NPASS Compound

Structure

NPC473859 OpenBabel07101719152D 26 28 0 0 1 0 0 0 0 0999 V2000 4.7260 0.7811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3245 1.1077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1031 -3.0953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7595 2.3998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5575 2.2740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3219 1.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2402 1.2639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4037 1.2639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2402 -1.2639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8077 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2428 0.8094 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.3219 -2.5278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9603 1.4554 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.3219 -1.5622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8077 -0.4828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4037 -1.2639 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8362 -0.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4435 -0.1351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4037 -2.8261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 0.4828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8785 1.1571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3618 -0.4334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1053 -3.7444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7260 -0.7811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 -2.0450 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 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 13 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 10 2 0 0 0 0 8 20 1 0 0 0 0 9 15 1 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 14 9 1 1 0 0 0 14 16 1 0 0 0 0 15 24 1 1 0 0 0 16 17 1 0 0 0 0 16 25 1 6 0 0 0 17 20 1 1 0 0 0 17 26 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 5 1 1 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.19
Volume:	371.002
LogP:	2.593
LogD:	2.062
LogS:	-3.497
# Rotatable Bonds:	4
TPSA:	85.36
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.358
Synthetic Accessibility Score:	5.259
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	5.385983968153596e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.771
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.41
Plasma Protein Binding (PPB):	79.8953857421875%
Volume Distribution (VD):	1.117
Pgp-substrate:	23.727079391479492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.409
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.657
CYP2C9-inhibitor:	0.056
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.393
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	9.59
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.869
Drug-inuced Liver Injury (DILI):	0.673
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.754
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.501
Carcinogencity:	0.204
Eye Corrosion:	0.02
Eye Irritation:	0.021
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC473859

Natural Product ID:	NPC473859
*Common Name:**	MPNJUHHXWPDZRT-DFQPLNLMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MPNJUHHXWPDZRT-DFQPLNLMSA-N
Standard InCHI:	InChI=1S/C20H28O6/c1-10-7-6-8-20(5)17(26-20)16-14(12(3)19(23)25-16)9-15(10)24-18(22)11(2)13(4)21/h7,11,13-17,21H,3,6,8-9H2,1-2,4-5H3/b10-7+/t11?,13?,14-,15-,16-,17+,20+/m0/s1
SMILES:	CC(C(C(=O)O[C@H]1C[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2O[C@@]2(CC/C=C/1C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453565
PubChem CID:	10090173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides 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
NPO40534	Inula verbascifolia subsp. methanea	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141872]
NPO33178	inula montbretiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]

☑ 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	9

Activity Type	# Activity
Cell Line	5
Individual Protein	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	11.7	ug.mL-1	PMID[528737]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	0.39	ug.mL-1	PMID[528737]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40.0	ug.mL-1	PMID[528737]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	25.4	ug.mL-1	PMID[528737]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	11.3	ug.mL-1	PMID[528737]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13.4	ug.mL-1	PMID[528737]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	14354.89	nM	PMID[528738]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[528738]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	14350.0	nM	PMID[528738]

☑ 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 NPC473859 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	224
0.1-0.2	1361
0.2-0.3	5054
0.3-0.4	9110
0.4-0.5	14555
0.5-0.6	7356
0.6-0.7	3595
0.7-0.8	1174
0.8-0.85	164
0.85-0.9	73
0.9-0.95	24
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC475659
0.9674	High Similarity	NPC288876
0.9556	High Similarity	NPC303942
0.9556	High Similarity	NPC57405
0.9341	High Similarity	NPC471147
0.9255	High Similarity	NPC475949
0.9239	High Similarity	NPC270013
0.9239	High Similarity	NPC14961
0.9231	High Similarity	NPC212486
0.9149	High Similarity	NPC473326
0.914	High Similarity	NPC279621
0.914	High Similarity	NPC476315
0.914	High Similarity	NPC230800
0.913	High Similarity	NPC474035
0.913	High Similarity	NPC81386
0.9111	High Similarity	NPC474032
0.9111	High Similarity	NPC151770
0.9082	High Similarity	NPC477513
0.9062	High Similarity	NPC471148
0.9032	High Similarity	NPC471142
0.9032	High Similarity	NPC477922
0.9022	High Similarity	NPC475838
0.9022	High Similarity	NPC475912
0.9022	High Similarity	NPC125674
0.9022	High Similarity	NPC228451
0.9011	High Similarity	NPC473619
0.8958	High Similarity	NPC474339
0.8958	High Similarity	NPC164598
0.8958	High Similarity	NPC201718
0.8947	High Similarity	NPC471144
0.8936	High Similarity	NPC477921
0.8925	High Similarity	NPC140543
0.8925	High Similarity	NPC473316
0.8925	High Similarity	NPC473330
0.8925	High Similarity	NPC474247
0.8913	High Similarity	NPC473321
0.8913	High Similarity	NPC184463
0.8913	High Similarity	NPC30515
0.8901	High Similarity	NPC166919
0.8889	High Similarity	NPC231889
0.8876	High Similarity	NPC38468
0.8876	High Similarity	NPC50362
0.8876	High Similarity	NPC319795
0.8866	High Similarity	NPC149371
0.883	High Similarity	NPC36954
0.8817	High Similarity	NPC162205
0.8817	High Similarity	NPC273579
0.8817	High Similarity	NPC476300
0.8817	High Similarity	NPC288240
0.8817	High Similarity	NPC295204
0.8817	High Similarity	NPC81419
0.8817	High Similarity	NPC179746
0.8804	High Similarity	NPC475748
0.8804	High Similarity	NPC51004
0.8791	High Similarity	NPC473715
0.8791	High Similarity	NPC202672
0.8778	High Similarity	NPC50637
0.8763	High Similarity	NPC264477
0.8763	High Similarity	NPC47880
0.8763	High Similarity	NPC477511
0.875	High Similarity	NPC474213
0.875	High Similarity	NPC208233
0.8737	High Similarity	NPC17585
0.8737	High Similarity	NPC35498
0.8723	High Similarity	NPC476267
0.871	High Similarity	NPC12172
0.871	High Similarity	NPC208886
0.8696	High Similarity	NPC307411
0.8687	High Similarity	NPC474741
0.8646	High Similarity	NPC471140
0.8632	High Similarity	NPC471141
0.8602	High Similarity	NPC251385
0.8602	High Similarity	NPC475855
0.8602	High Similarity	NPC49342
0.8602	High Similarity	NPC474232
0.8602	High Similarity	NPC474761
0.8602	High Similarity	NPC476004
0.8587	High Similarity	NPC476803
0.8586	High Similarity	NPC475871
0.8586	High Similarity	NPC475945
0.8571	High Similarity	NPC476270
0.8571	High Similarity	NPC469910
0.8571	High Similarity	NPC473332
0.8557	High Similarity	NPC279561
0.8556	High Similarity	NPC158756
0.8511	High Similarity	NPC475881
0.8511	High Similarity	NPC20713
0.8511	High Similarity	NPC70251
0.85	High Similarity	NPC471143
0.85	High Similarity	NPC477510
0.85	High Similarity	NPC100487
0.8485	Intermediate Similarity	NPC474747
0.8478	Intermediate Similarity	NPC266957
0.8478	Intermediate Similarity	NPC5130
0.8469	Intermediate Similarity	NPC477512
0.8462	Intermediate Similarity	NPC470755
0.8462	Intermediate Similarity	NPC255307
0.8462	Intermediate Similarity	NPC21469
0.8444	Intermediate Similarity	NPC272814
0.8421	Intermediate Similarity	NPC475302
0.8416	Intermediate Similarity	NPC243998
0.8404	Intermediate Similarity	NPC144133
0.8404	Intermediate Similarity	NPC179394
0.8404	Intermediate Similarity	NPC312042
0.8387	Intermediate Similarity	NPC475819
0.8387	Intermediate Similarity	NPC476805
0.8387	Intermediate Similarity	NPC281516
0.8384	Intermediate Similarity	NPC474742
0.837	Intermediate Similarity	NPC305475
0.837	Intermediate Similarity	NPC475461
0.8352	Intermediate Similarity	NPC141193
0.8352	Intermediate Similarity	NPC96259
0.8352	Intermediate Similarity	NPC476804
0.8352	Intermediate Similarity	NPC191476
0.8352	Intermediate Similarity	NPC114979
0.8351	Intermediate Similarity	NPC76862
0.8351	Intermediate Similarity	NPC470883
0.8351	Intermediate Similarity	NPC39859
0.8351	Intermediate Similarity	NPC158416
0.8333	Intermediate Similarity	NPC72813
0.8333	Intermediate Similarity	NPC194620
0.8333	Intermediate Similarity	NPC474421
0.8333	Intermediate Similarity	NPC326994
0.8333	Intermediate Similarity	NPC324327
0.8317	Intermediate Similarity	NPC203659
0.8316	Intermediate Similarity	NPC158061
0.8298	Intermediate Similarity	NPC295312
0.828	Intermediate Similarity	NPC475703
0.828	Intermediate Similarity	NPC186148
0.8265	Intermediate Similarity	NPC40812
0.8261	Intermediate Similarity	NPC47958
0.8261	Intermediate Similarity	NPC149725
0.8261	Intermediate Similarity	NPC304509
0.8252	Intermediate Similarity	NPC169888
0.8252	Intermediate Similarity	NPC233379
0.8252	Intermediate Similarity	NPC55972
0.8252	Intermediate Similarity	NPC474664
0.8252	Intermediate Similarity	NPC327286
0.8252	Intermediate Similarity	NPC14862
0.8247	Intermediate Similarity	NPC107476
0.8242	Intermediate Similarity	NPC169575
0.8242	Intermediate Similarity	NPC131669
0.8242	Intermediate Similarity	NPC473390
0.8242	Intermediate Similarity	NPC40746
0.8235	Intermediate Similarity	NPC9303
0.8235	Intermediate Similarity	NPC223450
0.8235	Intermediate Similarity	NPC475802
0.8235	Intermediate Similarity	NPC16313
0.8229	Intermediate Similarity	NPC165383
0.8222	Intermediate Similarity	NPC24417
0.8222	Intermediate Similarity	NPC141810
0.8218	Intermediate Similarity	NPC69171
0.8218	Intermediate Similarity	NPC472755
0.8218	Intermediate Similarity	NPC474165
0.8218	Intermediate Similarity	NPC110989
0.8218	Intermediate Similarity	NPC4620
0.8211	Intermediate Similarity	NPC71533
0.8211	Intermediate Similarity	NPC106510
0.8211	Intermediate Similarity	NPC469368
0.8202	Intermediate Similarity	NPC98557
0.8202	Intermediate Similarity	NPC167881
0.82	Intermediate Similarity	NPC110443
0.82	Intermediate Similarity	NPC133907
0.82	Intermediate Similarity	NPC46998
0.82	Intermediate Similarity	NPC128733
0.82	Intermediate Similarity	NPC185141
0.82	Intermediate Similarity	NPC472753
0.8191	Intermediate Similarity	NPC58219
0.8191	Intermediate Similarity	NPC153805
0.8191	Intermediate Similarity	NPC227379
0.8191	Intermediate Similarity	NPC177629
0.8191	Intermediate Similarity	NPC474471
0.8191	Intermediate Similarity	NPC287089
0.8182	Intermediate Similarity	NPC187761
0.8182	Intermediate Similarity	NPC255592
0.8182	Intermediate Similarity	NPC187268
0.8182	Intermediate Similarity	NPC261377
0.8182	Intermediate Similarity	NPC308567
0.8182	Intermediate Similarity	NPC83895
0.8173	Intermediate Similarity	NPC38154
0.8173	Intermediate Similarity	NPC475922
0.8173	Intermediate Similarity	NPC15218
0.8172	Intermediate Similarity	NPC150755
0.8172	Intermediate Similarity	NPC469483
0.8172	Intermediate Similarity	NPC470242
0.8172	Intermediate Similarity	NPC122502
0.8163	Intermediate Similarity	NPC476009
0.8163	Intermediate Similarity	NPC306041
0.8144	Intermediate Similarity	NPC71589
0.8144	Intermediate Similarity	NPC190294
0.8137	Intermediate Similarity	NPC475676
0.8137	Intermediate Similarity	NPC220964
0.8132	Intermediate Similarity	NPC229825
0.8125	Intermediate Similarity	NPC470373
0.8125	Intermediate Similarity	NPC476705
0.8125	Intermediate Similarity	NPC470379
0.8119	Intermediate Similarity	NPC472754
0.8119	Intermediate Similarity	NPC225353
0.8119	Intermediate Similarity	NPC183571
0.8119	Intermediate Similarity	NPC320019

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 NPC473859 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1965
0.2-0.3	3744
0.3-0.4	2139
0.4-0.5	716
0.5-0.6	302
0.6-0.7	66
0.7-0.8	12
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8876	High Similarity	NPD1733	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD46	Approved
0.8211	Intermediate Similarity	NPD6698	Approved
0.7938	Intermediate Similarity	NPD7983	Approved
0.781	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD6371	Approved
0.77	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD7838	Discovery
0.7551	Intermediate Similarity	NPD1695	Approved
0.7157	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4225	Approved
0.7129	Intermediate Similarity	NPD5785	Approved
0.7094	Intermediate Similarity	NPD8517	Approved
0.7094	Intermediate Similarity	NPD8513	Phase 3
0.7094	Intermediate Similarity	NPD8516	Approved
0.7094	Intermediate Similarity	NPD8515	Approved
0.7071	Intermediate Similarity	NPD5786	Approved
0.7054	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5344	Discontinued
0.6975	Remote Similarity	NPD7642	Approved
0.697	Remote Similarity	NPD5363	Approved
0.6952	Remote Similarity	NPD7839	Suspended
0.6939	Remote Similarity	NPD7154	Phase 3
0.6937	Remote Similarity	NPD6686	Approved
0.6923	Remote Similarity	NPD5282	Discontinued
0.6907	Remote Similarity	NPD5369	Approved
0.69	Remote Similarity	NPD4249	Approved
0.6897	Remote Similarity	NPD7115	Discovery
0.6842	Remote Similarity	NPD6053	Discontinued
0.6837	Remote Similarity	NPD4270	Approved
0.6837	Remote Similarity	NPD6435	Approved
0.6837	Remote Similarity	NPD4269	Approved
0.6833	Remote Similarity	NPD7830	Approved
0.6833	Remote Similarity	NPD7829	Approved
0.6832	Remote Similarity	NPD4251	Approved
0.6832	Remote Similarity	NPD4250	Approved
0.6803	Remote Similarity	NPD8074	Phase 3
0.6759	Remote Similarity	NPD6648	Approved
0.6726	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6101	Approved
0.6699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4822	Approved
0.6633	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4819	Approved
0.6633	Remote Similarity	NPD4821	Approved
0.6633	Remote Similarity	NPD4252	Approved
0.6633	Remote Similarity	NPD4820	Approved
0.6633	Remote Similarity	NPD5368	Approved
0.66	Remote Similarity	NPD5362	Discontinued
0.6571	Remote Similarity	NPD6411	Approved
0.6556	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5209	Approved
0.6491	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6008	Approved
0.6452	Remote Similarity	NPD8451	Approved
0.6452	Remote Similarity	NPD8273	Phase 1
0.6446	Remote Similarity	NPD6319	Approved
0.6429	Remote Similarity	NPD4268	Approved
0.6429	Remote Similarity	NPD7319	Approved
0.6429	Remote Similarity	NPD4271	Approved
0.6415	Remote Similarity	NPD7637	Suspended
0.6404	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8448	Approved
0.6393	Remote Similarity	NPD8444	Approved
0.6371	Remote Similarity	NPD7492	Approved
0.6364	Remote Similarity	NPD7638	Approved
0.6337	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD2204	Approved
0.632	Remote Similarity	NPD7507	Approved
0.632	Remote Similarity	NPD6616	Approved
0.6311	Remote Similarity	NPD6054	Approved
0.6311	Remote Similarity	NPD1694	Approved
0.6306	Remote Similarity	NPD7639	Approved
0.6306	Remote Similarity	NPD7640	Approved
0.6281	Remote Similarity	NPD7641	Discontinued
0.627	Remote Similarity	NPD7078	Approved
0.6263	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6016	Approved
0.626	Remote Similarity	NPD6015	Approved
0.625	Remote Similarity	NPD8390	Approved
0.625	Remote Similarity	NPD8392	Approved
0.625	Remote Similarity	NPD8391	Approved
0.624	Remote Similarity	NPD8299	Approved
0.624	Remote Similarity	NPD8342	Approved
0.624	Remote Similarity	NPD8341	Approved
0.624	Remote Similarity	NPD8340	Approved
0.6226	Remote Similarity	NPD5370	Suspended
0.622	Remote Similarity	NPD7736	Approved
0.6218	Remote Similarity	NPD4632	Approved
0.621	Remote Similarity	NPD5988	Approved
0.621	Remote Similarity	NPD6370	Approved
0.6179	Remote Similarity	NPD6059	Approved
0.6142	Remote Similarity	NPD8293	Discontinued
0.6134	Remote Similarity	NPD8297	Approved
0.6121	Remote Similarity	NPD5697	Approved
0.6117	Remote Similarity	NPD5332	Approved
0.6117	Remote Similarity	NPD5331	Approved
0.6117	Remote Similarity	NPD6110	Phase 1
0.6111	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4790	Discontinued
0.6077	Remote Similarity	NPD7260	Phase 2
0.6068	Remote Similarity	NPD6881	Approved
0.6068	Remote Similarity	NPD6899	Approved
0.6066	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6009	Approved
0.6066	Remote Similarity	NPD7500	Approved
0.6064	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6399	Phase 3
0.605	Remote Similarity	NPD6650	Approved
0.605	Remote Similarity	NPD6649	Approved
0.6034	Remote Similarity	NPD6402	Approved
0.6034	Remote Similarity	NPD5739	Approved
0.6034	Remote Similarity	NPD7128	Approved
0.6034	Remote Similarity	NPD6675	Approved
0.6032	Remote Similarity	NPD7604	Phase 2
0.6032	Remote Similarity	NPD8328	Phase 3
0.6019	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6014	Approved
0.6017	Remote Similarity	NPD6373	Approved
0.6017	Remote Similarity	NPD6372	Approved
0.6017	Remote Similarity	NPD6012	Approved
0.6017	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD8266	Approved
0.6	Remote Similarity	NPD8267	Approved
0.6	Remote Similarity	NPD8268	Approved
0.6	Remote Similarity	NPD8269	Approved
0.6	Remote Similarity	NPD5983	Phase 2
0.5983	Remote Similarity	NPD6412	Phase 2
0.5983	Remote Similarity	NPD5701	Approved
0.5966	Remote Similarity	NPD7102	Approved
0.5966	Remote Similarity	NPD4634	Approved
0.5966	Remote Similarity	NPD7290	Approved
0.5966	Remote Similarity	NPD6883	Approved
0.596	Remote Similarity	NPD8039	Approved
0.5957	Remote Similarity	NPD7331	Phase 2
0.5952	Remote Similarity	NPD8080	Discontinued
0.5943	Remote Similarity	NPD6422	Discontinued
0.5935	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6011	Approved
0.5932	Remote Similarity	NPD7320	Approved
0.5917	Remote Similarity	NPD6869	Approved
0.5917	Remote Similarity	NPD6617	Approved
0.5917	Remote Similarity	NPD8130	Phase 1
0.5917	Remote Similarity	NPD6847	Approved
0.5909	Remote Similarity	NPD6845	Suspended
0.5897	Remote Similarity	NPD5048	Discontinued
0.5873	Remote Similarity	NPD6921	Approved
0.5873	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6882	Approved
0.5842	Remote Similarity	NPD4756	Discovery
0.5841	Remote Similarity	NPD6084	Phase 2
0.5841	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD6421	Discontinued
0.582	Remote Similarity	NPD8133	Approved
0.5814	Remote Similarity	NPD6336	Discontinued
0.5804	Remote Similarity	NPD5695	Phase 3
0.5789	Remote Similarity	NPD5696	Approved
0.5785	Remote Similarity	NPD1719	Phase 1
0.5778	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD5211	Phase 2
0.5776	Remote Similarity	NPD7632	Discontinued
0.576	Remote Similarity	NPD7328	Approved
0.576	Remote Similarity	NPD7327	Approved
0.5755	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD8033	Approved
0.5748	Remote Similarity	NPD7503	Approved
0.5745	Remote Similarity	NPD3197	Phase 1
0.5741	Remote Similarity	NPD7524	Approved
0.5739	Remote Similarity	NPD5285	Approved
0.5739	Remote Similarity	NPD4696	Approved
0.5739	Remote Similarity	NPD5286	Approved
0.5727	Remote Similarity	NPD3168	Discontinued
0.5726	Remote Similarity	NPD6274	Approved
0.5725	Remote Similarity	NPD6033	Approved
0.5714	Remote Similarity	NPD7516	Approved
0.5704	Remote Similarity	NPD8415	Approved
0.5702	Remote Similarity	NPD7902	Approved
0.5702	Remote Similarity	NPD2067	Discontinued
0.5702	Remote Similarity	NPD4755	Approved
0.569	Remote Similarity	NPD1700	Approved
0.5684	Remote Similarity	NPD7341	Phase 2
0.5678	Remote Similarity	NPD5141	Approved
0.5669	Remote Similarity	NPD8294	Approved
0.5669	Remote Similarity	NPD8377	Approved
0.566	Remote Similarity	NPD6695	Phase 3
0.5656	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5225	Approved
0.5641	Remote Similarity	NPD5224	Approved
0.5641	Remote Similarity	NPD5226	Approved
0.5641	Remote Similarity	NPD4633	Approved
0.5639	Remote Similarity	NPD5956	Approved
0.5631	Remote Similarity	NPD3732	Approved
0.5625	Remote Similarity	NPD8380	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