Structure

Physi-Chem Properties

Molecular Weight:  250.08
Volume:  247.06
LogP:  3.841
LogD:  1.103
LogS:  -2.653
# Rotatable Bonds:  1
TPSA:  86.99
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.673
Synthetic Accessibility Score:  4.038
Fsp3:  0.308
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.628
MDCK Permeability:  2.3025816062727245e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.018
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.037
Plasma Protein Binding (PPB):  93.77281188964844%
Volume Distribution (VD):  0.949
Pgp-substrate:  6.198541164398193%

ADMET: Metabolism

CYP1A2-inhibitor:  0.227
CYP1A2-substrate:  0.571
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.065
CYP2C9-substrate:  0.167
CYP2D6-inhibitor:  0.03
CYP2D6-substrate:  0.125
CYP3A4-inhibitor:  0.051
CYP3A4-substrate:  0.067

ADMET: Excretion

Clearance (CL):  1.593
Half-life (T1/2):  0.888

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.598
Drug-inuced Liver Injury (DILI):  0.984
AMES Toxicity:  0.402
Rat Oral Acute Toxicity:  0.217
Maximum Recommended Daily Dose:  0.025
Skin Sensitization:  0.367
Carcinogencity:  0.953
Eye Corrosion:  0.004
Eye Irritation:  0.336
Respiratory Toxicity:  0.872

Download Data

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

  Natural Product: NPC264391

Natural Product ID:  NPC264391
Common Name*:   Citrinin
IUPAC Name:   n.a.
Synonyms:   Citrinin
Standard InCHIKey:  CQIUKKVOEOPUDV-IYSWYEEDSA-N
Standard InCHI:  InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1
SMILES:  C[C@@H]1[C@@H](C)OC=C2C1=C(C)C(=O)C(=C2O)C(=O)O
Synthetic Gene Cluster:   BGC0001338;
ChEMBL Identifier:   CHEMBL510139
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans

*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
NPO4343 Guanomyces polythrix Species n.a. Eukaryota n.a. n.a. n.a. PMID[10869195]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15730261]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15973055]
NPO32513 Penicillium citrinum Under-species n.a. n.a. n.a. n.a. n.a. PMID[18281952]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[18656987]
NPO19812 Pimelea simplex Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[21049973]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21053938]
NPO33186 penicillium citrinum hgy1-5 Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21761866]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. Moroccan n.a. PMID[23713692]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26295595]
NPO12352 Magnolia baillonii Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[3437284]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[7766039]
NPO19812 Pimelea simplex Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19551 Cocculus pendulus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19812 Pimelea simplex Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19551 Cocculus pendulus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11741 Glycosmis parviflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18223 Dictyostelium brefeldianum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18651 Piper lolot Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19551 Cocculus pendulus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19681 Hypoxis filiformis Species Hypoxidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19146 Cosmos bipinnatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4343 Guanomyces polythrix Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14131 Phyllanthus maderaspatensis Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18898 Madhuca utilis Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17984 Aplysia angasi Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10921 Cercospora ligustri Species Mycosphaerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12352 Magnolia baillonii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19611 Ipomoea tuberosa Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19812 Pimelea simplex Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13189 Carex folliculata Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16902 Dendroctonus brevicomis Species Curculionidae 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
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 31622.8 nM PMID[543294]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 12559.4 nM PMID[543294]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 10000.0 nM PMID[543296]
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 10000.0 nM PMID[543296]
NPT91 Cell Line KB Homo sapiens IC50 > 10000.0 nM PMID[543296]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 89125.1 nM PMID[543294]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 26242.19 nM PMID[543298]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 21727.01 nM PMID[543298]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 20511.62 nM PMID[543298]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 20989.4 nM PMID[543298]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 48305.88 nM PMID[543298]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 25118.86 nM PMID[543298]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 11117.32 nM PMID[543298]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 24154.61 nM PMID[543298]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 12274.39 nM PMID[543298]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 12823.31 nM PMID[543298]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 50118.72 nM PMID[543298]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 15275.66 nM PMID[543298]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 781.63 nM PMID[543298]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 16749.43 nM PMID[543298]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 13091.82 nM PMID[543298]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 17100.15 nM PMID[543298]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 14621.77 nM PMID[543298]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 43752.21 nM PMID[543298]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 59841.16 nM PMID[543298]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 13152.25 nM PMID[543298]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 23173.95 nM PMID[543298]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 21877.62 nM PMID[543298]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 43954.16 nM PMID[543298]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 24547.09 nM PMID[543298]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 15631.48 nM PMID[543298]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 20558.91 nM PMID[543298]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 24490.63 nM PMID[543298]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 12387.97 nM PMID[543298]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 26853.44 nM PMID[543298]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 5546.26 nM PMID[543298]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 23014.42 nM PMID[543298]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 20370.42 nM PMID[543298]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 15776.11 nM PMID[543298]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 32885.16 nM PMID[543298]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 16255.49 nM PMID[543298]
NPT168 Cell Line P388 Mus musculus GI50 n.a. 17021.59 nM PMID[543298]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 13304.54 nM PMID[543298]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 16255.49 nM PMID[543298]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 70469.31 nM PMID[543298]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 23823.19 nM PMID[543298]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 32583.67 nM PMID[543298]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 19098.53 nM PMID[543298]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 16865.53 nM PMID[543298]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 25822.6 nM PMID[543298]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 6998.42 nM PMID[543298]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 31988.95 nM PMID[543298]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 15739.83 nM PMID[543298]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 18749.95 nM PMID[543298]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 71779.43 nM PMID[543298]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 11455.13 nM PMID[543298]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 29241.52 nM PMID[543298]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 11803.21 nM PMID[543298]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 20323.57 nM PMID[543298]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 27289.78 nM PMID[543298]
NPT552 Cell Line P388/ADR Mus musculus GI50 n.a. 11508.0 nM PMID[543298]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 26977.39 nM PMID[543298]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 18578.04 nM PMID[543298]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 35809.64 nM PMID[543298]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 27478.94 nM PMID[543298]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 29716.66 nM PMID[543298]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 24547.09 nM PMID[543298]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 11194.38 nM PMID[543298]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 14825.18 nM PMID[543298]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 18197.01 nM PMID[543298]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 23280.91 nM PMID[543298]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 31768.74 nM PMID[543298]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 33884.42 nM PMID[543298]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 13182.57 nM PMID[543298]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 33884.42 nM PMID[543298]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 15240.53 nM PMID[543298]
NPT738 Cell Line SN12K1 Homo sapiens GI50 n.a. 15310.87 nM PMID[543298]
NPT1472 Individual Protein Solute carrier family 22 member 11 Homo sapiens Ki = 366400.0 nM PMID[543301]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 3.11 % PMID[543302]
NPT965 Organism Amaranthus hypochondriacus Amaranthus hypochondriacus IC50 = 55000.0 nM PMID[543290]
NPT117 Organism Echinochloa crus-galli Echinochloa crus-galli IC50 = 63000.0 nM PMID[543290]
NPT1 Others Radical scavenging activity IC50 = 160000.0 nM PMID[543291]
NPT141 Organism Agrobacterium tumefaciens Agrobacterium tumefaciens Activity = -26.0 % PMID[543292]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 25.0 ug.mL-1 PMID[543293]
NPT665 Individual Protein Solute carrier family 22 member 6 Homo sapiens Ki = 3080000.0 nM PMID[543295]
NPT669 Individual Protein Solute carrier family 22 member 8 Homo sapiens Ki = 15400.0 nM PMID[543299]
NPT665 Individual Protein Solute carrier family 22 member 6 Homo sapiens Ki = 3080000.0 nM PMID[543299]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 11.31 % PMID[543302]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 34.39 % PMID[543303]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 67.29 % PMID[543303]
NPT21772 PROTEIN COMPLEX GroEL/GroES Escherichia coli Inhibition = 99.0 % PMID[543304]
NPT21772 PROTEIN COMPLEX GroEL/GroES Escherichia coli Inhibition = 79.0 % PMID[543304]

☑ 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 NPC264391 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
0.7895 Intermediate Similarity NPC473277
0.7558 Intermediate Similarity NPC242233
0.7468 Intermediate Similarity NPC133098
0.7363 Intermediate Similarity NPC29798
0.7363 Intermediate Similarity NPC282644
0.7349 Intermediate Similarity NPC315765
0.7333 Intermediate Similarity NPC274075
0.7273 Intermediate Similarity NPC47220
0.7273 Intermediate Similarity NPC186332
0.7253 Intermediate Similarity NPC32552
0.7241 Intermediate Similarity NPC469884
0.7241 Intermediate Similarity NPC219966
0.7229 Intermediate Similarity NPC315394
0.72 Intermediate Similarity NPC68044
0.7172 Intermediate Similarity NPC232969
0.7172 Intermediate Similarity NPC199107
0.716 Intermediate Similarity NPC12815
0.716 Intermediate Similarity NPC238948
0.716 Intermediate Similarity NPC215745
0.7159 Intermediate Similarity NPC92633
0.7126 Intermediate Similarity NPC475083
0.7126 Intermediate Similarity NPC16488
0.7093 Intermediate Similarity NPC474980
0.7089 Intermediate Similarity NPC238223
0.7079 Intermediate Similarity NPC315395
0.7079 Intermediate Similarity NPC316426
0.7053 Intermediate Similarity NPC478233
0.7045 Intermediate Similarity NPC32676
0.7024 Intermediate Similarity NPC316324
0.7011 Intermediate Similarity NPC10080
0.7011 Intermediate Similarity NPC123908
0.701 Intermediate Similarity NPC469851
0.7 Intermediate Similarity NPC113370
0.7 Intermediate Similarity NPC476079
0.7 Intermediate Similarity NPC103743
0.7 Intermediate Similarity NPC142583
0.6966 Remote Similarity NPC15807
0.6966 Remote Similarity NPC471223
0.6966 Remote Similarity NPC281172
0.6966 Remote Similarity NPC307112
0.6966 Remote Similarity NPC67081
0.6962 Remote Similarity NPC132286
0.6962 Remote Similarity NPC251429
0.6923 Remote Similarity NPC26078
0.6923 Remote Similarity NPC473658
0.6914 Remote Similarity NPC203819
0.6914 Remote Similarity NPC59558
0.6905 Remote Similarity NPC51391
0.6905 Remote Similarity NPC4492
0.6889 Remote Similarity NPC472009
0.6889 Remote Similarity NPC278283
0.6889 Remote Similarity NPC291712
0.6882 Remote Similarity NPC142838
0.6882 Remote Similarity NPC114345
0.6882 Remote Similarity NPC6099
0.6882 Remote Similarity NPC303230
0.6882 Remote Similarity NPC166110
0.6875 Remote Similarity NPC79220
0.6848 Remote Similarity NPC142159
0.6848 Remote Similarity NPC51358
0.6848 Remote Similarity NPC87306
0.6848 Remote Similarity NPC307092
0.6848 Remote Similarity NPC95364
0.6835 Remote Similarity NPC469446
0.6835 Remote Similarity NPC315115
0.6829 Remote Similarity NPC126061
0.6813 Remote Similarity NPC477959
0.6813 Remote Similarity NPC472007
0.6813 Remote Similarity NPC473248
0.6813 Remote Similarity NPC23622
0.6813 Remote Similarity NPC86005
0.6809 Remote Similarity NPC248193
0.6786 Remote Similarity NPC315552
0.6774 Remote Similarity NPC131864
0.6774 Remote Similarity NPC473455
0.6774 Remote Similarity NPC71533
0.6774 Remote Similarity NPC106510
0.6774 Remote Similarity NPC265856
0.6771 Remote Similarity NPC93271
0.6771 Remote Similarity NPC135576
0.6762 Remote Similarity NPC321496
0.675 Remote Similarity NPC298249
0.6744 Remote Similarity NPC248624
0.6744 Remote Similarity NPC478122
0.6742 Remote Similarity NPC188717
0.6742 Remote Similarity NPC107498
0.6742 Remote Similarity NPC211455
0.6742 Remote Similarity NPC69469
0.6742 Remote Similarity NPC185949
0.6742 Remote Similarity NPC258985
0.6739 Remote Similarity NPC153570
0.6739 Remote Similarity NPC53454
0.6739 Remote Similarity NPC472008
0.6735 Remote Similarity NPC54705
0.6733 Remote Similarity NPC469852
0.6709 Remote Similarity NPC101670
0.6707 Remote Similarity NPC316029
0.6707 Remote Similarity NPC107848
0.6707 Remote Similarity NPC315597
0.6707 Remote Similarity NPC315285
0.6706 Remote Similarity NPC271986
0.6705 Remote Similarity NPC275766
0.6703 Remote Similarity NPC122502
0.6702 Remote Similarity NPC327760
0.6702 Remote Similarity NPC193396
0.6702 Remote Similarity NPC32944
0.6701 Remote Similarity NPC20066
0.6667 Remote Similarity NPC291260
0.6667 Remote Similarity NPC477117
0.6667 Remote Similarity NPC63326
0.6667 Remote Similarity NPC246458
0.6667 Remote Similarity NPC313444
0.6667 Remote Similarity NPC265980
0.6632 Remote Similarity NPC476049
0.6632 Remote Similarity NPC320552
0.663 Remote Similarity NPC313658
0.663 Remote Similarity NPC316138
0.6629 Remote Similarity NPC224455
0.6628 Remote Similarity NPC471061
0.6628 Remote Similarity NPC473536
0.6627 Remote Similarity NPC477087
0.6627 Remote Similarity NPC178575
0.6627 Remote Similarity NPC319163
0.6627 Remote Similarity NPC67076
0.6627 Remote Similarity NPC477086
0.6625 Remote Similarity NPC470033
0.66 Remote Similarity NPC235369
0.6598 Remote Similarity NPC473291
0.6596 Remote Similarity NPC316228
0.6596 Remote Similarity NPC327253
0.6596 Remote Similarity NPC313670
0.6593 Remote Similarity NPC470177
0.6588 Remote Similarity NPC199445
0.6588 Remote Similarity NPC260396
0.6585 Remote Similarity NPC236208
0.6562 Remote Similarity NPC143210
0.6559 Remote Similarity NPC143025
0.6559 Remote Similarity NPC475819
0.6559 Remote Similarity NPC260343
0.6559 Remote Similarity NPC119740
0.6559 Remote Similarity NPC137368
0.6559 Remote Similarity NPC150063
0.6552 Remote Similarity NPC108816
0.6552 Remote Similarity NPC93763
0.6548 Remote Similarity NPC316851
0.6548 Remote Similarity NPC477085
0.6538 Remote Similarity NPC263732
0.6538 Remote Similarity NPC269737
0.6538 Remote Similarity NPC15193
0.6535 Remote Similarity NPC95899
0.6535 Remote Similarity NPC291154
0.6531 Remote Similarity NPC287668
0.6526 Remote Similarity NPC472705
0.6522 Remote Similarity NPC164393
0.6522 Remote Similarity NPC478112
0.6512 Remote Similarity NPC225022
0.6512 Remote Similarity NPC238554
0.6509 Remote Similarity NPC66108
0.6506 Remote Similarity NPC318766
0.6506 Remote Similarity NPC472017
0.6505 Remote Similarity NPC469853
0.65 Remote Similarity NPC244456
0.65 Remote Similarity NPC471566
0.65 Remote Similarity NPC469657
0.65 Remote Similarity NPC471556
0.6495 Remote Similarity NPC214694
0.6495 Remote Similarity NPC12727
0.6495 Remote Similarity NPC170204
0.6495 Remote Similarity NPC272050
0.6494 Remote Similarity NPC86789
0.6489 Remote Similarity NPC225283
0.6489 Remote Similarity NPC118011
0.6489 Remote Similarity NPC256902
0.6489 Remote Similarity NPC280833
0.6489 Remote Similarity NPC36668
0.6489 Remote Similarity NPC478110
0.6489 Remote Similarity NPC118193
0.6486 Remote Similarity NPC154626
0.6484 Remote Similarity NPC212363
0.6484 Remote Similarity NPC472957
0.6484 Remote Similarity NPC472958
0.6484 Remote Similarity NPC163615
0.6484 Remote Similarity NPC38569
0.6477 Remote Similarity NPC139712
0.6476 Remote Similarity NPC478209
0.6471 Remote Similarity NPC476590
0.6471 Remote Similarity NPC177030
0.6471 Remote Similarity NPC470686
0.6471 Remote Similarity NPC122244
0.6471 Remote Similarity NPC114727
0.6465 Remote Similarity NPC300584
0.6465 Remote Similarity NPC161855
0.6463 Remote Similarity NPC287705
0.6458 Remote Similarity NPC271652
0.6458 Remote Similarity NPC159092
0.6458 Remote Similarity NPC109406
0.6458 Remote Similarity NPC61201
0.6452 Remote Similarity NPC241054
0.6452 Remote Similarity NPC125925
0.6452 Remote Similarity NPC160138

  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 NPC264391 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
0.6932 Remote Similarity NPD6110 Phase 1
0.6824 Remote Similarity NPD4756 Discovery
0.6809 Remote Similarity NPD5779 Approved
0.6809 Remote Similarity NPD5778 Approved
0.6526 Remote Similarity NPD7983 Approved
0.6526 Remote Similarity NPD7637 Suspended
0.6344 Remote Similarity NPD4249 Approved
0.6341 Remote Similarity NPD4247 Clinical (unspecified phase)
0.63 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6277 Remote Similarity NPD4251 Approved
0.6277 Remote Similarity NPD4250 Approved
0.6264 Remote Similarity NPD5209 Approved
0.6263 Remote Similarity NPD7839 Suspended
0.625 Remote Similarity NPD6698 Approved
0.625 Remote Similarity NPD46 Approved
0.6237 Remote Similarity NPD5363 Approved
0.6222 Remote Similarity NPD4252 Approved
0.6196 Remote Similarity NPD7154 Phase 3
0.6146 Remote Similarity NPD6101 Approved
0.6146 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6087 Remote Similarity NPD4269 Approved
0.6087 Remote Similarity NPD4270 Approved
0.6082 Remote Similarity NPD5785 Approved
0.6082 Remote Similarity NPD7838 Discovery
0.6061 Remote Similarity NPD5282 Discontinued
0.6024 Remote Similarity NPD3704 Approved
0.602 Remote Similarity NPD6411 Approved
0.6 Remote Similarity NPD5786 Approved
0.6 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5957 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5922 Remote Similarity NPD7640 Approved
0.5922 Remote Similarity NPD7639 Approved
0.5909 Remote Similarity NPD6053 Discontinued
0.587 Remote Similarity NPD5790 Clinical (unspecified phase)
0.587 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5859 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5851 Remote Similarity NPD5362 Discontinued
0.5825 Remote Similarity NPD4225 Approved
0.5825 Remote Similarity NPD7638 Approved
0.5824 Remote Similarity NPD4268 Approved
0.5824 Remote Similarity NPD4271 Approved
0.5824 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5816 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5816 Remote Similarity NPD5370 Suspended
0.5806 Remote Similarity NPD5369 Approved
0.5794 Remote Similarity NPD5048 Discontinued
0.5729 Remote Similarity NPD1694 Approved
0.5729 Remote Similarity NPD1696 Phase 3
0.5727 Remote Similarity NPD6371 Approved
0.5702 Remote Similarity NPD7500 Approved
0.5699 Remote Similarity NPD4822 Approved
0.5699 Remote Similarity NPD4819 Approved
0.5699 Remote Similarity NPD4821 Approved
0.5699 Remote Similarity NPD4820 Approved
0.5686 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5684 Remote Similarity NPD5331 Approved
0.5684 Remote Similarity NPD5332 Approved
0.5663 Remote Similarity NPD2664 Clinical (unspecified phase)
0.566 Remote Similarity NPD7632 Discontinued
0.5641 Remote Similarity NPD8513 Phase 3
0.5638 Remote Similarity NPD4790 Discontinued
0.5619 Remote Similarity NPD6648 Approved
0.5607 Remote Similarity NPD6647 Phase 2

  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