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18,19-epoxyxenic-19-methoxy-18-hydroxy-4-acetoxy-6,9,13-triene

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

Canonical Smiles	COC1OC(C2/C/1=C\C/C=C(/CC(C2C(CCC=C(C)C)C)OC(=O)C)\C)O
InChI	InChI=1S/C23H36O5/c1-14(2)9-7-11-16(4)20-19(27-17(5)24)13-15(3)10-8-12-18-21(20)22(25)28-23(18)26-6/h9-10,12,16,19-23,25H,7-8,11,13H2,1-6H3/b15-10+,18-12+
InChIKey	YQRVRXGVKYSYLV-XSDUGUOQSA-N
Formula	C₂₃H₃₆O₅
HBA	5
HBD	1
MW	392.54
Rotatable Bonds	6
TPSA	64.99
LogP	4.52
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.7
Exact Mass	392.26
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Padina pavonia	Dictyotaceae	Plantae	82389

Showing of synonyms

Awad NE, Selim MA, et al. (2008). Cytotoxic xenicane diterpenes from the brown alga Padina pavonia (L.) Gaill. Phytotherapy Research,2008,22,1610-1613. [View] [PubMed]

CPRiL: 276156

SMILES: C1OCC(C1=2)CCCC=CCC2

Level: 0

Mol. Weight: 164.25 g/mol

Antitumor

Absorption

Caco-2 (logPapp): -4.61
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.600
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.95

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.750
Plasma Protein Binding: 32.05
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 9.480
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.890
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.930
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 7.370
Micronucleos: Safe
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: -3.270
Rat (Acute): 2.500
Rat (Chronic Oral): 2.040
Fathead Minnow: 5.150
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 379.370
Hydration Free Energy: -4.930
Log(D) at pH=7.4: 3.690
Log(P): 5.37
Log S: -4.85
Log(Vapor Pressure): -6.04
Melting Point: 62.86
pKa Acid: 9.22
pKa Basic: 4.35

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9485
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9485
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7945
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7945
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7908
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7908
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7876
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7876
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7827
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7827
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7695
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7695
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7618
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7618
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7600
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7600
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7591
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7591
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7560
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7560
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7484
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7484
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7362
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7362
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7342
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7342
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7310
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7310
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7197
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7197
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7186
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7186
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7122
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7122
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7083
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7083
Quorum-sensing transcriptional activator	Q8XBD0	Q8XBD0_ECO57	Escherichia coli O157:H7	3	0.7064
Quorum-sensing transcriptional activator	Q8XBD0	Q8XBD0_ECO57	Escherichia coli O157:H7	3	0.7064
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7063
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7063

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