NPASS Compound

Structure

NPC472219 OpenBabel07101718222D 51 54 0 0 1 0 0 0 0 0999 V2000 10.2034 -7.8545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4239 7.7481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0412 7.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 5.8806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7484 3.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1515 3.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3531 -7.3636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3531 -6.3818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2034 -5.8909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2034 -4.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0536 -4.4182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0536 -3.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2034 -2.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2034 -1.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3531 -1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5028 -1.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6525 -1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8022 -1.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9520 -1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1017 -1.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2514 -1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4011 -1.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4344 5.3551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1310 4.4213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0617 1.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4846 1.1693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7006 0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8503 1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7006 2.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 2.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7006 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8503 -0.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0809 7.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7775 6.0847 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7880 3.6917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7006 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4846 2.7579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5508 1.4727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7006 0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 -0.4909 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5508 -1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5508 2.4545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9818 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8503 1.4727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8503 -1.4727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7006 -1.9636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5508 -0.4909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 34 1 0 0 0 0 3 34 1 0 0 0 0 7 44 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 2 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 23 42 1 0 0 0 0 24 25 2 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 27 1 0 0 0 0 26 38 1 0 0 0 0 27 39 1 0 0 0 0 28 29 1 0 0 0 0 28 37 1 0 0 0 0 29 44 1 0 0 0 0 30 31 1 0 0 0 0 30 43 1 0 0 0 0 31 45 1 0 0 0 0 32 40 2 0 0 0 0 32 41 1 0 0 0 0 33 37 1 0 0 0 0 33 46 1 0 0 0 0 34 35 1 0 0 0 0 35 4 1 1 0 0 0 36 5 1 6 0 0 0 36 38 1 0 0 0 0 37 51 1 6 0 0 0 38 43 1 6 0 0 0 39 40 1 0 0 0 0 39 43 1 6 0 0 0 40 45 1 0 0 0 0 41 46 1 1 0 0 0 41 47 1 0 0 0 0 42 48 2 0 0 0 0 42 51 1 0 0 0 0 43 6 1 6 0 0 0 44 45 1 1 0 0 0 45 49 1 1 0 0 0 46 44 1 1 0 0 0 46 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.16
Volume:	313.323
LogP:	3.439
LogD:	2.424
LogS:	-4.192
# Rotatable Bonds:	3
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	3.878
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.606
MDCK Permeability:	1.5455738321179524e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.23
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	94.7492446899414%
Volume Distribution (VD):	0.205
Pgp-substrate:	4.2761149406433105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.49
CYP1A2-substrate:	0.421
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.209
CYP2C9-inhibitor:	0.296
CYP2C9-substrate:	0.598
CYP2D6-inhibitor:	0.241
CYP2D6-substrate:	0.255
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	1.914
Half-life (T1/2):	0.54

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.924
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.467
Rat Oral Acute Toxicity:	0.123
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.882
Carcinogencity:	0.76
Eye Corrosion:	0.025
Eye Irritation:	0.759
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC472219

Natural Product ID:	NPC472219
*Common Name:**	PNSISTCNWNAKTQ-AIDPMJBASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PNSISTCNWNAKTQ-AIDPMJBASA-N
Standard InCHI:	InChI=1S/C46H76O5/c1-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-42(48)51-37-28-29-44(7)45(49)31-30-43(6)38(36(5)25-24-35(4)34(2)3)26-27-39(43)40(45)32-41(47)46(44,50)33-37/h12-13,15-16,24-25,32,34-39,41,47,49-50H,8-11,14,17-23,26-31,33H2,1-7H3/b13-12-,16-15-,25-24+/t35-,36+,37-,38+,39-,41-,43+,44+,45+,46-/m0/s1
SMILES:	CCCCC/C=CC/C=CCCCCCCCC(=O)O[C@H]1CC[C@]2([C@@](C1)(O)[C@@H](O)C=C1[C@]2(O)CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3353025
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001691] Steroid esters

*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
NPO33451	hericium erinaceum	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18835171]
NPO33451	hericium erinaceum	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25437304]

☑ 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
EC50	1

Activity Type	# Activity
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3942	Protein Family	Peroxisome proliferator-activated receptor	Homo sapiens	EC50	=	22300.0	nM	PMID[569902]

☑ 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 NPC472219 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	192
0.1-0.2	1113
0.2-0.3	3702
0.3-0.4	6943
0.4-0.5	13737
0.5-0.6	6195
0.6-0.7	5758
0.7-0.8	4494
0.8-0.85	495
0.85-0.9	60
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472218
1.0	High Similarity	NPC472217
0.951	High Similarity	NPC173905
0.951	High Similarity	NPC472216
0.951	High Similarity	NPC5475
0.951	High Similarity	NPC284828
0.9208	High Similarity	NPC222153
0.9048	High Similarity	NPC472214
0.9048	High Similarity	NPC472215
0.9	High Similarity	NPC119036
0.8942	High Similarity	NPC59530
0.8911	High Similarity	NPC167974
0.875	High Similarity	NPC473543
0.8716	High Similarity	NPC220293
0.87	High Similarity	NPC279974
0.8692	High Similarity	NPC101450
0.8679	High Similarity	NPC258323
0.8654	High Similarity	NPC36688
0.8654	High Similarity	NPC473523
0.8654	High Similarity	NPC474124
0.8641	High Similarity	NPC475617
0.8624	High Similarity	NPC962
0.8614	High Similarity	NPC471903
0.8614	High Similarity	NPC54248
0.8614	High Similarity	NPC276103
0.8611	High Similarity	NPC475480
0.8611	High Similarity	NPC473921
0.8611	High Similarity	NPC475668
0.86	High Similarity	NPC474922
0.8598	High Similarity	NPC218853
0.8586	High Similarity	NPC41554
0.8586	High Similarity	NPC97404
0.8585	High Similarity	NPC187435
0.8585	High Similarity	NPC473284
0.8585	High Similarity	NPC67321
0.8585	High Similarity	NPC64844
0.8585	High Similarity	NPC42847
0.8584	High Similarity	NPC67569
0.8571	High Similarity	NPC471293
0.8558	High Similarity	NPC475344
0.8558	High Similarity	NPC476471
0.8558	High Similarity	NPC477054
0.8558	High Similarity	NPC22388
0.8544	High Similarity	NPC473510
0.8532	High Similarity	NPC234042
0.8532	High Similarity	NPC152117
0.8532	High Similarity	NPC280782
0.8532	High Similarity	NPC470063
0.8519	High Similarity	NPC475563
0.8519	High Similarity	NPC475134
0.8515	High Similarity	NPC266899
0.8515	High Similarity	NPC53565
0.8509	High Similarity	NPC470265
0.8509	High Similarity	NPC23786
0.8509	High Similarity	NPC222688
0.8505	High Similarity	NPC295389
0.8491	Intermediate Similarity	NPC477877
0.8491	Intermediate Similarity	NPC231530
0.8491	Intermediate Similarity	NPC278628
0.8491	Intermediate Similarity	NPC323834
0.8491	Intermediate Similarity	NPC60315
0.8491	Intermediate Similarity	NPC166607
0.8485	Intermediate Similarity	NPC3345
0.8485	Intermediate Similarity	NPC80561
0.8485	Intermediate Similarity	NPC11216
0.8485	Intermediate Similarity	NPC291484
0.8485	Intermediate Similarity	NPC471896
0.8485	Intermediate Similarity	NPC204188
0.8485	Intermediate Similarity	NPC329596
0.8476	Intermediate Similarity	NPC475623
0.8476	Intermediate Similarity	NPC247957
0.8476	Intermediate Similarity	NPC473694
0.8476	Intermediate Similarity	NPC249187
0.8476	Intermediate Similarity	NPC475334
0.8468	Intermediate Similarity	NPC474734
0.8468	Intermediate Similarity	NPC179626
0.8468	Intermediate Similarity	NPC266728
0.8468	Intermediate Similarity	NPC49492
0.8462	Intermediate Similarity	NPC477053
0.8462	Intermediate Similarity	NPC477052
0.8462	Intermediate Similarity	NPC289670
0.8462	Intermediate Similarity	NPC115899
0.8462	Intermediate Similarity	NPC476897
0.8462	Intermediate Similarity	NPC477051
0.8455	Intermediate Similarity	NPC250109
0.8448	Intermediate Similarity	NPC293112
0.8447	Intermediate Similarity	NPC477854
0.844	Intermediate Similarity	NPC285410
0.844	Intermediate Similarity	NPC263827
0.844	Intermediate Similarity	NPC250481
0.8435	Intermediate Similarity	NPC41129
0.8435	Intermediate Similarity	NPC469789
0.8431	Intermediate Similarity	NPC12103
0.8431	Intermediate Similarity	NPC227583
0.8431	Intermediate Similarity	NPC288970
0.8431	Intermediate Similarity	NPC98457
0.8426	Intermediate Similarity	NPC257082
0.8426	Intermediate Similarity	NPC472534
0.8426	Intermediate Similarity	NPC143706
0.8416	Intermediate Similarity	NPC470957
0.8416	Intermediate Similarity	NPC470958
0.8411	Intermediate Similarity	NPC230541
0.8411	Intermediate Similarity	NPC475176
0.8407	Intermediate Similarity	NPC475041
0.8407	Intermediate Similarity	NPC477071
0.84	Intermediate Similarity	NPC26888
0.84	Intermediate Similarity	NPC189520
0.8396	Intermediate Similarity	NPC201763
0.8396	Intermediate Similarity	NPC475331
0.8396	Intermediate Similarity	NPC103298
0.8396	Intermediate Similarity	NPC475335
0.8396	Intermediate Similarity	NPC121518
0.8396	Intermediate Similarity	NPC160843
0.8396	Intermediate Similarity	NPC288502
0.8396	Intermediate Similarity	NPC201144
0.8396	Intermediate Similarity	NPC181104
0.8396	Intermediate Similarity	NPC80809
0.8393	Intermediate Similarity	NPC471854
0.8384	Intermediate Similarity	NPC470361
0.8384	Intermediate Similarity	NPC475921
0.8384	Intermediate Similarity	NPC474704
0.8381	Intermediate Similarity	NPC473788
0.8381	Intermediate Similarity	NPC136289
0.8381	Intermediate Similarity	NPC476081
0.8381	Intermediate Similarity	NPC475558
0.8378	Intermediate Similarity	NPC473882
0.8378	Intermediate Similarity	NPC67259
0.8378	Intermediate Similarity	NPC117712
0.8378	Intermediate Similarity	NPC147912
0.8365	Intermediate Similarity	NPC208358
0.8365	Intermediate Similarity	NPC230546
0.8365	Intermediate Similarity	NPC266955
0.8364	Intermediate Similarity	NPC472002
0.8364	Intermediate Similarity	NPC236217
0.835	Intermediate Similarity	NPC476879
0.835	Intermediate Similarity	NPC475033
0.835	Intermediate Similarity	NPC107243
0.835	Intermediate Similarity	NPC476878
0.835	Intermediate Similarity	NPC320306
0.835	Intermediate Similarity	NPC108078
0.835	Intermediate Similarity	NPC475032
0.835	Intermediate Similarity	NPC210337
0.835	Intermediate Similarity	NPC261807
0.8349	Intermediate Similarity	NPC129340
0.8349	Intermediate Similarity	NPC197428
0.8349	Intermediate Similarity	NPC475317
0.8349	Intermediate Similarity	NPC154856
0.8349	Intermediate Similarity	NPC6206
0.8349	Intermediate Similarity	NPC5284
0.8349	Intermediate Similarity	NPC52241
0.8349	Intermediate Similarity	NPC250956
0.8333	Intermediate Similarity	NPC8774
0.8333	Intermediate Similarity	NPC84383
0.8333	Intermediate Similarity	NPC306265
0.8333	Intermediate Similarity	NPC88701
0.8333	Intermediate Similarity	NPC163216
0.8333	Intermediate Similarity	NPC94529
0.8333	Intermediate Similarity	NPC472825
0.8319	Intermediate Similarity	NPC709
0.8319	Intermediate Similarity	NPC50774
0.8319	Intermediate Similarity	NPC45475
0.8318	Intermediate Similarity	NPC475494
0.8318	Intermediate Similarity	NPC475414
0.8318	Intermediate Similarity	NPC257353
0.8318	Intermediate Similarity	NPC472655
0.8318	Intermediate Similarity	NPC173172
0.8304	Intermediate Similarity	NPC474046
0.8304	Intermediate Similarity	NPC470628
0.8304	Intermediate Similarity	NPC259306
0.8302	Intermediate Similarity	NPC478057
0.8302	Intermediate Similarity	NPC475050
0.83	Intermediate Similarity	NPC148414
0.83	Intermediate Similarity	NPC175628
0.83	Intermediate Similarity	NPC111585
0.83	Intermediate Similarity	NPC469400
0.8291	Intermediate Similarity	NPC473635
0.8288	Intermediate Similarity	NPC317210
0.8288	Intermediate Similarity	NPC255017
0.8288	Intermediate Similarity	NPC251309
0.8286	Intermediate Similarity	NPC256247
0.8286	Intermediate Similarity	NPC155974
0.8286	Intermediate Similarity	NPC96784
0.8286	Intermediate Similarity	NPC235920
0.8286	Intermediate Similarity	NPC81530
0.8276	Intermediate Similarity	NPC11895
0.8276	Intermediate Similarity	NPC473979
0.8273	Intermediate Similarity	NPC470076
0.8269	Intermediate Similarity	NPC300179
0.8269	Intermediate Similarity	NPC102426
0.8269	Intermediate Similarity	NPC470067
0.8269	Intermediate Similarity	NPC470066
0.8269	Intermediate Similarity	NPC470068
0.8261	Intermediate Similarity	NPC202051
0.8261	Intermediate Similarity	NPC46570
0.8257	Intermediate Similarity	NPC10064
0.8257	Intermediate Similarity	NPC41405
0.8257	Intermediate Similarity	NPC141350
0.8257	Intermediate Similarity	NPC477070
0.8257	Intermediate Similarity	NPC475065
0.8257	Intermediate Similarity	NPC170221

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 NPC472219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1324
0.2-0.3	3606
0.3-0.4	2588
0.4-0.5	854
0.5-0.6	268
0.6-0.7	176
0.7-0.8	161
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.823	Intermediate Similarity	NPD7115	Discovery
0.819	Intermediate Similarity	NPD7640	Approved
0.819	Intermediate Similarity	NPD7639	Approved
0.8137	Intermediate Similarity	NPD6399	Phase 3
0.8095	Intermediate Similarity	NPD7638	Approved
0.8036	Intermediate Similarity	NPD8297	Approved
0.8	Intermediate Similarity	NPD6899	Approved
0.8	Intermediate Similarity	NPD6881	Approved
0.7982	Intermediate Similarity	NPD6675	Approved
0.7982	Intermediate Similarity	NPD7128	Approved
0.7982	Intermediate Similarity	NPD6402	Approved
0.7982	Intermediate Similarity	NPD5739	Approved
0.7965	Intermediate Similarity	NPD4632	Approved
0.7946	Intermediate Similarity	NPD8130	Phase 1
0.7928	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD5697	Approved
0.7864	Intermediate Similarity	NPD7637	Suspended
0.7863	Intermediate Similarity	NPD6319	Approved
0.7857	Intermediate Similarity	NPD6883	Approved
0.7857	Intermediate Similarity	NPD7290	Approved
0.7857	Intermediate Similarity	NPD7102	Approved
0.7838	Intermediate Similarity	NPD7320	Approved
0.7788	Intermediate Similarity	NPD6617	Approved
0.7788	Intermediate Similarity	NPD6847	Approved
0.7788	Intermediate Similarity	NPD6869	Approved
0.7788	Intermediate Similarity	NPD6650	Approved
0.7788	Intermediate Similarity	NPD6649	Approved
0.7768	Intermediate Similarity	NPD6013	Approved
0.7768	Intermediate Similarity	NPD6012	Approved
0.7768	Intermediate Similarity	NPD6014	Approved
0.7768	Intermediate Similarity	NPD6372	Approved
0.7768	Intermediate Similarity	NPD6373	Approved
0.7748	Intermediate Similarity	NPD5701	Approved
0.7719	Intermediate Similarity	NPD6882	Approved
0.7706	Intermediate Similarity	NPD5211	Phase 2
0.77	Intermediate Similarity	NPD4786	Approved
0.7692	Intermediate Similarity	NPD8034	Phase 2
0.7692	Intermediate Similarity	NPD8035	Phase 2
0.7686	Intermediate Similarity	NPD7507	Approved
0.7679	Intermediate Similarity	NPD6011	Approved
0.7664	Intermediate Similarity	NPD6084	Phase 2
0.7664	Intermediate Similarity	NPD6083	Phase 2
0.7658	Intermediate Similarity	NPD6008	Approved
0.7642	Intermediate Similarity	NPD7319	Approved
0.7607	Intermediate Similarity	NPD6009	Approved
0.7603	Intermediate Similarity	NPD7492	Approved
0.7589	Intermediate Similarity	NPD6412	Phase 2
0.7568	Intermediate Similarity	NPD5141	Approved
0.7563	Intermediate Similarity	NPD6054	Approved
0.7561	Intermediate Similarity	NPD7736	Approved
0.7547	Intermediate Similarity	NPD7748	Approved
0.7545	Intermediate Similarity	NPD7632	Discontinued
0.7544	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4634	Approved
0.7542	Intermediate Similarity	NPD7327	Approved
0.7542	Intermediate Similarity	NPD7328	Approved
0.7541	Intermediate Similarity	NPD6616	Approved
0.7525	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD6079	Approved
0.7523	Intermediate Similarity	NPD5286	Approved
0.7523	Intermediate Similarity	NPD4696	Approved
0.7523	Intermediate Similarity	NPD5285	Approved
0.7522	Intermediate Similarity	NPD6686	Approved
0.7522	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD5983	Phase 2
0.75	Intermediate Similarity	NPD8133	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.748	Intermediate Similarity	NPD7078	Approved
0.748	Intermediate Similarity	NPD8293	Discontinued
0.7479	Intermediate Similarity	NPD7516	Approved
0.7478	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7524	Approved
0.7456	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5778	Approved
0.7453	Intermediate Similarity	NPD5779	Approved
0.7453	Intermediate Similarity	NPD4202	Approved
0.7451	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6370	Approved
0.7431	Intermediate Similarity	NPD4225	Approved
0.7426	Intermediate Similarity	NPD6695	Phase 3
0.7417	Intermediate Similarity	NPD8377	Approved
0.7417	Intermediate Similarity	NPD6059	Approved
0.7417	Intermediate Similarity	NPD8294	Approved
0.7414	Intermediate Similarity	NPD6053	Discontinued
0.7398	Intermediate Similarity	NPD6336	Discontinued
0.7387	Intermediate Similarity	NPD5226	Approved
0.7387	Intermediate Similarity	NPD4633	Approved
0.7387	Intermediate Similarity	NPD5225	Approved
0.7387	Intermediate Similarity	NPD5224	Approved
0.7379	Intermediate Similarity	NPD3618	Phase 1
0.7364	Intermediate Similarity	NPD4700	Approved
0.7358	Intermediate Similarity	NPD7515	Phase 2
0.7355	Intermediate Similarity	NPD7503	Approved
0.7355	Intermediate Similarity	NPD6016	Approved
0.7355	Intermediate Similarity	NPD6015	Approved
0.7333	Intermediate Similarity	NPD7100	Approved
0.7333	Intermediate Similarity	NPD7101	Approved
0.7321	Intermediate Similarity	NPD5175	Approved
0.7321	Intermediate Similarity	NPD5174	Approved
0.7315	Intermediate Similarity	NPD5695	Phase 3
0.7308	Intermediate Similarity	NPD7750	Discontinued
0.73	Intermediate Similarity	NPD7525	Registered
0.7297	Intermediate Similarity	NPD5344	Discontinued
0.7297	Intermediate Similarity	NPD5223	Approved
0.7295	Intermediate Similarity	NPD5988	Approved
0.7281	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5696	Approved
0.725	Intermediate Similarity	NPD6335	Approved
0.7248	Intermediate Similarity	NPD5222	Approved
0.7248	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5221	Approved
0.7238	Intermediate Similarity	NPD5737	Approved
0.7238	Intermediate Similarity	NPD6672	Approved
0.7227	Intermediate Similarity	NPD6274	Approved
0.7222	Intermediate Similarity	NPD7900	Approved
0.7222	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8517	Approved
0.7213	Intermediate Similarity	NPD8516	Approved
0.7213	Intermediate Similarity	NPD8513	Phase 3
0.7213	Intermediate Similarity	NPD8515	Approved
0.7212	Intermediate Similarity	NPD6409	Approved
0.7212	Intermediate Similarity	NPD6684	Approved
0.7212	Intermediate Similarity	NPD7334	Approved
0.7212	Intermediate Similarity	NPD7146	Approved
0.7212	Intermediate Similarity	NPD5330	Approved
0.7212	Intermediate Similarity	NPD7521	Approved
0.7196	Intermediate Similarity	NPD6411	Approved
0.7196	Intermediate Similarity	NPD7983	Approved
0.7182	Intermediate Similarity	NPD5173	Approved
0.717	Intermediate Similarity	NPD4753	Phase 2
0.7167	Intermediate Similarity	NPD6317	Approved
0.7167	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6930	Phase 2
0.7129	Intermediate Similarity	NPD6931	Approved
0.7129	Intermediate Similarity	NPD7514	Phase 3
0.7107	Intermediate Similarity	NPD6313	Approved
0.7107	Intermediate Similarity	NPD6314	Approved
0.71	Intermediate Similarity	NPD6114	Approved
0.71	Intermediate Similarity	NPD6118	Approved
0.71	Intermediate Similarity	NPD6697	Approved
0.71	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6115	Approved
0.7097	Intermediate Similarity	NPD8328	Phase 3
0.7091	Intermediate Similarity	NPD4697	Phase 3
0.7087	Intermediate Similarity	NPD5362	Discontinued
0.7083	Intermediate Similarity	NPD6868	Approved
0.7075	Intermediate Similarity	NPD6903	Approved
0.7075	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6908	Approved
0.7073	Intermediate Similarity	NPD6909	Approved
0.7069	Intermediate Similarity	NPD4729	Approved
0.7069	Intermediate Similarity	NPD4730	Approved
0.7048	Intermediate Similarity	NPD6098	Approved
0.7043	Intermediate Similarity	NPD4768	Approved
0.7043	Intermediate Similarity	NPD4767	Approved
0.7037	Intermediate Similarity	NPD5281	Approved
0.7037	Intermediate Similarity	NPD5284	Approved
0.7034	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6929	Approved
0.7019	Intermediate Similarity	NPD3666	Approved
0.7019	Intermediate Similarity	NPD3668	Phase 3
0.7019	Intermediate Similarity	NPD3133	Approved
0.7019	Intermediate Similarity	NPD3665	Phase 1
0.7018	Intermediate Similarity	NPD4754	Approved
0.7009	Intermediate Similarity	NPD6080	Approved
0.7009	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6904	Approved
0.7009	Intermediate Similarity	NPD6051	Approved
0.7009	Intermediate Similarity	NPD6101	Approved
0.7009	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD5210	Approved
0.6981	Remote Similarity	NPD4251	Approved
0.6981	Remote Similarity	NPD4250	Approved
0.697	Remote Similarity	NPD6942	Approved
0.697	Remote Similarity	NPD7339	Approved
0.6961	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4822	Approved
0.6961	Remote Similarity	NPD4821	Approved
0.6961	Remote Similarity	NPD4820	Approved
0.6961	Remote Similarity	NPD7332	Phase 2
0.6961	Remote Similarity	NPD4819	Approved
0.6949	Remote Similarity	NPD6371	Approved
0.6949	Remote Similarity	NPD5250	Approved
0.6949	Remote Similarity	NPD5251	Approved
0.6949	Remote Similarity	NPD5249	Phase 3
0.6949	Remote Similarity	NPD5247	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