Structure

Physi-Chem Properties

Molecular Weight:  264.14
Volume:  269.578
LogP:  1.123
LogD:  1.275
LogS:  -3.122
# Rotatable Bonds:  0
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.533
Synthetic Accessibility Score:  4.545
Fsp3:  0.733
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.634
MDCK Permeability:  2.5592769816285e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.121
30% Bioavailability (F30%):  0.058

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.889
Plasma Protein Binding (PPB):  38.59888458251953%
Volume Distribution (VD):  1.154
Pgp-substrate:  66.60066986083984%

ADMET: Metabolism

CYP1A2-inhibitor:  0.406
CYP1A2-substrate:  0.532
CYP2C19-inhibitor:  0.16
CYP2C19-substrate:  0.69
CYP2C9-inhibitor:  0.067
CYP2C9-substrate:  0.244
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.083
CYP3A4-inhibitor:  0.28
CYP3A4-substrate:  0.268

ADMET: Excretion

Clearance (CL):  7.899
Half-life (T1/2):  0.712

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.217
Drug-inuced Liver Injury (DILI):  0.11
AMES Toxicity:  0.393
Rat Oral Acute Toxicity:  0.93
Maximum Recommended Daily Dose:  0.783
Skin Sensitization:  0.743
Carcinogencity:  0.886
Eye Corrosion:  0.393
Eye Irritation:  0.53
Respiratory Toxicity:  0.965

Download Data

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

  Natural Product: NPC201658

Natural Product ID:  NPC201658
Common Name*:   Coronopilin
IUPAC Name:   (3aS,6S,6aR,9aS,9bR)-6a-hydroxy-6,9a-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-azuleno[8,7-b]furan-2,9-dione
Synonyms:   Coronopilin
Standard InCHIKey:  GEUJJEYGSRWXPC-JISBIHODSA-N
Standard InCHI:  InChI=1S/C15H20O4/c1-8-4-5-10-9(2)13(17)19-12(10)14(3)11(16)6-7-15(8,14)18/h8,10,12,18H,2,4-7H2,1,3H3/t8-,10-,12+,14-,15+/m0/s1
SMILES:  C[C@H]1CC[C@H]2C(=C)C(=O)O[C@H]2[C@]2(C)C(=O)CC[C@@]12O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL248564
PubChem CID:   257278
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0002046] Ambrosanolides and secoambrosanolides

*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
NPO33469 Asteraceae Family Asteraceae Eukaryota n.a. n.a. n.a. PMID[18329753]
NPO16340 Heterostemma brownii Species Apocynaceae Eukaryota Stems n.a. n.a. PMID[9358639]
NPO29601 Abrus fruticulosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12932 Hymenoclea salsola n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO12932 Hymenoclea salsola n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO12932 Hymenoclea salsola n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29601 Abrus fruticulosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16152 Phlebia radiata Species Meruliaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO29601 Abrus fruticulosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16340 Heterostemma brownii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13843 Peronema canescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9557 Rumex bequaertii Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16262 Bacillus mojavensis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14970 Vitex polygama Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16152 Phlebia radiata Species Meruliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12932 Hymenoclea salsola n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12242 Lactuca tatarica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16668 Lonas annua Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2736 Penstemon diffusus Species Plantaginaceae 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
NPT91 Cell Line KB Homo sapiens pED50 = 5.26 n.a. PMID[475690]
NPT91 Cell Line KB Homo sapiens ED50 = 1.45 ug ml-1 PMID[475690]
NPT91 Cell Line KB Homo sapiens ED50 = 5.49 umol/L PMID[475693]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 11220.2 nM PMID[475694]
NPT3 Individual Protein Thioredoxin glutathione reductase Schistosoma mansoni Potency = 39810.7 nM PMID[475694]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency n.a. 11220.2 nM PMID[475694]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 100000.0 nM PMID[475694]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 35481.3 nM PMID[475694]
NPT484 Individual Protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 23934.1 nM PMID[475694]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 4159.11 nM PMID[475696]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 9.397 nM PMID[475696]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 3655.95 nM PMID[475696]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 5727.96 nM PMID[475696]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 4688.13 nM PMID[475696]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 10000.0 nM PMID[475696]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 23109.3 nM PMID[475694]
NPT102 Individual Protein Interleukin-8 Homo sapiens IC50 n.a. 40520.0 nM PMID[475694]
NPT102 Individual Protein Interleukin-8 Homo sapiens IC50 n.a. 7490.0 nM PMID[475694]
NPT477 Individual Protein DNA dC->dU-editing enzyme APOBEC-3G Homo sapiens Potency n.a. 19952.6 nM PMID[475694]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 29092.9 nM PMID[475694]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 39810.7 nM PMID[475694]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 8912.5 nM PMID[475694]
NPT1043 Individual Protein Glycoprotein hormones alpha chain Homo sapiens Potency n.a. 891.3 nM PMID[475694]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[475694]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 23109.3 nM PMID[475694]
NPT1283 Individual Protein Paired box protein Pax-8 Homo sapiens AC50 = 5430.0 nM PMID[475694]
NPT20967 CELL-LINE Platelet n.a. IC50 = 248900.0 nM PMID[475691]
NPT35 Others n.a. LogP = 1.42 n.a. PMID[475692]
NPT2 Others Unspecified Potency = 16360.1 nM PMID[475694]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[475694]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 7.03 % PMID[475695]
NPT2 Others Unspecified Potency n.a. 5011.9 nM PMID[475694]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[475694]
NPT2 Others Unspecified Potency n.a. 7079.5 nM PMID[475694]
NPT2 Others Unspecified Potency n.a. 10000.0 nM PMID[475694]
NPT2 Others Unspecified Potency n.a. 31622.8 nM PMID[475694]
NPT2 Others Unspecified Potency n.a. 29092.9 nM PMID[475694]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 18356.4 nM PMID[475694]

☑ 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 NPC201658 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
0.9419 High Similarity NPC473234
0.9419 High Similarity NPC308656
0.9419 High Similarity NPC60386
0.9419 High Similarity NPC473263
0.9419 High Similarity NPC473273
0.9294 High Similarity NPC12872
0.9294 High Similarity NPC168679
0.9195 High Similarity NPC153590
0.9136 High Similarity NPC6823
0.9036 High Similarity NPC245665
0.9 High Similarity NPC170143
0.9 High Similarity NPC311904
0.9 High Similarity NPC213947
0.9 High Similarity NPC108475
0.8977 High Similarity NPC200237
0.8941 High Similarity NPC238593
0.8889 High Similarity NPC91771
0.8889 High Similarity NPC142529
0.8851 High Similarity NPC155935
0.875 High Similarity NPC297474
0.875 High Similarity NPC35809
0.875 High Similarity NPC54065
0.8736 High Similarity NPC79549
0.8721 High Similarity NPC56593
0.8721 High Similarity NPC309757
0.8721 High Similarity NPC236692
0.8706 High Similarity NPC156485
0.8675 High Similarity NPC73052
0.8675 High Similarity NPC293418
0.8675 High Similarity NPC290508
0.8667 High Similarity NPC167219
0.8667 High Similarity NPC473331
0.8652 High Similarity NPC57304
0.8652 High Similarity NPC35959
0.8652 High Similarity NPC286341
0.8652 High Similarity NPC29821
0.8652 High Similarity NPC191339
0.8652 High Similarity NPC171360
0.8652 High Similarity NPC133888
0.8652 High Similarity NPC184063
0.8652 High Similarity NPC293001
0.8652 High Similarity NPC63193
0.8636 High Similarity NPC215556
0.8621 High Similarity NPC118601
0.8605 High Similarity NPC284534
0.8605 High Similarity NPC300082
0.8605 High Similarity NPC204105
0.8588 High Similarity NPC54468
0.8539 High Similarity NPC19087
0.8539 High Similarity NPC216284
0.8523 High Similarity NPC178875
0.8511 High Similarity NPC171759
0.8444 Intermediate Similarity NPC155215
0.8427 Intermediate Similarity NPC38392
0.8409 Intermediate Similarity NPC24728
0.8395 Intermediate Similarity NPC143979
0.8395 Intermediate Similarity NPC320537
0.8372 Intermediate Similarity NPC215294
0.837 Intermediate Similarity NPC90121
0.837 Intermediate Similarity NPC275960
0.837 Intermediate Similarity NPC193645
0.837 Intermediate Similarity NPC163228
0.837 Intermediate Similarity NPC48803
0.8352 Intermediate Similarity NPC258216
0.8315 Intermediate Similarity NPC207114
0.8315 Intermediate Similarity NPC471149
0.8315 Intermediate Similarity NPC217983
0.8313 Intermediate Similarity NPC208223
0.8295 Intermediate Similarity NPC67493
0.8295 Intermediate Similarity NPC304558
0.8295 Intermediate Similarity NPC187661
0.828 Intermediate Similarity NPC24956
0.828 Intermediate Similarity NPC18019
0.8235 Intermediate Similarity NPC51507
0.8222 Intermediate Similarity NPC283409
0.8202 Intermediate Similarity NPC190753
0.8191 Intermediate Similarity NPC474313
0.8191 Intermediate Similarity NPC169205
0.8182 Intermediate Similarity NPC33570
0.8182 Intermediate Similarity NPC21471
0.8172 Intermediate Similarity NPC472873
0.8172 Intermediate Similarity NPC476053
0.8125 Intermediate Similarity NPC477950
0.8118 Intermediate Similarity NPC19841
0.8111 Intermediate Similarity NPC53158
0.8105 Intermediate Similarity NPC141191
0.8085 Intermediate Similarity NPC185553
0.8085 Intermediate Similarity NPC126156
0.8068 Intermediate Similarity NPC224386
0.8068 Intermediate Similarity NPC194859
0.8065 Intermediate Similarity NPC127019
0.8046 Intermediate Similarity NPC246076
0.8043 Intermediate Similarity NPC300312
0.8043 Intermediate Similarity NPC131209
0.8043 Intermediate Similarity NPC123177
0.8043 Intermediate Similarity NPC74103
0.8043 Intermediate Similarity NPC70595
0.8043 Intermediate Similarity NPC261607
0.8043 Intermediate Similarity NPC150978
0.8043 Intermediate Similarity NPC133698
0.8043 Intermediate Similarity NPC111114
0.8023 Intermediate Similarity NPC74673
0.8023 Intermediate Similarity NPC258965
0.8023 Intermediate Similarity NPC69271
0.8023 Intermediate Similarity NPC156658
0.8022 Intermediate Similarity NPC472872
0.8 Intermediate Similarity NPC477949
0.8 Intermediate Similarity NPC471150
0.7979 Intermediate Similarity NPC67584
0.7979 Intermediate Similarity NPC52044
0.7979 Intermediate Similarity NPC170120
0.7979 Intermediate Similarity NPC475900
0.7979 Intermediate Similarity NPC213698
0.7978 Intermediate Similarity NPC235792
0.7957 Intermediate Similarity NPC135776
0.7955 Intermediate Similarity NPC111409
0.7955 Intermediate Similarity NPC128246
0.7952 Intermediate Similarity NPC48641
0.7935 Intermediate Similarity NPC301969
0.7935 Intermediate Similarity NPC37607
0.7935 Intermediate Similarity NPC253144
0.7931 Intermediate Similarity NPC47635
0.7917 Intermediate Similarity NPC45125
0.7912 Intermediate Similarity NPC91248
0.7907 Intermediate Similarity NPC182550
0.7901 Intermediate Similarity NPC5714
0.7895 Intermediate Similarity NPC213078
0.7895 Intermediate Similarity NPC476009
0.7889 Intermediate Similarity NPC9231
0.7889 Intermediate Similarity NPC470242
0.7872 Intermediate Similarity NPC262133
0.7872 Intermediate Similarity NPC470013
0.7872 Intermediate Similarity NPC477131
0.7872 Intermediate Similarity NPC470010
0.7872 Intermediate Similarity NPC323008
0.7872 Intermediate Similarity NPC198853
0.7849 Intermediate Similarity NPC475925
0.7849 Intermediate Similarity NPC284185
0.7835 Intermediate Similarity NPC471381
0.7835 Intermediate Similarity NPC186861
0.7826 Intermediate Similarity NPC117405
0.7826 Intermediate Similarity NPC212664
0.7826 Intermediate Similarity NPC52198
0.7816 Intermediate Similarity NPC276356
0.7812 Intermediate Similarity NPC181151
0.7812 Intermediate Similarity NPC161493
0.7805 Intermediate Similarity NPC18543
0.7802 Intermediate Similarity NPC270270
0.78 Intermediate Similarity NPC44004
0.7789 Intermediate Similarity NPC469873
0.7778 Intermediate Similarity NPC161957
0.7778 Intermediate Similarity NPC165162
0.7766 Intermediate Similarity NPC475788
0.7742 Intermediate Similarity NPC129419
0.7732 Intermediate Similarity NPC221615
0.7727 Intermediate Similarity NPC126248
0.7717 Intermediate Similarity NPC224652
0.7701 Intermediate Similarity NPC470244
0.7701 Intermediate Similarity NPC470239
0.77 Intermediate Similarity NPC203659
0.77 Intermediate Similarity NPC309190
0.7692 Intermediate Similarity NPC107787
0.7692 Intermediate Similarity NPC162071
0.7692 Intermediate Similarity NPC64153
0.7677 Intermediate Similarity NPC225353
0.7667 Intermediate Similarity NPC165287
0.7667 Intermediate Similarity NPC115786
0.7647 Intermediate Similarity NPC255082
0.7647 Intermediate Similarity NPC179922
0.764 Intermediate Similarity NPC89555
0.7634 Intermediate Similarity NPC32922
0.7634 Intermediate Similarity NPC268298
0.7614 Intermediate Similarity NPC223904
0.7614 Intermediate Similarity NPC302426
0.7604 Intermediate Similarity NPC304886
0.76 Intermediate Similarity NPC110989
0.7582 Intermediate Similarity NPC245434
0.7582 Intermediate Similarity NPC78089
0.7579 Intermediate Similarity NPC472874
0.7576 Intermediate Similarity NPC150923
0.7576 Intermediate Similarity NPC206079
0.7576 Intermediate Similarity NPC474742
0.7556 Intermediate Similarity NPC39588
0.7553 Intermediate Similarity NPC469368
0.7553 Intermediate Similarity NPC71533
0.7553 Intermediate Similarity NPC106510
0.7551 Intermediate Similarity NPC54843
0.7549 Intermediate Similarity NPC26617
0.7528 Intermediate Similarity NPC281949
0.7528 Intermediate Similarity NPC35089
0.7528 Intermediate Similarity NPC10276
0.7528 Intermediate Similarity NPC25684
0.7528 Intermediate Similarity NPC301477
0.7525 Intermediate Similarity NPC100487
0.7525 Intermediate Similarity NPC294259
0.75 Intermediate Similarity NPC70555
0.75 Intermediate Similarity NPC474590
0.75 Intermediate Similarity NPC477920
0.75 Intermediate Similarity NPC474747
0.75 Intermediate Similarity NPC472013

  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 NPC201658 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
0.837 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD5785 Approved
0.7549 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD1695 Approved
0.7333 Intermediate Similarity NPD5369 Approved
0.7333 Intermediate Similarity NPD6371 Approved
0.7204 Intermediate Similarity NPD5363 Approved
0.7065 Intermediate Similarity NPD4270 Approved
0.7065 Intermediate Similarity NPD4269 Approved
0.697 Remote Similarity NPD5282 Discontinued
0.6947 Remote Similarity NPD5786 Approved
0.6863 Remote Similarity NPD4225 Approved
0.6848 Remote Similarity NPD4252 Approved
0.6842 Remote Similarity NPD1694 Approved
0.6809 Remote Similarity NPD5362 Discontinued
0.6786 Remote Similarity NPD7115 Discovery
0.6733 Remote Similarity NPD5695 Phase 3
0.6702 Remote Similarity NPD6435 Approved
0.6702 Remote Similarity NPD5209 Approved
0.67 Remote Similarity NPD6399 Phase 3
0.6699 Remote Similarity NPD5696 Approved
0.6667 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1733 Clinical (unspecified phase)
0.663 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6602 Remote Similarity NPD6084 Phase 2
0.6602 Remote Similarity NPD6083 Phase 2
0.6526 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6489 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6489 Remote Similarity NPD5368 Approved
0.6489 Remote Similarity NPD4820 Approved
0.6489 Remote Similarity NPD4821 Approved
0.6489 Remote Similarity NPD4819 Approved
0.6489 Remote Similarity NPD4822 Approved
0.6465 Remote Similarity NPD6903 Approved
0.6458 Remote Similarity NPD4788 Approved
0.6458 Remote Similarity NPD7154 Phase 3
0.6436 Remote Similarity NPD8035 Phase 2
0.6436 Remote Similarity NPD5693 Phase 1
0.6436 Remote Similarity NPD6411 Approved
0.6436 Remote Similarity NPD8034 Phase 2
0.6429 Remote Similarity NPD6053 Discontinued
0.6429 Remote Similarity NPD7521 Approved
0.6429 Remote Similarity NPD6684 Approved
0.6429 Remote Similarity NPD7334 Approved
0.6429 Remote Similarity NPD6409 Approved
0.6429 Remote Similarity NPD4249 Approved
0.6429 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7146 Approved
0.6429 Remote Similarity NPD5330 Approved
0.6422 Remote Similarity NPD5697 Approved
0.6408 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6881 Approved
0.6364 Remote Similarity NPD7320 Approved
0.6364 Remote Similarity NPD4250 Approved
0.6364 Remote Similarity NPD6899 Approved
0.6364 Remote Similarity NPD4251 Approved
0.6339 Remote Similarity NPD6650 Approved
0.6339 Remote Similarity NPD6649 Approved
0.6337 Remote Similarity NPD5207 Approved
0.633 Remote Similarity NPD6008 Approved
0.633 Remote Similarity NPD5739 Approved
0.633 Remote Similarity NPD6675 Approved
0.633 Remote Similarity NPD7128 Approved
0.633 Remote Similarity NPD6402 Approved
0.6306 Remote Similarity NPD6013 Approved
0.6306 Remote Similarity NPD6012 Approved
0.6306 Remote Similarity NPD6373 Approved
0.6306 Remote Similarity NPD6372 Approved
0.6306 Remote Similarity NPD6014 Approved
0.63 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6289 Remote Similarity NPD5332 Approved
0.6289 Remote Similarity NPD5331 Approved
0.6277 Remote Similarity NPD4802 Phase 2
0.6277 Remote Similarity NPD4238 Approved
0.6277 Remote Similarity NPD4268 Approved
0.6277 Remote Similarity NPD4271 Approved
0.6275 Remote Similarity NPD5284 Approved
0.6275 Remote Similarity NPD7637 Suspended
0.6275 Remote Similarity NPD5281 Approved
0.6273 Remote Similarity NPD5701 Approved
0.625 Remote Similarity NPD7102 Approved
0.625 Remote Similarity NPD5210 Approved
0.625 Remote Similarity NPD7290 Approved
0.625 Remote Similarity NPD6883 Approved
0.625 Remote Similarity NPD4790 Discontinued
0.625 Remote Similarity NPD4629 Approved
0.6238 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6238 Remote Similarity NPD6101 Approved
0.6238 Remote Similarity NPD4753 Phase 2
0.6226 Remote Similarity NPD7638 Approved
0.6224 Remote Similarity NPD3666 Approved
0.6224 Remote Similarity NPD3665 Phase 1
0.6224 Remote Similarity NPD3133 Approved
0.6216 Remote Similarity NPD6011 Approved
0.6214 Remote Similarity NPD5778 Approved
0.6214 Remote Similarity NPD5779 Approved
0.6195 Remote Similarity NPD6847 Approved
0.6195 Remote Similarity NPD6869 Approved
0.6195 Remote Similarity NPD6617 Approved
0.6195 Remote Similarity NPD8130 Phase 1
0.6186 Remote Similarity NPD3667 Approved
0.618 Remote Similarity NPD229 Approved
0.6176 Remote Similarity NPD6698 Approved
0.6176 Remote Similarity NPD46 Approved
0.6168 Remote Similarity NPD7640 Approved
0.6168 Remote Similarity NPD7639 Approved
0.6162 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6001 Approved
0.614 Remote Similarity NPD8297 Approved
0.614 Remote Similarity NPD6882 Approved
0.6139 Remote Similarity NPD5737 Approved
0.6139 Remote Similarity NPD6672 Approved
0.6116 Remote Similarity NPD7492 Approved
0.61 Remote Similarity NPD3618 Phase 1
0.6078 Remote Similarity NPD6080 Approved
0.6078 Remote Similarity NPD5370 Suspended
0.6078 Remote Similarity NPD6904 Approved
0.6078 Remote Similarity NPD6673 Approved
0.6071 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6071 Remote Similarity NPD6686 Approved
0.6066 Remote Similarity NPD6616 Approved
0.6061 Remote Similarity NPD4786 Approved
0.6055 Remote Similarity NPD5211 Phase 2
0.605 Remote Similarity NPD6319 Approved
0.605 Remote Similarity NPD6054 Approved
0.602 Remote Similarity NPD4221 Approved
0.602 Remote Similarity NPD4223 Phase 3
0.6019 Remote Similarity NPD5286 Approved
0.6019 Remote Similarity NPD5692 Phase 3
0.6019 Remote Similarity NPD4696 Approved
0.6019 Remote Similarity NPD5285 Approved
0.6016 Remote Similarity NPD7078 Approved
0.6 Remote Similarity NPD6015 Approved
0.6 Remote Similarity NPD6016 Approved
0.6 Remote Similarity NPD7748 Approved
0.6 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6 Remote Similarity NPD3198 Approved
0.5983 Remote Similarity NPD6274 Approved
0.5981 Remote Similarity NPD7902 Approved
0.5981 Remote Similarity NPD4755 Approved
0.598 Remote Similarity NPD5208 Approved
0.5968 Remote Similarity NPD7736 Approved
0.5962 Remote Similarity NPD6050 Approved
0.5962 Remote Similarity NPD7983 Approved
0.5962 Remote Similarity NPD5694 Approved
0.5962 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5957 Remote Similarity NPD3702 Approved
0.595 Remote Similarity NPD5988 Approved
0.595 Remote Similarity NPD6370 Approved
0.5946 Remote Similarity NPD5141 Approved
0.5941 Remote Similarity NPD5690 Phase 2
0.5941 Remote Similarity NPD6098 Approved
0.5941 Remote Similarity NPD5279 Phase 3
0.5922 Remote Similarity NPD6051 Approved
0.592 Remote Similarity NPD7319 Approved
0.5917 Remote Similarity NPD6059 Approved
0.5913 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5909 Remote Similarity NPD5224 Approved
0.5909 Remote Similarity NPD4633 Approved
0.5909 Remote Similarity NPD5225 Approved
0.5909 Remote Similarity NPD5226 Approved
0.5905 Remote Similarity NPD4202 Approved
0.59 Remote Similarity NPD4197 Approved
0.59 Remote Similarity NPD3668 Phase 3
0.5887 Remote Similarity NPD8293 Discontinued
0.5872 Remote Similarity NPD4700 Approved
0.5865 Remote Similarity NPD7838 Discovery
0.5856 Remote Similarity NPD6052 Approved
0.5856 Remote Similarity NPD5174 Approved
0.5856 Remote Similarity NPD5175 Approved
0.5843 Remote Similarity NPD9496 Clinical (unspecified phase)
0.5842 Remote Similarity NPD5329 Approved
0.5841 Remote Similarity NPD6412 Phase 2
0.5833 Remote Similarity NPD7100 Approved
0.5833 Remote Similarity NPD7101 Approved
0.5826 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5826 Remote Similarity NPD4634 Approved
0.5825 Remote Similarity NPD4518 Approved
0.5818 Remote Similarity NPD5223 Approved
0.5818 Remote Similarity NPD1700 Approved
0.5816 Remote Similarity NPD4695 Discontinued
0.5812 Remote Similarity NPD4632 Approved
0.5812 Remote Similarity NPD8133 Approved
0.581 Remote Similarity NPD6079 Approved
0.581 Remote Similarity NPD7515 Phase 2
0.5806 Remote Similarity NPD7507 Approved
0.5806 Remote Similarity NPD5777 Approved
0.58 Remote Similarity NPD6695 Phase 3
0.5798 Remote Similarity NPD6317 Approved
0.5789 Remote Similarity NPD8039 Approved
0.5784 Remote Similarity NPD4693 Phase 3
0.5784 Remote Similarity NPD4690 Approved
0.5784 Remote Similarity NPD4694 Approved
0.5784 Remote Similarity NPD4688 Approved
0.5784 Remote Similarity NPD4138 Approved
0.5784 Remote Similarity NPD5205 Approved
0.5784 Remote Similarity NPD5280 Approved
0.5784 Remote Similarity NPD4689 Approved
0.5776 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5769 Remote Similarity NPD5328 Approved

  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