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5-(2-(furan-3-yl)ethyl)-3,4,4a,5,6,7,8,8a-octahydro-8 hydroxy-5,6,8a-trimethylnaphthalene-1-carboxylic acid

Family: Plantae - Sapindaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Diterpene

Canonical Smiles	OC(=O)C1=CCCC2C1(C)C(O)CC(C2(C)CCc1cocc1)C
InChI	InChI=1S/C20H28O4/c1-13-11-17(21)20(3)15(18(22)23)5-4-6-16(20)19(13,2)9-7-14-8-10-24-12-14/h5,8,10,12-13,16-17,21H,4,6-7,9,11H2,1-3H3,(H,22,23)
InChIKey	XWKYXEIGWQYOCY-UHFFFAOYSA-N
Formula	C₂₀H₂₈O₄
HBA	3
HBD	2
MW	332.44
Rotatable Bonds	4
TPSA	70.67
LogP	4.05
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.65
Exact Mass	332.2
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dodonaea angustifolia	Sapindaceae	Plantae	379228

Showing of synonyms

Bekele D, Gebreyesus T. (2009). Phytochemical investigation on the leaves of Dodonaea viscosa var. angustifolia. M.Sc. Thesis-3, Addis Ababa University, Ethiopia,2009. [View] [PubMed]

Pubchem: 45359865

Chebi: 181045

Nmrshiftdb2: 70013571

No compound-protein relationship available.

SMILES: c1occc1CCC(CCC2)C(C23)CCC=C3

Level: 1

Mol. Weight: 332.44 g/mol

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 332.44 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 332.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.19
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.68
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.16

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.81
Plasma Protein Binding: 17.36
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: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.79
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.56
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.19
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.25
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: 2.57
Rat (Acute): 2.23
Rat (Chronic Oral): 2.18
Fathead Minnow: 4.02
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: 361.79
Hydration Free Energy: -7.75
Log(D) at pH=7.4: 1.4
Log(P): 3.84
Log S: -4.12
Log(Vapor Pressure): -8.06
Melting Point: 147.75
pKa Acid: 3.23
pKa Basic: 7.72

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.8251
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.8251
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7894
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7894
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7815
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7815
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7790
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7790
Alpha/beta hydrolase fold protein	D2J2T6	D2J2T6_9RHIZ	Ochrobactrum sp. T63	3	0.7743
Alpha/beta hydrolase fold protein	D2J2T6	D2J2T6_9RHIZ	Ochrobactrum sp. T63	3	0.7743
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7682
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7682
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7647
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7647
Cytochrome P450 3A4	P08684	CP3A4_HUMAN	Homo sapiens	3	0.7467
Cytochrome P450 3A4	P08684	CP3A4_HUMAN	Homo sapiens	3	0.7467
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7396
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7396
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7361
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7361
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	2	0.7273
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	2	0.7273
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7218
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7218
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7154
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7154
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7149
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7149
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7142
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7142
Interleukin enhancer-binding factor 2	Q9CXY6	ILF2_MOUSE	Mus musculus	2	0.7127
Interleukin enhancer-binding factor 2	Q9CXY6	ILF2_MOUSE	Mus musculus	2	0.7127
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7049
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7049
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	3	0.7016
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	3	0.7016
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7012
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7012

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