ganoderol B was first documented in 2005 (PMID: 16000773). Based on a literature review a significant number of articles have been published on Ganoderol B (PMID: 33691545) (PMID: 28912878) (PMID: 28875673) (PMID: 23790868) (PMID: 29748985) (PMID: 17313101).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262311102D          

 32 35  0  0  0  0            999 V2000
   -2.1243   -2.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4105   -2.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6952   -2.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -1.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4063   -1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -0.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6883    0.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0294   -0.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1161    0.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8795    0.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1367    1.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9425    1.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1999    2.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6511    3.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085    2.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2657    3.4976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206    1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707    0.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8121   -0.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2962   -0.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8079   -1.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0227   -1.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080   -2.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229   -0.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229   -1.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8352   -1.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5465   -1.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5478   -2.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2657   -2.8649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3716   -3.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -2.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099   -3.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 25  1  0  0  0  0
  1 31  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 22  1  0  0  0  0
  5  6  2  0  0  0  0
  5 25  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 19  1  0  0  0  0
  8 22  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  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 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 31  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END


  Mrv2104 05262311102D          

 32 35  0  0  0  0            999 V2000
   -2.1243   -2.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4105   -2.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6952   -2.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938   -1.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4063   -1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -0.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6883    0.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0294   -0.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1161    0.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8795    0.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1367    1.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9425    1.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1999    2.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6511    3.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085    2.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2657    3.4976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206    1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707    0.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8121   -0.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2962   -0.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8079   -1.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0227   -1.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080   -2.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229   -0.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229   -1.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8352   -1.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5465   -1.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5478   -2.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2657   -2.8649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3716   -3.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -2.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099   -3.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 25  1  0  0  0  0
  1 31  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 22  1  0  0  0  0
  5  6  2  0  0  0  0
  5 25  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 19  1  0  0  0  0
  8 22  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  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 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 31  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336967

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC\C=C(/C)CO)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3=CCC12C

> <INCHI_IDENTIFIER>
InChI=1/C30H48O2/c1-20(19-31)9-8-10-21(2)22-13-17-30(7)24-11-12-25-27(3,4)26(32)15-16-28(25,5)23(24)14-18-29(22,30)6/h9,11,14,21-22,25-26,31-32H,8,10,12-13,15-19H2,1-7H3/b20-9+

> <INCHI_KEY>
AOXXVRDKZLRGTJ-AWQFTUOYNA-N

> <FORMULA>
C30H48O2

> <MOLECULAR_WEIGHT>
440.712

> <EXACT_MASS>
440.365430786

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.75037766836122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(5E)-7-hydroxy-6-methylhept-5-en-2-yl]-3a,6,6,9a,11a-pentamethyl-1H,2H,3H,3aH,5H,5aH,6H,7H,8H,9H,9aH,11H,11aH-cyclopenta[a]phenanthren-7-ol

> <JCHEM_LOGP>
6.063979707666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.618794118233346

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.64402356141891

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7785394526847345

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
137.43599999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-[(5E)-7-hydroxy-6-methylhept-5-en-2-yl]-3a,6,6,9a,11a-pentamethyl-1H,2H,3H,5H,5aH,7H,8H,9H,11H-cyclopenta[a]phenanthren-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -3.965  -4.583   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.633  -5.353   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.298  -4.583   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.295  -3.050   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.625  -2.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.628  -0.734   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.285   0.041   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.055  -0.734   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.217   0.788   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.508   1.510   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.989   2.973   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.493   3.289   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.973   4.750   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.949   5.900   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.483   5.065   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.963   6.529   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.972   2.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.999   1.194   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.516  -0.272   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.420  -1.520   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.508  -2.762   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.042  -2.277   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.202  -3.815   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.963  -1.499   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.963  -3.042   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.292  -2.272   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.620  -3.040   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.623  -4.572   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -7.963  -5.348   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.294  -6.524   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.298  -5.353   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.312  -6.529   0.000  0.00  0.00           C+0
CONECT    1    2   25   31                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   22                                                  
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19   22                                             
CONECT    9    8                                                            
CONECT   10   11   18                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   18                                                            
CONECT   18   10   17   19                                                  
CONECT   19    8   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22    4    8   21   23                                             
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25    1    5   24   26                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28                                                            
CONECT   30   31                                                            
CONECT   31    1   28   30   32                                             
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₂

Average Mass

440.7120 Da

Monoisotopic Mass

440.36543 Da

IUPAC Name

1-[(5E)-7-hydroxy-6-methylhept-5-en-2-yl]-3a,6,6,9a,11a-pentamethyl-1H,2H,3H,3aH,5H,5aH,6H,7H,8H,9H,9aH,11H,11aH-cyclopenta[a]phenanthren-7-ol

Traditional Name

1-[(5E)-7-hydroxy-6-methylhept-5-en-2-yl]-3a,6,6,9a,11a-pentamethyl-1H,2H,3H,5H,5aH,7H,8H,9H,11H-cyclopenta[a]phenanthren-7-ol

CAS Registry Number

Not Available

SMILES

CC(CC\C=C(/C)CO)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3=CCC12C

InChI Identifier

InChI=1/C30H48O2/c1-20(19-31)9-8-10-21(2)22-13-17-30(7)24-11-12-25-27(3,4)26(32)15-16-28(25,5)23(24)14-18-29(22,30)6/h9,11,14,21-22,25-26,31-32H,8,10,12-13,15-19H2,1-7H3/b20-9+

InChI Key

AOXXVRDKZLRGTJ-AWQFTUOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	6.06	ChemAxon
pKa (Strongest Acidic)	16.64	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.44 m³·mol⁻¹	ChemAxon
Polarizability	54.75 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	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

Ganodermadiol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu M, Shen CE, Lin QF, Zhong JY, Zhou YF, Liu BC, Xu JH, Zhang ZQ, Li P: Sterols and triterpenoids from Ganoderma lucidum and their reversal activities of tumor multidrug resistance. Nat Prod Res. 2021 Mar 10:1-4. doi: 10.1080/14786419.2021.1878514. [PubMed:33691545 ]
Zheng DS, Chen LS: Triterpenoids from Ganoderma lucidum inhibit the activation of EBV antigens as telomerase inhibitors. Exp Ther Med. 2017 Oct;14(4):3273-3278. doi: 10.3892/etm.2017.4883. Epub 2017 Aug 3. [PubMed:28912878 ]
Liu LY, Kang J, Wu CH, Li Y, Chen RY: [Triterpenoids from Ganoderma theaecolum]. Zhongguo Zhong Yao Za Zhi. 2016 Mar;41(6):1075-1080. doi: 10.4268/cjcmm20160617. [PubMed:28875673 ]
Peng XR, Liu JQ, Han ZH, Yuan XX, Luo HR, Qiu MH: Protective effects of triterpenoids from Ganoderma resinaceum on H(2)O(2)-induced toxicity in HepG2 cells. Food Chem. 2013 Nov 15;141(2):920-6. doi: 10.1016/j.foodchem.2013.03.071. Epub 2013 Mar 27. [PubMed:23790868 ]
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Showing NP-Card for Ganoderol B (NP0336967)

MOL for NP0336967 (Ganoderol B)

3D MOL for NP0336967 (Ganoderol B)

3D SDF for NP0336967 (Ganoderol B)

3D-SDF for NP0336967 (Ganoderol B)

PDB for NP0336967 (Ganoderol B)

3D PDB for NP0336967 (Ganoderol B)

SMILES for NP0336967 (Ganoderol B)

INCHI for NP0336967 (Ganoderol B)

Structure for NP0336967 (Ganoderol B)

3D Structure for NP0336967 (Ganoderol B)