NPASS Compound

Structure

NPC272359 OpenBabel07101719252D 35 40 0 0 1 0 0 0 0 0999 V2000 3.7624 0.5102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1856 4.6959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2345 4.3869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1225 2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1006 1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4533 1.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7698 2.7396 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9777 3.7177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7208 3.0486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 21 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 19 31 1 0 0 0 0 19 32 1 0 0 0 0 20 1 1 1 0 0 0 20 22 1 0 0 0 0 21 33 2 0 0 0 0 21 34 1 0 0 0 0 22 29 1 6 0 0 0 23 27 1 0 0 0 0 23 31 1 6 0 0 0 24 30 1 1 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 34 1 6 0 0 0 26 12 1 6 0 0 0 26 28 1 0 0 0 0 26 35 1 0 0 0 0 28 35 1 0 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 31 32 1 1 0 0 0 32 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.39
Volume:	534.423
LogP:	8.024
LogD:	5.689
LogS:	-7.103
# Rotatable Bonds:	6
TPSA:	38.83
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	5.568
Fsp3:	0.969
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.096
MDCK Permeability:	1.993848491110839e-05
Pgp-inhibitor:	0.481
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.586
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	95.03431701660156%
Volume Distribution (VD):	1.188
Pgp-substrate:	2.3524880409240723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.2
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.111
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.455
CYP3A4-inhibitor:	0.677
CYP3A4-substrate:	0.77

ADMET: Excretion

Clearance (CL):	3.694
Half-life (T1/2):	0.043

ADMET: Toxicity

hERG Blockers:	0.81
Human Hepatotoxicity (H-HT):	0.347
Drug-inuced Liver Injury (DILI):	0.807
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.708
Skin Sensitization:	0.945
Carcinogencity:	0.052
Eye Corrosion:	0.894
Eye Irritation:	0.146
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC272359

Natural Product ID:	NPC272359
*Common Name:**	PLCWLUBXTCUJSK-FQWGTIQDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PLCWLUBXTCUJSK-FQWGTIQDSA-N
Standard InCHI:	InChI=1S/C32H52O3/c1-20(9-12-26-28(5,6)35-26)22-13-15-30(8)24-11-10-23-27(3,4)25(34-21(2)33)14-16-31(23)19-32(24,31)18-17-29(22,30)7/h20,22-26H,9-19H2,1-8H3/t20-,22-,23+,24+,25+,26-,29-,30+,31-,32+/m1/s1
SMILES:	CC(=O)O[C@H]1CC[C@]23[C@H](C1(C)C)CC[C@@H]1[C@@]3(C2)CC[C@]2([C@@]1(C)CC[C@@H]2[C@@H](CC[C@H]1OC1(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467418
PubChem CID:	479215
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO33324	borrichia frutescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988597]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	128.0	ug.mL-1	PMID[450058]

☑ 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 NPC272359 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	448
0.1-0.2	5158
0.2-0.3	18047
0.3-0.4	7311
0.4-0.5	5264
0.5-0.6	4972
0.6-0.7	1261
0.7-0.8	222
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8611	High Similarity	NPC195530
0.8553	High Similarity	NPC47808
0.8533	High Similarity	NPC212453
0.8514	High Similarity	NPC186851
0.8312	Intermediate Similarity	NPC220379
0.8312	Intermediate Similarity	NPC477287
0.8267	Intermediate Similarity	NPC478105
0.8243	Intermediate Similarity	NPC474123
0.8125	Intermediate Similarity	NPC139206
0.8108	Intermediate Similarity	NPC473279
0.8101	Intermediate Similarity	NPC73515
0.8101	Intermediate Similarity	NPC190940
0.8077	Intermediate Similarity	NPC305835
0.8077	Intermediate Similarity	NPC476176
0.8025	Intermediate Similarity	NPC319909
0.8	Intermediate Similarity	NPC286719
0.8	Intermediate Similarity	NPC473238
0.8	Intermediate Similarity	NPC477284
0.8	Intermediate Similarity	NPC477286
0.8	Intermediate Similarity	NPC472341
0.7975	Intermediate Similarity	NPC261616
0.7975	Intermediate Similarity	NPC304194
0.7975	Intermediate Similarity	NPC206735
0.7949	Intermediate Similarity	NPC471045
0.7949	Intermediate Similarity	NPC471769
0.7901	Intermediate Similarity	NPC111582
0.7901	Intermediate Similarity	NPC477285
0.7895	Intermediate Similarity	NPC74639
0.7875	Intermediate Similarity	NPC58631
0.7875	Intermediate Similarity	NPC12933
0.7867	Intermediate Similarity	NPC127283
0.7867	Intermediate Similarity	NPC8004
0.7838	Intermediate Similarity	NPC470830
0.7838	Intermediate Similarity	NPC299948
0.7838	Intermediate Similarity	NPC241085
0.7821	Intermediate Similarity	NPC474404
0.7821	Intermediate Similarity	NPC171658
0.7821	Intermediate Similarity	NPC471151
0.7808	Intermediate Similarity	NPC475884
0.7808	Intermediate Similarity	NPC473230
0.7792	Intermediate Similarity	NPC212733
0.7778	Intermediate Similarity	NPC60018
0.7778	Intermediate Similarity	NPC473276
0.7778	Intermediate Similarity	NPC154043
0.7778	Intermediate Similarity	NPC202688
0.7778	Intermediate Similarity	NPC474380
0.7778	Intermediate Similarity	NPC13494
0.7778	Intermediate Similarity	NPC41577
0.7765	Intermediate Similarity	NPC472233
0.7765	Intermediate Similarity	NPC472234
0.7733	Intermediate Similarity	NPC282454
0.7727	Intermediate Similarity	NPC470031
0.7714	Intermediate Similarity	NPC204173
0.7692	Intermediate Similarity	NPC4209
0.7692	Intermediate Similarity	NPC471046
0.7692	Intermediate Similarity	NPC470145
0.7683	Intermediate Similarity	NPC5280
0.7683	Intermediate Similarity	NPC473742
0.7662	Intermediate Similarity	NPC167702
0.7662	Intermediate Similarity	NPC280026
0.764	Intermediate Similarity	NPC252056
0.7639	Intermediate Similarity	NPC69149
0.7632	Intermediate Similarity	NPC109457
0.7632	Intermediate Similarity	NPC100586
0.7632	Intermediate Similarity	NPC157422
0.7625	Intermediate Similarity	NPC73013
0.7625	Intermediate Similarity	NPC201276
0.7625	Intermediate Similarity	NPC80891
0.7619	Intermediate Similarity	NPC215968
0.7619	Intermediate Similarity	NPC155531
0.7619	Intermediate Similarity	NPC477283
0.7619	Intermediate Similarity	NPC103782
0.7619	Intermediate Similarity	NPC114378
0.7595	Intermediate Similarity	NPC317913
0.7595	Intermediate Similarity	NPC298168
0.7595	Intermediate Similarity	NPC476233
0.7595	Intermediate Similarity	NPC207010
0.7595	Intermediate Similarity	NPC475031
0.7595	Intermediate Similarity	NPC143133
0.759	Intermediate Similarity	NPC239362
0.759	Intermediate Similarity	NPC475509
0.7586	Intermediate Similarity	NPC473066
0.7568	Intermediate Similarity	NPC476928
0.7568	Intermediate Similarity	NPC48079
0.7564	Intermediate Similarity	NPC72444
0.7564	Intermediate Similarity	NPC273366
0.7561	Intermediate Similarity	NPC289486
0.7561	Intermediate Similarity	NPC61107
0.7531	Intermediate Similarity	NPC474714
0.7531	Intermediate Similarity	NPC477851
0.75	Intermediate Similarity	NPC171426
0.75	Intermediate Similarity	NPC80089
0.75	Intermediate Similarity	NPC324700
0.75	Intermediate Similarity	NPC114891
0.75	Intermediate Similarity	NPC98270
0.75	Intermediate Similarity	NPC34046
0.75	Intermediate Similarity	NPC266651
0.75	Intermediate Similarity	NPC224802
0.7471	Intermediate Similarity	NPC10274
0.7467	Intermediate Similarity	NPC472741
0.7442	Intermediate Similarity	NPC56777
0.7442	Intermediate Similarity	NPC201607
0.7436	Intermediate Similarity	NPC472945
0.7436	Intermediate Similarity	NPC477508
0.7436	Intermediate Similarity	NPC472944
0.7432	Intermediate Similarity	NPC142712
0.7416	Intermediate Similarity	NPC151214
0.7416	Intermediate Similarity	NPC191915
0.7412	Intermediate Similarity	NPC168231
0.7412	Intermediate Similarity	NPC131365
0.7407	Intermediate Similarity	NPC320144
0.7403	Intermediate Similarity	NPC470071
0.7403	Intermediate Similarity	NPC1340
0.7403	Intermediate Similarity	NPC252182
0.7403	Intermediate Similarity	NPC157777
0.7403	Intermediate Similarity	NPC197701
0.7403	Intermediate Similarity	NPC469940
0.7403	Intermediate Similarity	NPC187471
0.7403	Intermediate Similarity	NPC131506
0.7391	Intermediate Similarity	NPC470030
0.7381	Intermediate Similarity	NPC471044
0.7381	Intermediate Similarity	NPC473336
0.7381	Intermediate Similarity	NPC474996
0.7375	Intermediate Similarity	NPC84868
0.7368	Intermediate Similarity	NPC196197
0.7368	Intermediate Similarity	NPC254037
0.7368	Intermediate Similarity	NPC66407
0.7368	Intermediate Similarity	NPC129829
0.7368	Intermediate Similarity	NPC107919
0.7361	Intermediate Similarity	NPC218585
0.7361	Intermediate Similarity	NPC71460
0.7361	Intermediate Similarity	NPC83088
0.7361	Intermediate Similarity	NPC148174
0.7349	Intermediate Similarity	NPC472504
0.7342	Intermediate Similarity	NPC91387
0.7342	Intermediate Similarity	NPC270306
0.7342	Intermediate Similarity	NPC231680
0.7333	Intermediate Similarity	NPC84383
0.7326	Intermediate Similarity	NPC5943
0.7326	Intermediate Similarity	NPC202937
0.7324	Intermediate Similarity	NPC95958
0.7317	Intermediate Similarity	NPC472951
0.7317	Intermediate Similarity	NPC16449
0.7317	Intermediate Similarity	NPC475456
0.7317	Intermediate Similarity	NPC472943
0.7308	Intermediate Similarity	NPC109510
0.7308	Intermediate Similarity	NPC232112
0.7303	Intermediate Similarity	NPC472232
0.7303	Intermediate Similarity	NPC472231
0.7297	Intermediate Similarity	NPC477603
0.7284	Intermediate Similarity	NPC185465
0.7284	Intermediate Similarity	NPC243594
0.7284	Intermediate Similarity	NPC329117
0.7284	Intermediate Similarity	NPC31031
0.7284	Intermediate Similarity	NPC478128
0.7273	Intermediate Similarity	NPC77756
0.7273	Intermediate Similarity	NPC477929
0.7273	Intermediate Similarity	NPC477850
0.7273	Intermediate Similarity	NPC231945
0.7273	Intermediate Similarity	NPC192192
0.7262	Intermediate Similarity	NPC259173
0.7262	Intermediate Similarity	NPC15821
0.7253	Intermediate Similarity	NPC156377
0.7241	Intermediate Similarity	NPC4309
0.7229	Intermediate Similarity	NPC48756
0.7229	Intermediate Similarity	NPC280781
0.7222	Intermediate Similarity	NPC84218
0.7222	Intermediate Similarity	NPC477495
0.7215	Intermediate Similarity	NPC478130
0.7215	Intermediate Similarity	NPC55508
0.7209	Intermediate Similarity	NPC302111
0.72	Intermediate Similarity	NPC44122
0.72	Intermediate Similarity	NPC84562
0.7195	Intermediate Similarity	NPC153987
0.7195	Intermediate Similarity	NPC44083
0.7191	Intermediate Similarity	NPC52756
0.7179	Intermediate Similarity	NPC156277
0.7179	Intermediate Similarity	NPC127094
0.7179	Intermediate Similarity	NPC151018
0.7179	Intermediate Similarity	NPC58057
0.7179	Intermediate Similarity	NPC320549
0.7176	Intermediate Similarity	NPC299963
0.7162	Intermediate Similarity	NPC159654
0.7162	Intermediate Similarity	NPC281540
0.7162	Intermediate Similarity	NPC167995
0.7162	Intermediate Similarity	NPC118937
0.716	Intermediate Similarity	NPC474574
0.716	Intermediate Similarity	NPC133596
0.716	Intermediate Similarity	NPC64081
0.716	Intermediate Similarity	NPC23884
0.716	Intermediate Similarity	NPC11907
0.716	Intermediate Similarity	NPC477918
0.7159	Intermediate Similarity	NPC24705
0.7159	Intermediate Similarity	NPC56962
0.7158	Intermediate Similarity	NPC97260
0.7158	Intermediate Similarity	NPC476837
0.7158	Intermediate Similarity	NPC139181
0.7143	Intermediate Similarity	NPC252032
0.7143	Intermediate Similarity	NPC476734
0.7143	Intermediate Similarity	NPC178541

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 NPC272359 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	4575
0.2-0.3	3073
0.3-0.4	603
0.4-0.5	207
0.5-0.6	224
0.6-0.7	32
0.7-0.8	10
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
0.7692	Intermediate Similarity	NPD6117	Approved
0.7662	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5777	Approved
0.7595	Intermediate Similarity	NPD6116	Phase 1
0.75	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD6118	Approved
0.75	Intermediate Similarity	NPD6115	Approved
0.75	Intermediate Similarity	NPD6697	Approved
0.7368	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3702	Approved
0.7051	Intermediate Similarity	NPD4787	Phase 1
0.7013	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5360	Phase 3
0.7	Intermediate Similarity	NPD8034	Phase 2
0.7	Intermediate Similarity	NPD8035	Phase 2
0.6923	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4224	Phase 2
0.675	Remote Similarity	NPD6081	Approved
0.6707	Remote Similarity	NPD3703	Phase 2
0.6706	Remote Similarity	NPD6928	Phase 2
0.6625	Remote Similarity	NPD4789	Approved
0.6625	Remote Similarity	NPD4245	Approved
0.6625	Remote Similarity	NPD4244	Approved
0.6543	Remote Similarity	NPD4758	Discontinued
0.6512	Remote Similarity	NPD7525	Registered
0.65	Remote Similarity	NPD3698	Phase 2
0.6444	Remote Similarity	NPD8308	Discontinued
0.6421	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6051	Approved
0.641	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6001	Approved
0.6304	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3671	Phase 1
0.6279	Remote Similarity	NPD5364	Discontinued
0.6264	Remote Similarity	NPD7146	Approved
0.6264	Remote Similarity	NPD5330	Approved
0.6264	Remote Similarity	NPD7521	Approved
0.6264	Remote Similarity	NPD7334	Approved
0.6264	Remote Similarity	NPD6684	Approved
0.6264	Remote Similarity	NPD6409	Approved
0.6224	Remote Similarity	NPD7638	Approved
0.6211	Remote Similarity	NPD6399	Phase 3
0.6176	Remote Similarity	NPD6008	Approved
0.6162	Remote Similarity	NPD8418	Phase 2
0.6162	Remote Similarity	NPD7639	Approved
0.6162	Remote Similarity	NPD7640	Approved
0.6146	Remote Similarity	NPD7748	Approved
0.6146	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7900	Approved
0.6129	Remote Similarity	NPD6903	Approved
0.6129	Remote Similarity	NPD6672	Approved
0.6129	Remote Similarity	NPD5737	Approved
0.6087	Remote Similarity	NPD6098	Approved
0.6042	Remote Similarity	NPD8171	Discontinued
0.604	Remote Similarity	NPD7632	Discontinued
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.598	Remote Similarity	NPD7986	Approved
0.598	Remote Similarity	NPD7911	Approved
0.598	Remote Similarity	NPD7912	Approved
0.598	Remote Similarity	NPD7987	Approved
0.5977	Remote Similarity	NPD8143	Approved
0.5977	Remote Similarity	NPD8144	Approved
0.596	Remote Similarity	NPD7902	Approved
0.5934	Remote Similarity	NPD4788	Approved
0.593	Remote Similarity	NPD6942	Approved
0.593	Remote Similarity	NPD7339	Approved
0.5918	Remote Similarity	NPD7991	Discontinued
0.5905	Remote Similarity	NPD6881	Approved
0.5905	Remote Similarity	NPD6899	Approved
0.5905	Remote Similarity	NPD7320	Approved
0.5895	Remote Similarity	NPD6673	Approved
0.5895	Remote Similarity	NPD6904	Approved
0.5895	Remote Similarity	NPD5328	Approved
0.5895	Remote Similarity	NPD6080	Approved
0.5888	Remote Similarity	NPD8130	Phase 1
0.587	Remote Similarity	NPD4786	Approved
0.5865	Remote Similarity	NPD8040	Discontinued
0.5849	Remote Similarity	NPD6372	Approved
0.5849	Remote Similarity	NPD6373	Approved
0.5843	Remote Similarity	NPD7645	Phase 2
0.5833	Remote Similarity	NPD8297	Approved
0.581	Remote Similarity	NPD5701	Approved
0.581	Remote Similarity	NPD5697	Approved
0.581	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7990	Approved
0.581	Remote Similarity	NPD7989	Approved
0.58	Remote Similarity	NPD6084	Phase 2
0.58	Remote Similarity	NPD6083	Phase 2
0.5794	Remote Similarity	NPD6883	Approved
0.5794	Remote Similarity	NPD7290	Approved
0.5794	Remote Similarity	NPD7102	Approved
0.5789	Remote Similarity	NPD5208	Approved
0.5784	Remote Similarity	NPD1700	Approved
0.5783	Remote Similarity	NPD6705	Phase 1
0.5778	Remote Similarity	NPD4748	Discontinued
0.5773	Remote Similarity	NPD6079	Approved
0.5773	Remote Similarity	NPD7515	Phase 2
0.5769	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7115	Discovery
0.5755	Remote Similarity	NPD6011	Approved
0.5745	Remote Similarity	NPD3618	Phase 1
0.5741	Remote Similarity	NPD6650	Approved
0.5741	Remote Similarity	NPD6617	Approved
0.5741	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6869	Approved
0.5741	Remote Similarity	NPD6649	Approved
0.5741	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD4202	Approved
0.5701	Remote Similarity	NPD6013	Approved
0.5701	Remote Similarity	NPD6014	Approved
0.5701	Remote Similarity	NPD6012	Approved
0.5701	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6882	Approved
0.5684	Remote Similarity	NPD3573	Approved
0.5682	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.567	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.567	Remote Similarity	NPD6700	Approved
0.566	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD3667	Approved
0.5648	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD2254	Approved
0.5647	Remote Similarity	NPD2686	Approved
0.5647	Remote Similarity	NPD2687	Approved
0.5636	Remote Similarity	NPD8133	Approved
0.5632	Remote Similarity	NPD6926	Approved
0.5632	Remote Similarity	NPD6924	Approved
0.5614	Remote Similarity	NPD8294	Approved
0.5614	Remote Similarity	NPD8377	Approved
0.5612	Remote Similarity	NPD6702	Approved
0.5612	Remote Similarity	NPD5693	Phase 1
0.5612	Remote Similarity	NPD6050	Approved
0.5612	Remote Similarity	NPD6703	Approved
0.56	Remote Similarity	NPD5695	Phase 3

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