NPASS Compound

Structure

NPC239517 OpenBabel07101718222D 45 47 0 0 1 0 0 0 0 0999 V2000 17.7033 -9.7117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.6814 -9.5038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.9905 -8.5528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.3213 -7.8096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.6303 -6.8586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.9612 -6.1154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5155 -1.6309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4291 -1.2242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7065 -1.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.2702 -5.1644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2381 -1.8120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7930 -1.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.6011 -4.4212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1517 -1.4052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9840 -0.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.9101 -3.4702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9607 -1.9930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0704 -1.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.2410 -2.7270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8742 -1.5863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.0888 -0.0547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.2228 0.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3479 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0947 0.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2614 -0.6810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 17.5500 -1.7760 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.9787 -0.5918 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.1002 0.7931 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 16.8809 -1.0328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 15.4796 -0.2238 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.5015 -0.0159 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.8923 -0.1850 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3659 0.3135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.5281 -1.5681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1697 -0.0040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4311 1.5363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 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 15.8863 -1.1374 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.7583 -0.6850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 33 1 0 0 0 0 24 27 1 0 0 0 0 24 28 2 0 0 0 0 25 28 1 0 0 0 0 25 29 1 0 0 0 0 26 32 1 0 0 0 0 27 2 1 1 0 0 0 27 43 1 0 0 0 0 28 37 1 0 0 0 0 29 38 1 6 0 0 0 30 39 1 6 0 0 0 31 40 1 1 0 0 0 32 36 1 0 0 0 0 32 41 1 6 0 0 0 33 30 1 6 0 0 0 33 44 1 0 0 0 0 34 23 1 1 0 0 0 34 35 1 0 0 0 0 34 44 1 0 0 0 0 35 26 1 6 0 0 0 35 45 1 0 0 0 0 36 31 1 1 0 0 0 36 45 1 0 0 0 0 37 42 2 0 0 0 0 37 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	638.48
Volume:	687.887
LogP:	8.344
LogD:	4.484
LogS:	-6.147
# Rotatable Bonds:	25
TPSA:	132.75
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.07
Synthetic Accessibility Score:	4.828
Fsp3:	0.892
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.368
MDCK Permeability:	9.782061169971712e-06
Pgp-inhibitor:	0.129
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.525

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	98.45036315917969%
Volume Distribution (VD):	0.814
Pgp-substrate:	3.051628351211548%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.204
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.984
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.119
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	3.377
Half-life (T1/2):	0.108

ADMET: Toxicity

hERG Blockers:	0.577
Human Hepatotoxicity (H-HT):	0.502
Drug-inuced Liver Injury (DILI):	0.054
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.746
Skin Sensitization:	0.965
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.577

Download Data

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

Natural Product: NPC239517

Natural Product ID:	NPC239517
*Common Name:**	Asimitrin
IUPAC Name:	(2S)-4-[(2R,13R)-2,13-dihydroxy-13-[(2S,3R,5R)-3-hydroxy-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Synonyms:	Asimitrin
Standard InCHIKey:	NNTXABWKPQWPML-SDNTZQKYSA-N
Standard InCHI:	InChI=1S/C37H66O8/c1-3-4-5-6-7-11-14-17-20-30(39)33-22-23-34(44-33)35-26-32(41)36(45-35)31(40)21-18-15-12-9-8-10-13-16-19-29(38)25-28-24-27(2)43-37(28)42/h24,27,29-36,38-41H,3-23,25-26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+,35+,36-/m0/s1
SMILES:	CCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H]1O[C@H]([C@@H](C1)O)[C@@H](CCCCCCCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446217
PubChem CID:	11422308
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11087592]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15730242]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1593281]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30028612]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8676130]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8946743]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7697	Asimina triloba	Species	Annonaceae	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	6
Others	1

Activity Type	# Activity
Cell Line	6
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.19	ug ml-1	PMID[543539]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	2.12	ug ml-1	PMID[543539]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.19	10'-4 ug/ml	PMID[543539]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	1.72	10'-6 ug/ml	PMID[543539]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	=	2.11	10'-4 ug/ml	PMID[543539]
NPT376	Cell Line	A498	Homo sapiens	ED50	=	7.5	10'-1 ug/ml	PMID[543539]
NPT140	Organism	Artemia	Artemia	LC50	=	0.0207	ug.mL-1	PMID[543539]

☑ 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 NPC239517 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	211
0.1-0.2	1493
0.2-0.3	5801
0.3-0.4	13726
0.4-0.5	11417
0.5-0.6	6808
0.6-0.7	2573
0.7-0.8	480
0.8-0.85	24
0.85-0.9	35
0.9-0.95	80
0.95-1	49

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC318963
0.9881	High Similarity	NPC20621
0.9881	High Similarity	NPC81778
0.9881	High Similarity	NPC40066
0.9881	High Similarity	NPC473504
0.9881	High Similarity	NPC91067
0.9881	High Similarity	NPC42598
0.9881	High Similarity	NPC93794
0.9762	High Similarity	NPC133730
0.9762	High Similarity	NPC151403
0.9762	High Similarity	NPC169511
0.9762	High Similarity	NPC191929
0.9762	High Similarity	NPC274446
0.9762	High Similarity	NPC20339
0.9762	High Similarity	NPC21208
0.9762	High Similarity	NPC48338
0.9762	High Similarity	NPC320569
0.9762	High Similarity	NPC171135
0.9762	High Similarity	NPC320458
0.9762	High Similarity	NPC473905
0.9762	High Similarity	NPC81045
0.9762	High Similarity	NPC287164
0.9762	High Similarity	NPC40376
0.9762	High Similarity	NPC233551
0.9762	High Similarity	NPC39754
0.9762	High Similarity	NPC100454
0.9762	High Similarity	NPC280621
0.9762	High Similarity	NPC234077
0.9762	High Similarity	NPC242364
0.9762	High Similarity	NPC172821
0.9762	High Similarity	NPC261952
0.9762	High Similarity	NPC61257
0.9643	High Similarity	NPC476583
0.9643	High Similarity	NPC20533
0.9643	High Similarity	NPC178215
0.9643	High Similarity	NPC258068
0.9524	High Similarity	NPC25703
0.9524	High Similarity	NPC231096
0.9524	High Similarity	NPC62118
0.9524	High Similarity	NPC473840
0.9524	High Similarity	NPC134865
0.9524	High Similarity	NPC293136
0.9524	High Similarity	NPC107717
0.9524	High Similarity	NPC132940
0.9524	High Similarity	NPC240695
0.9524	High Similarity	NPC114694
0.9524	High Similarity	NPC219652
0.9524	High Similarity	NPC232555
0.9524	High Similarity	NPC241360
0.9524	High Similarity	NPC103523
0.9524	High Similarity	NPC171174
0.9524	High Similarity	NPC142117
0.9524	High Similarity	NPC475581
0.9524	High Similarity	NPC282815
0.9419	High Similarity	NPC477011
0.9405	High Similarity	NPC475268
0.9405	High Similarity	NPC202055
0.9405	High Similarity	NPC473156
0.9405	High Similarity	NPC39279
0.9405	High Similarity	NPC77871
0.9405	High Similarity	NPC329838
0.9405	High Similarity	NPC292809
0.9405	High Similarity	NPC470400
0.9405	High Similarity	NPC9678
0.9405	High Similarity	NPC66346
0.9405	High Similarity	NPC110710
0.9405	High Similarity	NPC473651
0.9405	High Similarity	NPC283085
0.9405	High Similarity	NPC132496
0.9405	High Similarity	NPC329615
0.9405	High Similarity	NPC235809
0.9405	High Similarity	NPC319036
0.9405	High Similarity	NPC107986
0.9405	High Similarity	NPC82795
0.9405	High Similarity	NPC25764
0.9405	High Similarity	NPC471567
0.9405	High Similarity	NPC103284
0.9405	High Similarity	NPC120398
0.9405	High Similarity	NPC473671
0.9405	High Similarity	NPC223871
0.9405	High Similarity	NPC477014
0.9405	High Similarity	NPC231009
0.9405	High Similarity	NPC477013
0.9405	High Similarity	NPC1083
0.9405	High Similarity	NPC473478
0.9405	High Similarity	NPC286338
0.9405	High Similarity	NPC473669
0.9405	High Similarity	NPC39167
0.931	High Similarity	NPC473904
0.9302	High Similarity	NPC89001
0.9294	High Similarity	NPC210218
0.9294	High Similarity	NPC134807
0.9294	High Similarity	NPC204686
0.9294	High Similarity	NPC134885
0.9294	High Similarity	NPC219498
0.9294	High Similarity	NPC308412
0.9294	High Similarity	NPC473687
0.9294	High Similarity	NPC477015
0.9294	High Similarity	NPC279267
0.9294	High Similarity	NPC69082
0.9286	High Similarity	NPC156804
0.9286	High Similarity	NPC163093
0.9195	High Similarity	NPC130359
0.9195	High Similarity	NPC139418
0.9195	High Similarity	NPC477016
0.9195	High Similarity	NPC477017
0.9195	High Similarity	NPC280612
0.9195	High Similarity	NPC14901
0.9186	High Similarity	NPC154097
0.9186	High Similarity	NPC473649
0.9186	High Similarity	NPC473995
0.9186	High Similarity	NPC159750
0.9186	High Similarity	NPC470401
0.9176	High Similarity	NPC322529
0.907	High Similarity	NPC112685
0.907	High Similarity	NPC47937
0.9048	High Similarity	NPC11332
0.9048	High Similarity	NPC73310
0.9048	High Similarity	NPC473712
0.9048	High Similarity	NPC473780
0.9048	High Similarity	NPC329829
0.9048	High Similarity	NPC131002
0.9048	High Similarity	NPC475159
0.9048	High Similarity	NPC180363
0.9048	High Similarity	NPC145914
0.9048	High Similarity	NPC473529
0.9048	High Similarity	NPC65930
0.9048	High Similarity	NPC94875
0.8953	High Similarity	NPC477018
0.8953	High Similarity	NPC182383
0.8953	High Similarity	NPC100921
0.8941	High Similarity	NPC144415
0.8941	High Similarity	NPC253801
0.8889	High Similarity	NPC473520
0.8889	High Similarity	NPC473663
0.8889	High Similarity	NPC475173
0.8889	High Similarity	NPC473723
0.8889	High Similarity	NPC11456
0.8889	High Similarity	NPC473561
0.8851	High Similarity	NPC309211
0.8851	High Similarity	NPC477010
0.8778	High Similarity	NPC473707
0.875	High Similarity	NPC477012
0.8298	Intermediate Similarity	NPC36954
0.828	Intermediate Similarity	NPC81419
0.828	Intermediate Similarity	NPC179746
0.828	Intermediate Similarity	NPC476300
0.8261	Intermediate Similarity	NPC473619
0.8229	Intermediate Similarity	NPC187268
0.8172	Intermediate Similarity	NPC473321
0.8172	Intermediate Similarity	NPC184463
0.8172	Intermediate Similarity	NPC208886
0.8172	Intermediate Similarity	NPC12172
0.8172	Intermediate Similarity	NPC30515
0.8163	Intermediate Similarity	NPC86077
0.8085	Intermediate Similarity	NPC288240
0.8085	Intermediate Similarity	NPC295204
0.8085	Intermediate Similarity	NPC273579
0.8085	Intermediate Similarity	NPC162205
0.8085	Intermediate Similarity	NPC475912
0.8065	Intermediate Similarity	NPC51004
0.8041	Intermediate Similarity	NPC473326
0.8022	Intermediate Similarity	NPC469483
0.8021	Intermediate Similarity	NPC279621
0.8021	Intermediate Similarity	NPC476315
0.7957	Intermediate Similarity	NPC92974
0.7957	Intermediate Similarity	NPC295312
0.7957	Intermediate Similarity	NPC307411
0.7955	Intermediate Similarity	NPC133226
0.7955	Intermediate Similarity	NPC470147
0.7917	Intermediate Similarity	NPC471141
0.7917	Intermediate Similarity	NPC270013
0.7917	Intermediate Similarity	NPC471142
0.7917	Intermediate Similarity	NPC14961
0.7912	Intermediate Similarity	NPC21469
0.7895	Intermediate Similarity	NPC212486
0.7889	Intermediate Similarity	NPC284472
0.7889	Intermediate Similarity	NPC286770
0.7889	Intermediate Similarity	NPC229799
0.7889	Intermediate Similarity	NPC116543
0.7872	Intermediate Similarity	NPC473448
0.7872	Intermediate Similarity	NPC478003
0.7872	Intermediate Similarity	NPC158388
0.7872	Intermediate Similarity	NPC474761
0.7872	Intermediate Similarity	NPC474232
0.7872	Intermediate Similarity	NPC478004
0.7872	Intermediate Similarity	NPC476004
0.7857	Intermediate Similarity	NPC471144
0.7849	Intermediate Similarity	NPC58219
0.7849	Intermediate Similarity	NPC177629
0.7849	Intermediate Similarity	NPC202672
0.7849	Intermediate Similarity	NPC473715
0.7843	Intermediate Similarity	NPC26617
0.7841	Intermediate Similarity	NPC470149
0.7841	Intermediate Similarity	NPC470148
0.7841	Intermediate Similarity	NPC180725
0.7835	Intermediate Similarity	NPC306041
0.7835	Intermediate Similarity	NPC477921
0.7816	Intermediate Similarity	NPC475711
0.7816	Intermediate Similarity	NPC474026

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 NPC239517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	2273
0.2-0.3	3862
0.3-0.4	1983
0.4-0.5	606
0.5-0.6	195
0.6-0.7	37
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8065	Intermediate Similarity	NPD6698	Approved
0.8065	Intermediate Similarity	NPD46	Approved
0.7843	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7838	Discovery
0.7423	Intermediate Similarity	NPD7983	Approved
0.7264	Intermediate Similarity	NPD6686	Approved
0.7157	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6371	Approved
0.7064	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4251	Approved
0.6837	Remote Similarity	NPD4250	Approved
0.6735	Remote Similarity	NPD4249	Approved
0.67	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6634	Remote Similarity	NPD5785	Approved
0.6598	Remote Similarity	NPD7154	Phase 3
0.6542	Remote Similarity	NPD5344	Discontinued
0.6525	Remote Similarity	NPD8517	Approved
0.6525	Remote Similarity	NPD8515	Approved
0.6525	Remote Similarity	NPD8516	Approved
0.6525	Remote Similarity	NPD8513	Phase 3
0.6465	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5363	Approved
0.6458	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3197	Phase 1
0.6429	Remote Similarity	NPD5362	Discontinued
0.6404	Remote Similarity	NPD6053	Discontinued
0.6321	Remote Similarity	NPD7839	Suspended
0.6316	Remote Similarity	NPD4756	Discovery
0.6311	Remote Similarity	NPD7507	Approved
0.6286	Remote Similarity	NPD5282	Discontinued
0.6283	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7830	Approved
0.6281	Remote Similarity	NPD7829	Approved
0.626	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD4268	Approved
0.625	Remote Similarity	NPD4271	Approved
0.6228	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7638	Approved
0.62	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5779	Approved
0.619	Remote Similarity	NPD5778	Approved
0.6186	Remote Similarity	NPD7115	Discovery
0.6162	Remote Similarity	NPD4270	Approved
0.6162	Remote Similarity	NPD6435	Approved
0.6162	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4269	Approved
0.616	Remote Similarity	NPD7319	Approved
0.6148	Remote Similarity	NPD7642	Approved
0.6147	Remote Similarity	NPD7639	Approved
0.6147	Remote Similarity	NPD6648	Approved
0.6147	Remote Similarity	NPD7640	Approved
0.6134	Remote Similarity	NPD7641	Discontinued
0.6122	Remote Similarity	NPD4820	Approved
0.6122	Remote Similarity	NPD4252	Approved
0.6122	Remote Similarity	NPD4819	Approved
0.6122	Remote Similarity	NPD4821	Approved
0.6122	Remote Similarity	NPD4822	Approved
0.6116	Remote Similarity	NPD8033	Approved
0.61	Remote Similarity	NPD6110	Phase 1
0.6078	Remote Similarity	NPD5786	Approved
0.6077	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4790	Discontinued
0.6061	Remote Similarity	NPD5369	Approved
0.6033	Remote Similarity	NPD8377	Approved
0.6033	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD7328	Approved
0.5984	Remote Similarity	NPD8296	Approved
0.5984	Remote Similarity	NPD8380	Approved
0.5984	Remote Similarity	NPD8379	Approved
0.5984	Remote Similarity	NPD8378	Approved
0.5984	Remote Similarity	NPD8335	Approved
0.5984	Remote Similarity	NPD8444	Approved
0.598	Remote Similarity	NPD1694	Approved
0.5965	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6412	Phase 2
0.596	Remote Similarity	NPD5368	Approved
0.5952	Remote Similarity	NPD3730	Approved
0.5952	Remote Similarity	NPD3728	Approved
0.595	Remote Similarity	NPD7516	Approved
0.5948	Remote Similarity	NPD6421	Discontinued
0.5941	Remote Similarity	NPD5331	Approved
0.5941	Remote Similarity	NPD5332	Approved
0.5938	Remote Similarity	NPD8039	Approved
0.592	Remote Similarity	NPD8273	Phase 1
0.592	Remote Similarity	NPD8451	Approved
0.5918	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD2204	Approved
0.5873	Remote Similarity	NPD8448	Approved
0.5862	Remote Similarity	NPD9119	Approved
0.5862	Remote Similarity	NPD69	Approved
0.5854	Remote Similarity	NPD8268	Approved
0.5854	Remote Similarity	NPD8269	Approved
0.5854	Remote Similarity	NPD8266	Approved
0.5854	Remote Similarity	NPD8267	Approved
0.5847	Remote Similarity	NPD8297	Approved
0.5842	Remote Similarity	NPD5209	Approved
0.5824	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD7260	Phase 2
0.5798	Remote Similarity	NPD8133	Approved
0.5794	Remote Similarity	NPD7637	Suspended
0.5785	Remote Similarity	NPD7505	Discontinued
0.5785	Remote Similarity	NPD7500	Approved
0.5778	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD6319	Approved
0.5769	Remote Similarity	NPD6845	Suspended
0.5765	Remote Similarity	NPD3196	Approved
0.5765	Remote Similarity	NPD3195	Phase 2
0.5765	Remote Similarity	NPD3194	Approved
0.5765	Remote Similarity	NPD4266	Approved
0.5763	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD3704	Approved
0.576	Remote Similarity	NPD8328	Phase 3
0.5755	Remote Similarity	NPD5370	Suspended
0.5755	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6101	Approved
0.5748	Remote Similarity	NPD7078	Approved
0.5747	Remote Similarity	NPD9118	Approved
0.5741	Remote Similarity	NPD6399	Phase 3
0.5736	Remote Similarity	NPD8391	Approved
0.5736	Remote Similarity	NPD8392	Approved
0.5736	Remote Similarity	NPD8390	Approved
0.5726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7503	Approved
0.5714	Remote Similarity	NPD8341	Approved
0.5714	Remote Similarity	NPD7492	Approved
0.5714	Remote Similarity	NPD8340	Approved
0.5714	Remote Similarity	NPD8299	Approved
0.5714	Remote Similarity	NPD8342	Approved
0.5703	Remote Similarity	NPD7736	Approved
0.5682	Remote Similarity	NPD6109	Phase 1
0.568	Remote Similarity	NPD8080	Discontinued
0.5678	Remote Similarity	NPD2067	Discontinued
0.5676	Remote Similarity	NPD7902	Approved
0.5669	Remote Similarity	NPD6616	Approved
0.5667	Remote Similarity	NPD4632	Approved
0.5656	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6411	Approved
0.5647	Remote Similarity	NPD3172	Approved
0.5645	Remote Similarity	NPD6054	Approved
0.5641	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6650	Approved
0.563	Remote Similarity	NPD6649	Approved
0.5625	Remote Similarity	NPD8293	Discontinued
0.5614	Remote Similarity	NPD7632	Discontinued
0.5603	Remote Similarity	NPD6008	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