NPASS Compound

Structure

NPC472621 OpenBabel07101718292D 31 35 0 0 1 0 0 0 0 0999 V2000 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.1340 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 2 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 -2.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 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 3.4641 -3.0000 0.0000 C 0 0 1 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 2 23 1 0 0 0 0 3 23 1 0 0 0 0 6 7 1 0 0 0 0 6 19 1 0 0 0 0 7 24 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 1 1 1 0 0 0 12 30 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 21 1 0 0 0 0 15 21 2 0 0 0 0 15 26 1 0 0 0 0 16 31 1 0 0 0 0 17 23 1 0 0 0 0 17 24 1 1 0 0 0 18 24 1 6 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 27 1 1 0 0 0 20 25 1 1 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 22 29 2 0 0 0 0 22 30 1 0 0 0 0 24 4 1 1 0 0 0 25 5 1 6 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.24
Volume:	440.369
LogP:	4.876
LogD:	3.704
LogS:	-4.149
# Rotatable Bonds:	0
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	4.793
Fsp3:	0.72
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.008
MDCK Permeability:	1.7870597730507143e-05
Pgp-inhibitor:	0.926
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.517
Plasma Protein Binding (PPB):	92.0923843383789%
Volume Distribution (VD):	1.036
Pgp-substrate:	7.603910446166992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.131
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.298
CYP2C9-inhibitor:	0.272
CYP2C9-substrate:	0.627
CYP2D6-inhibitor:	0.088
CYP2D6-substrate:	0.271
CYP3A4-inhibitor:	0.183
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	12.114
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.759
Human Hepatotoxicity (H-HT):	0.816
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.512
Carcinogencity:	0.293
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC472621

Natural Product ID:	NPC472621
*Common Name:**	YMGGKEHLQJSJSU-CJVWRCMMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YMGGKEHLQJSJSU-CJVWRCMMSA-N
Standard InCHI:	InChI=1S/C25H34O6/c1-12-8-14-13-9-18-24(4)7-6-19(27)23(2,3)17(24)11-20(28)25(18,5)31-16(13)10-15(26)21(14)22(29)30-12/h10,12,17-20,26-28H,6-9,11H2,1-5H3/t12-,17+,18+,19+,20+,24+,25-/m1/s1
SMILES:	C[C@H]1OC(=O)c2c(C1)c1C[C@@H]3[C@](Oc1cc2O)(C)[C@@H](O)C[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581317
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO32870	penicillium funiculosum gwt2-24	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26046820]

☑ 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	5
MIC	2

Activity Type	# Activity
Cell Line	4
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[538898]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[538898]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[538898]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[538898]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	600.0	ug.mL-1	PMID[538898]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	600.0	ug.mL-1	PMID[538898]
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	57000.0	nM	PMID[538898]

☑ 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 NPC472621 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	393
0.1-0.2	1522
0.2-0.3	3154
0.3-0.4	6490
0.4-0.5	9836
0.5-0.6	6446
0.6-0.7	5151
0.7-0.8	7630
0.8-0.85	1862
0.85-0.9	193
0.9-0.95	14
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC472622
0.9625	High Similarity	NPC472619
0.9509	High Similarity	NPC294149
0.9506	High Similarity	NPC472620
0.9367	High Similarity	NPC472617
0.9313	High Similarity	NPC473022
0.9187	High Similarity	NPC472618
0.9141	High Similarity	NPC125465
0.9125	High Similarity	NPC470339
0.9068	High Similarity	NPC472055
0.8994	High Similarity	NPC472799
0.8944	High Similarity	NPC272196
0.8931	High Similarity	NPC167903
0.8929	High Similarity	NPC63105
0.8916	High Similarity	NPC102810
0.8909	High Similarity	NPC469394
0.8889	High Similarity	NPC239118
0.8889	High Similarity	NPC4950
0.8882	High Similarity	NPC164427
0.8882	High Similarity	NPC4547
0.8876	High Similarity	NPC324220
0.8876	High Similarity	NPC312630
0.8868	High Similarity	NPC473131
0.8868	High Similarity	NPC470675
0.8862	High Similarity	NPC251144
0.8862	High Similarity	NPC241387
0.8862	High Similarity	NPC298778
0.8855	High Similarity	NPC474024
0.8848	High Similarity	NPC293319
0.883	High Similarity	NPC208069
0.883	High Similarity	NPC475161
0.883	High Similarity	NPC477860
0.8817	High Similarity	NPC474345
0.8812	High Similarity	NPC113608
0.8812	High Similarity	NPC470337
0.8812	High Similarity	NPC470338
0.8812	High Similarity	NPC268992
0.8812	High Similarity	NPC51824
0.8805	High Similarity	NPC150928
0.8795	High Similarity	NPC472452
0.879	High Similarity	NPC473132
0.879	High Similarity	NPC470676
0.879	High Similarity	NPC473023
0.879	High Similarity	NPC473135
0.8788	High Similarity	NPC476295
0.8788	High Similarity	NPC12461
0.8786	High Similarity	NPC221140
0.8786	High Similarity	NPC473686
0.8786	High Similarity	NPC475352
0.8786	High Similarity	NPC475220
0.8786	High Similarity	NPC229817
0.878	High Similarity	NPC97812
0.8779	High Similarity	NPC473631
0.8779	High Similarity	NPC475662
0.8779	High Similarity	NPC293227
0.8779	High Similarity	NPC473717
0.8773	High Similarity	NPC473990
0.8773	High Similarity	NPC474373
0.8772	High Similarity	NPC84494
0.8772	High Similarity	NPC245059
0.8765	High Similarity	NPC478050
0.8765	High Similarity	NPC46958
0.8765	High Similarity	NPC477674
0.8757	High Similarity	NPC213052
0.875	High Similarity	NPC474021
0.875	High Similarity	NPC478148
0.875	High Similarity	NPC241874
0.875	High Similarity	NPC474023
0.875	High Similarity	NPC477670
0.8743	High Similarity	NPC225419
0.8743	High Similarity	NPC117854
0.8743	High Similarity	NPC218226
0.8743	High Similarity	NPC6588
0.8743	High Similarity	NPC249977
0.8743	High Similarity	NPC477154
0.8742	High Similarity	NPC237440
0.8742	High Similarity	NPC270160
0.8727	High Similarity	NPC206605
0.8727	High Similarity	NPC211107
0.8727	High Similarity	NPC473961
0.8727	High Similarity	NPC15374
0.8726	High Similarity	NPC470673
0.8726	High Similarity	NPC470674
0.8726	High Similarity	NPC117716
0.8721	High Similarity	NPC470452
0.8721	High Similarity	NPC470453
0.8721	High Similarity	NPC164047
0.8721	High Similarity	NPC470448
0.872	High Similarity	NPC321399
0.872	High Similarity	NPC470810
0.872	High Similarity	NPC174953
0.8712	High Similarity	NPC158542
0.8706	High Similarity	NPC68381
0.8704	High Similarity	NPC68727
0.8704	High Similarity	NPC477958
0.8704	High Similarity	NPC477687
0.8704	High Similarity	NPC477671
0.8704	High Similarity	NPC175192
0.8698	High Similarity	NPC4200
0.8698	High Similarity	NPC118128
0.8696	High Similarity	NPC87708
0.8696	High Similarity	NPC180944
0.8696	High Similarity	NPC217447
0.8696	High Similarity	NPC475790
0.8696	High Similarity	NPC256141
0.8696	High Similarity	NPC273483
0.869	High Similarity	NPC300307
0.869	High Similarity	NPC297195
0.869	High Similarity	NPC291795
0.869	High Similarity	NPC207574
0.8688	High Similarity	NPC179178
0.8683	High Similarity	NPC272502
0.8683	High Similarity	NPC13481
0.8683	High Similarity	NPC178173
0.8683	High Similarity	NPC207575
0.8683	High Similarity	NPC43319
0.8675	High Similarity	NPC100849
0.8675	High Similarity	NPC186686
0.8675	High Similarity	NPC474240
0.8671	High Similarity	NPC260946
0.8667	High Similarity	NPC472632
0.8667	High Similarity	NPC117985
0.8667	High Similarity	NPC471211
0.8667	High Similarity	NPC471212
0.8667	High Similarity	NPC18380
0.8667	High Similarity	NPC471210
0.8667	High Similarity	NPC3629
0.8667	High Similarity	NPC137232
0.8667	High Similarity	NPC472906
0.8663	High Similarity	NPC473785
0.8659	High Similarity	NPC85121
0.8659	High Similarity	NPC218818
0.8659	High Similarity	NPC210459
0.8659	High Similarity	NPC195167
0.8655	High Similarity	NPC475246
0.8655	High Similarity	NPC469345
0.865	High Similarity	NPC208152
0.865	High Similarity	NPC78492
0.865	High Similarity	NPC472050
0.865	High Similarity	NPC477675
0.8647	High Similarity	NPC469393
0.8642	High Similarity	NPC192189
0.8642	High Similarity	NPC477669
0.8639	High Similarity	NPC315306
0.8639	High Similarity	NPC313717
0.8639	High Similarity	NPC193698
0.8639	High Similarity	NPC313304
0.8634	High Similarity	NPC204561
0.8634	High Similarity	NPC312549
0.8634	High Similarity	NPC305965
0.8634	High Similarity	NPC317715
0.8634	High Similarity	NPC72958
0.8634	High Similarity	NPC148945
0.8634	High Similarity	NPC209142
0.8634	High Similarity	NPC48671
0.8634	High Similarity	NPC471677
0.8634	High Similarity	NPC477672
0.8634	High Similarity	NPC309512
0.8634	High Similarity	NPC477673
0.8634	High Similarity	NPC78835
0.8634	High Similarity	NPC149526
0.8634	High Similarity	NPC70016
0.8634	High Similarity	NPC232645
0.8634	High Similarity	NPC215921
0.8634	High Similarity	NPC474417
0.8634	High Similarity	NPC316960
0.8631	High Similarity	NPC476306
0.8625	High Similarity	NPC233267
0.8625	High Similarity	NPC473016
0.8625	High Similarity	NPC472628
0.8625	High Similarity	NPC291049
0.8623	High Similarity	NPC99216
0.8623	High Similarity	NPC475888
0.8623	High Similarity	NPC7752
0.8623	High Similarity	NPC475979
0.8616	High Similarity	NPC91902
0.8616	High Similarity	NPC470670
0.8616	High Similarity	NPC473133
0.8616	High Similarity	NPC47388
0.8614	High Similarity	NPC474033
0.8614	High Similarity	NPC474034
0.8614	High Similarity	NPC201800
0.8614	High Similarity	NPC472402
0.8614	High Similarity	NPC472964
0.8614	High Similarity	NPC52204
0.8606	High Similarity	NPC155302
0.8606	High Similarity	NPC475784
0.8606	High Similarity	NPC471976
0.8606	High Similarity	NPC299436
0.8606	High Similarity	NPC36217
0.8606	High Similarity	NPC161947
0.8606	High Similarity	NPC292863
0.8606	High Similarity	NPC184326
0.8606	High Similarity	NPC476280
0.8606	High Similarity	NPC472630
0.8606	High Similarity	NPC297212
0.8606	High Similarity	NPC472631
0.8605	High Similarity	NPC477683
0.8605	High Similarity	NPC470334
0.8605	High Similarity	NPC477682

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 NPC472621 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	950
0.2-0.3	1818
0.3-0.4	2511
0.4-0.5	1931
0.5-0.6	1004
0.6-0.7	427
0.7-0.8	154
0.8-0.85	26
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD6959	Discontinued
0.8528	High Similarity	NPD7819	Suspended
0.8485	Intermediate Similarity	NPD7075	Discontinued
0.8471	Intermediate Similarity	NPD5844	Phase 1
0.8415	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD6166	Phase 2
0.8402	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD7473	Discontinued
0.8314	Intermediate Similarity	NPD7074	Phase 3
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD6232	Discontinued
0.8256	Intermediate Similarity	NPD7054	Approved
0.8256	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6801	Discontinued
0.8242	Intermediate Similarity	NPD1934	Approved
0.8232	Intermediate Similarity	NPD4380	Phase 2
0.8228	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD7472	Approved
0.8182	Intermediate Similarity	NPD7411	Suspended
0.8148	Intermediate Similarity	NPD2532	Approved
0.8148	Intermediate Similarity	NPD2534	Approved
0.8148	Intermediate Similarity	NPD2533	Approved
0.8125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD8312	Approved
0.8125	Intermediate Similarity	NPD8313	Approved
0.8121	Intermediate Similarity	NPD6599	Discontinued
0.8114	Intermediate Similarity	NPD7251	Discontinued
0.8111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7768	Phase 2
0.8084	Intermediate Similarity	NPD1465	Phase 2
0.8081	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7808	Phase 3
0.8059	Intermediate Similarity	NPD5494	Approved
0.8057	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD6797	Phase 2
0.8047	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4628	Phase 3
0.7989	Intermediate Similarity	NPD7228	Approved
0.7987	Intermediate Similarity	NPD6099	Approved
0.7987	Intermediate Similarity	NPD6100	Approved
0.7941	Intermediate Similarity	NPD3749	Approved
0.7937	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3817	Phase 2
0.7927	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6559	Discontinued
0.7889	Intermediate Similarity	NPD8150	Discontinued
0.7888	Intermediate Similarity	NPD1549	Phase 2
0.787	Intermediate Similarity	NPD2801	Approved
0.7866	Intermediate Similarity	NPD6799	Approved
0.7865	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8151	Discontinued
0.7844	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3750	Approved
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD3882	Suspended
0.7772	Intermediate Similarity	NPD7783	Phase 2
0.7772	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD1511	Approved
0.7738	Intermediate Similarity	NPD7458	Discontinued
0.773	Intermediate Similarity	NPD2800	Approved
0.7725	Intermediate Similarity	NPD5403	Approved
0.7719	Intermediate Similarity	NPD5402	Approved
0.7706	Intermediate Similarity	NPD37	Approved
0.7705	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD8434	Phase 2
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7688	Intermediate Similarity	NPD6651	Approved
0.7684	Intermediate Similarity	NPD7435	Discontinued
0.7684	Intermediate Similarity	NPD3751	Discontinued
0.7674	Intermediate Similarity	NPD4967	Phase 2
0.7674	Intermediate Similarity	NPD4966	Approved
0.7674	Intermediate Similarity	NPD4965	Approved
0.7665	Intermediate Similarity	NPD1512	Approved
0.7665	Intermediate Similarity	NPD6273	Approved
0.7657	Intermediate Similarity	NPD3787	Discontinued
0.7657	Intermediate Similarity	NPD5710	Approved
0.7657	Intermediate Similarity	NPD5711	Approved
0.7654	Intermediate Similarity	NPD2796	Approved
0.7633	Intermediate Similarity	NPD3226	Approved
0.7622	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7240	Approved
0.7605	Intermediate Similarity	NPD5401	Approved
0.7593	Intermediate Similarity	NPD1510	Phase 2
0.7576	Intermediate Similarity	NPD7003	Approved
0.7558	Intermediate Similarity	NPD8455	Phase 2
0.7547	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2935	Discontinued
0.7546	Intermediate Similarity	NPD1551	Phase 2
0.7545	Intermediate Similarity	NPD7390	Discontinued
0.7541	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6779	Approved
0.7526	Intermediate Similarity	NPD6778	Approved
0.7526	Intermediate Similarity	NPD6776	Approved
0.7526	Intermediate Similarity	NPD6782	Approved
0.7526	Intermediate Similarity	NPD6777	Approved
0.7526	Intermediate Similarity	NPD6781	Approved
0.7526	Intermediate Similarity	NPD6780	Approved
0.7516	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5124	Phase 1
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7697	Approved
0.75	Intermediate Similarity	NPD7698	Approved
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD7696	Phase 3
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7485	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3748	Approved
0.7469	Intermediate Similarity	NPD1607	Approved
0.7461	Intermediate Similarity	NPD8320	Phase 1
0.7461	Intermediate Similarity	NPD8319	Approved
0.746	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7229	Phase 3
0.7453	Intermediate Similarity	NPD1240	Approved
0.7449	Intermediate Similarity	NPD7874	Approved
0.7449	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7701	Phase 2
0.7386	Intermediate Similarity	NPD919	Approved
0.7378	Intermediate Similarity	NPD2799	Discontinued
0.7371	Intermediate Similarity	NPD7871	Phase 2
0.7371	Intermediate Similarity	NPD7870	Phase 2
0.7365	Intermediate Similarity	NPD8166	Discontinued
0.7358	Intermediate Similarity	NPD6823	Phase 2
0.7356	Intermediate Similarity	NPD5761	Phase 2
0.7356	Intermediate Similarity	NPD5760	Phase 2
0.7348	Intermediate Similarity	NPD7286	Phase 2
0.7346	Intermediate Similarity	NPD4060	Phase 1
0.7333	Intermediate Similarity	NPD5406	Approved
0.7333	Intermediate Similarity	NPD5408	Approved
0.7333	Intermediate Similarity	NPD5405	Approved
0.7333	Intermediate Similarity	NPD5404	Approved
0.733	Intermediate Similarity	NPD7699	Phase 2
0.733	Intermediate Similarity	NPD7700	Phase 2
0.7323	Intermediate Similarity	NPD7801	Approved
0.7312	Intermediate Similarity	NPD4908	Phase 1
0.731	Intermediate Similarity	NPD920	Approved
0.7305	Intermediate Similarity	NPD1243	Approved
0.7305	Intermediate Similarity	NPD6674	Discontinued
0.7301	Intermediate Similarity	NPD230	Phase 1
0.7283	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.7268	Intermediate Similarity	NPD5953	Discontinued
0.7267	Intermediate Similarity	NPD4625	Phase 3
0.7263	Intermediate Similarity	NPD6535	Approved
0.7263	Intermediate Similarity	NPD6534	Approved
0.7262	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1613	Approved
0.7239	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7685	Pre-registration
0.7209	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7177	Discontinued
0.7195	Intermediate Similarity	NPD6355	Discontinued
0.7193	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5763	Approved
0.7186	Intermediate Similarity	NPD5762	Approved
0.7176	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD4363	Phase 3
0.7173	Intermediate Similarity	NPD4360	Phase 2
0.716	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD7497	Discontinued
0.7135	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4140	Approved
0.7121	Intermediate Similarity	NPD7584	Approved
0.7118	Intermediate Similarity	NPD6190	Approved
0.7117	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6798	Discontinued
0.7113	Intermediate Similarity	NPD8285	Discontinued
0.7108	Intermediate Similarity	NPD7097	Phase 1
0.7107	Intermediate Similarity	NPD4749	Approved
0.7099	Intermediate Similarity	NPD6832	Phase 2
0.7095	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD447	Suspended
0.7087	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8032	Phase 2
0.7069	Intermediate Similarity	NPD1653	Approved
0.7059	Intermediate Similarity	NPD4110	Phase 3
0.7059	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7680	Approved
0.7053	Intermediate Similarity	NPD4287	Approved
0.7044	Intermediate Similarity	NPD7930	Approved
0.7044	Intermediate Similarity	NPD1608	Approved
0.7037	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3926	Phase 2
0.703	Intermediate Similarity	NPD943	Approved
0.7024	Intermediate Similarity	NPD2438	Suspended
0.7022	Intermediate Similarity	NPD4288	Approved
0.7022	Intermediate Similarity	NPD5353	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