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Agathic acid

Family: Fungi - Bionectriaceae
Kingdom: Fungi
Class: Terpenoid
- Subclass: Diterpene

Canonical Smiles	OC(=O)/C=C(/CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O)\C
InChI	InChI=1S/C20H30O4/c1-13(12-17(21)22)6-8-15-14(2)7-9-16-19(15,3)10-5-11-20(16,4)18(23)24/h12,15-16H,2,5-11H2,1,3-4H3,(H,21,22)(H,23,24)/b13-12+/t15-,16+,19+,20-/m0/s1
InChIKey	QYCOHMYDSOZCQD-GWEOMKHGSA-N
Formula	C₂₀H₃₀O₄
HBA	2
HBD	2
MW	334.46
Rotatable Bonds	5
TPSA	74.6
LogP	4.66
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.7
Exact Mass	334.21
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Bionectria sp.	Bionectriaceae	Fungi	—

Showing of synonyms

Kamdem RST, Wang H, et al. (2018). Induction of new metabolites from the endophytic fungus Bionectria sp. through bacterial co-culture.. Fitoterapia,2018, 124, 132-136. [View] [PubMed]

Pubchem: 6436877

Cas: 640-28-8

Nmrshiftdb2: 60067646

Chembl: CHEMBL457162

CPRiL: 221717

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

Level: 0

Mol. Weight: 334.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.0
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.08
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.4

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.14
Plasma Protein Binding: 93.46
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: 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: -2.45
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.39
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.39
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 2.05
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: -1.37
Rat (Acute): 2.45
Rat (Chronic Oral): 2.13
Fathead Minnow: 3.81
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 381.22
Hydration Free Energy: -5.34
Log(D) at pH=7.4: -0.39
Log(P): 4.76
Log S: -4.85
Log(Vapor Pressure): -9.88
Melting Point: 207.27
pKa Acid: 4.7
pKa Basic: 7.44

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9786
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9434
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.9269
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.9139
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8872
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8823
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8667
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8417
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.8263
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.8054
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7963
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7928
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7908
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	4	0.7873
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7837
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7816
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7813
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7796
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7682
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7676
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7651
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7491
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7482
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7458
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7457
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7400
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7383
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7343
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7290
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7284
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	2	0.7283
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7250
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7245
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7221
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7208
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7194
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7178
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7174
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	3	0.7134
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7118
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7110
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7081
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7080
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7067
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7064
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7059
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7042
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	2	0.7008

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