NP-MRD: Showing NP-Card for (1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate (NP0309335)

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Record Information

Version

2.0

Created at

2022-09-11 03:52:11 UTC

Updated at

2022-09-11 03:52:11 UTC

NP-MRD ID

NP0309335

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate

Description

Phorbol 12,13-diacetate belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. (1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate is found in Croton tiglium. (1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate was first documented in 2010 (PMID: 20561511). Based on a literature review a small amount of articles have been published on Phorbol 12,13-diacetate (PMID: 34095301) (PMID: 31607483) (PMID: 31342263) (PMID: 21307262).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205522D          

 32 35  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112205522D          

 32 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0309335

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H](OC(C)=O)[C@]2(OC(C)=O)[C@H]([C@@H]3C=C(CO)C[C@@]4(O)[C@@H](C=C(C)C4=O)[C@@]13O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O8/c1-11-7-17-22(29,19(11)28)9-15(10-25)8-16-18-21(5,6)24(18,32-14(4)27)20(31-13(3)26)12(2)23(16,17)30/h7-8,12,16-18,20,25,29-30H,9-10H2,1-6H3/t12-,16+,17-,18-,20-,22-,23-,24-/m1/s1

> <INCHI_KEY>
OMHXSAMFEJVCPT-XQOWHXTBSA-N

> <FORMULA>
C24H32O8

> <MOLECULAR_WEIGHT>
448.512

> <EXACT_MASS>
448.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.20288803015681

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,6R,10S,11R,13S,14R,15R)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl acetate

> <JCHEM_LOGP>
0.10136807633333501

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.933225968355181

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.57037025950111

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7316135464888243

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
114.08040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6R,10S,11R,13S,14R,15R)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.371  -5.496   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.128  -5.846   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.576  -7.319   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.181  -4.721   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.734  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.766  -2.898   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.819  -4.023   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.214  -1.425   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.179  -2.625   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.161  -0.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.384   1.223   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.714   1.999   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.592   3.534   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.201   4.196   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.150   1.443   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.610  -0.027   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.686   1.075   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.091  -0.452   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.305   0.496   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.144  -1.991   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.420  -2.853   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.696  -2.517   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.749  -1.303   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.339  -0.650   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.839  -1.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.443   0.417   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.129  -1.841   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.786  -2.124   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.910  -3.176   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.561  -4.676   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.298  -5.557   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.685  -5.729   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   23                                             
CONECT    9    8                                                            
CONECT   10    8   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22    8   16                                                  
CONECT   24   10   25   28                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25    5   24   29                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
Phorbol 12,13-diacetic acid	Generator
4 beta-Phorbol-12,13-diacetate	MeSH
Phorbol-10,11-diacetate	MeSH
Phorbol-12,13-diacetate	MeSH
Phorbol-12,13-diacetate, (1ar-(1aalpha,1bbeta,4abeta,7abeta,7balpha,8alpha,9beta,9aalpha))-isomer	MeSH

Chemical Formula

C₂₄H₃₂O₈

Average Mass

448.5120 Da

Monoisotopic Mass

448.20972 Da

IUPAC Name

(1S,2S,6R,10S,11R,13S,14R,15R)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl acetate

Traditional Name

(1S,2S,6R,10S,11R,13S,14R,15R)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-13-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H](OC(C)=O)[C@]2(OC(C)=O)[C@H]([C@@H]3C=C(CO)C[C@@]4(O)[C@@H](C=C(C)C4=O)[C@@]13O)C2(C)C

InChI Identifier

InChI=1S/C24H32O8/c1-11-7-17-22(29,19(11)28)9-15(10-25)8-16-18-21(5,6)24(18,32-14(4)27)20(31-13(3)26)12(2)23(16,17)30/h7-8,12,16-18,20,25,29-30H,9-10H2,1-6H3/t12-,16+,17-,18-,20-,22-,23-,24-/m1/s1

InChI Key

OMHXSAMFEJVCPT-XQOWHXTBSA-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
Croton tiglium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Phorbol esters

Alternative Parents

Substituents

Phorbol ester
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	0.1	ChemAxon
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.08 m³·mol⁻¹	ChemAxon
Polarizability	47.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

65245

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72293

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xing S, Nong F, Qin J, Huang H, Zhan R, Chen W: Gentiopicroside Produces Endothelium-Independent Vasodilation by Deactivating the PI3K/Akt/Rho-Kinase Pathway in Isolated Rat Thoracic Aorta. Biomed Res Int. 2021 May 14;2021:5565748. doi: 10.1155/2021/5565748. eCollection 2021. [PubMed:34095301 ]
Kamboj K, Jana S, Sharma SK: Mechanisms of protein kinase C-induced sustained activation of extracellular signal-regulated kinase in the hippocampus. Biochem Biophys Res Commun. 2019 Dec 3;520(2):453-458. doi: 10.1016/j.bbrc.2019.10.046. Epub 2019 Oct 10. [PubMed:31607483 ]
da Silva LC, de Carvalho TC, Pereira I, Marana JC, Laviola BG, Abdelnur PV, Vaz BG: Molecularly Imprinted Polymer-Coated Probe Electrospray Ionization Mass Spectrometry Determines Phorbol Esters and Deoxyphorbol Metabolites in Jatropha curcas Leaves. J Am Soc Mass Spectrom. 2019 Oct;30(10):2051-2059. doi: 10.1007/s13361-019-02269-5. Epub 2019 Jul 24. [PubMed:31342263 ]
Cheng SJ, Chen CC, Yang HW, Chang YT, Bai SW, Chen CC, Yen CT, Min MY: Role of extracellular signal-regulated kinase in synaptic transmission and plasticity of a nociceptive input on capsular central amygdaloid neurons in normal and acid-induced muscle pain mice. J Neurosci. 2011 Feb 9;31(6):2258-70. doi: 10.1523/JNEUROSCI.5564-10.2011. [PubMed:21307262 ]
Li CY, Shi HB, Chen ZN, Ye HB, Song NY, Yin SK: Protein kinase A and C signaling induces bilirubin potentiation of GABA/glycinergic synaptic transmission in rat ventral cochlear nucleus neurons. Brain Res. 2010 Aug 12;1348:30-41. doi: 10.1016/j.brainres.2010.06.022. Epub 2010 Jun 16. [PubMed:20561511 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate (NP0309335)

MOL for NP0309335 ((1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate)

3D MOL for NP0309335 ((1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate)

3D SDF for NP0309335 ((1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate)

3D-SDF for NP0309335 ((1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate)

PDB for NP0309335 ((1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate)

3D PDB for NP0309335 ((1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate)

SMILES for NP0309335 ((1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate)

INCHI for NP0309335 ((1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate)

Structure for NP0309335 ((1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate)

3D Structure for NP0309335 ((1s,2s,6r,10s,11r,13s,14r,15r)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate)