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Agathadiol

Family: Animalia - Apidae
Kingdom: Animalia
Class: Terpenoid
- Subclass: Diterpenoid

Canonical Smiles	OC/C=C(/CCC1C(=C)CCC2C1(C)CCCC2(C)CO)\C
InChI	InChI=1S/C20H34O2/c1-15(10-13-21)6-8-17-16(2)7-9-18-19(3,14-22)11-5-12-20(17,18)4/h10,17-18,21-22H,2,5-9,11-14H2,1,3-4H3/b15-10+
InChIKey	MJHWZTRFACWHTA-XNTDXEJSSA-N
Formula	C₂₀H₃₄O₂
HBA	2
HBD	2
MW	306.49
Rotatable Bonds	5
TPSA	40.46
LogP	4.48
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.8
Exact Mass	306.26
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Apis species	Apidae	Animalia	7459

Showing of synonyms

Piccinelli AL, Mencherini T, et al. (2013). Chemical composition and antioxidant activity of Algerian propolis. Journal of Agricultural and Food Chemistry,2013,61(21),5080-5088. [View] [PubMed]

Pubchem: 5316778

Nmrshiftdb2: 60067614

No compound-protein relationship available.

SMILES: C=C(C1)CCC(C12)CCCC2

Level: 0

Mol. Weight: 306.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.58
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.35
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.46

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.95
Plasma Protein Binding: 25.22
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: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.48
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.2
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.91
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.19
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 2.85
Rat (Acute): 2.48
Rat (Chronic Oral): 1.89
Fathead Minnow: 4.57
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 347.87
Hydration Free Energy: -4.08
Log(D) at pH=7.4: 3.6
Log(P): 4.3
Log S: -4.67
Log(Vapor Pressure): -6.19
Melting Point: 90.36
pKa Acid: 11.9
pKa Basic: 7.45

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8670
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8670
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.8646
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.8646
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8620
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8620
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	4	0.8477
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	4	0.8477
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8473
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8473
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8442
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8442
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8362
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8362
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8331
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8331
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8315
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8315
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8238
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8238
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8218
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8218
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8207
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8207
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8196
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8196
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8156
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8156
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.8113
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.8113
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	3	0.8113
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	3	0.8113
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	3	0.8002
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	3	0.8002
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7956
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7956
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7934
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7934
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7906
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7906
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7883
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7883
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7857
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7857
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7849
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7849
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7837
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7837
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7695
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7695
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7677
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7677
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	3	0.7676
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	3	0.7676
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7655
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7655
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7638
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7638
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7621
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7621
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7576
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7576
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7576
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7576
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7503
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7503
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7480
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7480
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7428
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7428
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7394
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7394
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7381
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7381
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7328
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7328
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7324
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7324
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7321
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7321
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7285
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7285
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7249
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7249
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7233
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7233
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7173
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7173
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7164
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7164
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7156
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7156
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7136
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7136
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7133
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7133
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7113
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7113
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7104
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7104
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7087
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7087
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	3	0.7085
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	3	0.7085
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7045
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7045
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7008
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7008

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