NP-MRD: Showing NP-Card for antcin b (NP0231189)

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Record Information

Version

2.0

Created at

2022-09-06 11:55:40 UTC

Updated at

2022-09-06 11:55:40 UTC

NP-MRD ID

NP0231189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

antcin b

Description

Zhankuic acid A, also known as zhankuate a, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. antcin b is found in Taiwanofungus camphoratus. antcin b was first documented in 2019 (PMID: 31623176). Based on a literature review a small amount of articles have been published on zhankuic acid A (PMID: 33525984) (PMID: 33951534) (PMID: 34577615) (PMID: 30277103).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062213552D          

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 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  2  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0231189

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O5/c1-15(17(3)27(33)34)7-8-16(2)19-9-10-20-25-23(31)13-21-18(4)22(30)11-12-28(21,5)26(25)24(32)14-29(19,20)6/h16-21H,1,7-14H2,2-6H3,(H,33,34)/t16-,17?,18+,19-,20+,21+,28+,29-/m1/s1

> <INCHI_KEY>
DVORYMAGXQGBQK-QCMFUGJUSA-N

> <FORMULA>
C29H40O5

> <MOLECULAR_WEIGHT>
468.634

> <EXACT_MASS>
468.287574388

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.783815444766624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-2-methyl-3-methylidene-6-[(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-5,9,17-trioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]heptanoic acid

> <JCHEM_LOGP>
5.360250265666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.098058860636957

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.845053571718457

> <JCHEM_PKA_STRONGEST_BASIC>
-6.725365011436457

> <JCHEM_POLAR_SURFACE_AREA>
88.50999999999999

> <JCHEM_REFRACTIVITY>
131.3001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-2-methyl-3-methylidene-6-[(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-5,9,17-trioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]heptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.784  -9.261   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.784  -7.721   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.451  -6.951   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.883  -7.721   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.217  -6.951   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.217  -5.411   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.550  -7.721   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.957  -7.094   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.988  -8.239   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.218  -9.572   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.694 -11.037   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.663 -12.181   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.157 -11.861   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.126 -13.006   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.681 -10.397   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.711  -9.252   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.247  -8.776   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.139 -13.646   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.633 -13.326   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.108 -14.790   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.584 -16.255   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.091 -16.575   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.567 -18.040   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -7.121 -15.431   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.628 -15.751   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.645 -13.966   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.676 -12.822   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.200 -11.357   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.230 -10.213   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.118  -6.951   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.118  -5.411   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.452  -7.721   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.785  -6.951   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.452  -9.261   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10    7   17                                             
CONECT   17   16                                                            
CONECT   18   12   19   20   26                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   18   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   11   29                                                  
CONECT   29   28                                                            
CONECT   30    2   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
4alpha-Methylergosta-8,24(28)-dien-3,7,11-trione-26-Oic acid	ChEBI
4a-Methylergosta-8,24(28)-dien-3,7,11-trione-26-Oate	Generator
4a-Methylergosta-8,24(28)-dien-3,7,11-trione-26-Oic acid	Generator
4alpha-Methylergosta-8,24(28)-dien-3,7,11-trione-26-Oate	Generator
4Α-methylergosta-8,24(28)-dien-3,7,11-trione-26-Oate	Generator
4Α-methylergosta-8,24(28)-dien-3,7,11-trione-26-Oic acid	Generator
Zhankuate a	Generator
4-Methylergosta-8,24(28)-dien-3,7,11-trione-26-Oic acid	MeSH

Chemical Formula

C₂₉H₄₀O₅

Average Mass

468.6340 Da

Monoisotopic Mass

468.28757 Da

IUPAC Name

(6R)-2-methyl-3-methylidene-6-[(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-5,9,17-trioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]heptanoic acid

Traditional Name

(6R)-2-methyl-3-methylidene-6-[(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-5,9,17-trioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]heptanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H40O5/c1-15(17(3)27(33)34)7-8-16(2)19-9-10-20-25-23(31)13-21-18(4)22(30)11-12-28(21,5)26(25)24(32)14-29(19,20)6/h16-21H,1,7-14H2,2-6H3,(H,33,34)/t16-,17?,18+,19-,20+,21+,28+,29-/m1/s1

InChI Key

DVORYMAGXQGBQK-QCMFUGJUSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Taiwanofungus camphoratus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
Bile acid, alcohol, or derivatives
Steroid acid
3-oxosteroid
11-oxosteroid
Oxosteroid
3-oxo-5-alpha-steroid
7-oxosteroid
Medium-chain fatty acid
Cyclohexenone
Fatty acyl
Fatty acid
Unsaturated fatty acid
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:66503 )
monocarboxylic acid (CHEBI:66503 )
7-oxo steroid (CHEBI:66503 )
ergostanoid (CHEBI:66503 )
steroid acid (CHEBI:66503 )
11-oxo steroid (CHEBI:66503 )

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	5.36	ChemAxon
pKa (Strongest Acidic)	4.85	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.51 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	131.3 m³·mol⁻¹	ChemAxon
Polarizability	53.78 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

C00044021

Chemspider ID

8180422

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10004842

PDB ID

Not Available

ChEBI ID

66503

Good Scents ID

Not Available

References

General References

Purawarga Matada GS, Dhiwar PS, Abbas N, Singh E, Ghara A, Das A, Bhargava SV: Molecular docking and molecular dynamic studies: screening of phytochemicals against EGFR, HER2, estrogen and NF-KB receptors for their potential use in breast cancer. J Biomol Struct Dyn. 2021 Feb 2:1-11. doi: 10.1080/07391102.2021.1877823. [PubMed:33525984 ]
Cheng KC, Chen CF, Hung CC, Lam SH, Hung HY, Li YC, Chen FA, Shieh PC, Kuo PC, Wu TS: Bioactive naphthoquinones and triterpenoids from the fruiting bodies of Taiwanofungus salmoneus. Bioorg Chem. 2021 Jul;112:104939. doi: 10.1016/j.bioorg.2021.104939. Epub 2021 Apr 23. [PubMed:33951534 ]
Yu KH, Hung CC, Wu TS, Chen CF, Wu IT, Kuo PC, Lam SH, Hung HY: Chemoreversal Agents from Taiwanofungus Genus and Their More Potent Methyl Derivatives Targeting Signal Transducer and Activator of Transcription 3 (STAT3) Phosphorylation. Pharmaceuticals (Basel). 2021 Sep 10;14(9):916. doi: 10.3390/ph14090916. [PubMed:34577615 ]
Hung HY, Hung CC, Liang JW, Chen CF, Chen HY, Shieh PC, Kuo PC, Wu TS: Constituents and Anti-Multidrug Resistance Activity of Taiwanofungus camphoratus on Human Cervical Cancer Cells. Molecules. 2019 Oct 16;24(20):3730. doi: 10.3390/molecules24203730. [PubMed:31623176 ]
Chen YF, Chang CH, Huang ZN, Su YC, Chang SJ, Jan JS: The JAK inhibitor antcin H exhibits direct anticancer activity while enhancing chemotherapy against LMP1-expressed lymphoma. Leuk Lymphoma. 2019 May;60(5):1193-1203. doi: 10.1080/10428194.2018.1512709. Epub 2018 Oct 2. [PubMed:30277103 ]
LOTUS database [Link]

Showing NP-Card for antcin b (NP0231189)

MOL for NP0231189 (antcin b)

3D MOL for NP0231189 (antcin b)

3D SDF for NP0231189 (antcin b)

3D-SDF for NP0231189 (antcin b)

PDB for NP0231189 (antcin b)

3D PDB for NP0231189 (antcin b)

SMILES for NP0231189 (antcin b)

INCHI for NP0231189 (antcin b)

Structure for NP0231189 (antcin b)

3D Structure for NP0231189 (antcin b)