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Torulosal

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

Canonical Smiles	C=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/C20H32O2/c1-6-19(4,22)13-10-16-15(2)8-9-17-18(3,14-21)11-7-12-20(16,17)5/h6,14,16-17,22H,1-2,7-13H2,3-5H3/t16-,17-,18+,19-,20+/m0/s1
InChIKey	GLJXUJMLZHNKJU-UHZRXMQZSA-N
Formula	C₂₀H₃₂O₂
HBA	2
HBD	1
MW	304.47
Rotatable Bonds	5
TPSA	37.3
LogP	4.68
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.75
Exact Mass	304.24
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: 101306776

Cas: 1857-21-2

Zinc: ZINC000238757537

Nmrshiftdb2: 60069578

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 304.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.62
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.34
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.43

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.73
Plasma Protein Binding: 65.43
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: Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.42
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.31
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.33
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.51
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: -2.6
Rat (Acute): 3.44
Rat (Chronic Oral): 1.43
Fathead Minnow: 3.92
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: 335.5
Hydration Free Energy: -2.63
Log(D) at pH=7.4: 3.91
Log(P): 4.17
Log S: -4.79
Log(Vapor Pressure): -5.8
Melting Point: 88.82
pKa Acid: 9.08
pKa Basic: 6.33

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	0.9892
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9892
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9446
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9446
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8749
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8749
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8585
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8585
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8536
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8536
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8164
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8164
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8070
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8070
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7955
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7955
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7928
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7928
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7914
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7914
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7902
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7902
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7891
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7891
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7881
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7881
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7867
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7867
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7863
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7863
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7840
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7840
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7839
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7839
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7796
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7796
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7785
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7785
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7745
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7745
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7728
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7728
Retinoic acid receptor RXR	Q8T5C6	RXR_BIOGL	Biomphalaria glabrata	3	0.7713
Retinoic acid receptor RXR	Q8T5C6	RXR_BIOGL	Biomphalaria glabrata	3	0.7713
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7692
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7692
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	2	0.7689
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	2	0.7689
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7686
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7686
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7682
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7682
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7641
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7641
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7604
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7604
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7546
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7546
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7541
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7541
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7539
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7539
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7534
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7534
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7524
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7524
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7511
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7511
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7488
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7488
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7484
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7484
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7458
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7458
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7457
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7457
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7442
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7442
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7392
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7392
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7389
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7389
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7375
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7375
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7362
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7362
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7328
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7328
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7320
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7320
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7313
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7313
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7301
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7301
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	2	0.7278
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	2	0.7278
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7250
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7250
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	2	0.7244
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	2	0.7244
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7238
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7238
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7237
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7237
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7235
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7235
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7233
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7233
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	2	0.7225
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	2	0.7225
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	2	0.7224
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	2	0.7224
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7189
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7189
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7185
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7185
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7178
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7178
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7176
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7176
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7134
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7134
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7127
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7127
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7122
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7122
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7102
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7102
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7094
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7094
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7079
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7079
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	2	0.7067
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	2	0.7067
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7058
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7058
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7026
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7026
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7016
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7016
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7009
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7009
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7007
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7007
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7004
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7004

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