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Barbaloin B

Family: Plantae - Asphodelaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Anthrone

Canonical Smiles	OCc1cc(O)c2c(c1)[C@@H](C1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1c(C2=O)c(O)ccc1
InChI	InChI=1S/C21H22O9/c22-6-8-4-10-14(21-20(29)19(28)17(26)13(7-23)30-21)9-2-1-3-11(24)15(9)18(27)16(10)12(25)5-8/h1-5,13-14,17,19-26,28-29H,6-7H2/t13-,14+,17-,19+,20-,21?/m1/s1
InChIKey	AFHJQYHRLPMKHU-LJSIEZAASA-N
Formula	C₂₁H₂₂O₉
HBA	9
HBD	7
MW	418.4
Rotatable Bonds	3
TPSA	167.91
LogP	-0.89
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	418.13
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aloe turkanensis	Asphodelaceae	Plantae	1811903
2	Aloe scabrifolia	Asphodelaceae	Plantae	25641

Showing of synonyms

Reynolds T. (1996). Chemotaxonomy of Aloe turkanensis and Aloe scabrifolia from Kenya. Biochemical Systematics and Ecology,1996,24(4),347-352. [View] [PubMed]

Pubchem: 89483142

No compound-protein relationship available.

SMILES: O1CCCCC1C(c(c23)cccc3)c4c(C2=O)cccc4

Level: 1

Mol. Weight: 418.4 g/mol

SMILES: c1cccc(c12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 418.4 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 418.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.39
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.79
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.15

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.7
Plasma Protein Binding: 69.11
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: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.64
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.05
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.72
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.85
Micronucleos: Toxic
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: -31.7
Rat (Acute): 2.64
Rat (Chronic Oral): 4.27
Fathead Minnow: 3.82
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 572.3
Hydration Free Energy: -9.06
Log(D) at pH=7.4: -0.35
Log(P): 0.56
Log S: -2.58
Log(Vapor Pressure): -12.05
Melting Point: 182.93
pKa Acid: 4.21
pKa Basic: 7.26

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8849
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8849
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.8504
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.8504
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.8321
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.8321
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8232
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8232
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7829
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7829
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7601
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7601
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7586
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7586
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7469
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7469
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7460
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7460
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7434
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7434
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7430
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7430
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7306
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7306
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7286
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7286
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7190
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7190
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7185
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7185
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7185
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7185
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7182
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7182
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	3	0.7159
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	3	0.7159
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7157
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7157
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7155
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7155
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7037
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7037
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7031
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7031

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