Barbaloin A - Compound Card

Barbaloin A

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Barbaloin A

Structure
Zoomed Structure
  • 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-NETPXSOISA-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: 168314870

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 418.4 g/mol

Structure

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

Level: 0

Mol. Weight: 418.4 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 418.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.35
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
-0.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
69.2
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
11.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.98
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
-31.51
Rat (Acute)
2.63
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
571.59
Hydration Free Energy
-9.04
Log(D) at pH=7.4
-0.36
Log(P)
0.69
Log S
-2.58
Log(Vapor Pressure)
-12.03
Melting Point
183.88
pKa Acid
4.21
pKa Basic
7.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8803
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8803
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8571
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8571
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7973
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7973
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.7856
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.7856
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.7764
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.7764
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7686
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7686
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7661
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7661
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7472
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7472
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7310
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7310
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7299
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7299
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7271
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7271
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7267
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7267
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7266
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7266
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7240
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7240
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7200
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7200
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7198
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7198
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7118
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7118
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7117
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7117
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7115
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7115
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7042
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7042
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7036
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7036
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7032
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7032
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7024
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7024
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7011
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7011
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7005
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7005

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