NPASS Compound

Structure

NPC288471 OpenBabel07101719252D 42 43 0 0 1 0 0 0 0 0999 V2000 -2.6646 9.8749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4353 0.1022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5890 -1.3638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6646 8.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5109 8.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5109 7.4317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3573 6.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3573 5.9658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2036 5.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2036 4.4999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0500 4.0112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0500 3.0340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2036 2.5453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7427 0.1022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3573 -2.8297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0960 -1.3534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9719 1.0794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5890 -0.3865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3573 -1.8524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2032 -0.9559 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2036 1.5681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8963 -0.3865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2036 -1.3638 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6432 -1.4446 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2036 -0.3865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3573 0.1022 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3694 -0.7906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5109 -0.3865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9719 0.1022 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2036 -3.3183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1981 -2.3253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8183 1.5681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0500 1.0794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8963 -1.3638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0500 -1.8524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7453 -2.4165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3253 -0.9938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5109 -1.3638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3573 1.0794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0500 0.1022 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 -1.8183 0.5908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 18 1 0 0 0 0 3 18 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 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 21 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 32 1 0 0 0 0 19 15 1 6 0 0 0 19 23 1 0 0 0 0 19 38 1 0 0 0 0 20 16 1 1 0 0 0 20 24 1 0 0 0 0 20 41 1 0 0 0 0 21 33 2 0 0 0 0 21 39 1 0 0 0 0 22 34 2 0 0 0 0 22 40 1 0 0 0 0 23 25 1 0 0 0 0 23 35 1 1 0 0 0 24 27 1 0 0 0 0 24 36 1 6 0 0 0 25 26 1 0 0 0 0 25 40 1 6 0 0 0 26 28 1 0 0 0 0 26 39 1 1 0 0 0 27 29 1 1 0 0 0 27 37 1 0 0 0 0 28 38 1 0 0 0 0 28 42 1 1 0 0 0 29 17 1 6 0 0 0 29 41 1 0 0 0 0 29 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	606.33
Volume:	599.391
LogP:	2.97
LogD:	1.242
LogS:	-3.037
# Rotatable Bonds:	20
TPSA:	201.67
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.072
Synthetic Accessibility Score:	4.744
Fsp3:	0.862
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:	-5.623
MDCK Permeability:	9.19163430808112e-05
Pgp-inhibitor:	0.639
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.884
20% Bioavailability (F20%):	0.778
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	90.18907928466797%
Volume Distribution (VD):	0.653
Pgp-substrate:	5.672150135040283%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.057
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.125
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.371
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	4.3
Half-life (T1/2):	0.738

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.342
Drug-inuced Liver Injury (DILI):	0.303
AMES Toxicity:	0.209
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.925
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC288471

Natural Product ID:	NPC288471
*Common Name:**	Physaloside A
IUPAC Name:	[(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-(3-methylbut-2-enoyloxy)oxan-3-yl] dodecanoate
Synonyms:
Standard InCHIKey:	KWJCIFYBGHTTIJ-XXSCEOMOSA-N
Standard InCHI:	InChI=1S/C29H50O13/c1-4-5-6-7-8-9-10-11-12-13-21(33)39-26-25(40-22(34)14-18(2)3)23(35)19(15-30)38-28(26)42-29(17-32)27(37)24(36)20(16-31)41-29/h14,19-20,23-28,30-32,35-37H,4-13,15-17H2,1-3H3/t19-,20+,23-,24+,25+,26-,27-,28-,29-/m1/s1
SMILES:	CCCCCCCCCCCC(=O)O[C@H]1[C@H](O[C@@H]([C@H]([C@@H]1OC(=O)C=C(C)C)O)CO)O[C@@]1(CO)O[C@H]([C@@H]([C@H]1O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447892
PubChem CID:	21575480
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*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
NPO8282	Physalis viscosa	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730264]
NPO8282	Physalis viscosa	Species	Solanaceae	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
IC50	5
Others	6

Activity Type	# Activity
Cell Line	1
Organism	4
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	800000.0	nM	PMID[455982]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IC50	>	413000.0	nM	PMID[455982]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IC50	>	413000.0	nM	PMID[455982]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	52000.0	nM	PMID[455982]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	IC50	=	57000.0	nM	PMID[455982]
NPT27	Others	Unspecified	""	Ratio IC50	=	10.0	n.a.	PMID[455982]
NPT2	Others	Unspecified	""	Ratio IC50	=	8.0	n.a.	PMID[455982]

☑ 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 NPC288471 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	176
0.1-0.2	1933
0.2-0.3	6482
0.3-0.4	13795
0.4-0.5	10182
0.5-0.6	7431
0.6-0.7	2287
0.7-0.8	399
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8736	High Similarity	NPC477349
0.8539	High Similarity	NPC44682
0.8539	High Similarity	NPC163409
0.8539	High Similarity	NPC238264
0.8539	High Similarity	NPC477345
0.8539	High Similarity	NPC477348
0.8352	Intermediate Similarity	NPC475375
0.8352	Intermediate Similarity	NPC473765
0.8352	Intermediate Similarity	NPC476066
0.8352	Intermediate Similarity	NPC475164
0.8352	Intermediate Similarity	NPC475241
0.8352	Intermediate Similarity	NPC475540
0.8352	Intermediate Similarity	NPC475593
0.8352	Intermediate Similarity	NPC475525
0.8352	Intermediate Similarity	NPC473605
0.8228	Intermediate Similarity	NPC185419
0.8228	Intermediate Similarity	NPC184550
0.8222	Intermediate Similarity	NPC320089
0.8152	Intermediate Similarity	NPC54731
0.8152	Intermediate Similarity	NPC306041
0.8125	Intermediate Similarity	NPC308096
0.8125	Intermediate Similarity	NPC291228
0.8046	Intermediate Similarity	NPC329615
0.8046	Intermediate Similarity	NPC471567
0.8046	Intermediate Similarity	NPC120398
0.8046	Intermediate Similarity	NPC329838
0.8046	Intermediate Similarity	NPC477014
0.8046	Intermediate Similarity	NPC477013
0.8022	Intermediate Similarity	NPC475173
0.8022	Intermediate Similarity	NPC473561
0.8022	Intermediate Similarity	NPC473520
0.8022	Intermediate Similarity	NPC473723
0.8022	Intermediate Similarity	NPC473663
0.8	Intermediate Similarity	NPC21693
0.8	Intermediate Similarity	NPC473904
0.8	Intermediate Similarity	NPC469469
0.8	Intermediate Similarity	NPC236649
0.8	Intermediate Similarity	NPC118078
0.7978	Intermediate Similarity	NPC233551
0.7978	Intermediate Similarity	NPC21208
0.7978	Intermediate Similarity	NPC320458
0.7978	Intermediate Similarity	NPC280621
0.7978	Intermediate Similarity	NPC20339
0.7978	Intermediate Similarity	NPC48338
0.7978	Intermediate Similarity	NPC40376
0.7978	Intermediate Similarity	NPC89001
0.7978	Intermediate Similarity	NPC473905
0.7955	Intermediate Similarity	NPC47937
0.7955	Intermediate Similarity	NPC477015
0.7949	Intermediate Similarity	NPC206601
0.7931	Intermediate Similarity	NPC163093
0.7931	Intermediate Similarity	NPC156804
0.7912	Intermediate Similarity	NPC473707
0.7889	Intermediate Similarity	NPC139418
0.7889	Intermediate Similarity	NPC477017
0.7889	Intermediate Similarity	NPC477016
0.7865	Intermediate Similarity	NPC258068
0.7865	Intermediate Similarity	NPC473995
0.7865	Intermediate Similarity	NPC476583
0.7865	Intermediate Similarity	NPC178215
0.7865	Intermediate Similarity	NPC20533
0.7841	Intermediate Similarity	NPC322529
0.7841	Intermediate Similarity	NPC182383
0.7826	Intermediate Similarity	NPC238090
0.7826	Intermediate Similarity	NPC472196
0.7826	Intermediate Similarity	NPC472195
0.7816	Intermediate Similarity	NPC156089
0.7816	Intermediate Similarity	NPC470313
0.7816	Intermediate Similarity	NPC473500
0.7816	Intermediate Similarity	NPC38295
0.7802	Intermediate Similarity	NPC239517
0.7802	Intermediate Similarity	NPC473311
0.7789	Intermediate Similarity	NPC472015
0.7766	Intermediate Similarity	NPC143446
0.7753	Intermediate Similarity	NPC114694
0.7753	Intermediate Similarity	NPC473840
0.7753	Intermediate Similarity	NPC232555
0.7753	Intermediate Similarity	NPC293136
0.7753	Intermediate Similarity	NPC134865
0.7753	Intermediate Similarity	NPC241360
0.7753	Intermediate Similarity	NPC231096
0.7753	Intermediate Similarity	NPC107717
0.7753	Intermediate Similarity	NPC142117
0.7753	Intermediate Similarity	NPC132940
0.7753	Intermediate Similarity	NPC171174
0.7753	Intermediate Similarity	NPC282815
0.7753	Intermediate Similarity	NPC219652
0.7753	Intermediate Similarity	NPC475581
0.7753	Intermediate Similarity	NPC240695
0.7753	Intermediate Similarity	NPC103523
0.7753	Intermediate Similarity	NPC208473
0.7753	Intermediate Similarity	NPC25703
0.7753	Intermediate Similarity	NPC62118
0.775	Intermediate Similarity	NPC285003
0.775	Intermediate Similarity	NPC241265
0.7742	Intermediate Similarity	NPC159698
0.7717	Intermediate Similarity	NPC472197
0.7701	Intermediate Similarity	NPC180363
0.7701	Intermediate Similarity	NPC131002
0.7701	Intermediate Similarity	NPC475159
0.7701	Intermediate Similarity	NPC473712
0.7701	Intermediate Similarity	NPC473780
0.7701	Intermediate Similarity	NPC329829
0.7701	Intermediate Similarity	NPC473529
0.7701	Intermediate Similarity	NPC145914
0.7701	Intermediate Similarity	NPC65930
0.7701	Intermediate Similarity	NPC73310
0.7701	Intermediate Similarity	NPC11332
0.7701	Intermediate Similarity	NPC94875
0.77	Intermediate Similarity	NPC219900
0.77	Intermediate Similarity	NPC177524
0.77	Intermediate Similarity	NPC392
0.7692	Intermediate Similarity	NPC81778
0.7692	Intermediate Similarity	NPC473504
0.7692	Intermediate Similarity	NPC91067
0.7692	Intermediate Similarity	NPC42598
0.7692	Intermediate Similarity	NPC40066
0.7692	Intermediate Similarity	NPC280612
0.7692	Intermediate Similarity	NPC477011
0.7692	Intermediate Similarity	NPC20621
0.7692	Intermediate Similarity	NPC93794
0.7692	Intermediate Similarity	NPC318963
0.7684	Intermediate Similarity	NPC472290
0.7674	Intermediate Similarity	NPC163362
0.7674	Intermediate Similarity	NPC127295
0.7667	Intermediate Similarity	NPC475186
0.7667	Intermediate Similarity	NPC118077
0.764	Intermediate Similarity	NPC110710
0.764	Intermediate Similarity	NPC283085
0.764	Intermediate Similarity	NPC39167
0.764	Intermediate Similarity	NPC103284
0.764	Intermediate Similarity	NPC77871
0.764	Intermediate Similarity	NPC292809
0.764	Intermediate Similarity	NPC470124
0.764	Intermediate Similarity	NPC473478
0.764	Intermediate Similarity	NPC473651
0.764	Intermediate Similarity	NPC475268
0.764	Intermediate Similarity	NPC473156
0.764	Intermediate Similarity	NPC66346
0.764	Intermediate Similarity	NPC39279
0.764	Intermediate Similarity	NPC286338
0.764	Intermediate Similarity	NPC107986
0.764	Intermediate Similarity	NPC473671
0.764	Intermediate Similarity	NPC231009
0.764	Intermediate Similarity	NPC9678
0.764	Intermediate Similarity	NPC100921
0.764	Intermediate Similarity	NPC132496
0.764	Intermediate Similarity	NPC319036
0.764	Intermediate Similarity	NPC223871
0.764	Intermediate Similarity	NPC82795
0.764	Intermediate Similarity	NPC1083
0.764	Intermediate Similarity	NPC477018
0.764	Intermediate Similarity	NPC25764
0.764	Intermediate Similarity	NPC470400
0.764	Intermediate Similarity	NPC235809
0.764	Intermediate Similarity	NPC473669
0.764	Intermediate Similarity	NPC202055
0.7634	Intermediate Similarity	NPC11456
0.7625	Intermediate Similarity	NPC50228
0.7625	Intermediate Similarity	NPC97736
0.7614	Intermediate Similarity	NPC253801
0.7614	Intermediate Similarity	NPC144415
0.759	Intermediate Similarity	NPC477308
0.759	Intermediate Similarity	NPC477305
0.759	Intermediate Similarity	NPC477309
0.759	Intermediate Similarity	NPC477315
0.759	Intermediate Similarity	NPC477304
0.759	Intermediate Similarity	NPC477313
0.759	Intermediate Similarity	NPC477312
0.759	Intermediate Similarity	NPC477316
0.7586	Intermediate Similarity	NPC280367
0.7582	Intermediate Similarity	NPC81045
0.7582	Intermediate Similarity	NPC320569
0.7582	Intermediate Similarity	NPC39754
0.7582	Intermediate Similarity	NPC191929
0.7582	Intermediate Similarity	NPC274446
0.7582	Intermediate Similarity	NPC287164
0.7582	Intermediate Similarity	NPC151403
0.7582	Intermediate Similarity	NPC242364
0.7582	Intermediate Similarity	NPC169511
0.7582	Intermediate Similarity	NPC171135
0.7582	Intermediate Similarity	NPC61257
0.7582	Intermediate Similarity	NPC133730
0.7582	Intermediate Similarity	NPC100454
0.7582	Intermediate Similarity	NPC172821
0.7582	Intermediate Similarity	NPC261952
0.7582	Intermediate Similarity	NPC234077
0.7556	Intermediate Similarity	NPC134807
0.7556	Intermediate Similarity	NPC309211
0.7556	Intermediate Similarity	NPC219498
0.7556	Intermediate Similarity	NPC112685
0.7556	Intermediate Similarity	NPC134885
0.7556	Intermediate Similarity	NPC477010
0.7556	Intermediate Similarity	NPC473687
0.7556	Intermediate Similarity	NPC69082
0.7556	Intermediate Similarity	NPC279267
0.7556	Intermediate Similarity	NPC308412
0.7556	Intermediate Similarity	NPC210218
0.7556	Intermediate Similarity	NPC204686
0.7553	Intermediate Similarity	NPC294293

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 NPC288471 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	2608
0.2-0.3	3893
0.3-0.4	1574
0.4-0.5	609
0.5-0.6	242
0.6-0.7	33
0.7-0.8	2
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
0.7802	Intermediate Similarity	NPD6698	Approved
0.7802	Intermediate Similarity	NPD46	Approved
0.77	Intermediate Similarity	NPD6686	Approved
0.6981	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.69	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8516	Approved
0.6726	Remote Similarity	NPD8517	Approved
0.6726	Remote Similarity	NPD8515	Approved
0.6726	Remote Similarity	NPD8513	Phase 3
0.6701	Remote Similarity	NPD7838	Discovery
0.6638	Remote Similarity	NPD7507	Approved
0.6633	Remote Similarity	NPD7983	Approved
0.6604	Remote Similarity	NPD6412	Phase 2
0.6604	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8133	Approved
0.6471	Remote Similarity	NPD898	Approved
0.6471	Remote Similarity	NPD897	Approved
0.6471	Remote Similarity	NPD896	Approved
0.6471	Remote Similarity	NPD7319	Approved
0.6466	Remote Similarity	NPD7830	Approved
0.6466	Remote Similarity	NPD7829	Approved
0.641	Remote Similarity	NPD3730	Approved
0.641	Remote Similarity	NPD3728	Approved
0.6325	Remote Similarity	NPD7642	Approved
0.6316	Remote Similarity	NPD7328	Approved
0.6316	Remote Similarity	NPD7327	Approved
0.6316	Remote Similarity	NPD7641	Discontinued
0.6293	Remote Similarity	NPD8444	Approved
0.6282	Remote Similarity	NPD895	Approved
0.6282	Remote Similarity	NPD889	Approved
0.6282	Remote Similarity	NPD894	Approved
0.6282	Remote Similarity	NPD887	Approved
0.6273	Remote Similarity	NPD6371	Approved
0.6261	Remote Similarity	NPD7516	Approved
0.625	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2267	Suspended
0.6237	Remote Similarity	NPD7329	Approved
0.6214	Remote Similarity	NPD7839	Suspended
0.6207	Remote Similarity	NPD8377	Approved
0.6207	Remote Similarity	NPD8294	Approved
0.6167	Remote Similarity	NPD8074	Phase 3
0.6154	Remote Similarity	NPD8380	Approved
0.6154	Remote Similarity	NPD8335	Approved
0.6154	Remote Similarity	NPD8379	Approved
0.6154	Remote Similarity	NPD7503	Approved
0.6154	Remote Similarity	NPD2269	Approved
0.6154	Remote Similarity	NPD8033	Approved
0.6154	Remote Similarity	NPD8378	Approved
0.6154	Remote Similarity	NPD8296	Approved
0.6111	Remote Similarity	NPD3181	Approved
0.6083	Remote Similarity	NPD8451	Approved
0.6061	Remote Similarity	NPD4251	Approved
0.6061	Remote Similarity	NPD4250	Approved
0.605	Remote Similarity	NPD8328	Phase 3
0.604	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD8448	Approved
0.6026	Remote Similarity	NPD904	Phase 3
0.6026	Remote Similarity	NPD905	Approved
0.602	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5344	Discontinued
0.5979	Remote Similarity	NPD7154	Phase 3
0.596	Remote Similarity	NPD4249	Approved
0.5943	Remote Similarity	NPD7638	Approved
0.5943	Remote Similarity	NPD4225	Approved
0.593	Remote Similarity	NPD3197	Phase 1
0.5893	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7640	Approved
0.5888	Remote Similarity	NPD7639	Approved
0.5887	Remote Similarity	NPD8392	Approved
0.5887	Remote Similarity	NPD8390	Approved
0.5887	Remote Similarity	NPD8391	Approved
0.5877	Remote Similarity	NPD6053	Discontinued
0.5875	Remote Similarity	NPD892	Phase 3
0.5875	Remote Similarity	NPD891	Phase 3
0.5875	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD888	Phase 3
0.5875	Remote Similarity	NPD893	Approved
0.5868	Remote Similarity	NPD8341	Approved
0.5868	Remote Similarity	NPD8340	Approved
0.5868	Remote Similarity	NPD8299	Approved
0.5868	Remote Similarity	NPD8342	Approved
0.5833	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8080	Discontinued
0.5814	Remote Similarity	NPD8961	Approved
0.5812	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.581	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.578	Remote Similarity	NPD8084	Approved
0.578	Remote Similarity	NPD8139	Approved
0.578	Remote Similarity	NPD8086	Approved
0.578	Remote Similarity	NPD8085	Approved
0.578	Remote Similarity	NPD8083	Approved
0.578	Remote Similarity	NPD8082	Approved
0.578	Remote Similarity	NPD8138	Approved
0.5772	Remote Similarity	NPD8293	Discontinued
0.5769	Remote Similarity	NPD5778	Approved
0.5769	Remote Similarity	NPD5779	Approved
0.5765	Remote Similarity	NPD6123	Approved
0.5728	Remote Similarity	NPD5785	Approved
0.5727	Remote Similarity	NPD8275	Approved
0.5727	Remote Similarity	NPD8276	Approved
0.5726	Remote Similarity	NPD7736	Approved
0.5714	Remote Similarity	NPD6435	Approved
0.5714	Remote Similarity	NPD5282	Discontinued
0.5702	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6370	Approved
0.57	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD4756	Discovery
0.5678	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD8081	Approved
0.5664	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD5362	Discontinued
0.5657	Remote Similarity	NPD6110	Phase 1
0.5641	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD847	Phase 1
0.5631	Remote Similarity	NPD1695	Approved
0.5625	Remote Similarity	NPD4271	Approved
0.5625	Remote Similarity	NPD8393	Approved
0.5625	Remote Similarity	NPD4268	Approved
0.562	Remote Similarity	NPD8267	Approved
0.562	Remote Similarity	NPD8269	Approved
0.562	Remote Similarity	NPD8266	Approved
0.562	Remote Similarity	NPD8268	Approved
0.562	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.561	Remote Similarity	NPD7492	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