NPASS Compound

Structure

CID189730 OpenBabel06191715572D 33 38 0 0 1 0 0 0 0 0999 V2000 2.5880 3.5251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4376 -1.0932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8286 -4.0995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8587 -4.1025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3110 -3.2580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3711 -3.2640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8234 -2.4195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7008 -1.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6214 -1.3034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1717 -0.0142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5293 1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8300 1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8376 -2.4307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4466 1.0843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8535 -2.4225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9759 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 1.9517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0120 -1.9402 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8172 -0.3534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0923 0.2912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5293 0.4801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8300 0.4801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6676 -1.9505 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6796 -0.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6736 -0.9806 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0060 -0.9702 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5306 -2.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6736 -0.9868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 3.0006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4376 -0.0443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6542 0.1368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0576 0.1958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 30 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 16 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 22 2 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 31 1 0 0 0 0 14 32 1 0 0 0 0 15 18 1 0 0 0 0 17 29 1 0 0 0 0 18 26 1 1 0 0 0 19 20 2 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 24 2 0 0 0 0 21 30 1 0 0 0 0 22 24 1 0 0 0 0 22 33 1 0 0 0 0 23 25 1 6 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 1 0 0 0 25 28 1 0 0 0 0 26 16 1 1 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.15
Volume:	444.717
LogP:	3.753
LogD:	3.553
LogS:	-5.29
# Rotatable Bonds:	4
TPSA:	86.61
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	3.865
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.378
MDCK Permeability:	6.0022306570317596e-05
Pgp-inhibitor:	0.836
Pgp-substrate:	0.889
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.583
Plasma Protein Binding (PPB):	95.36222076416016%
Volume Distribution (VD):	0.784
Pgp-substrate:	2.621577024459839%

ADMET: Metabolism

CYP1A2-inhibitor:	0.563
CYP1A2-substrate:	0.732
CYP2C19-inhibitor:	0.93
CYP2C19-substrate:	0.674
CYP2C9-inhibitor:	0.888
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.967
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.98
CYP3A4-substrate:	0.828

ADMET: Excretion

Clearance (CL):	11.167
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.488
Human Hepatotoxicity (H-HT):	0.672
Drug-inuced Liver Injury (DILI):	0.191
AMES Toxicity:	0.287
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.074
Carcinogencity:	0.919
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC189730

Natural Product ID:	NPC189730
*Common Name:**	4'-Demethoxy-3',4'-Methylenedioxyrocaglaol
IUPAC Name:	(1R,3S,3aR,8bS)-3a-(1,3-benzodioxol-5-yl)-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1,8b-diol
Synonyms:
Standard InCHIKey:	ZPHNJERYFDKEMS-LHVBDCGNSA-N
Standard InCHI:	InChI=1S/C26H24O7/c1-29-17-11-21(30-2)24-22(12-17)33-26(16-8-9-19-20(10-16)32-14-31-19)18(13-23(27)25(24,26)28)15-6-4-3-5-7-15/h3-12,18,23,27-28H,13-14H2,1-2H3/t18-,23+,25+,26-/m0/s1
SMILES:	COc1cc(c2c(c1)O[C@@]1(c3ccc4c(c3)OCO4)[C@@H](C[C@H]([C@@]21O)O)c1ccccc1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332223
PubChem CID:	10623340
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0003109] Flavaglines

*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
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	Leaf Diffusate	n.a.	n.a.	Database[FooDB]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27623	Citrus japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20222	Franseria ambrosioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23171	Hygrophorus olivaceoalbus	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23092	Ammodendron karelinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28052	Miriquidica leucophaea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27623	Citrus japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19682	Duguetia chrysocarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20667	Cereus queretaroensis	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22318	Sechium edule	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13294	Pinus yunnanensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18179	Leucopaxillus amarus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21632	Chlorobium phaeovibrioides	Species	Chlorobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO993	Phaseolus coccineus	Species	Fabaceae	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

Activity Type	# Activity
ED50	3

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.0067	uM	PMID[463363]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	ED50	=	0.33	uM	PMID[463363]
NPT27	Others	Unspecified		ED50	>	50.0	uM	PMID[463363]

☑ 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 NPC189730 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	480
0.1-0.2	1576
0.2-0.3	3962
0.3-0.4	10047
0.4-0.5	8892
0.5-0.6	5447
0.6-0.7	8407
0.7-0.8	3107
0.8-0.85	674
0.85-0.9	99
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC164152
0.9241	High Similarity	NPC475621
0.9122	High Similarity	NPC184607
0.908	High Similarity	NPC23593
0.9054	High Similarity	NPC470937
0.9018	High Similarity	NPC107739
0.897	High Similarity	NPC236089
0.8963	High Similarity	NPC263955
0.894	High Similarity	NPC162193
0.8909	High Similarity	NPC29587
0.8882	High Similarity	NPC20360
0.8874	High Similarity	NPC180953
0.8824	High Similarity	NPC301961
0.8824	High Similarity	NPC166584
0.8816	High Similarity	NPC324492
0.8816	High Similarity	NPC317053
0.8808	High Similarity	NPC179521
0.88	High Similarity	NPC302506
0.8766	High Similarity	NPC286235
0.8766	High Similarity	NPC240521
0.8766	High Similarity	NPC51328
0.8766	High Similarity	NPC55158
0.8758	High Similarity	NPC327412
0.8758	High Similarity	NPC320970
0.8758	High Similarity	NPC328567
0.8758	High Similarity	NPC320671
0.875	High Similarity	NPC474749
0.875	High Similarity	NPC42716
0.875	High Similarity	NPC11422
0.875	High Similarity	NPC178014
0.8742	High Similarity	NPC298317
0.8742	High Similarity	NPC81638
0.8742	High Similarity	NPC474808
0.8742	High Similarity	NPC255566
0.8726	High Similarity	NPC159922
0.8716	High Similarity	NPC25695
0.8716	High Similarity	NPC172818
0.871	High Similarity	NPC238140
0.8701	High Similarity	NPC130449
0.8701	High Similarity	NPC71726
0.8701	High Similarity	NPC270751
0.8701	High Similarity	NPC248132
0.8693	High Similarity	NPC226540
0.8693	High Similarity	NPC211758
0.8693	High Similarity	NPC87794
0.8684	High Similarity	NPC470097
0.8684	High Similarity	NPC471415
0.8684	High Similarity	NPC114119
0.8675	High Similarity	NPC80326
0.8675	High Similarity	NPC174522
0.8667	High Similarity	NPC226547
0.8667	High Similarity	NPC46591
0.8667	High Similarity	NPC177868
0.8658	High Similarity	NPC185908
0.8636	High Similarity	NPC39657
0.8627	High Similarity	NPC307466
0.8627	High Similarity	NPC181615
0.8618	High Similarity	NPC12728
0.8618	High Similarity	NPC185071
0.8609	High Similarity	NPC58137
0.8609	High Similarity	NPC476334
0.8609	High Similarity	NPC300798
0.86	High Similarity	NPC292487
0.8599	High Similarity	NPC51543
0.859	High Similarity	NPC472709
0.859	High Similarity	NPC98624
0.859	High Similarity	NPC472710
0.8571	High Similarity	NPC99515
0.8571	High Similarity	NPC260397
0.8571	High Similarity	NPC190714
0.8571	High Similarity	NPC93610
0.8571	High Similarity	NPC112861
0.8571	High Similarity	NPC241846
0.8562	High Similarity	NPC317237
0.8562	High Similarity	NPC44530
0.8562	High Similarity	NPC277951
0.8562	High Similarity	NPC172171
0.8562	High Similarity	NPC239254
0.8553	High Similarity	NPC472562
0.8553	High Similarity	NPC246947
0.8544	High Similarity	NPC87363
0.8543	High Similarity	NPC184797
0.8543	High Similarity	NPC56091
0.8543	High Similarity	NPC309124
0.8535	High Similarity	NPC324517
0.8535	High Similarity	NPC329343
0.8535	High Similarity	NPC321972
0.8533	High Similarity	NPC477938
0.8533	High Similarity	NPC474039
0.8533	High Similarity	NPC283949
0.8526	High Similarity	NPC55715
0.8526	High Similarity	NPC35877
0.8526	High Similarity	NPC95392
0.8523	High Similarity	NPC189474
0.8523	High Similarity	NPC174191
0.8523	High Similarity	NPC18576
0.8523	High Similarity	NPC150534
0.8514	High Similarity	NPC196937
0.8514	High Similarity	NPC136750
0.8514	High Similarity	NPC266848
0.8514	High Similarity	NPC58585
0.8506	High Similarity	NPC279298
0.8506	High Similarity	NPC22150
0.8506	High Similarity	NPC475096
0.8506	High Similarity	NPC18979
0.8506	High Similarity	NPC205316
0.8506	High Similarity	NPC475868
0.8506	High Similarity	NPC43508
0.8506	High Similarity	NPC38041
0.8506	High Similarity	NPC469586
0.8506	High Similarity	NPC476301
0.8497	Intermediate Similarity	NPC274721
0.8497	Intermediate Similarity	NPC155392
0.8497	Intermediate Similarity	NPC135767
0.8497	Intermediate Similarity	NPC265154
0.8487	Intermediate Similarity	NPC87725
0.8487	Intermediate Similarity	NPC312199
0.8487	Intermediate Similarity	NPC263261
0.8481	Intermediate Similarity	NPC302610
0.8477	Intermediate Similarity	NPC473739
0.8477	Intermediate Similarity	NPC232164
0.8477	Intermediate Similarity	NPC9068
0.8477	Intermediate Similarity	NPC193666
0.8477	Intermediate Similarity	NPC236306
0.8477	Intermediate Similarity	NPC123526
0.8477	Intermediate Similarity	NPC88640
0.8462	Intermediate Similarity	NPC175976
0.8462	Intermediate Similarity	NPC226153
0.8462	Intermediate Similarity	NPC304048
0.8456	Intermediate Similarity	NPC47181
0.8456	Intermediate Similarity	NPC31530
0.8452	Intermediate Similarity	NPC252286
0.8452	Intermediate Similarity	NPC154971
0.8452	Intermediate Similarity	NPC33832
0.8452	Intermediate Similarity	NPC125755
0.8452	Intermediate Similarity	NPC212890
0.8446	Intermediate Similarity	NPC104077
0.8446	Intermediate Similarity	NPC65183
0.8446	Intermediate Similarity	NPC259742
0.8446	Intermediate Similarity	NPC261812
0.8446	Intermediate Similarity	NPC7744
0.8446	Intermediate Similarity	NPC147616
0.8446	Intermediate Similarity	NPC72046
0.8446	Intermediate Similarity	NPC219671
0.8442	Intermediate Similarity	NPC79429
0.8442	Intermediate Similarity	NPC118385
0.8442	Intermediate Similarity	NPC84181
0.8442	Intermediate Similarity	NPC473045
0.8442	Intermediate Similarity	NPC217635
0.8442	Intermediate Similarity	NPC477701
0.8442	Intermediate Similarity	NPC141569
0.8442	Intermediate Similarity	NPC25292
0.8442	Intermediate Similarity	NPC472712
0.8442	Intermediate Similarity	NPC283995
0.8442	Intermediate Similarity	NPC187774
0.8442	Intermediate Similarity	NPC472713
0.8442	Intermediate Similarity	NPC166884
0.8442	Intermediate Similarity	NPC129417
0.8442	Intermediate Similarity	NPC473046
0.8442	Intermediate Similarity	NPC470235
0.8442	Intermediate Similarity	NPC471667
0.8431	Intermediate Similarity	NPC287124
0.8431	Intermediate Similarity	NPC230538
0.8431	Intermediate Similarity	NPC107161
0.8431	Intermediate Similarity	NPC36531
0.8431	Intermediate Similarity	NPC189115
0.8431	Intermediate Similarity	NPC41782
0.8431	Intermediate Similarity	NPC475084
0.8431	Intermediate Similarity	NPC253878
0.8431	Intermediate Similarity	NPC103637
0.8431	Intermediate Similarity	NPC229172
0.8428	Intermediate Similarity	NPC78809
0.8421	Intermediate Similarity	NPC284464
0.8421	Intermediate Similarity	NPC254759
0.8421	Intermediate Similarity	NPC160283
0.8421	Intermediate Similarity	NPC291101
0.8421	Intermediate Similarity	NPC27495
0.8421	Intermediate Similarity	NPC266197
0.8411	Intermediate Similarity	NPC101807
0.8408	Intermediate Similarity	NPC470826
0.8408	Intermediate Similarity	NPC470098
0.8408	Intermediate Similarity	NPC473266
0.84	Intermediate Similarity	NPC142547
0.84	Intermediate Similarity	NPC148893
0.84	Intermediate Similarity	NPC126409
0.84	Intermediate Similarity	NPC61946
0.84	Intermediate Similarity	NPC135777
0.84	Intermediate Similarity	NPC25333
0.84	Intermediate Similarity	NPC99572
0.84	Intermediate Similarity	NPC49235
0.8397	Intermediate Similarity	NPC227902
0.8397	Intermediate Similarity	NPC114505
0.8397	Intermediate Similarity	NPC224674
0.8397	Intermediate Similarity	NPC275284
0.8397	Intermediate Similarity	NPC99183
0.8397	Intermediate Similarity	NPC193473
0.8397	Intermediate Similarity	NPC213074
0.8397	Intermediate Similarity	NPC31325
0.8397	Intermediate Similarity	NPC15956
0.8389	Intermediate Similarity	NPC263064

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 NPC189730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	879
0.2-0.3	1952
0.3-0.4	2811
0.4-0.5	1692
0.5-0.6	966
0.6-0.7	408
0.7-0.8	60
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD7199	Phase 2
0.8303	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD4965	Approved
0.816	Intermediate Similarity	NPD4967	Phase 2
0.816	Intermediate Similarity	NPD4966	Approved
0.8079	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1613	Approved
0.8061	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD3027	Phase 3
0.7975	Intermediate Similarity	NPD37	Approved
0.7836	Intermediate Similarity	NPD7228	Approved
0.7815	Intermediate Similarity	NPD4908	Phase 1
0.7815	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6674	Discontinued
0.7748	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2861	Phase 2
0.763	Intermediate Similarity	NPD3818	Discontinued
0.7622	Intermediate Similarity	NPD1653	Approved
0.7564	Intermediate Similarity	NPD5735	Approved
0.7557	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3620	Phase 2
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3705	Approved
0.7467	Intermediate Similarity	NPD1091	Approved
0.7467	Intermediate Similarity	NPD1610	Phase 2
0.7458	Intermediate Similarity	NPD7685	Pre-registration
0.7443	Intermediate Similarity	NPD7074	Phase 3
0.7438	Intermediate Similarity	NPD5763	Approved
0.7438	Intermediate Similarity	NPD5762	Approved
0.7386	Intermediate Similarity	NPD7054	Approved
0.7345	Intermediate Similarity	NPD7472	Approved
0.7337	Intermediate Similarity	NPD1934	Approved
0.7317	Intermediate Similarity	NPD5058	Phase 3
0.7314	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6166	Phase 2
0.731	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5844	Phase 1
0.7267	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1357	Approved
0.7263	Intermediate Similarity	NPD6559	Discontinued
0.7261	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4749	Approved
0.7246	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6002	Phase 3
0.7222	Intermediate Similarity	NPD6004	Phase 3
0.7222	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7808	Phase 3
0.7222	Intermediate Similarity	NPD6005	Phase 3
0.7222	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7028	Phase 2
0.7207	Intermediate Similarity	NPD6797	Phase 2
0.72	Intermediate Similarity	NPD1548	Phase 1
0.7197	Intermediate Similarity	NPD4625	Phase 3
0.7195	Intermediate Similarity	NPD3892	Phase 2
0.7193	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6353	Approved
0.7188	Intermediate Similarity	NPD6653	Approved
0.7179	Intermediate Similarity	NPD3018	Phase 2
0.7173	Intermediate Similarity	NPD7680	Approved
0.717	Intermediate Similarity	NPD4140	Approved
0.7168	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7251	Discontinued
0.7161	Intermediate Similarity	NPD3094	Phase 2
0.7143	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7549	Discontinued
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7266	Discontinued
0.711	Intermediate Similarity	NPD3882	Suspended
0.7102	Intermediate Similarity	NPD3787	Discontinued
0.7095	Intermediate Similarity	NPD5283	Phase 1
0.7093	Intermediate Similarity	NPD2801	Approved
0.7093	Intermediate Similarity	NPD8455	Phase 2
0.7086	Intermediate Similarity	NPD5494	Approved
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7053	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD3817	Phase 2
0.7045	Intermediate Similarity	NPD8127	Discontinued
0.7032	Intermediate Similarity	NPD5327	Phase 3
0.7032	Intermediate Similarity	NPD2983	Phase 2
0.7032	Intermediate Similarity	NPD2982	Phase 2
0.7019	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD5124	Phase 1
0.7012	Intermediate Similarity	NPD1375	Discontinued
0.6988	Remote Similarity	NPD7466	Approved
0.6968	Remote Similarity	NPD2981	Phase 2
0.6954	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3751	Discontinued
0.6937	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6798	Discontinued
0.6928	Remote Similarity	NPD1652	Phase 2
0.6923	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3657	Discovery
0.691	Remote Similarity	NPD7229	Phase 3
0.691	Remote Similarity	NPD6232	Discontinued
0.6906	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3092	Approved
0.6899	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4624	Approved
0.6897	Remote Similarity	NPD2978	Approved
0.6897	Remote Similarity	NPD2977	Approved
0.689	Remote Similarity	NPD7033	Discontinued
0.689	Remote Similarity	NPD5588	Approved
0.6889	Remote Similarity	NPD7473	Discontinued
0.6886	Remote Similarity	NPD4110	Phase 3
0.6886	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6331	Phase 2
0.6879	Remote Similarity	NPD8651	Approved
0.6875	Remote Similarity	NPD7095	Approved
0.6864	Remote Similarity	NPD7212	Phase 2
0.6864	Remote Similarity	NPD7213	Phase 3
0.6864	Remote Similarity	NPD1511	Approved
0.686	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3384	Approved
0.6839	Remote Similarity	NPD3383	Approved
0.6839	Remote Similarity	NPD3382	Approved
0.6829	Remote Similarity	NPD4536	Approved
0.6829	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4538	Approved
0.6829	Remote Similarity	NPD7097	Phase 1
0.6826	Remote Similarity	NPD5177	Phase 3
0.6824	Remote Similarity	NPD7447	Phase 1
0.6821	Remote Similarity	NPD4675	Approved
0.6821	Remote Similarity	NPD4678	Approved
0.6816	Remote Similarity	NPD3051	Approved
0.6791	Remote Similarity	NPD4663	Approved
0.679	Remote Similarity	NPD6233	Phase 2
0.6784	Remote Similarity	NPD1512	Approved
0.6784	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD2970	Approved
0.6778	Remote Similarity	NPD2969	Approved
0.6776	Remote Similarity	NPD7157	Approved
0.6774	Remote Similarity	NPD5126	Approved
0.6774	Remote Similarity	NPD5846	Approved
0.6774	Remote Similarity	NPD5125	Phase 3
0.6774	Remote Similarity	NPD6516	Phase 2
0.6763	Remote Similarity	NPD4005	Discontinued
0.6761	Remote Similarity	NPD2563	Approved
0.6761	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2560	Approved
0.6757	Remote Similarity	NPD2684	Approved
0.6755	Remote Similarity	NPD6843	Phase 3
0.6755	Remote Similarity	NPD6842	Approved
0.6755	Remote Similarity	NPD6841	Approved
0.6755	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2238	Phase 2
0.6747	Remote Similarity	NPD6100	Approved
0.6747	Remote Similarity	NPD2161	Phase 2
0.6747	Remote Similarity	NPD6099	Approved
0.6746	Remote Similarity	NPD2677	Approved
0.6733	Remote Similarity	NPD228	Approved
0.6726	Remote Similarity	NPD4237	Approved
0.6726	Remote Similarity	NPD4236	Phase 3
0.6724	Remote Similarity	NPD4380	Phase 2
0.672	Remote Similarity	NPD4578	Approved
0.672	Remote Similarity	NPD4577	Approved
0.6707	Remote Similarity	NPD3540	Phase 1
0.6706	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5761	Phase 2
0.6705	Remote Similarity	NPD5760	Phase 2
0.6705	Remote Similarity	NPD4210	Discontinued
0.6705	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1465	Phase 2
0.6689	Remote Similarity	NPD290	Approved
0.6689	Remote Similarity	NPD7843	Approved
0.6688	Remote Similarity	NPD422	Phase 1
0.6687	Remote Similarity	NPD5960	Phase 3
0.6687	Remote Similarity	NPD6584	Phase 3
0.6687	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6273	Approved
0.6686	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4628	Phase 3
0.6686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7075	Discontinued
0.6684	Remote Similarity	NPD8053	Approved
0.6684	Remote Similarity	NPD8054	Approved
0.6667	Remote Similarity	NPD2424	Discontinued
0.6667	Remote Similarity	NPD2157	Approved
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD7906	Approved
0.6667	Remote Similarity	NPD6671	Approved
0.6649	Remote Similarity	NPD7007	Discovery
0.6648	Remote Similarity	NPD6801	Discontinued
0.6648	Remote Similarity	NPD2489	Approved
0.6648	Remote Similarity	NPD27	Approved
0.6647	Remote Similarity	NPD3539	Phase 1
0.6647	Remote Similarity	NPD6190	Approved
0.6646	Remote Similarity	NPD1558	Phase 1
0.6646	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7741	Discontinued
0.6645	Remote Similarity	NPD3091	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