2D

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- Double-bond stereo
- 8 of 8 defined stereocentres

(1aR,1bS,4aR,7aR,7bR,8R,9R,9aS)-9a-Acetoxy-7b-hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl (2Z,4E)-octa-2,4-dienoate

ChemSpider ID: 558784
Molecular Formula: C₃₀H₄₀O₇
Average mass: 512.634399 Da
Monoisotopic mass: 512.277405 Da
Systematic name

(1aR,1bS,4aR,7aR,7bR,8R,9R,9aS)-9a-Acetoxy-7b-hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl (2Z,4E)-2,4-octadienoate
SMILES and InChIs

SMILES:

O=C(O[C@H]2[C@]4(OC(=O)C)[C@H]([C@@H]1/C=C(/CO)C[C@H]3C(=O)\C(=C/[C@H]3[C@@]1(O)[C@@H]2C)C)C4(C)C)/C=C\C=C\CCC Copied

Std. InChI:

InChI=1S/C30H40O7/c1-7-8-9-10-11-12-24(33)36-27-18(3)29(35)22-13-17(2)25(34)21(22)14-20(16-31)15-23(29)26-28(5,6)30(26,27)37-19(4)32/h9-13,15,18,21-23,26-27,31,35H,7-8,14,16H2,1-6H3/b10-9+,12-11-/t18-,21-,22-,23+,26-,27-,29+,30-/m1/s1 Copied

Std. InChIKey:

ALKHEZOKTHCOBM-GTBZSHDQSA-N Copied
Cite this record
CSID:558784, http://www.chemspider.com/Chemical-Structure.558784.html (accessed 12:33, May 18, 2013) Copied

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

(1aR,1bS,4aR,7aR,7bR,8R,9R,9aS)-9a-Acetoxy-7b-hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl (2Z,4E)-octa-2,4-dienoate

2,4-octadienoic acid, (1aR,1bS,4aR,7aR,7bR,8R,9R,9aS)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-7b-hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester, (2Z,4E)-

(1aR,1bS,4aR,7aR,7bR,8R,9R,9aS)-9a-(acetyloxy)-7b-hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl rel-(2Z,4E)-octa-2,4

(1aR,1bS,4aR,7aR,7bR,8R,9R,9aS)-9a-acetoxy-7b-hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl (2Z,4E)-octa-2,4-dienoat

12-O-2Z,4E-Octadienoyl-4-deoxyphorbol 13-acetate

13-O-Acetyl-12-O-(2'Z,4'E-octadienoyl)-4α-deoxyphorbol

13-O-Acetyl-12-O-(Z,E)-2,4-octadienoyl-4-desoxyphorbol

4-deoxy-4α-phorbol 13-acetate 12-(2Z,4E)-octa-2,4-dienoate

70028-76-1 [RN]

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Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

CHEBI:743 [DBID]

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Properties

Predicted - ACD/Labs
Predicted - ChemAxon

Predicted data is generated using the ACD/Labs’ ACD/PhysChem Suite, for more information see their website.

ACD/LogP:	5.089	# of Rule of 5 Violations:	2
ACD/LogD (pH 5.5):	5.09	ACD/LogD (pH 7.4):	5.09
ACD/BCF (pH 5.5):	4342.17	ACD/BCF (pH 7.4):	4342.16
ACD/KOC (pH 5.5):	13978.61	ACD/KOC (pH 7.4):	13978.59
#H bond acceptors:	7	#H bond donors:	2
#Freely Rotating Bonds:	11	Polar Surface Area:	110.13 Å²
Index of Refraction:	1.577	Molar Refractivity:	138.766 cm³
Molar Volume:	419.013 cm³	Polarizability:	55.011 10^-24cm³
Surface Tension:	51.7309989929199 dyne/cm	Density:	1.223 g/cm³
Flash Point:	199.62 °C	Enthalpy of Vaporization:	106.919 kJ/mol
Boiling Point:	630.8 °C at 760 mmHg	Vapour Pressure:	0 mmHg at 25°C

Click to predict properties on the Chemicalize site

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Category	Target	PDB Code	LASSO Score
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.10
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.03
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Serine Proteases	Thrombin	1ba8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.01
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Serine Proteases	Trypsin	1bju	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Kinases	HSP90, human heat shock protein 90	1uy6	0.00
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00

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(1aR,1bS,4aR,7aR,7bR,8R,9R,9aS)-9a-Acetoxy-7b-hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl (2Z,4E)-octa-2,4-dienoate

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Std. InChIKey:

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(1aR,1bS,4aR,7aR,7bR,8R,9R,9aS)-9a-Acetoxy-7b-hydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl (2Z,4E)-octa-2,4-dienoate

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