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Imbricatoloic acid

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

Canonical Smiles	O=CC[C@H](CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O)C
InChI	InChI=1S/C20H32O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h13-14,16-17H,2,5-12H2,1,3-4H3,(H,22,23)/t14-,16-,17+,19+,20-/m0/s1
InChIKey	HYXULMWPHCMLGR-BEUFEYIVSA-N
Formula	C₂₀H₃₂O₃
HBA	2
HBD	1
MW	320.47
Rotatable Bonds	6
TPSA	54.37
LogP	4.86
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.8
Exact Mass	320.24
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: 14830084

Zinc: ZINC000034375331

Nmrshiftdb2: 60067385

Chembl: CHEMBL3780554

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 320.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.52
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.710
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.96

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.690
Plasma Protein Binding: 84.92
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: 0.450
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.410
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.160
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 3.410
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: -2.100
Rat (Acute): 3.930
Rat (Chronic Oral): 1.420
Fathead Minnow: 3.920
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 356.730
Hydration Free Energy: -4.500
Log(D) at pH=7.4: 2.440
Log(P): 4.56
Log S: -4.45
Log(Vapor Pressure): -7.34
Melting Point: 119.37
pKa Acid: 5.19
pKa Basic: 7.73

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	0.9941
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9941
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9600
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9600
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.9466
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.9466
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8993
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8993
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8750
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8750
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8453
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8453
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.8213
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.8213
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8068
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8068
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7981
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7981
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7978
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7978
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7940
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7940
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7914
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7914
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7817
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7817
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7800
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7800
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7775
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7775
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7732
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7732
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7677
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7677
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7670
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7670
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7649
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7649
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7648
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7648
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7625
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7625
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7586
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7586
12-oxophytodienoate reductase 1	Q9XG54	OPR1_SOLLC	Solanum lycopersicum	3	0.7586
12-oxophytodienoate reductase 1	Q9XG54	OPR1_SOLLC	Solanum lycopersicum	3	0.7586
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7563
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7563
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7542
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7542
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7534
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7534
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7527
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7527
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7426
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7426
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7410
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7410
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7386
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7386
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7348
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7348
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7345
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7345
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7337
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7337
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	2	0.7327
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	2	0.7327
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7324
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7324
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7319
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7319
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7292
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7292
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	2	0.7290
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	2	0.7290
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	2	0.7278
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	2	0.7278
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7276
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7276
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7266
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7266
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7241
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7241
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7194
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7194
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7182
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7182
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7174
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7174
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7161
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7161
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7146
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7146
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7137
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7137
Gibberellin receptor GID1	Q6L545	GID1_ORYSJ	Oryza sativa subsp. japonica	3	0.7126
Gibberellin receptor GID1	Q6L545	GID1_ORYSJ	Oryza sativa subsp. japonica	3	0.7126
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7122
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7122
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7120
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7120
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7096
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7096
Lactaldehyde dehydrogenase	P25553	ALDA_ECOLI	Escherichia coli	3	0.7089
Lactaldehyde dehydrogenase	P25553	ALDA_ECOLI	Escherichia coli	3	0.7089
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7081
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7081
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	2	0.7065
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	2	0.7065
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7063
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7063
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7057
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7057
Gibberellin receptor GID1A	Q9MAA7	GID1A_ARATH	Arabidopsis thaliana	3	0.7051
Gibberellin receptor GID1A	Q9MAA7	GID1A_ARATH	Arabidopsis thaliana	3	0.7051
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7045
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7045
Pyrrolysine--tRNA ligase	Q8PWY1	PYLS_METMA	Methanosarcina mazei	2	0.7045
Pyrrolysine--tRNA ligase	Q8PWY1	PYLS_METMA	Methanosarcina mazei	2	0.7045
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7038
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7038
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7025
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7025
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7011
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7011
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7008
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7008
Cytochrome b-c1 complex subunit 1, mitochondrial	P31800	QCR1_BOVIN	Bos taurus	3	0.7006
Cytochrome b-c1 complex subunit 1, mitochondrial	P31800	QCR1_BOVIN	Bos taurus	3	0.7006
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7003
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7003
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7001
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7001

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