NPASS Compound

Structure

NPC473928 OpenBabel07101718222D 42 45 0 0 1 0 0 0 0 0999 V2000 -0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1945 -1.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 -4.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9792 -5.0914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 -4.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 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 -2.5472 -2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 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 -1.2601 -1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8855 -0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2308 -3.6974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 -1.8781 -3.1622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 -4.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5546 -0.1896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 -3.4895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -4.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 -0.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -2.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 31 1 0 0 0 0 8 32 1 0 0 0 0 11 13 1 0 0 0 0 11 21 2 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 16 23 1 0 0 0 0 16 32 1 0 0 0 0 17 27 1 0 0 0 0 17 33 1 0 0 0 0 18 1 1 6 0 0 0 18 24 1 0 0 0 0 18 29 1 0 0 0 0 19 35 2 0 0 0 0 19 41 1 0 0 0 0 20 36 2 0 0 0 0 20 42 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 0 0 0 0 22 34 1 1 0 0 0 23 29 1 0 0 0 0 23 37 1 6 0 0 0 24 15 1 1 0 0 0 24 41 1 0 0 0 0 25 32 1 6 0 0 0 25 34 1 0 0 0 0 26 30 1 0 0 0 0 26 38 2 0 0 0 0 27 34 1 0 0 0 0 27 39 2 0 0 0 0 28 15 1 1 0 0 0 28 31 1 0 0 0 0 28 42 1 0 0 0 0 29 33 1 1 0 0 0 31 40 1 0 0 0 0 32 33 1 6 0 0 0 33 9 1 1 0 0 0 34 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	588.37
Volume:	619.534
LogP:	3.594
LogD:	2.994
LogS:	-4.353
# Rotatable Bonds:	9
TPSA:	127.2
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	5.425
Fsp3:	0.824
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.002
MDCK Permeability:	2.454185414535459e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.087
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.139
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.795
Plasma Protein Binding (PPB):	76.08167266845703%
Volume Distribution (VD):	1.094
Pgp-substrate:	13.114253044128418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.813
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.352
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.748
CYP3A4-substrate:	0.541

ADMET: Excretion

Clearance (CL):	3.43
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.291
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.333
Maximum Recommended Daily Dose:	0.529
Skin Sensitization:	0.047
Carcinogencity:	0.543
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.893

Download Data

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

Natural Product: NPC473928

Natural Product ID:	NPC473928
*Common Name:**	18-Deoxyleucopaxillone A
IUPAC Name:	[(2S,3R,5R)-5-acetyloxy-6-hydroxy-2-[(8S,9R,10R,13R,14S,16R,17R)-16-hydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptan-3-yl] acetate
Synonyms:
Standard InCHIKey:	FPHUJUDWFIGFAH-XKCFRZITSA-N
Standard InCHI:	InChI=1S/C34H52O8/c1-18(24(41-19(2)35)15-28(31(6,7)40)42-20(3)36)29-23(37)16-32(8)25-13-11-21-22(12-14-26(38)30(21,4)5)34(25,10)27(39)17-33(29,32)9/h11,18,22-25,28-29,37,40H,12-17H2,1-10H3/t18-,22-,23-,24-,25+,28-,29+,32+,33-,34+/m1/s1
SMILES:	CC(=O)O[C@@H]([C@H]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1CCC(=O)C2(C)C)C)C)C)C[C@H](C(O)(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455422
PubChem CID:	44566409
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568769]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[17190463]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	10.6	ug.mL-1	PMID[545644]

☑ 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 NPC473928 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	197
0.1-0.2	1145
0.2-0.3	4962
0.3-0.4	11954
0.4-0.5	9079
0.5-0.6	5692
0.6-0.7	6134
0.7-0.8	3238
0.8-0.85	258
0.85-0.9	36
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9175	High Similarity	NPC167974
0.8911	High Similarity	NPC196528
0.8854	High Similarity	NPC174051
0.8854	High Similarity	NPC67831
0.8842	High Similarity	NPC154101
0.883	High Similarity	NPC476733
0.883	High Similarity	NPC215029
0.8812	High Similarity	NPC149124
0.8812	High Similarity	NPC75531
0.88	High Similarity	NPC473163
0.8763	High Similarity	NPC469599
0.8762	High Similarity	NPC280782
0.8723	High Similarity	NPC470417
0.87	High Similarity	NPC474327
0.8679	High Similarity	NPC250109
0.8646	High Similarity	NPC262870
0.8641	High Similarity	NPC144459
0.8627	High Similarity	NPC471293
0.8617	High Similarity	NPC90652
0.86	High Similarity	NPC218383
0.8586	High Similarity	NPC57416
0.8586	High Similarity	NPC107243
0.8558	High Similarity	NPC258323
0.8544	High Similarity	NPC231530
0.8544	High Similarity	NPC278628
0.8544	High Similarity	NPC181265
0.8542	High Similarity	NPC171441
0.8529	High Similarity	NPC117185
0.8529	High Similarity	NPC140723
0.8526	High Similarity	NPC255176
0.8505	High Similarity	NPC962
0.8485	Intermediate Similarity	NPC42042
0.8476	Intermediate Similarity	NPC41405
0.8476	Intermediate Similarity	NPC118225
0.8476	Intermediate Similarity	NPC304495
0.8462	Intermediate Similarity	NPC59530
0.8462	Intermediate Similarity	NPC44063
0.8447	Intermediate Similarity	NPC235889
0.8447	Intermediate Similarity	NPC255309
0.844	Intermediate Similarity	NPC471854
0.8438	Intermediate Similarity	NPC54689
0.8438	Intermediate Similarity	NPC474570
0.8431	Intermediate Similarity	NPC22388
0.8426	Intermediate Similarity	NPC473898
0.8416	Intermediate Similarity	NPC83709
0.8411	Intermediate Similarity	NPC475524
0.8411	Intermediate Similarity	NPC100267
0.84	Intermediate Similarity	NPC475894
0.8396	Intermediate Similarity	NPC27551
0.8396	Intermediate Similarity	NPC114961
0.8384	Intermediate Similarity	NPC69548
0.8384	Intermediate Similarity	NPC184848
0.8381	Intermediate Similarity	NPC94529
0.8367	Intermediate Similarity	NPC152897
0.8367	Intermediate Similarity	NPC470376
0.8367	Intermediate Similarity	NPC470375
0.8367	Intermediate Similarity	NPC66429
0.8367	Intermediate Similarity	NPC206810
0.8367	Intermediate Similarity	NPC243866
0.8365	Intermediate Similarity	NPC63023
0.8365	Intermediate Similarity	NPC96377
0.8365	Intermediate Similarity	NPC95243
0.8365	Intermediate Similarity	NPC162033
0.8364	Intermediate Similarity	NPC311554
0.8364	Intermediate Similarity	NPC257457
0.8351	Intermediate Similarity	NPC289213
0.8351	Intermediate Similarity	NPC471896
0.8349	Intermediate Similarity	NPC266728
0.8349	Intermediate Similarity	NPC49492
0.8333	Intermediate Similarity	NPC477944
0.8333	Intermediate Similarity	NPC194100
0.8333	Intermediate Similarity	NPC73455
0.8333	Intermediate Similarity	NPC183546
0.8333	Intermediate Similarity	NPC294480
0.8333	Intermediate Similarity	NPC200944
0.8333	Intermediate Similarity	NPC52634
0.8318	Intermediate Similarity	NPC43775
0.8317	Intermediate Similarity	NPC477813
0.8317	Intermediate Similarity	NPC477854
0.8302	Intermediate Similarity	NPC258543
0.8302	Intermediate Similarity	NPC470257
0.8302	Intermediate Similarity	NPC241927
0.8302	Intermediate Similarity	NPC2766
0.8302	Intermediate Similarity	NPC472216
0.8302	Intermediate Similarity	NPC284828
0.8302	Intermediate Similarity	NPC5475
0.8302	Intermediate Similarity	NPC173905
0.83	Intermediate Similarity	NPC155676
0.83	Intermediate Similarity	NPC49371
0.8298	Intermediate Similarity	NPC82902
0.8286	Intermediate Similarity	NPC220974
0.8269	Intermediate Similarity	NPC100955
0.8269	Intermediate Similarity	NPC121566
0.8269	Intermediate Similarity	NPC223741
0.8269	Intermediate Similarity	NPC473175
0.8265	Intermediate Similarity	NPC189520
0.8265	Intermediate Similarity	NPC150383
0.8257	Intermediate Similarity	NPC471398
0.8257	Intermediate Similarity	NPC473882
0.8252	Intermediate Similarity	NPC185530
0.8247	Intermediate Similarity	NPC474704
0.8247	Intermediate Similarity	NPC32830
0.8247	Intermediate Similarity	NPC477943
0.8247	Intermediate Similarity	NPC475921
0.8241	Intermediate Similarity	NPC170487
0.8241	Intermediate Similarity	NPC221144
0.8241	Intermediate Similarity	NPC234042
0.8241	Intermediate Similarity	NPC207251
0.8241	Intermediate Similarity	NPC152117
0.8235	Intermediate Similarity	NPC230546
0.8229	Intermediate Similarity	NPC96496
0.8229	Intermediate Similarity	NPC317590
0.8229	Intermediate Similarity	NPC312215
0.8224	Intermediate Similarity	NPC197428
0.8224	Intermediate Similarity	NPC154856
0.8224	Intermediate Similarity	NPC5284
0.8224	Intermediate Similarity	NPC52241
0.8224	Intermediate Similarity	NPC475317
0.8224	Intermediate Similarity	NPC101450
0.8224	Intermediate Similarity	NPC473627
0.8218	Intermediate Similarity	NPC469432
0.8218	Intermediate Similarity	NPC18509
0.8214	Intermediate Similarity	NPC471406
0.8211	Intermediate Similarity	NPC474218
0.8208	Intermediate Similarity	NPC472218
0.8208	Intermediate Similarity	NPC295389
0.8208	Intermediate Similarity	NPC472219
0.8208	Intermediate Similarity	NPC472217
0.82	Intermediate Similarity	NPC469329
0.82	Intermediate Similarity	NPC279974
0.82	Intermediate Similarity	NPC263347
0.82	Intermediate Similarity	NPC30677
0.82	Intermediate Similarity	NPC180557
0.82	Intermediate Similarity	NPC37787
0.82	Intermediate Similarity	NPC473415
0.819	Intermediate Similarity	NPC210178
0.819	Intermediate Similarity	NPC475494
0.8182	Intermediate Similarity	NPC148458
0.8173	Intermediate Similarity	NPC26478
0.8173	Intermediate Similarity	NPC236390
0.8173	Intermediate Similarity	NPC191892
0.8165	Intermediate Similarity	NPC260665
0.8165	Intermediate Similarity	NPC202889
0.8165	Intermediate Similarity	NPC255017
0.8165	Intermediate Similarity	NPC317210
0.8163	Intermediate Similarity	NPC111585
0.8163	Intermediate Similarity	NPC123854
0.8163	Intermediate Similarity	NPC320026
0.8163	Intermediate Similarity	NPC148414
0.8163	Intermediate Similarity	NPC175628
0.8148	Intermediate Similarity	NPC250481
0.8148	Intermediate Similarity	NPC285410
0.8148	Intermediate Similarity	NPC231589
0.8148	Intermediate Similarity	NPC214797
0.8148	Intermediate Similarity	NPC263827
0.8148	Intermediate Similarity	NPC118860
0.8144	Intermediate Similarity	NPC44181
0.8144	Intermediate Similarity	NPC28227
0.8142	Intermediate Similarity	NPC475182
0.8137	Intermediate Similarity	NPC197386
0.8137	Intermediate Similarity	NPC471582
0.8137	Intermediate Similarity	NPC119036
0.8137	Intermediate Similarity	NPC153792
0.8137	Intermediate Similarity	NPC271387
0.8131	Intermediate Similarity	NPC218853
0.8131	Intermediate Similarity	NPC265655
0.8131	Intermediate Similarity	NPC246205
0.8125	Intermediate Similarity	NPC469994
0.8125	Intermediate Similarity	NPC324063
0.8125	Intermediate Similarity	NPC161738
0.8125	Intermediate Similarity	NPC475041
0.8125	Intermediate Similarity	NPC319570
0.8125	Intermediate Similarity	NPC5292
0.8125	Intermediate Similarity	NPC155011
0.8125	Intermediate Similarity	NPC212843
0.8125	Intermediate Similarity	NPC473168
0.8125	Intermediate Similarity	NPC195640
0.8125	Intermediate Similarity	NPC61520
0.8119	Intermediate Similarity	NPC173272
0.8119	Intermediate Similarity	NPC322063
0.8119	Intermediate Similarity	NPC477853
0.8113	Intermediate Similarity	NPC43285
0.8113	Intermediate Similarity	NPC165873
0.8113	Intermediate Similarity	NPC58370
0.8113	Intermediate Similarity	NPC475294
0.8113	Intermediate Similarity	NPC83744
0.8108	Intermediate Similarity	NPC239273
0.81	Intermediate Similarity	NPC159410
0.81	Intermediate Similarity	NPC7165
0.81	Intermediate Similarity	NPC473172
0.81	Intermediate Similarity	NPC240617
0.8095	Intermediate Similarity	NPC470104
0.8095	Intermediate Similarity	NPC477812
0.8095	Intermediate Similarity	NPC472228
0.8095	Intermediate Similarity	NPC13385
0.8095	Intermediate Similarity	NPC472227
0.8095	Intermediate Similarity	NPC29705
0.8095	Intermediate Similarity	NPC137657
0.8091	Intermediate Similarity	NPC116024
0.8091	Intermediate Similarity	NPC326542

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 NPC473928 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1471
0.2-0.3	4037
0.3-0.4	2295
0.4-0.5	642
0.5-0.6	187
0.6-0.7	174
0.7-0.8	128
0.8-0.85	39
0.85-0.9	15
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8942	High Similarity	NPD8297	Approved
0.8725	High Similarity	NPD6402	Approved
0.8725	High Similarity	NPD7128	Approved
0.8725	High Similarity	NPD5739	Approved
0.8725	High Similarity	NPD6675	Approved
0.8654	High Similarity	NPD6372	Approved
0.8654	High Similarity	NPD6373	Approved
0.8586	High Similarity	NPD6084	Phase 2
0.8586	High Similarity	NPD6083	Phase 2
0.8558	High Similarity	NPD7320	Approved
0.8558	High Similarity	NPD6899	Approved
0.8558	High Similarity	NPD6881	Approved
0.8491	Intermediate Similarity	NPD6649	Approved
0.8491	Intermediate Similarity	NPD8130	Phase 1
0.8491	Intermediate Similarity	NPD6650	Approved
0.8462	Intermediate Similarity	NPD5701	Approved
0.8462	Intermediate Similarity	NPD5697	Approved
0.8411	Intermediate Similarity	NPD6882	Approved
0.8396	Intermediate Similarity	NPD6883	Approved
0.8396	Intermediate Similarity	NPD7290	Approved
0.8396	Intermediate Similarity	NPD7102	Approved
0.8367	Intermediate Similarity	NPD6399	Phase 3
0.8318	Intermediate Similarity	NPD6869	Approved
0.8318	Intermediate Similarity	NPD6617	Approved
0.8318	Intermediate Similarity	NPD6847	Approved
0.8302	Intermediate Similarity	NPD6013	Approved
0.8302	Intermediate Similarity	NPD6012	Approved
0.8302	Intermediate Similarity	NPD6014	Approved
0.8218	Intermediate Similarity	NPD4755	Approved
0.8214	Intermediate Similarity	NPD6319	Approved
0.8208	Intermediate Similarity	NPD6011	Approved
0.82	Intermediate Similarity	NPD5695	Phase 3
0.8165	Intermediate Similarity	NPD4632	Approved
0.8148	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5696	Approved
0.8125	Intermediate Similarity	NPD7521	Approved
0.8125	Intermediate Similarity	NPD6409	Approved
0.8125	Intermediate Similarity	NPD6684	Approved
0.8125	Intermediate Similarity	NPD5330	Approved
0.8125	Intermediate Similarity	NPD7146	Approved
0.8125	Intermediate Similarity	NPD7334	Approved
0.8113	Intermediate Similarity	NPD6412	Phase 2
0.8061	Intermediate Similarity	NPD4753	Phase 2
0.8058	Intermediate Similarity	NPD5286	Approved
0.8058	Intermediate Similarity	NPD5285	Approved
0.8058	Intermediate Similarity	NPD4700	Approved
0.8058	Intermediate Similarity	NPD4696	Approved
0.7959	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6903	Approved
0.7938	Intermediate Similarity	NPD6098	Approved
0.7917	Intermediate Similarity	NPD3665	Phase 1
0.7917	Intermediate Similarity	NPD3666	Approved
0.7917	Intermediate Similarity	NPD3133	Approved
0.7917	Intermediate Similarity	NPD4786	Approved
0.7905	Intermediate Similarity	NPD5225	Approved
0.7905	Intermediate Similarity	NPD4633	Approved
0.7905	Intermediate Similarity	NPD5226	Approved
0.7905	Intermediate Similarity	NPD5211	Phase 2
0.7905	Intermediate Similarity	NPD5224	Approved
0.7879	Intermediate Similarity	NPD6904	Approved
0.7879	Intermediate Similarity	NPD6673	Approved
0.7879	Intermediate Similarity	NPD5328	Approved
0.7879	Intermediate Similarity	NPD6080	Approved
0.7857	Intermediate Similarity	NPD6274	Approved
0.785	Intermediate Similarity	NPD4767	Approved
0.785	Intermediate Similarity	NPD4768	Approved
0.783	Intermediate Similarity	NPD5175	Approved
0.783	Intermediate Similarity	NPD5174	Approved
0.7822	Intermediate Similarity	NPD4202	Approved
0.781	Intermediate Similarity	NPD5223	Approved
0.7807	Intermediate Similarity	NPD7100	Approved
0.7807	Intermediate Similarity	NPD7101	Approved
0.7797	Intermediate Similarity	NPD8293	Discontinued
0.7788	Intermediate Similarity	NPD6009	Approved
0.7778	Intermediate Similarity	NPD7492	Approved
0.7778	Intermediate Similarity	NPD6672	Approved
0.7778	Intermediate Similarity	NPD5737	Approved
0.7757	Intermediate Similarity	NPD5141	Approved
0.7739	Intermediate Similarity	NPD6059	Approved
0.7739	Intermediate Similarity	NPD6054	Approved
0.7731	Intermediate Similarity	NPD7736	Approved
0.7727	Intermediate Similarity	NPD4634	Approved
0.7723	Intermediate Similarity	NPD5284	Approved
0.7723	Intermediate Similarity	NPD6079	Approved
0.7723	Intermediate Similarity	NPD5281	Approved
0.7719	Intermediate Similarity	NPD6335	Approved
0.7712	Intermediate Similarity	NPD7507	Approved
0.7712	Intermediate Similarity	NPD6616	Approved
0.7708	Intermediate Similarity	NPD4221	Approved
0.7708	Intermediate Similarity	NPD4223	Phase 3
0.7708	Intermediate Similarity	NPD3667	Approved
0.7708	Intermediate Similarity	NPD6435	Approved
0.7706	Intermediate Similarity	NPD4730	Approved
0.7706	Intermediate Similarity	NPD4729	Approved
0.7692	Intermediate Similarity	NPD7604	Phase 2
0.7685	Intermediate Similarity	NPD6008	Approved
0.7672	Intermediate Similarity	NPD5983	Phase 2
0.7672	Intermediate Similarity	NPD6908	Approved
0.7672	Intermediate Similarity	NPD6909	Approved
0.767	Intermediate Similarity	NPD4629	Approved
0.767	Intermediate Similarity	NPD5210	Approved
0.767	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD4754	Approved
0.7653	Intermediate Similarity	NPD5329	Approved
0.7647	Intermediate Similarity	NPD7078	Approved
0.7632	Intermediate Similarity	NPD6317	Approved
0.7632	Intermediate Similarity	NPD7115	Discovery
0.7607	Intermediate Similarity	NPD6370	Approved
0.76	Intermediate Similarity	NPD5208	Approved
0.7573	Intermediate Similarity	NPD7748	Approved
0.7568	Intermediate Similarity	NPD5251	Approved
0.7568	Intermediate Similarity	NPD5247	Approved
0.7568	Intermediate Similarity	NPD5249	Phase 3
0.7568	Intermediate Similarity	NPD5250	Approved
0.7568	Intermediate Similarity	NPD5248	Approved
0.7565	Intermediate Similarity	NPD6313	Approved
0.7565	Intermediate Similarity	NPD6314	Approved
0.7563	Intermediate Similarity	NPD6336	Discontinued
0.7551	Intermediate Similarity	NPD4197	Approved
0.7549	Intermediate Similarity	NPD8035	Phase 2
0.7549	Intermediate Similarity	NPD6050	Approved
0.7549	Intermediate Similarity	NPD8034	Phase 2
0.7549	Intermediate Similarity	NPD5693	Phase 1
0.7545	Intermediate Similarity	NPD5128	Approved
0.7524	Intermediate Similarity	NPD7902	Approved
0.7521	Intermediate Similarity	NPD6015	Approved
0.7521	Intermediate Similarity	NPD6016	Approved
0.7521	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD5368	Approved
0.7458	Intermediate Similarity	NPD5988	Approved
0.7451	Intermediate Similarity	NPD5692	Phase 3
0.7449	Intermediate Similarity	NPD4788	Approved
0.7434	Intermediate Similarity	NPD6053	Discontinued
0.7429	Intermediate Similarity	NPD4697	Phase 3
0.7429	Intermediate Similarity	NPD5222	Approved
0.7429	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5221	Approved
0.74	Intermediate Similarity	NPD4693	Phase 3
0.74	Intermediate Similarity	NPD4690	Approved
0.74	Intermediate Similarity	NPD5205	Approved
0.74	Intermediate Similarity	NPD4689	Approved
0.74	Intermediate Similarity	NPD4688	Approved
0.74	Intermediate Similarity	NPD4138	Approved
0.74	Intermediate Similarity	NPD3618	Phase 1
0.7387	Intermediate Similarity	NPD6686	Approved
0.7379	Intermediate Similarity	NPD7515	Phase 2
0.7379	Intermediate Similarity	NPD5694	Approved
0.7379	Intermediate Similarity	NPD6411	Approved
0.7373	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8133	Approved
0.7358	Intermediate Similarity	NPD5173	Approved
0.7353	Intermediate Similarity	NPD6051	Approved
0.7345	Intermediate Similarity	NPD5216	Approved
0.7345	Intermediate Similarity	NPD5217	Approved
0.7345	Intermediate Similarity	NPD5215	Approved
0.7321	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7638	Approved
0.7282	Intermediate Similarity	NPD5207	Approved
0.7257	Intermediate Similarity	NPD5135	Approved
0.7257	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5169	Approved
0.725	Intermediate Similarity	NPD8328	Phase 3
0.7241	Intermediate Similarity	NPD6868	Approved
0.7238	Intermediate Similarity	NPD6001	Approved
0.7238	Intermediate Similarity	NPD7900	Approved
0.7238	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5690	Phase 2
0.7228	Intermediate Similarity	NPD5279	Phase 3
0.7228	Intermediate Similarity	NPD4694	Approved
0.7228	Intermediate Similarity	NPD5280	Approved
0.7222	Intermediate Similarity	NPD7640	Approved
0.7222	Intermediate Similarity	NPD7639	Approved
0.72	Intermediate Similarity	NPD3668	Phase 3
0.7193	Intermediate Similarity	NPD5127	Approved
0.7184	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6101	Approved
0.7158	Intermediate Similarity	NPD3702	Approved
0.7154	Intermediate Similarity	NPD6033	Approved
0.7143	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD8377	Approved
0.7143	Intermediate Similarity	NPD8294	Approved
0.7119	Intermediate Similarity	NPD7327	Approved
0.7119	Intermediate Similarity	NPD7328	Approved
0.7083	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8378	Approved
0.7083	Intermediate Similarity	NPD8335	Approved
0.7083	Intermediate Similarity	NPD8379	Approved
0.7083	Intermediate Similarity	NPD7503	Approved
0.7083	Intermediate Similarity	NPD8380	Approved
0.7083	Intermediate Similarity	NPD8296	Approved
0.7083	Intermediate Similarity	NPD8033	Approved
0.708	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4692	Approved
0.7071	Intermediate Similarity	NPD4139	Approved
0.7071	Intermediate Similarity	NPD5369	Approved
0.7059	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7516	Approved
0.7041	Intermediate Similarity	NPD4195	Approved
0.7034	Intermediate Similarity	NPD8295	Clinical (unspecified phase)

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