Aloesaponol I - Compound Card

Aloesaponol I

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Aloesaponol I

Structure
Zoomed Structure
  • Family: Plantae - Liliaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COC(=O)c1c(O)cc2c(c1C)c(O)c1c(c2)CC(CC1=O)O
InChI InChI=1S/C17H16O6/c1-7-13-9(5-11(19)14(7)17(22)23-2)3-8-4-10(18)6-12(20)15(8)16(13)21/h3,5,10,18-19,21H,4,6H2,1-2H3
InChIKey HMBXOSGHDRHNNU-UHFFFAOYSA-N
Formula C17H16O6
HBA 6
HBD 3
MW 316.31
Rotatable Bonds 1
TPSA 104.06
LogP 1.84
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 316.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aloe dawei Asphodelaceae Plantae 1331517
2 Aloe secundiflora Asphodelaceae Plantae 1593107
3 Aloe berhana Asphodelaceae Plantae 1593069
4 Aloe saponaria Asphodelaceae Plantae 1155789
5 Aloe graminicola Liliaceae Plantae 330741
6 Aloe species Liliaceae Plantae 117795

Showing of synonyms

  • Yenesew A, Ogur JA, et al. (1993). (R)-Prechrysophanol from Aloe graminicola.. Phytochemistry,1993,34(5),1442-1444. [View] [PubMed]
  • Dagne E, Casser I, et al. (1992). Aloechrysone, a dihydroanthracenone from Aloe berhana.. Phytochemistry,1992,31(5),1791-1793. [View] [PubMed]
  • Dagne E, Yenesew A, et al. (1994). Anthraquinones, pre-anthraquinones and isoeleutherol in the roots of Aloe species.. Phytochemistry,1994,35(2),401-406. [View] [PubMed]
  • Abdissa N, Induli M, et al. (2014). Cytotoxic quinones from the roots of Aloe dawei. Molecules,2014,19(3),3264-3273. [View] [PubMed]
  • Induli M, Cheloti M, et al. (2012). Naphthoquinones from the roots of Aloe secundiflora. Phytochemistry Letters,2012,5(3),506-509. [View] [PubMed]
  • Dagne E. (1996). Review of the chemistry of Aloes of Africa. Bulletin of the Chemical Society of Ethiopia,1996,10(1),89-103. [View] [PubMed]
Pubchem: 44631015
Nmrshiftdb2: 70004751

No compound-protein relationship available.

Structure

SMILES: O=C1CCCc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 316.31 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.780
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.020
Plasma Protein Binding
46.35
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
7.790
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.460
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.770
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.860
Micronucleos
Toxic
NR-AhR
Toxic
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
3.740
Rat (Acute)
2.440
Rat (Chronic Oral)
3.220
Fathead Minnow
4.070
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
430.420
Hydration Free Energy
-10.160
Log(D) at pH=7.4
2.400
Log(P)
3.29
Log S
-4.53
Log(Vapor Pressure)
-7.09
Melting Point
180.01
pKa Acid
7.08
pKa Basic
5.22
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9233
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9233
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9102
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9102
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8992
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8992
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8867
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8867
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8785
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8785
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8783
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8783
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8686
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8686
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8635
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8635
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8627
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8627
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8592
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8592
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8502
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8502
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8466
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8466
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8455
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8455
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8420
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8420
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8259
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8259
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8245
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8245
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8220
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8220
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8219
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8219
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8196
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8196
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8187
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8187
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 4 0.8126
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 4 0.8126
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.8055
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.8055
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8001
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8001
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7966
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7966
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7908
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7908
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7785
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7785
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7753
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7753
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7709
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7709
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7692
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7692
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7683
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7683
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7642
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7642
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7599
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7599
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7579
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7579
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7568
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7568
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7541
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7541
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7522
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7522
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7334
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7334
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7334
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7334
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7283
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7283
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7230
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7230
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 4 0.7226
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 4 0.7226
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7189
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7189
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7119
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7119
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7113
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7113
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7111
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7111
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7104
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7104
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7080
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7080
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7072
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7072
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7070
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7070
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7026
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7026
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7010
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7010
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7004
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7004
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7002
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7002

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