Asphodelin A 4'-O-beta-D-glucoside - Compound Card

Asphodelin A 4'-O-beta-D-glucoside

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Asphodelin A 4'-O-beta-D-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Liliaceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Arylcoumarin Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2ccc(c(c2)O)c2c(=O)oc3c(c2O)ccc(c3)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C21H20O11/c22-7-14-17(26)18(27)19(28)21(32-14)30-9-2-4-10(12(24)6-9)15-16(25)11-3-1-8(23)5-13(11)31-20(15)29/h1-6,14,17-19,21-28H,7H2/t14-,17-,18+,19-,21-/m1/s1
InChIKey OEZWCAHAQBRTTP-FKRBRYKNSA-N
Formula C21H20O11
HBA 11
HBD 7
MW 448.38
Rotatable Bonds 4
TPSA 190.28
LogP -0.24
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 448.1
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Asphodelus microcarpus Liliaceae Plantae 49697

Showing of synonyms

  • El-Seedi HR (2007). Antimicrobial arylcoumarins from Asphodelus microcarpus. Journal of Natural Products,2007,70(1),118-120. [View] [PubMed]
Pubchem: 54679753
Chebi: 65454
Nmrshiftdb2: 70093291
Metabolights: MTBLC65454

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(=O)c(c2)-c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1ccccc1-c(c2)c(=O)oc(c23)cccc3

Level: 1

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 448.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 448.38 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-6.53
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.490
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.900
Plasma Protein Binding
80.53
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
11.040
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.480
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.860
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.070
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
-74.390
Rat (Acute)
2.520
Rat (Chronic Oral)
4.140
Fathead Minnow
3.960
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
615.140
Hydration Free Energy
-4.680
Log(D) at pH=7.4
-0.110
Log(P)
-0.2
Log S
-3.83
Log(Vapor Pressure)
-12.7
Melting Point
207.87
pKa Acid
4.62
pKa Basic
7.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9487
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9487
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9474
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9474
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9312
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9312
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9237
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9237
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9155
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9155
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.9154
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.9154
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8901
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8901
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8820
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8820
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8813
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8813
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8798
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8798
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8731
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8731
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.8693
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.8693
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8688
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8688
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8681
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8681
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8672
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8672
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8659
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8659
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8617
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8617
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8587
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8587
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8579
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8579
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 3 0.8548
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 3 0.8548
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8474
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8474
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.8403
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.8403
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8224
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8224
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8140
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8140
Pyridoxal kinase, putative C4LVZ4 C4LVZ4_ENTHI Entamoeba histolytica 3 0.8112
Pyridoxal kinase, putative C4LVZ4 C4LVZ4_ENTHI Entamoeba histolytica 3 0.8112
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8108
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8108
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7979
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7979
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7953
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7953
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7949
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7949
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7898
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7898
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7894
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7894
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7883
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7883
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7881
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7881
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7876
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7876
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7876
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7876
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7829
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7829
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7823
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7823
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7781
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7781
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7715
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7715
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7714
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7714
Macrophage colony-stimulating factor 1 receptor P07333 CSF1R_HUMAN Homo sapiens 4 0.7647
Macrophage colony-stimulating factor 1 receptor P07333 CSF1R_HUMAN Homo sapiens 4 0.7647
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 4 0.7598
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 4 0.7598
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7576
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7576
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7550
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7550
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7543
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7543
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7530
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7530
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7510
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7510
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7487
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7487
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7458
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7458
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7433
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7433
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7421
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7421
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7401
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7401
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7332
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7332
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 3 0.7330
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 3 0.7330
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7327
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7327
Bromodomain protein, putative Q8I240 Q8I240_PLAF7 Plasmodium falciparum 4 0.7265
Bromodomain protein, putative Q8I240 Q8I240_PLAF7 Plasmodium falciparum 4 0.7265
Uncharacterized protein Q7DBA6 Q7DBA6_ECO57 Escherichia coli O157:H7 4 0.7255
Uncharacterized protein Q7DBA6 Q7DBA6_ECO57 Escherichia coli O157:H7 4 0.7255
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7213
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7213
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7204
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7204
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7187
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7187
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7186
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7186
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7180
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7180
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7171
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7171
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7158
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7158
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic P80030 FABI_BRANA Brassica napus 4 0.7139
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic P80030 FABI_BRANA Brassica napus 4 0.7139
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7137
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7137
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7134
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7134
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7129
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7129
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7114
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7114
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7106
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7106
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7104
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7104
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7096
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7096
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7095
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7095
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7092
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7092
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7086
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7086
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7074
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7074
Putative N-acetyl glucosaminyl transferase Q6U8B0 Q6U8B0_RAOTE Raoultella terrigena 3 0.7067
Putative N-acetyl glucosaminyl transferase Q6U8B0 Q6U8B0_RAOTE Raoultella terrigena 3 0.7067
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7061
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7061
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7059
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7059
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7050
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7050
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7042
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7042
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7029
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7029
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7019
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7019

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