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14alpha,15beta-diacetoxy-3beta,7beta-dibenzoyloxy-17-hydroxy-9-oxo-2betaHjatropha-5E,11E-diene

Family: Plantae - Euphorbiaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Diterpenoid

Canonical Smiles	OC/C/1=C\[C@H]2[C@@H](OC(=O)c3ccccc3)[C@@H](C[C@]2(OC(=O)C)[C@H](OC(=O)C)C(C)/C=C/C(C(=O)C[C@H]1OC(=O)c1ccccc1)(C)C)C
InChI	InChI=1S/C38H44O10/c1-23-17-18-37(5,6)32(42)20-31(46-35(43)27-13-9-7-10-14-27)29(22-39)19-30-33(47-36(44)28-15-11-8-12-16-28)24(2)21-38(30,48-26(4)41)34(23)45-25(3)40/h7-19,23-24,30-31,33-34,39H,20-22H2,1-6H3/b18-17+,29-19+/t23?,24-,30+,31-,33+,34-,38-/m1/s1
InChIKey	ADONXPDCJFWYAQ-XLTDOXTRSA-N
Formula	C₃₈H₄₄O₁₀
HBA	10
HBD	1
MW	660.76
Rotatable Bonds	7
TPSA	142.5
LogP	5.44
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	48
Formal Charge	0
Fraction CSP3	0.45
Exact Mass	660.29
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Euphorbia helioscopia	Euphorbiaceae	Plantae	154990

Showing of synonyms

Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]

Pubchem: 162959697

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC2CCC(C23)CCC=CCC(=O)CC(C=C3)OC(=O)c4ccccc4

Level: 2

Mol. Weight: 660.76 g/mol

SMILES: c1ccccc1C(=O)OC2CCC(C23)CCC=CCC(=O)CCC=C3

Level: 1

Mol. Weight: 660.76 g/mol

SMILES: c1ccccc1C(=O)OC(C=C2)CC(=O)CC=CCCC(C23)CCC3

Level: 1

Mol. Weight: 660.76 g/mol

SMILES: C1CCC(C12)CCC=CCC(=O)CCC=C2

Level: 0

Mol. Weight: 660.76 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 660.76 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.76
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.36
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 60.34

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.81
Plasma Protein Binding: 101.04
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 10.23
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.71
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.6
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.7
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -114583.58
Rat (Acute): 3.65
Rat (Chronic Oral): 3.07
Fathead Minnow: 159.93
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 7741.5
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 3.97
Log(P): 6.44
Log S: -5.64
Log(Vapor Pressure): -284.31
Melting Point: 154.96
pKa Acid: 7.98
pKa Basic: 1.78

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8901
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8901
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8803
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8803
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8582
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8582
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8214
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8214
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8207
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8207
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8202
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8202
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8177
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8177
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8037
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8037
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8025
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8025
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7973
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7973
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7830
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7830
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7761
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7761
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7728
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7728
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7688
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7688
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7687
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7687
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7648
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7648
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7616
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7616
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7556
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7556
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7552
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7552
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	2	0.7546
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	2	0.7546
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7521
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7521
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7512
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7512
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7501
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7501
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7496
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7496
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7494
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7494
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7412
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7412
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7335
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7335
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7335
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7335
Putative HMP/thiamine-binding protein YkoF	O34911	YKOF_BACSU	Bacillus subtilis	2	0.7330
Putative HMP/thiamine-binding protein YkoF	O34911	YKOF_BACSU	Bacillus subtilis	2	0.7330
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7270
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7270
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	3	0.7266
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	3	0.7266
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7256
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7256
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	2	0.7227
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	2	0.7227
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7220
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7220
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7187
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7187
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7179
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7179
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7142
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7142
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7142
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7142
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7123
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7123
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7097
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7097
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	2	0.7084
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	2	0.7084
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7078
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7078
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7077
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7077
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7030
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7030
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7002
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7002
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7001
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7001

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