NP-MRD: Showing NP-Card for (1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate (NP0178756)

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Record Information

Version

2.0

Created at

2022-09-03 16:48:29 UTC

Updated at

2022-09-03 16:48:29 UTC

NP-MRD ID

NP0178756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate

Description

Kansuiphorin C belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. (1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate is found in Euphorbia kansui. (1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate was first documented in 2010 (PMID: 19844773). Based on a literature review a small amount of articles have been published on Kansuiphorin C (PMID: 33349474) (PMID: 31765764) (PMID: 30947126) (PMID: 23109850).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032218482D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032218482D          

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 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 16 26  1  0  0  0  0
  5 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  1  0  0  0
 12 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
  9 31  1  0  0  0  0
 31 32  1  6  0  0  0
 29 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H]2[C@H]([C@H]3C=C(C)[C@@H](OC(=O)C4=CC=CC=C4)[C@]4(O)[C@@H](OC(C)=O)C(C)=C[C@@]14C3=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O6/c1-15-12-20-22-21(27(22,5)6)13-17(3)28(23(20)31)14-16(2)25(34-18(4)30)29(28,33)24(15)35-26(32)19-10-8-7-9-11-19/h7-12,14,17,20-22,24-25,33H,13H2,1-6H3/t17-,20-,21-,22+,24-,25+,28+,29+/m1/s1

> <INCHI_KEY>
IDDLQFSLFADOOA-ISFUUBDKSA-N

> <FORMULA>
C29H34O6

> <MOLECULAR_WEIGHT>
478.585

> <EXACT_MASS>
478.235538815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.31443836585775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,5R,6R,9R,10R,12R,14R)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-6-yl benzoate

> <JCHEM_LOGP>
4.509864442000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.305115655984814

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.138929747202347

> <JCHEM_PKA_STRONGEST_BASIC>
-4.04990818003786

> <JCHEM_POLAR_SURFACE_AREA>
89.90000000000002

> <JCHEM_REFRACTIVITY>
131.2257

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,6R,9R,10R,12R,14R)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-6-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.958  -1.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.892  -2.929   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.192  -3.755   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.473  -3.642   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.773  -2.816   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.858  -1.275   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.675  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.359  -0.910   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.329  -2.188   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.484  -3.024   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.389  -1.778   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.676  -3.891   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.094  -5.357   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.615  -5.886   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.426  -7.414   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.304  -5.009   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.964  -5.768   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.951  -7.307   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.278  -8.088   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.611  -8.066   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.598  -9.606   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.742 -10.365   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.069  -9.584   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.056  -8.044   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.716  -7.285   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.224  -3.400   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.969  -4.293   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.892  -2.880   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.917  -1.341   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.698  -0.315   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.175  -0.764   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.230   0.452   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.238  -2.132   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.514  -1.269   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.485  -3.035   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   26   31                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   16    5    9   27                                             
CONECT   27   26                                                            
CONECT   28   12   29   33                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30    9   32                                                  
CONECT   32   31                                                            
CONECT   33   29   28   34   35                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₆

Average Mass

478.5850 Da

Monoisotopic Mass

478.23554 Da

IUPAC Name

(1S,4S,5R,6R,9R,10R,12R,14R)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-6-yl benzoate

Traditional Name

(1S,4S,5R,6R,9R,10R,12R,14R)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-6-yl benzoate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H]2[C@H]([C@H]3C=C(C)[C@@H](OC(=O)C4=CC=CC=C4)[C@]4(O)[C@@H](OC(C)=O)C(C)=C[C@@]14C3=O)C2(C)C

InChI Identifier

InChI=1S/C29H34O6/c1-15-12-20-22-21(27(22,5)6)13-17(3)28(23(20)31)14-16(2)25(34-18(4)30)29(28,33)24(15)35-26(32)19-10-8-7-9-11-19/h7-12,14,17,20-22,24-25,33H,13H2,1-6H3/t17-,20-,21-,22+,24-,25+,28+,29+/m1/s1

InChI Key

IDDLQFSLFADOOA-ISFUUBDKSA-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
Euphorbia kansui	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Ingenane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tertiary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	4.51	ChemAxon
pKa (Strongest Acidic)	12.14	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.23 m³·mol⁻¹	ChemAxon
Polarizability	51.31 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

C00030594

Chemspider ID

58802358

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155487900

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhou SK, Zhang Y, Ju YH, Zhang Q, Luo D, Cao YD, Yao WF, Tang YP, Zhang L: Comparison of content-toxicity-activity of six ingenane-type diterpenoids between Euphorbia kansui before and after stir-fried with vinegar by using UFLC-MS/MS, zebrafish embryos and HT-29 cells. J Pharm Biomed Anal. 2021 Feb 20;195:113828. doi: 10.1016/j.jpba.2020.113828. Epub 2020 Dec 7. [PubMed:33349474 ]
Zhang Y, Lou JW, Kang A, Zhang Q, Zhou SK, Bao BH, Cao YD, Yao WF, Tang YP, Zhang L: Kansuiphorin C and Kansuinin A ameliorate malignant ascites by modulating gut microbiota and related metabolic functions. J Ethnopharmacol. 2020 Mar 1;249:112423. doi: 10.1016/j.jep.2019.112423. Epub 2019 Nov 22. [PubMed:31765764 ]
Zhang Y, Lou JW, Zhang Q, Li ZL, Bao BH, Cao YD, Yao WF, Tang YP, Zhang L: Determination of kansuiphorin C and kansuinin A in rat feces using UFLC-MS/MS and its application in the comparative excretion study on normal and malignant ascites rats. J Pharm Biomed Anal. 2019 Jun 5;170:254-263. doi: 10.1016/j.jpba.2019.03.054. Epub 2019 Mar 26. [PubMed:30947126 ]
Zhang L, Gao L, Li Z, Yan X, Yang Y, Tang Y, Cao Y, Ding A: Bio-guided isolation of the cytotoxic terpenoids from the roots of Euphorbia kansui against human normal cell lines L-O2 and GES-1. Int J Mol Sci. 2012;13(9):11247-11259. doi: 10.3390/ijms130911247. Epub 2012 Sep 10. [PubMed:23109850 ]
Shu X, Yu L, Tang Y, Zhang L, Ding A, Luo D, Duan JA, Shen X: Bioassay-guided separation of the proinflammatory constituents from the roots of Euphorbia kansui. J Nat Med. 2010 Jan;64(1):98-103. doi: 10.1007/s11418-009-0366-0. Epub 2009 Oct 21. [PubMed:19844773 ]
LOTUS database [Link]

Showing NP-Card for (1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate (NP0178756)

MOL for NP0178756 ((1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate)

3D MOL for NP0178756 ((1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate)

3D SDF for NP0178756 ((1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate)

3D-SDF for NP0178756 ((1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate)

PDB for NP0178756 ((1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate)

3D PDB for NP0178756 ((1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate)

SMILES for NP0178756 ((1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate)

INCHI for NP0178756 ((1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate)

Structure for NP0178756 ((1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate)

3D Structure for NP0178756 ((1s,4s,5r,6r,9r,10r,12r,14r)-4-(acetyloxy)-5-hydroxy-3,7,11,11,14-pentamethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl benzoate)