NPASS Compound

Structure

NPC294149 OpenBabel07101719522D 35 39 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 0.0000 -5.0000 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 -4.4641 -2.0000 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 -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 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 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 0 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 1.7321 -2.0000 0.0000 C 0 0 0 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 1.7321 -3.0000 0.0000 C 0 0 1 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 1.7321 -5.0000 0.0000 O 0 0 0 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 0.8660 -3.5000 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 13 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 7 8 2 0 0 0 0 7 19 1 0 0 0 0 8 26 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 1 1 6 0 0 0 12 23 1 0 0 0 0 12 33 1 0 0 0 0 13 28 2 0 0 0 0 13 34 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 15 29 1 0 0 0 0 16 35 1 0 0 0 0 17 25 1 0 0 0 0 17 26 1 6 0 0 0 18 26 1 1 0 0 0 18 27 1 0 0 0 0 19 25 1 0 0 0 0 19 30 2 0 0 0 0 20 27 1 6 0 0 0 20 31 1 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 34 1 6 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 26 5 1 6 0 0 0 27 6 1 1 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.21
Volume:	484.632
LogP:	3.822
LogD:	2.514
LogS:	-4.201
# Rotatable Bonds:	2
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.582
Synthetic Accessibility Score:	5.09
Fsp3:	0.593
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:	-5.296
MDCK Permeability:	3.095968713751063e-05
Pgp-inhibitor:	0.973
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.05
20% Bioavailability (F20%):	0.161
30% Bioavailability (F30%):	0.479

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.696
Plasma Protein Binding (PPB):	82.52892303466797%
Volume Distribution (VD):	0.959
Pgp-substrate:	15.487676620483398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.087
CYP1A2-substrate:	0.245
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.273
CYP2C9-inhibitor:	0.448
CYP2C9-substrate:	0.283
CYP2D6-inhibitor:	0.595
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.683
CYP3A4-substrate:	0.469

ADMET: Excretion

Clearance (CL):	3.543
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.83
Human Hepatotoxicity (H-HT):	0.866
Drug-inuced Liver Injury (DILI):	0.249
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.345
Carcinogencity:	0.735
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC294149

Natural Product ID:	NPC294149
*Common Name:**	DYQKBALSPZQWQD-FWEFFTEASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DYQKBALSPZQWQD-FWEFFTEASA-N
Standard InCHI:	InChI=1S/C27H32O8/c1-12-23(34-13(2)28)21-14-9-18-26(5)8-7-19(30)25(3,4)17(26)11-20(31)27(18,6)35-16(14)10-15(29)22(21)24(32)33-12/h7-8,10,12,17-18,20,23,29,31H,9,11H2,1-6H3/t12-,17+,18+,20+,23+,26+,27-/m1/s1
SMILES:	CC(=O)O[C@H]1[C@@H](C)OC(=O)c2c1c1C[C@@H]3[C@](Oc1cc2O)(C)[C@@H](O)C[C@@H]1[C@]3(C)C=CC(=O)C1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581316
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]
NPO33271	penicillium verruculosum	Species	Aspergillaceae	Eukaryota	n.a.	Indonesian	n.a.	PMID[26115570]

☑ 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[456163]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[456163]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[456163]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[456163]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	600.0	ug.mL-1	PMID[456163]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	600.0	ug.mL-1	PMID[456163]
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	55000.0	nM	PMID[456163]

☑ 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 NPC294149 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	391
0.1-0.2	1499
0.2-0.3	3091
0.3-0.4	6435
0.4-0.5	9967
0.5-0.6	6249
0.6-0.7	4918
0.7-0.8	6803
0.8-0.85	2916
0.85-0.9	405
0.9-0.95	17
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC472620
0.9753	High Similarity	NPC472619
0.9571	High Similarity	NPC472622
0.9509	High Similarity	NPC472621
0.9444	High Similarity	NPC473022
0.9222	High Similarity	NPC251144
0.9222	High Similarity	NPC241387
0.9202	High Similarity	NPC472618
0.9118	High Similarity	NPC312630
0.9118	High Similarity	NPC324220
0.9085	High Similarity	NPC472055
0.907	High Similarity	NPC475161
0.907	High Similarity	NPC477860
0.9048	High Similarity	NPC207574
0.9048	High Similarity	NPC291795
0.9048	High Similarity	NPC102810
0.9048	High Similarity	NPC297195
0.9042	High Similarity	NPC178173
0.9042	High Similarity	NPC469394
0.9024	High Similarity	NPC472617
0.9024	High Similarity	NPC470339
0.9006	High Similarity	NPC469345
0.8994	High Similarity	NPC241874
0.896	High Similarity	NPC208069
0.8947	High Similarity	NPC232412
0.8947	High Similarity	NPC86809
0.8947	High Similarity	NPC98667
0.8929	High Similarity	NPC207575
0.8929	High Similarity	NPC13481
0.8929	High Similarity	NPC125465
0.8916	High Similarity	NPC3629
0.8914	High Similarity	NPC197972
0.8902	High Similarity	NPC164427
0.8895	High Similarity	NPC46958
0.8895	High Similarity	NPC475246
0.8889	High Similarity	NPC469393
0.8889	High Similarity	NPC154986
0.8882	High Similarity	NPC313717
0.8882	High Similarity	NPC315306
0.8882	High Similarity	NPC103307
0.8876	High Similarity	NPC474024
0.8876	High Similarity	NPC225419
0.8869	High Similarity	NPC475979
0.8869	High Similarity	NPC293319
0.8862	High Similarity	NPC473961
0.8855	High Similarity	NPC471976
0.8844	High Similarity	NPC477682
0.8844	High Similarity	NPC477683
0.8841	High Similarity	NPC477958
0.8837	High Similarity	NPC3718
0.8837	High Similarity	NPC63105
0.8837	High Similarity	NPC68381
0.8834	High Similarity	NPC470340
0.883	High Similarity	NPC212038
0.883	High Similarity	NPC262580
0.883	High Similarity	NPC289396
0.883	High Similarity	NPC271848
0.883	High Similarity	NPC81332
0.8802	High Similarity	NPC97812
0.8802	High Similarity	NPC117985
0.88	High Similarity	NPC475148
0.88	High Similarity	NPC475656
0.8795	High Similarity	NPC4950
0.8795	High Similarity	NPC239118
0.8793	High Similarity	NPC473785
0.8793	High Similarity	NPC245059
0.8793	High Similarity	NPC473607
0.8793	High Similarity	NPC84494
0.8788	High Similarity	NPC472050
0.878	High Similarity	NPC192189
0.878	High Similarity	NPC472799
0.8779	High Similarity	NPC213052
0.8773	High Similarity	NPC470675
0.8773	High Similarity	NPC473131
0.8773	High Similarity	NPC70016
0.8773	High Similarity	NPC215921
0.8772	High Similarity	NPC298778
0.8772	High Similarity	NPC477670
0.8772	High Similarity	NPC313304
0.8772	High Similarity	NPC74559
0.8772	High Similarity	NPC193698
0.8765	High Similarity	NPC218226
0.8765	High Similarity	NPC6588
0.8765	High Similarity	NPC477154
0.8765	High Similarity	NPC117854
0.8757	High Similarity	NPC294722
0.8757	High Similarity	NPC471788
0.8757	High Similarity	NPC105591
0.875	High Similarity	NPC474034
0.875	High Similarity	NPC474033
0.875	High Similarity	NPC220912
0.875	High Similarity	NPC472964
0.875	High Similarity	NPC472402
0.8743	High Similarity	NPC321399
0.8743	High Similarity	NPC470448
0.8743	High Similarity	NPC164047
0.8743	High Similarity	NPC470453
0.8743	High Similarity	NPC470452
0.8736	High Similarity	NPC470334
0.8736	High Similarity	NPC476199
0.8736	High Similarity	NPC476210
0.8735	High Similarity	NPC158542
0.8728	High Similarity	NPC474345
0.8728	High Similarity	NPC162248
0.8727	High Similarity	NPC68727
0.8727	High Similarity	NPC477671
0.8727	High Similarity	NPC477687
0.8727	High Similarity	NPC175192
0.8721	High Similarity	NPC271385
0.8721	High Similarity	NPC5029
0.8721	High Similarity	NPC118128
0.8721	High Similarity	NPC111536
0.8721	High Similarity	NPC30432
0.8721	High Similarity	NPC76128
0.872	High Similarity	NPC470338
0.872	High Similarity	NPC256141
0.872	High Similarity	NPC167903
0.872	High Similarity	NPC113608
0.872	High Similarity	NPC268992
0.872	High Similarity	NPC475790
0.872	High Similarity	NPC51824
0.872	High Similarity	NPC180944
0.872	High Similarity	NPC470337
0.8715	High Similarity	NPC264302
0.8713	High Similarity	NPC188079
0.8713	High Similarity	NPC54903
0.8713	High Similarity	NPC288813
0.8713	High Similarity	NPC177480
0.8713	High Similarity	NPC286074
0.8713	High Similarity	NPC222455
0.8713	High Similarity	NPC326877
0.8706	High Similarity	NPC120593
0.8706	High Similarity	NPC43319
0.8706	High Similarity	NPC272502
0.8706	High Similarity	NPC471213
0.8701	High Similarity	NPC221140
0.8701	High Similarity	NPC473686
0.8701	High Similarity	NPC229817
0.8701	High Similarity	NPC475220
0.8701	High Similarity	NPC87583
0.8701	High Similarity	NPC475352
0.8698	High Similarity	NPC186686
0.8698	High Similarity	NPC205265
0.8698	High Similarity	NPC472281
0.8698	High Similarity	NPC469395
0.8698	High Similarity	NPC12461
0.8698	High Similarity	NPC476295
0.8693	High Similarity	NPC473717
0.8693	High Similarity	NPC475662
0.8693	High Similarity	NPC293227
0.8693	High Similarity	NPC473631
0.869	High Similarity	NPC471210
0.869	High Similarity	NPC134783
0.869	High Similarity	NPC92589
0.869	High Similarity	NPC57715
0.869	High Similarity	NPC228383
0.869	High Similarity	NPC471211
0.869	High Similarity	NPC471212
0.869	High Similarity	NPC472632
0.869	High Similarity	NPC472634
0.8686	High Similarity	NPC299149
0.8686	High Similarity	NPC277710
0.8686	High Similarity	NPC153578
0.8686	High Similarity	NPC114257
0.8686	High Similarity	NPC473729
0.8683	High Similarity	NPC474373
0.8683	High Similarity	NPC210459
0.8683	High Similarity	NPC186113
0.8683	High Similarity	NPC473990
0.8678	High Similarity	NPC475233
0.8678	High Similarity	NPC478050
0.8675	High Similarity	NPC471787
0.8675	High Similarity	NPC4547
0.8675	High Similarity	NPC146636
0.8675	High Similarity	NPC20530
0.8675	High Similarity	NPC78492
0.8675	High Similarity	NPC215917
0.8675	High Similarity	NPC10754
0.8675	High Similarity	NPC208152
0.8675	High Similarity	NPC477674
0.8671	High Similarity	NPC476139
0.8671	High Similarity	NPC476152
0.8671	High Similarity	NPC471969
0.8671	High Similarity	NPC472054
0.8671	High Similarity	NPC476311
0.8671	High Similarity	NPC475080
0.8667	High Similarity	NPC155686
0.8667	High Similarity	NPC223701
0.8667	High Similarity	NPC326592
0.8667	High Similarity	NPC469405
0.8667	High Similarity	NPC112701
0.8667	High Similarity	NPC7989
0.8667	High Similarity	NPC472583
0.8667	High Similarity	NPC109594
0.8663	High Similarity	NPC472276
0.8659	High Similarity	NPC263384
0.8659	High Similarity	NPC471676
0.8659	High Similarity	NPC474023
0.8659	High Similarity	NPC471677
0.8659	High Similarity	NPC474021

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 NPC294149 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	934
0.2-0.3	1854
0.3-0.4	2511
0.4-0.5	1889
0.5-0.6	1008
0.6-0.7	416
0.7-0.8	167
0.8-0.85	30
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD7819	Suspended
0.8623	High Similarity	NPD7075	Discontinued
0.858	High Similarity	NPD6959	Discontinued
0.8488	Intermediate Similarity	NPD7473	Discontinued
0.8485	Intermediate Similarity	NPD4380	Phase 2
0.8448	Intermediate Similarity	NPD7074	Phase 3
0.8443	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD6166	Phase 2
0.843	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD7054	Approved
0.8391	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD5844	Phase 1
0.8383	Intermediate Similarity	NPD6801	Discontinued
0.8362	Intermediate Similarity	NPD8312	Approved
0.8362	Intermediate Similarity	NPD8313	Approved
0.8343	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7472	Approved
0.8343	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD6232	Discontinued
0.8304	Intermediate Similarity	NPD5494	Approved
0.8294	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD1934	Approved
0.8249	Intermediate Similarity	NPD7251	Discontinued
0.8225	Intermediate Similarity	NPD1465	Phase 2
0.8222	Intermediate Similarity	NPD8150	Discontinued
0.8214	Intermediate Similarity	NPD7411	Suspended
0.8202	Intermediate Similarity	NPD7808	Phase 3
0.8192	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8192	Intermediate Similarity	NPD6797	Phase 2
0.8155	Intermediate Similarity	NPD6599	Discontinued
0.8146	Intermediate Similarity	NPD6559	Discontinued
0.8125	Intermediate Similarity	NPD3818	Discontinued
0.8122	Intermediate Similarity	NPD8434	Phase 2
0.8114	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD2532	Approved
0.8072	Intermediate Similarity	NPD2534	Approved
0.8072	Intermediate Similarity	NPD2533	Approved
0.807	Intermediate Similarity	NPD3817	Phase 2
0.807	Intermediate Similarity	NPD5402	Approved
0.8049	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2801	Approved
0.7979	Intermediate Similarity	NPD8151	Discontinued
0.7977	Intermediate Similarity	NPD3749	Approved
0.7964	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4628	Phase 3
0.7939	Intermediate Similarity	NPD3750	Approved
0.7927	Intermediate Similarity	NPD1549	Phase 2
0.7927	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD7228	Approved
0.7921	Intermediate Similarity	NPD3751	Discontinued
0.7919	Intermediate Similarity	NPD3882	Suspended
0.7919	Intermediate Similarity	NPD7768	Phase 2
0.7906	Intermediate Similarity	NPD7435	Discontinued
0.7904	Intermediate Similarity	NPD6799	Approved
0.7882	Intermediate Similarity	NPD3226	Approved
0.7879	Intermediate Similarity	NPD2800	Approved
0.787	Intermediate Similarity	NPD5403	Approved
0.7866	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7783	Phase 2
0.7806	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6100	Approved
0.7805	Intermediate Similarity	NPD6099	Approved
0.7798	Intermediate Similarity	NPD1511	Approved
0.7772	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2346	Discontinued
0.7751	Intermediate Similarity	NPD5401	Approved
0.7749	Intermediate Similarity	NPD6781	Approved
0.7749	Intermediate Similarity	NPD6780	Approved
0.7749	Intermediate Similarity	NPD6779	Approved
0.7749	Intermediate Similarity	NPD6778	Approved
0.7749	Intermediate Similarity	NPD6776	Approved
0.7749	Intermediate Similarity	NPD6782	Approved
0.7749	Intermediate Similarity	NPD6777	Approved
0.773	Intermediate Similarity	NPD6651	Approved
0.772	Intermediate Similarity	NPD7697	Approved
0.772	Intermediate Similarity	NPD7696	Phase 3
0.772	Intermediate Similarity	NPD7698	Approved
0.7706	Intermediate Similarity	NPD1512	Approved
0.7697	Intermediate Similarity	NPD3787	Discontinued
0.7697	Intermediate Similarity	NPD2796	Approved
0.768	Intermediate Similarity	NPD8320	Phase 1
0.768	Intermediate Similarity	NPD8319	Approved
0.7674	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7458	Discontinued
0.7665	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7874	Approved
0.7653	Intermediate Similarity	NPD7701	Phase 2
0.7647	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD37	Approved
0.7636	Intermediate Similarity	NPD3748	Approved
0.7636	Intermediate Similarity	NPD1510	Phase 2
0.7627	Intermediate Similarity	NPD6234	Discontinued
0.7614	Intermediate Similarity	NPD4966	Approved
0.7614	Intermediate Similarity	NPD4967	Phase 2
0.7614	Intermediate Similarity	NPD4965	Approved
0.7598	Intermediate Similarity	NPD5710	Approved
0.7598	Intermediate Similarity	NPD5711	Approved
0.759	Intermediate Similarity	NPD7870	Phase 2
0.759	Intermediate Similarity	NPD2935	Discontinued
0.759	Intermediate Similarity	NPD7871	Phase 2
0.7582	Intermediate Similarity	NPD7286	Phase 2
0.7577	Intermediate Similarity	NPD6823	Phase 2
0.756	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD920	Approved
0.7554	Intermediate Similarity	NPD7240	Approved
0.7552	Intermediate Similarity	NPD7699	Phase 2
0.7552	Intermediate Similarity	NPD7700	Phase 2
0.7542	Intermediate Similarity	NPD7199	Phase 2
0.7542	Intermediate Similarity	NPD8127	Discontinued
0.7538	Intermediate Similarity	NPD7801	Approved
0.753	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7487	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD6535	Approved
0.7485	Intermediate Similarity	NPD7390	Discontinued
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7474	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7685	Pre-registration
0.743	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD919	Approved
0.7425	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD8166	Discontinued
0.7412	Intermediate Similarity	NPD7003	Approved
0.7412	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7229	Phase 3
0.7401	Intermediate Similarity	NPD5761	Phase 2
0.7401	Intermediate Similarity	NPD5760	Phase 2
0.7378	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD230	Phase 1
0.7349	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5124	Phase 1
0.7341	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7584	Approved
0.7333	Intermediate Similarity	NPD8285	Discontinued
0.7295	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2313	Discontinued
0.7268	Intermediate Similarity	NPD3926	Phase 2
0.7267	Intermediate Similarity	NPD6190	Approved
0.7257	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD1247	Approved
0.7251	Intermediate Similarity	NPD1243	Approved
0.7246	Intermediate Similarity	NPD447	Suspended
0.7234	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4360	Phase 2
0.7216	Intermediate Similarity	NPD4363	Phase 3
0.7216	Intermediate Similarity	NPD1653	Approved
0.7186	Intermediate Similarity	NPD1613	Approved
0.7186	Intermediate Similarity	NPD943	Approved
0.7186	Intermediate Similarity	NPD4060	Phase 1
0.7186	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5408	Approved
0.7176	Intermediate Similarity	NPD5406	Approved
0.7176	Intermediate Similarity	NPD5404	Approved
0.7176	Intermediate Similarity	NPD5405	Approved
0.7169	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6213	Phase 3
0.7165	Intermediate Similarity	NPD6212	Phase 3
0.716	Intermediate Similarity	NPD7097	Phase 1
0.7157	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7585	Approved
0.7129	Intermediate Similarity	NPD7907	Approved
0.7118	Intermediate Similarity	NPD7033	Discontinued
0.7118	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4111	Phase 1
0.7115	Intermediate Similarity	NPD4665	Approved
0.7108	Intermediate Similarity	NPD4625	Phase 3
0.7101	Intermediate Similarity	NPD8404	Phase 2
0.71	Intermediate Similarity	NPD7497	Discontinued
0.71	Intermediate Similarity	NPD7680	Approved
0.7098	Intermediate Similarity	NPD4287	Approved
0.709	Intermediate Similarity	NPD6764	Approved
0.709	Intermediate Similarity	NPD8368	Discontinued
0.709	Intermediate Similarity	NPD6765	Approved
0.7087	Intermediate Similarity	NPD7930	Approved
0.7079	Intermediate Similarity	NPD7583	Approved
0.7072	Intermediate Similarity	NPD4288	Approved
0.7072	Intermediate Similarity	NPD5353	Approved
0.7059	Intermediate Similarity	NPD7177	Discontinued
0.7052	Intermediate Similarity	NPD6674	Discontinued
0.7048	Intermediate Similarity	NPD8366	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