NPASS Compound

Structure

NPC166919 OpenBabel07101718182D 21 23 0 0 1 0 0 0 0 0999 V2000 4.7377 2.0298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5459 2.2571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9529 -3.6806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7794 -0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3047 -1.5506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7794 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3932 -1.2545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3932 1.2545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7794 2.0298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2161 -1.2545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2161 1.2545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3047 1.5506 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8299 -0.4792 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2161 2.8051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7794 -2.0298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 0.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5122 3.7165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7325 -1.9296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3896 -2.9053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3047 2.5089 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 9 2 0 0 0 0 3 19 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 7 1 0 0 0 0 5 10 1 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 6 1 1 0 0 0 11 12 1 0 0 0 0 12 8 1 6 0 0 0 12 20 1 0 0 0 0 13 16 1 1 0 0 0 13 21 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 2 1 1 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.13
Volume:	293.028
LogP:	2.394
LogD:	1.533
LogS:	-3.366
# Rotatable Bonds:	2
TPSA:	65.13
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.419
Synthetic Accessibility Score:	4.686
Fsp3:	0.625
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:	-4.766
MDCK Permeability:	2.0254983610357158e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.842
30% Bioavailability (F30%):	0.854

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	78.4112777709961%
Volume Distribution (VD):	1.8
Pgp-substrate:	13.701471328735352%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.492
CYP2C19-inhibitor:	0.327
CYP2C19-substrate:	0.728
CYP2C9-inhibitor:	0.287
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.386
CYP3A4-inhibitor:	0.28
CYP3A4-substrate:	0.412

ADMET: Excretion

Clearance (CL):	8.204
Half-life (T1/2):	0.73

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.522
Drug-inuced Liver Injury (DILI):	0.466
AMES Toxicity:	0.581
Rat Oral Acute Toxicity:	0.419
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.966
Carcinogencity:	0.726
Eye Corrosion:	0.501
Eye Irritation:	0.816
Respiratory Toxicity:	0.819

Download Data

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

Natural Product: NPC166919

Natural Product ID:	NPC166919
*Common Name:**	Hirusutolide
IUPAC Name:	n.a.
Synonyms:	Hirusutolide
Standard InCHIKey:	JXOSBNBCTRYGNH-JHMSBIDHSA-N
Standard InCHI:	InChI=1S/C16H20O5/c1-9-11-6-4-10(15(18)19-3)5-7-13-16(2,21-13)8-12(11)20-14(9)17/h4,11-13H,1,5-8H2,2-3H3/b10-4+/t11-,12+,13-,16-/m1/s1
SMILES:	C=C1[C@H]2C/C=C(CC[C@@H]3[C@@](C)(C[C@@H]2OC1=O)O3)/C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489197
PubChem CID:	44579872
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]

☑ 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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	7.0	umol/L	PMID[478597]

☑ 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 NPC166919 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	240
0.1-0.2	1542
0.2-0.3	5607
0.3-0.4	11694
0.4-0.5	12963
0.5-0.6	6449
0.6-0.7	3063
0.7-0.8	923
0.8-0.85	131
0.85-0.9	48
0.9-0.95	29
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC50637
0.954	High Similarity	NPC473330
0.954	High Similarity	NPC473316
0.954	High Similarity	NPC140543
0.9529	High Similarity	NPC151770
0.9419	High Similarity	NPC312042
0.9318	High Similarity	NPC476267
0.9294	High Similarity	NPC475703
0.9294	High Similarity	NPC231889
0.9277	High Similarity	NPC272814
0.9205	High Similarity	NPC475838
0.9205	High Similarity	NPC228451
0.9205	High Similarity	NPC125674
0.9195	High Similarity	NPC475748
0.9101	High Similarity	NPC474247
0.9101	High Similarity	NPC471147
0.9059	High Similarity	NPC38468
0.9059	High Similarity	NPC50362
0.9059	High Similarity	NPC319795
0.9036	High Similarity	NPC141810
0.9022	High Similarity	NPC288876
0.9	High Similarity	NPC475659
0.8977	High Similarity	NPC251385
0.8977	High Similarity	NPC49342
0.8977	High Similarity	NPC62815
0.8925	High Similarity	NPC264477
0.8925	High Similarity	NPC477511
0.8913	High Similarity	NPC208233
0.8913	High Similarity	NPC473326
0.8913	High Similarity	NPC279561
0.8901	High Similarity	NPC279621
0.8901	High Similarity	NPC17585
0.8901	High Similarity	NPC230800
0.8901	High Similarity	NPC473859
0.8901	High Similarity	NPC35498
0.8889	High Similarity	NPC303942
0.8889	High Similarity	NPC57405
0.8876	High Similarity	NPC20713
0.8837	High Similarity	NPC474547
0.8795	High Similarity	NPC617
0.8791	High Similarity	NPC471141
0.8791	High Similarity	NPC270013
0.8791	High Similarity	NPC14961
0.8778	High Similarity	NPC212486
0.8764	High Similarity	NPC469718
0.8764	High Similarity	NPC144133
0.8764	High Similarity	NPC179394
0.8764	High Similarity	NPC475855
0.8764	High Similarity	NPC329857
0.8736	High Similarity	NPC284902
0.8721	High Similarity	NPC138647
0.8721	High Similarity	NPC470238
0.8696	High Similarity	NPC476315
0.8681	High Similarity	NPC474035
0.8681	High Similarity	NPC81386
0.8646	High Similarity	NPC477510
0.8646	High Similarity	NPC471143
0.8636	High Similarity	NPC5130
0.8617	High Similarity	NPC477512
0.8605	High Similarity	NPC170377
0.8602	High Similarity	NPC471140
0.8587	High Similarity	NPC474947
0.8571	High Similarity	NPC475912
0.8571	High Similarity	NPC270126
0.8571	High Similarity	NPC476300
0.8556	High Similarity	NPC473619
0.8556	High Similarity	NPC51004
0.8554	High Similarity	NPC476028
0.8554	High Similarity	NPC171204
0.8554	High Similarity	NPC141789
0.8539	High Similarity	NPC202672
0.8526	High Similarity	NPC474339
0.8526	High Similarity	NPC164598
0.8523	High Similarity	NPC305475
0.8523	High Similarity	NPC475461
0.8511	High Similarity	NPC474213
0.8495	Intermediate Similarity	NPC476275
0.8471	Intermediate Similarity	NPC281132
0.8471	Intermediate Similarity	NPC474510
0.8469	Intermediate Similarity	NPC477513
0.8462	Intermediate Similarity	NPC184463
0.8462	Intermediate Similarity	NPC473321
0.8462	Intermediate Similarity	NPC30515
0.8444	Intermediate Similarity	NPC295312
0.8444	Intermediate Similarity	NPC474032
0.8444	Intermediate Similarity	NPC307411
0.8438	Intermediate Similarity	NPC149371
0.8434	Intermediate Similarity	NPC235906
0.8409	Intermediate Similarity	NPC215364
0.8409	Intermediate Similarity	NPC255307
0.8387	Intermediate Similarity	NPC471142
0.8387	Intermediate Similarity	NPC36954
0.8372	Intermediate Similarity	NPC281949
0.8372	Intermediate Similarity	NPC207188
0.8372	Intermediate Similarity	NPC25684
0.8372	Intermediate Similarity	NPC301477
0.837	Intermediate Similarity	NPC162205
0.837	Intermediate Similarity	NPC273579
0.837	Intermediate Similarity	NPC179746
0.837	Intermediate Similarity	NPC81419
0.837	Intermediate Similarity	NPC295204
0.837	Intermediate Similarity	NPC288240
0.8333	Intermediate Similarity	NPC47880
0.8333	Intermediate Similarity	NPC476270
0.8333	Intermediate Similarity	NPC201718
0.8333	Intermediate Similarity	NPC473715
0.8333	Intermediate Similarity	NPC475902
0.8316	Intermediate Similarity	NPC471144
0.8315	Intermediate Similarity	NPC150755
0.8315	Intermediate Similarity	NPC122502
0.8295	Intermediate Similarity	NPC114979
0.8295	Intermediate Similarity	NPC191476
0.828	Intermediate Similarity	NPC474338
0.828	Intermediate Similarity	NPC477131
0.8265	Intermediate Similarity	NPC474741
0.8261	Intermediate Similarity	NPC12172
0.8261	Intermediate Similarity	NPC208886
0.8247	Intermediate Similarity	NPC471148
0.8242	Intermediate Similarity	NPC4986
0.8242	Intermediate Similarity	NPC475971
0.8229	Intermediate Similarity	NPC475949
0.8222	Intermediate Similarity	NPC266957
0.8222	Intermediate Similarity	NPC160138
0.8193	Intermediate Similarity	NPC476355
0.8191	Intermediate Similarity	NPC477922
0.8191	Intermediate Similarity	NPC304886
0.8182	Intermediate Similarity	NPC257358
0.8182	Intermediate Similarity	NPC40746
0.8182	Intermediate Similarity	NPC169575
0.8182	Intermediate Similarity	NPC250315
0.8182	Intermediate Similarity	NPC223450
0.8182	Intermediate Similarity	NPC128429
0.8182	Intermediate Similarity	NPC318468
0.8182	Intermediate Similarity	NPC170286
0.8182	Intermediate Similarity	NPC474703
0.8182	Intermediate Similarity	NPC53867
0.8182	Intermediate Similarity	NPC131669
0.8182	Intermediate Similarity	NPC474472
0.8182	Intermediate Similarity	NPC473390
0.8182	Intermediate Similarity	NPC243998
0.8172	Intermediate Similarity	NPC135776
0.8172	Intermediate Similarity	NPC165383
0.8152	Intermediate Similarity	NPC476004
0.8152	Intermediate Similarity	NPC80875
0.8152	Intermediate Similarity	NPC474761
0.8152	Intermediate Similarity	NPC469368
0.8144	Intermediate Similarity	NPC473332
0.8132	Intermediate Similarity	NPC224652
0.8118	Intermediate Similarity	NPC476794
0.8118	Intermediate Similarity	NPC470240
0.8118	Intermediate Similarity	NPC97516
0.8111	Intermediate Similarity	NPC469676
0.8111	Intermediate Similarity	NPC204048
0.8111	Intermediate Similarity	NPC107787
0.8111	Intermediate Similarity	NPC470242
0.8111	Intermediate Similarity	NPC64153
0.8111	Intermediate Similarity	NPC474045
0.8111	Intermediate Similarity	NPC261253
0.8105	Intermediate Similarity	NPC301596
0.8105	Intermediate Similarity	NPC299396
0.8105	Intermediate Similarity	NPC172998
0.8105	Intermediate Similarity	NPC477921
0.8095	Intermediate Similarity	NPC155587
0.809	Intermediate Similarity	NPC96259
0.809	Intermediate Similarity	NPC476804
0.809	Intermediate Similarity	NPC115786
0.809	Intermediate Similarity	NPC141193
0.8072	Intermediate Similarity	NPC58956
0.8072	Intermediate Similarity	NPC295633
0.8072	Intermediate Similarity	NPC269206
0.8068	Intermediate Similarity	NPC173609
0.8068	Intermediate Similarity	NPC229825
0.8065	Intermediate Similarity	NPC70251
0.8065	Intermediate Similarity	NPC475881
0.8065	Intermediate Similarity	NPC221282
0.8065	Intermediate Similarity	NPC133698
0.8046	Intermediate Similarity	NPC474739
0.8043	Intermediate Similarity	NPC78008
0.8041	Intermediate Similarity	NPC469551
0.8	Intermediate Similarity	NPC149725
0.8	Intermediate Similarity	NPC47958
0.8	Intermediate Similarity	NPC304509
0.8	Intermediate Similarity	NPC78089
0.8	Intermediate Similarity	NPC235792
0.8	Intermediate Similarity	NPC197903
0.8	Intermediate Similarity	NPC67584
0.8	Intermediate Similarity	NPC470755
0.8	Intermediate Similarity	NPC234339
0.8	Intermediate Similarity	NPC273197
0.8	Intermediate Similarity	NPC123360
0.8	Intermediate Similarity	NPC99395
0.798	Intermediate Similarity	NPC475871
0.798	Intermediate Similarity	NPC475945
0.7979	Intermediate Similarity	NPC475302
0.7978	Intermediate Similarity	NPC475842
0.7978	Intermediate Similarity	NPC59097
0.7978	Intermediate Similarity	NPC116543
0.7976	Intermediate Similarity	NPC140287
0.7959	Intermediate Similarity	NPC474742
0.7959	Intermediate Similarity	NPC15993

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 NPC166919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	2082
0.2-0.3	3878
0.3-0.4	2038
0.4-0.5	616
0.5-0.6	260
0.6-0.7	48
0.7-0.8	6
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9059	High Similarity	NPD1733	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD1695	Approved
0.7766	Intermediate Similarity	NPD6698	Approved
0.7766	Intermediate Similarity	NPD46	Approved
0.7449	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7838	Discovery
0.7229	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6371	Approved
0.7143	Intermediate Similarity	NPD6008	Approved
0.7097	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD1694	Approved
0.697	Remote Similarity	NPD7983	Approved
0.6909	Remote Similarity	NPD6053	Discontinued
0.6832	Remote Similarity	NPD5282	Discontinued
0.6827	Remote Similarity	NPD6648	Approved
0.6762	Remote Similarity	NPD5344	Discontinued
0.6759	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5209	Approved
0.6733	Remote Similarity	NPD5778	Approved
0.6733	Remote Similarity	NPD5779	Approved
0.6731	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5785	Approved
0.6697	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4249	Approved
0.6577	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4225	Approved
0.6566	Remote Similarity	NPD4251	Approved
0.6566	Remote Similarity	NPD4250	Approved
0.6562	Remote Similarity	NPD6435	Approved
0.6531	Remote Similarity	NPD5363	Approved
0.6486	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5786	Approved
0.6415	Remote Similarity	NPD7638	Approved
0.6381	Remote Similarity	NPD7839	Suspended
0.6379	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7639	Approved
0.6355	Remote Similarity	NPD7640	Approved
0.6354	Remote Similarity	NPD4820	Approved
0.6354	Remote Similarity	NPD4822	Approved
0.6354	Remote Similarity	NPD4819	Approved
0.6354	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4821	Approved
0.6354	Remote Similarity	NPD5368	Approved
0.6344	Remote Similarity	NPD8039	Approved
0.6333	Remote Similarity	NPD7642	Approved
0.6327	Remote Similarity	NPD5362	Discontinued
0.6303	Remote Similarity	NPD8517	Approved
0.6303	Remote Similarity	NPD8513	Phase 3
0.6303	Remote Similarity	NPD8515	Approved
0.6303	Remote Similarity	NPD8516	Approved
0.6289	Remote Similarity	NPD5369	Approved
0.6275	Remote Similarity	NPD6101	Approved
0.6275	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4269	Approved
0.6224	Remote Similarity	NPD4270	Approved
0.6198	Remote Similarity	NPD7830	Approved
0.6198	Remote Similarity	NPD7829	Approved
0.6161	Remote Similarity	NPD5697	Approved
0.6154	Remote Similarity	NPD5693	Phase 1
0.6154	Remote Similarity	NPD6411	Approved
0.6146	Remote Similarity	NPD4271	Approved
0.6146	Remote Similarity	NPD4268	Approved
0.6139	Remote Similarity	NPD6684	Approved
0.6139	Remote Similarity	NPD5330	Approved
0.6139	Remote Similarity	NPD7521	Approved
0.6139	Remote Similarity	NPD6409	Approved
0.6139	Remote Similarity	NPD7334	Approved
0.6139	Remote Similarity	NPD7146	Approved
0.6132	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6881	Approved
0.6106	Remote Similarity	NPD6899	Approved
0.6098	Remote Similarity	NPD7507	Approved
0.6095	Remote Similarity	NPD6399	Phase 3
0.6087	Remote Similarity	NPD6649	Approved
0.6087	Remote Similarity	NPD6650	Approved
0.6078	Remote Similarity	NPD3573	Approved
0.6071	Remote Similarity	NPD5739	Approved
0.6071	Remote Similarity	NPD7128	Approved
0.6071	Remote Similarity	NPD6402	Approved
0.6071	Remote Similarity	NPD6675	Approved
0.6053	Remote Similarity	NPD6372	Approved
0.6053	Remote Similarity	NPD6013	Approved
0.6053	Remote Similarity	NPD6373	Approved
0.6053	Remote Similarity	NPD6014	Approved
0.6053	Remote Similarity	NPD6012	Approved
0.6048	Remote Similarity	NPD8074	Phase 3
0.6038	Remote Similarity	NPD7900	Approved
0.6038	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4252	Approved
0.6019	Remote Similarity	NPD5737	Approved
0.6019	Remote Similarity	NPD6903	Approved
0.6019	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6672	Approved
0.6018	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6883	Approved
0.5984	Remote Similarity	NPD7260	Phase 2
0.5983	Remote Similarity	NPD4632	Approved
0.5981	Remote Similarity	NPD5695	Phase 3
0.598	Remote Similarity	NPD6422	Discontinued
0.5979	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6011	Approved
0.5965	Remote Similarity	NPD7320	Approved
0.5963	Remote Similarity	NPD5696	Approved
0.5952	Remote Similarity	NPD7319	Approved
0.595	Remote Similarity	NPD6319	Approved
0.5948	Remote Similarity	NPD8130	Phase 1
0.5948	Remote Similarity	NPD6847	Approved
0.5948	Remote Similarity	NPD6869	Approved
0.5948	Remote Similarity	NPD6617	Approved
0.5941	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7641	Discontinued
0.5905	Remote Similarity	NPD5207	Approved
0.5897	Remote Similarity	NPD6882	Approved
0.5897	Remote Similarity	NPD8297	Approved
0.5889	Remote Similarity	NPD7341	Phase 2
0.5888	Remote Similarity	NPD6001	Approved
0.5887	Remote Similarity	NPD7492	Approved
0.5876	Remote Similarity	NPD4756	Discovery
0.5872	Remote Similarity	NPD7902	Approved
0.5872	Remote Similarity	NPD6083	Phase 2
0.5872	Remote Similarity	NPD6084	Phase 2
0.5862	Remote Similarity	NPD2067	Discontinued
0.5849	Remote Similarity	NPD7637	Suspended
0.5842	Remote Similarity	NPD5332	Approved
0.5842	Remote Similarity	NPD5331	Approved
0.584	Remote Similarity	NPD6616	Approved
0.584	Remote Similarity	NPD8273	Phase 1
0.584	Remote Similarity	NPD8451	Approved
0.5833	Remote Similarity	NPD6009	Approved
0.5826	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.582	Remote Similarity	NPD6054	Approved
0.5814	Remote Similarity	NPD6845	Suspended
0.5812	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6080	Approved
0.581	Remote Similarity	NPD6904	Approved
0.581	Remote Similarity	NPD6673	Approved
0.581	Remote Similarity	NPD6051	Approved
0.5806	Remote Similarity	NPD7604	Phase 2
0.5804	Remote Similarity	NPD7632	Discontinued
0.5804	Remote Similarity	NPD5211	Phase 2
0.58	Remote Similarity	NPD4790	Discontinued
0.5794	Remote Similarity	NPD7078	Approved
0.5794	Remote Similarity	NPD8448	Approved
0.5772	Remote Similarity	NPD6016	Approved
0.5772	Remote Similarity	NPD6015	Approved
0.5772	Remote Similarity	NPD5983	Phase 2
0.5766	Remote Similarity	NPD5285	Approved
0.5766	Remote Similarity	NPD4696	Approved
0.5766	Remote Similarity	NPD5286	Approved
0.5761	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5692	Phase 3
0.575	Remote Similarity	NPD6274	Approved
0.5748	Remote Similarity	NPD7736	Approved
0.5743	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD7748	Approved
0.5739	Remote Similarity	NPD6412	Phase 2
0.5727	Remote Similarity	NPD4755	Approved
0.5726	Remote Similarity	NPD6370	Approved
0.5726	Remote Similarity	NPD5988	Approved
0.5714	Remote Similarity	NPD5208	Approved
0.5702	Remote Similarity	NPD5141	Approved
0.5701	Remote Similarity	NPD6050	Approved
0.5701	Remote Similarity	NPD5281	Approved
0.5701	Remote Similarity	NPD5694	Approved
0.5701	Remote Similarity	NPD5284	Approved
0.5691	Remote Similarity	NPD6059	Approved
0.5686	Remote Similarity	NPD6110	Phase 1
0.5678	Remote Similarity	NPD2204	Approved
0.5678	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD8293	Discontinued
0.5664	Remote Similarity	NPD4633	Approved
0.5664	Remote Similarity	NPD5224	Approved
0.5664	Remote Similarity	NPD5225	Approved
0.5664	Remote Similarity	NPD5226	Approved
0.566	Remote Similarity	NPD5370	Suspended
0.5659	Remote Similarity	NPD8392	Approved
0.5659	Remote Similarity	NPD8391	Approved
0.5659	Remote Similarity	NPD8390	Approved
0.5645	Remote Similarity	NPD8444	Approved
0.5645	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD8342	Approved
0.5635	Remote Similarity	NPD8341	Approved
0.5635	Remote Similarity	NPD8299	Approved
0.5635	Remote Similarity	NPD8340	Approved
0.5631	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4700	Approved
0.5614	Remote Similarity	NPD5174	Approved
0.5614	Remote Similarity	NPD5175	Approved
0.561	Remote Similarity	NPD7101	Approved
0.561	Remote Similarity	NPD7100	Approved
0.5607	Remote Similarity	NPD3168	Discontinued

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