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Torulosol

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

Canonical Smiles	C=CC(CCC1C(=C)CCC2C1(C)CCCC2(C)CO)(O)C
InChI	InChI=1S/C20H34O2/c1-6-19(4,22)13-10-16-15(2)8-9-17-18(3,14-21)11-7-12-20(16,17)5/h6,16-17,21-22H,1-2,7-14H2,3-5H3
InChIKey	IERFAZQCIAZODG-UHFFFAOYSA-N
Formula	C₂₀H₃₄O₂
HBA	2
HBD	2
MW	306.49
Rotatable Bonds	5
TPSA	40.46
LogP	4.47
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: 349315

Cas: 1438-65-9

Nmrshiftdb2: 60069579

Comptox: DTXSID90325173

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): -4.6
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.36
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.05

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.72
Plasma Protein Binding: 22.11
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: Non-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: 13.59
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.31
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.21
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.12
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: 3.07
Rat (Acute): 2.91
Rat (Chronic Oral): 1.85
Fathead Minnow: 4.09
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: 325.19
Hydration Free Energy: -3.17
Log(D) at pH=7.4: 3.91
Log(P): 4.08
Log S: -4.5
Log(Vapor Pressure): -5.79
Melting Point: 91.03
pKa Acid: 10.61
pKa Basic: 7.19

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	0.9151
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9151
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8724
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8724
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	3	0.8613
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	3	0.8613
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8518
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8518
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8457
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8457
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8444
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8444
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8417
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8417
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8357
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8357
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.8136
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.8136
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8040
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8040
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.8007
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.8007
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7986
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7986
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	3	0.7898
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	3	0.7898
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7893
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7893
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7861
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7861
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7818
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7818
Lanosterol synthase	P48449	ERG7_HUMAN	Homo sapiens	3	0.7816
Lanosterol synthase	P48449	ERG7_HUMAN	Homo sapiens	3	0.7816
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7766
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7766
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7744
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7744
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7624
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7624
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7607
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7607
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7606
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7606
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7604
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7604
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7604
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7604
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7602
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7602
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7552
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7552
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7531
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7531
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7512
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7512
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7481
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7481
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7466
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7466
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7436
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7436
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7412
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7412
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7390
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7390
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7388
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7388
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7367
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7367
Thyroid hormone receptor alpha	P04625	THA_CHICK	Gallus gallus	3	0.7335
Thyroid hormone receptor alpha	P04625	THA_CHICK	Gallus gallus	3	0.7335
Putative cytochrome P450 120	Q59990	CP120_SYNY3	Synechocystis sp	3	0.7323
Putative cytochrome P450 120	Q59990	CP120_SYNY3	Synechocystis sp	3	0.7323
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7321
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7321
Retinoic acid receptor RXR-alpha	P28700	RXRA_MOUSE	Mus musculus	3	0.7314
Retinoic acid receptor RXR-alpha	P28700	RXRA_MOUSE	Mus musculus	3	0.7314
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7308
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7308
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7295
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7295
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	3	0.7289
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	3	0.7289
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7188
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7188
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7182
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7182
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7162
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7162
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7136
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7136
Vitamin D3 receptor	P11473	VDR_HUMAN	Homo sapiens	4	0.7102
Vitamin D3 receptor	P11473	VDR_HUMAN	Homo sapiens	4	0.7102
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7092
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7092
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7092
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7092
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7091
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7091
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7085
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7085
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7085
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7085
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7064
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7064
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	3	0.7059
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	3	0.7059
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7058
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7058
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7025
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7025
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7007
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7007

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