Structure

Physi-Chem Properties

Molecular Weight:  154.03
Volume:  139.767
LogP:  1.333
LogD:  1.514
LogS:  -1.627
# Rotatable Bonds:  0
TPSA:  59.67
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.558
Synthetic Accessibility Score:  3.402
Fsp3:  0.286
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.683
MDCK Permeability:  3.2485437259310856e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.705

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.235
Plasma Protein Binding (PPB):  80.2275161743164%
Volume Distribution (VD):  1.274
Pgp-substrate:  29.027484893798828%

ADMET: Metabolism

CYP1A2-inhibitor:  0.547
CYP1A2-substrate:  0.448
CYP2C19-inhibitor:  0.075
CYP2C19-substrate:  0.066
CYP2C9-inhibitor:  0.056
CYP2C9-substrate:  0.764
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.483
CYP3A4-inhibitor:  0.013
CYP3A4-substrate:  0.163

ADMET: Excretion

Clearance (CL):  14.074
Half-life (T1/2):  0.875

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.344
Drug-inuced Liver Injury (DILI):  0.864
AMES Toxicity:  0.38
Rat Oral Acute Toxicity:  0.052
Maximum Recommended Daily Dose:  0.021
Skin Sensitization:  0.237
Carcinogencity:  0.53
Eye Corrosion:  0.022
Eye Irritation:  0.653
Respiratory Toxicity:  0.514

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC471611

Natural Product ID:  NPC471611
Common Name*:   Patulin
IUPAC Name:   4-hydroxy-4,6-dihydrofuro[3,2-c]pyran-2-one
Synonyms:   SCH-351633
Standard InCHIKey:  ZRWPUFFVAOMMNM-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2
SMILES:  C1C=C2C(=CC(=O)O2)C(O1)O
Synthetic Gene Cluster:   BGC0000120;
ChEMBL Identifier:   CHEMBL294018
PubChem CID:   4696
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000086] Pyrans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO14094 Aspergillus ochraceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[11170686]
NPO14094 Aspergillus ochraceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16156520]
NPO41354 Aspergillus clavatonanicus + Pytium ultimum Species n.a. n.a. n.a. n.a. n.a. PMID[18317751]
NPO14094 Aspergillus ochraceus Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21043476]
NPO14094 Aspergillus ochraceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT5224 Individual Protein NS3 Hepatitis C virus IC50 = 3.8 ug.mL-1 PMID[492088]
NPT5224 Individual Protein NS3 Hepatitis C virus IC50 = 3800.0 nM PMID[492089]
NPT306 Cell Line PC-3 Homo sapiens FC = 0.23 n.a. PMID[492093]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 2238.7 nM PMID[492094]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 891.3 nM PMID[492094]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 1995.3 nM PMID[492094]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens Potency = 31622.8 nM PMID[492094]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens Potency = 39810.7 nM PMID[492094]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 12589.3 nM PMID[492094]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 7943.3 nM PMID[492094]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 1122.0 nM PMID[492094]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 12589.3 nM PMID[492094]
NPT546 Individual Protein Retinoid X receptor alpha Homo sapiens Potency n.a. 12589.3 nM PMID[492096]
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency n.a. 8912.5 nM PMID[492096]
NPT540 Individual Protein Bile acid receptor FXR Homo sapiens Potency n.a. 19952.6 nM PMID[492096]
NPT249 Individual Protein Glucocorticoid receptor Homo sapiens Potency n.a. 6309.6 nM PMID[492096]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Potency n.a. 25118.9 nM PMID[492096]
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 6309.6 nM PMID[492096]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 35481.3 nM PMID[492094]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 25118.9 nM PMID[492096]
NPT249 Individual Protein Glucocorticoid receptor Homo sapiens Potency n.a. 31622.8 nM PMID[492096]
NPT546 Individual Protein Retinoid X receptor alpha Homo sapiens Potency n.a. 19952.6 nM PMID[492096]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 50118.7 nM PMID[492094]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 618.02 nM PMID[492097]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 1145.51 nM PMID[492097]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 3118.89 nM PMID[492097]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 3083.19 nM PMID[492097]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 243.78 nM PMID[492097]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 563.64 nM PMID[492097]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 1004.62 nM PMID[492097]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 1116.86 nM PMID[492097]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 410.2 nM PMID[492097]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 1020.94 nM PMID[492097]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 1039.92 nM PMID[492097]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 368.13 nM PMID[492097]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 10592.54 nM PMID[492097]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 732.82 nM PMID[492097]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 3019.95 nM PMID[492097]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 615.18 nM PMID[492097]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 7396.05 nM PMID[492097]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 3828.25 nM PMID[492097]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 881.05 nM PMID[492097]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 297.85 nM PMID[492097]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 1291.22 nM PMID[492097]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 974.99 nM PMID[492097]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 364.75 nM PMID[492097]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 267.3 nM PMID[492097]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 3169.57 nM PMID[492097]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 189.23 nM PMID[492097]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 309.03 nM PMID[492097]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 2844.46 nM PMID[492097]
NPT168 Cell Line P388 Mus musculus GI50 n.a. 134.59 nM PMID[492097]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 2275.1 nM PMID[492097]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 1370.88 nM PMID[492097]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 4102.04 nM PMID[492097]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 1150.8 nM PMID[492097]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 4275.63 nM PMID[492097]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 668.34 nM PMID[492097]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 222.84 nM PMID[492097]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 1321.3 nM PMID[492097]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 1489.36 nM PMID[492097]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 296.48 nM PMID[492097]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 1078.95 nM PMID[492097]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 10303.86 nM PMID[492097]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 1158.78 nM PMID[492097]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 820.35 nM PMID[492097]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 851.14 nM PMID[492097]
NPT552 Cell Line P388/ADR Mus musculus GI50 n.a. 318.42 nM PMID[492097]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 2937.65 nM PMID[492097]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 2098.94 nM PMID[492097]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 722.77 nM PMID[492097]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 2317.39 nM PMID[492097]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 158.49 nM PMID[492097]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 456.04 nM PMID[492097]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 3491.4 nM PMID[492097]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 1972.42 nM PMID[492097]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 990.83 nM PMID[492097]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 280.54 nM PMID[492097]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 509.33 nM PMID[492097]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 1981.53 nM PMID[492097]
NPT738 Cell Line SN12K1 Homo sapiens GI50 n.a. 997.7 nM PMID[492097]
NPT155 Individual Protein Aryl hydrocarbon receptor Homo sapiens Potency n.a. 12589.3 nM PMID[492096]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 5.33 % PMID[492098]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 145.8 nM PMID[492094]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 103.2 nM PMID[492094]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 4327.7 nM PMID[492096]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 31622.8 nM PMID[492094]
NPT2 Others Unspecified IC50 = 24700.0 nM PMID[492090]
NPT141 Organism Agrobacterium tumefaciens Agrobacterium tumefaciens Activity = -66.0 % PMID[492091]
NPT25088 PROTEIN FAMILY Janus Kinase (JAK) Homo sapiens Inhibition > 65.0 % PMID[492092]
NPT25088 PROTEIN FAMILY Janus Kinase (JAK) Homo sapiens Inhibition = 25.0 % PMID[492092]
NPT207 Protein Family MAP kinase p38 Homo sapiens Inhibition = 25.0 % PMID[492092]
NPT2 Others Unspecified Potency = 316.2 nM PMID[492094]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 17782.8 nM PMID[492094]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 35481.3 nM PMID[492094]
NPT2 Others Unspecified Potency = 22387.2 nM PMID[492094]
NPT24749 ORGANISM Ebolavirus Ebolavirus Inhibition = 89.0 % PMID[492095]
NPT27 Others Unspecified Inhibition = 20.0 % PMID[492095]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens Potency n.a. 19952.6 nM PMID[492096]
NPT888 Individual Protein 78 kDa glucose-regulated protein Homo sapiens Potency n.a. 5011.9 nM PMID[492094]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -1.78 % PMID[492098]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 79.09 % PMID[492099]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 81.5 % PMID[492099]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[492094]
NPT2 Others Unspecified Potency n.a. 3162.3 nM PMID[492094]
NPT610 Others Molecular identity unknown Potency n.a. 12589.3 nM PMID[492096]
NPT2 Others Unspecified Potency n.a. 1122.0 nM PMID[492094]
NPT2 Others Unspecified Potency n.a. 14125.4 nM PMID[492094]
NPT21772 PROTEIN COMPLEX GroEL/GroES Escherichia coli Inhibition = 107.0 % PMID[492100]
NPT21772 PROTEIN COMPLEX GroEL/GroES Escherichia coli Inhibition = 70.0 % PMID[492100]
NPT2 Others Unspecified Potency n.a. 8912.5 nM Open TG-GATES in vivo data: Biochemistry
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[2016706]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC471611 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.8116 Intermediate Similarity NPC178575
0.7969 Intermediate Similarity NPC98519
0.7903 Intermediate Similarity NPC51846
0.7692 Intermediate Similarity NPC130953
0.7692 Intermediate Similarity NPC476585
0.7647 Intermediate Similarity NPC470033
0.7536 Intermediate Similarity NPC132286
0.7463 Intermediate Similarity NPC475073
0.7429 Intermediate Similarity NPC238223
0.7391 Intermediate Similarity NPC37382
0.7385 Intermediate Similarity NPC189700
0.7302 Intermediate Similarity NPC218486
0.7246 Intermediate Similarity NPC476586
0.7222 Intermediate Similarity NPC59558
0.7206 Intermediate Similarity NPC2328
0.7049 Intermediate Similarity NPC234084
0.7 Intermediate Similarity NPC476589
0.7 Intermediate Similarity NPC282760
0.7 Intermediate Similarity NPC470123
0.6974 Remote Similarity NPC470705
0.6957 Remote Similarity NPC473737
0.6957 Remote Similarity NPC476584
0.6842 Remote Similarity NPC478193
0.6842 Remote Similarity NPC478196
0.6842 Remote Similarity NPC478194
0.6842 Remote Similarity NPC478192
0.6842 Remote Similarity NPC478191
0.6842 Remote Similarity NPC478195
0.6818 Remote Similarity NPC150717
0.6818 Remote Similarity NPC221763
0.6812 Remote Similarity NPC15193
0.68 Remote Similarity NPC316851
0.6774 Remote Similarity NPC126184
0.6761 Remote Similarity NPC471566
0.6761 Remote Similarity NPC7940
0.6761 Remote Similarity NPC471556
0.6761 Remote Similarity NPC273600
0.6761 Remote Similarity NPC471565
0.6719 Remote Similarity NPC191643
0.6712 Remote Similarity NPC280374
0.6712 Remote Similarity NPC287705
0.6707 Remote Similarity NPC475706
0.6707 Remote Similarity NPC126518
0.6667 Remote Similarity NPC324170
0.6667 Remote Similarity NPC323251
0.6667 Remote Similarity NPC309408
0.6627 Remote Similarity NPC163606
0.6623 Remote Similarity NPC206507
0.6623 Remote Similarity NPC210258
0.6623 Remote Similarity NPC147621
0.6623 Remote Similarity NPC315552
0.662 Remote Similarity NPC475618
0.6567 Remote Similarity NPC230296
0.6522 Remote Similarity NPC133600
0.6522 Remote Similarity NPC302564
0.6494 Remote Similarity NPC470686
0.6486 Remote Similarity NPC474823
0.6471 Remote Similarity NPC319423
0.6471 Remote Similarity NPC135863
0.6463 Remote Similarity NPC474028
0.6463 Remote Similarity NPC474439
0.6456 Remote Similarity NPC315394
0.6447 Remote Similarity NPC316185
0.6438 Remote Similarity NPC475675
0.6438 Remote Similarity NPC146811
0.6438 Remote Similarity NPC475555
0.6429 Remote Similarity NPC474424
0.6418 Remote Similarity NPC173157
0.641 Remote Similarity NPC161038
0.64 Remote Similarity NPC475004
0.6386 Remote Similarity NPC475714
0.6377 Remote Similarity NPC187770
0.6377 Remote Similarity NPC223679
0.6377 Remote Similarity NPC474084
0.6364 Remote Similarity NPC116366
0.6353 Remote Similarity NPC211892
0.6349 Remote Similarity NPC128520
0.6316 Remote Similarity NPC315285
0.6316 Remote Similarity NPC202011
0.6316 Remote Similarity NPC315597
0.631 Remote Similarity NPC470800
0.6301 Remote Similarity NPC96414
0.6286 Remote Similarity NPC97570
0.6282 Remote Similarity NPC315843
0.6279 Remote Similarity NPC45409
0.6269 Remote Similarity NPC135537
0.6267 Remote Similarity NPC470032
0.6267 Remote Similarity NPC63873
0.6267 Remote Similarity NPC477117
0.6265 Remote Similarity NPC471298
0.625 Remote Similarity NPC474729
0.625 Remote Similarity NPC275530
0.625 Remote Similarity NPC474723
0.625 Remote Similarity NPC68110
0.625 Remote Similarity NPC473756
0.6235 Remote Similarity NPC329630
0.6232 Remote Similarity NPC129150
0.6232 Remote Similarity NPC293437
0.6232 Remote Similarity NPC249850
0.6216 Remote Similarity NPC201356
0.6216 Remote Similarity NPC315115
0.6216 Remote Similarity NPC276299
0.6207 Remote Similarity NPC475739
0.6207 Remote Similarity NPC474629
0.619 Remote Similarity NPC471297
0.619 Remote Similarity NPC473315
0.619 Remote Similarity NPC142111
0.6173 Remote Similarity NPC209135
0.6173 Remote Similarity NPC474816
0.6164 Remote Similarity NPC90463
0.6154 Remote Similarity NPC275316
0.6143 Remote Similarity NPC254095
0.6136 Remote Similarity NPC225283
0.6119 Remote Similarity NPC327103
0.6118 Remote Similarity NPC471302
0.6118 Remote Similarity NPC473308
0.6118 Remote Similarity NPC471301
0.6111 Remote Similarity NPC59646
0.6111 Remote Similarity NPC242069
0.6111 Remote Similarity NPC55376
0.6104 Remote Similarity NPC476037
0.6098 Remote Similarity NPC179933
0.6092 Remote Similarity NPC118077
0.6092 Remote Similarity NPC475186
0.6081 Remote Similarity NPC182794
0.6076 Remote Similarity NPC107654
0.6076 Remote Similarity NPC476590
0.6076 Remote Similarity NPC114727
0.6071 Remote Similarity NPC471296
0.6071 Remote Similarity NPC251026
0.6067 Remote Similarity NPC327253
0.6067 Remote Similarity NPC475879
0.6067 Remote Similarity NPC3436
0.6053 Remote Similarity NPC313444
0.6049 Remote Similarity NPC262747
0.6047 Remote Similarity NPC470124
0.6047 Remote Similarity NPC474860
0.6047 Remote Similarity NPC471300
0.6047 Remote Similarity NPC471223
0.6047 Remote Similarity NPC67081
0.6044 Remote Similarity NPC104925
0.6044 Remote Similarity NPC298973
0.6044 Remote Similarity NPC470521
0.6044 Remote Similarity NPC469697
0.6044 Remote Similarity NPC470255
0.6029 Remote Similarity NPC151761
0.6029 Remote Similarity NPC159535
0.6027 Remote Similarity NPC179087
0.6027 Remote Similarity NPC132243
0.6027 Remote Similarity NPC210303
0.6027 Remote Similarity NPC44343
0.6026 Remote Similarity NPC133098
0.6026 Remote Similarity NPC293114
0.6023 Remote Similarity NPC472810
0.6023 Remote Similarity NPC472809
0.6 Remote Similarity NPC470520
0.6 Remote Similarity NPC188717
0.6 Remote Similarity NPC211455
0.6 Remote Similarity NPC294938
0.5978 Remote Similarity NPC170204
0.5977 Remote Similarity NPC208473
0.5974 Remote Similarity NPC151481
0.5955 Remote Similarity NPC470734
0.5952 Remote Similarity NPC475944
0.5949 Remote Similarity NPC329890
0.5949 Remote Similarity NPC284006
0.5946 Remote Similarity NPC470808
0.5942 Remote Similarity NPC478117
0.5942 Remote Similarity NPC25038
0.5938 Remote Similarity NPC87137
0.5934 Remote Similarity NPC469939
0.5934 Remote Similarity NPC472812
0.5934 Remote Similarity NPC320552
0.5934 Remote Similarity NPC282644
0.5934 Remote Similarity NPC29798
0.593 Remote Similarity NPC475035
0.5926 Remote Similarity NPC127118
0.5926 Remote Similarity NPC301207
0.5926 Remote Similarity NPC209113
0.5926 Remote Similarity NPC238554
0.5926 Remote Similarity NPC225022
0.5915 Remote Similarity NPC21946
0.5914 Remote Similarity NPC162346
0.5909 Remote Similarity NPC221467
0.5909 Remote Similarity NPC142583
0.5909 Remote Similarity NPC15789
0.5904 Remote Similarity NPC271632
0.5897 Remote Similarity NPC476012
0.5897 Remote Similarity NPC329904
0.5897 Remote Similarity NPC473361
0.5897 Remote Similarity NPC316029
0.589 Remote Similarity NPC26810
0.5889 Remote Similarity NPC118078
0.5889 Remote Similarity NPC474098
0.5889 Remote Similarity NPC475995
0.5882 Remote Similarity NPC310450
0.5882 Remote Similarity NPC475046
0.5882 Remote Similarity NPC313677
0.5882 Remote Similarity NPC11383
0.5882 Remote Similarity NPC474959

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC471611 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.6707 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6471 Remote Similarity NPD9118 Approved
0.6377 Remote Similarity NPD9119 Approved
0.6377 Remote Similarity NPD69 Approved
0.5955 Remote Similarity NPD689 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data