NPASS Compound

Structure

NPC474325 OpenBabel07101718182D 25 29 0 0 1 0 0 0 0 0999 V2000 -2.9027 4.5699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0812 3.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5232 0.5458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9599 -0.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0900 2.3208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1327 -0.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1327 1.5457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7927 -0.1809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0881 0.7326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9115 1.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4285 0.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4285 1.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3272 2.9674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8369 0.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8369 1.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3184 2.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7927 1.6462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0299 0.9996 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6142 2.6301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.5058 3.9513 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4970 1.9554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6102 0.0748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6102 1.3904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3770 3.2767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 16 1 0 0 0 0 3 4 1 0 0 0 0 3 10 1 0 0 0 0 4 20 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 20 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 1 0 0 0 14 15 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 17 12 1 6 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 1 0 0 0 19 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	343.14
Volume:	336.163
LogP:	2.366
LogD:	2.061
LogS:	-2.834
# Rotatable Bonds:	3
TPSA:	68.23
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.651
Synthetic Accessibility Score:	4.248
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.756
MDCK Permeability:	4.6421326260315254e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.615
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.608

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	68.6794662475586%
Volume Distribution (VD):	2.492
Pgp-substrate:	22.739233016967773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.775
CYP1A2-substrate:	0.288
CYP2C19-inhibitor:	0.174
CYP2C19-substrate:	0.666
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.452
CYP2D6-inhibitor:	0.966
CYP2D6-substrate:	0.533
CYP3A4-inhibitor:	0.691
CYP3A4-substrate:	0.398

ADMET: Excretion

Clearance (CL):	17.304
Half-life (T1/2):	0.515

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.28
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.893
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.052
Carcinogencity:	0.892
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC474325

Natural Product ID:	NPC474325
*Common Name:**	UEHWEXPUCDLSTI-NOENWEJRSA-N
IUPAC Name:	n.a.
Synonyms:	1-O-Propanoyllycorine
Standard InCHIKey:	UEHWEXPUCDLSTI-NOENWEJRSA-N
Standard InCHI:	InChI=1S/C19H21NO5/c1-2-16(22)25-19-13(21)5-10-3-4-20-8-11-6-14-15(24-9-23-14)7-12(11)17(19)18(10)20/h5-7,13,17-19,21H,2-4,8-9H2,1H3/t13-,17-,18+,19+/m0/s1
SMILES:	CCC(=O)OC1C(C=C2CCN3C2C1C4=CC5=C(C=C4C3)OCO5)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465296
PubChem CID:	44570339
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004120] Lycorine-type amaryllidaceae alkaloids

*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
NPO25024	Lycoris traubii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19013823]
NPO25024	Lycoris traubii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
Others	3

Activity Type	# Activity
Cell Line	1
Organism	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	4.99	ug.mL-1	PMID[486200]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	1.34	ug.mL-1	PMID[486200]
NPT2	Others	Unspecified		Ratio IC50	=	3.7	n.a.	PMID[486200]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.37	ug.mL-1	PMID[486200]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.3	ug.mL-1	PMID[486200]
NPT2	Others	Unspecified		Ratio IC50	=	13.5	n.a.	PMID[486200]
NPT2	Others	Unspecified		Ratio IC50	=	16.6	n.a.	PMID[486200]

☑ 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 NPC474325 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	215
0.1-0.2	1082
0.2-0.3	3139
0.3-0.4	10395
0.4-0.5	8868
0.5-0.6	12961
0.6-0.7	4912
0.7-0.8	936
0.8-0.85	108
0.85-0.9	32
0.9-0.95	32
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC237044
0.9938	High Similarity	NPC474745
0.9876	High Similarity	NPC304675
0.9758	High Similarity	NPC475981
0.9758	High Similarity	NPC474746
0.9641	High Similarity	NPC230098
0.9627	High Similarity	NPC475845
0.9568	High Similarity	NPC474708
0.9565	High Similarity	NPC474324
0.9565	High Similarity	NPC190332
0.9565	High Similarity	NPC57812
0.9565	High Similarity	NPC181653
0.9444	High Similarity	NPC100566
0.9379	High Similarity	NPC320104
0.9337	High Similarity	NPC474470
0.9042	High Similarity	NPC225597
0.9042	High Similarity	NPC477640
0.9042	High Similarity	NPC470739
0.9036	High Similarity	NPC266176
0.9036	High Similarity	NPC82533
0.9036	High Similarity	NPC475686
0.9036	High Similarity	NPC158148
0.9036	High Similarity	NPC58766
0.9036	High Similarity	NPC290759
0.9018	High Similarity	NPC249274
0.9018	High Similarity	NPC4304
0.9018	High Similarity	NPC205167
0.8982	High Similarity	NPC474475
0.8982	High Similarity	NPC311991
0.8935	High Similarity	NPC187678
0.8916	High Similarity	NPC476002
0.8902	High Similarity	NPC215829
0.8902	High Similarity	NPC97072
0.887	High Similarity	NPC33256
0.883	High Similarity	NPC15919
0.883	High Similarity	NPC148693
0.883	High Similarity	NPC294790
0.883	High Similarity	NPC118633
0.8671	High Similarity	NPC244554
0.8659	High Similarity	NPC78733
0.8639	High Similarity	NPC252960
0.8596	High Similarity	NPC65403
0.858	High Similarity	NPC9867
0.8571	High Similarity	NPC218614
0.8547	High Similarity	NPC2314
0.8538	High Similarity	NPC75958
0.8537	High Similarity	NPC223124
0.8521	High Similarity	NPC247972
0.8497	Intermediate Similarity	NPC49353
0.8494	Intermediate Similarity	NPC147091
0.8466	Intermediate Similarity	NPC275132
0.8441	Intermediate Similarity	NPC80472
0.8424	Intermediate Similarity	NPC148898
0.8415	Intermediate Similarity	NPC223125
0.8412	Intermediate Similarity	NPC180306
0.8393	Intermediate Similarity	NPC92191
0.8393	Intermediate Similarity	NPC111485
0.8393	Intermediate Similarity	NPC59028
0.8391	Intermediate Similarity	NPC128560
0.8391	Intermediate Similarity	NPC229166
0.8391	Intermediate Similarity	NPC199465
0.8362	Intermediate Similarity	NPC248642
0.8362	Intermediate Similarity	NPC116284
0.8352	Intermediate Similarity	NPC32154
0.8352	Intermediate Similarity	NPC126284
0.8343	Intermediate Similarity	NPC241704
0.8324	Intermediate Similarity	NPC162694
0.8315	Intermediate Similarity	NPC156576
0.8314	Intermediate Similarity	NPC210918
0.8313	Intermediate Similarity	NPC210148
0.8313	Intermediate Similarity	NPC233029
0.8304	Intermediate Similarity	NPC276944
0.8304	Intermediate Similarity	NPC238530
0.8304	Intermediate Similarity	NPC231198
0.8304	Intermediate Similarity	NPC232514
0.8303	Intermediate Similarity	NPC274026
0.8295	Intermediate Similarity	NPC114364
0.8295	Intermediate Similarity	NPC320223
0.8293	Intermediate Similarity	NPC475959
0.8284	Intermediate Similarity	NPC477080
0.8242	Intermediate Similarity	NPC94499
0.8235	Intermediate Similarity	NPC165797
0.8218	Intermediate Similarity	NPC474953
0.8208	Intermediate Similarity	NPC150879
0.8208	Intermediate Similarity	NPC301189
0.8208	Intermediate Similarity	NPC298186
0.8204	Intermediate Similarity	NPC133011
0.8204	Intermediate Similarity	NPC82285
0.8198	Intermediate Similarity	NPC16805
0.8198	Intermediate Similarity	NPC302527
0.8198	Intermediate Similarity	NPC167546
0.8177	Intermediate Similarity	NPC237579
0.8166	Intermediate Similarity	NPC31311
0.8166	Intermediate Similarity	NPC146288
0.8166	Intermediate Similarity	NPC234392
0.8156	Intermediate Similarity	NPC102760
0.8156	Intermediate Similarity	NPC233718
0.815	Intermediate Similarity	NPC24264
0.815	Intermediate Similarity	NPC476432
0.8146	Intermediate Similarity	NPC99179
0.814	Intermediate Similarity	NPC59567
0.8136	Intermediate Similarity	NPC283999
0.8136	Intermediate Similarity	NPC35680
0.8132	Intermediate Similarity	NPC82763
0.8122	Intermediate Similarity	NPC214116
0.8107	Intermediate Similarity	NPC41178
0.8107	Intermediate Similarity	NPC138487
0.8107	Intermediate Similarity	NPC216459
0.8103	Intermediate Similarity	NPC247389
0.8103	Intermediate Similarity	NPC298979
0.8101	Intermediate Similarity	NPC312918
0.8101	Intermediate Similarity	NPC476574
0.8101	Intermediate Similarity	NPC477561
0.8101	Intermediate Similarity	NPC155442
0.8092	Intermediate Similarity	NPC225774
0.8087	Intermediate Similarity	NPC319549
0.8072	Intermediate Similarity	NPC428
0.8072	Intermediate Similarity	NPC476571
0.8072	Intermediate Similarity	NPC24233
0.8072	Intermediate Similarity	NPC147390
0.8072	Intermediate Similarity	NPC135538
0.8072	Intermediate Similarity	NPC246587
0.8068	Intermediate Similarity	NPC57272
0.8046	Intermediate Similarity	NPC219341
0.8046	Intermediate Similarity	NPC124657
0.8035	Intermediate Similarity	NPC233650
0.8021	Intermediate Similarity	NPC267414
0.8012	Intermediate Similarity	NPC179825
0.8012	Intermediate Similarity	NPC191376
0.8012	Intermediate Similarity	NPC321505
0.8011	Intermediate Similarity	NPC135772
0.8	Intermediate Similarity	NPC130926
0.8	Intermediate Similarity	NPC474607
0.8	Intermediate Similarity	NPC185838
0.8	Intermediate Similarity	NPC210140
0.7989	Intermediate Similarity	NPC78222
0.7989	Intermediate Similarity	NPC63152
0.7989	Intermediate Similarity	NPC136508
0.7989	Intermediate Similarity	NPC134858
0.7989	Intermediate Similarity	NPC253043
0.7989	Intermediate Similarity	NPC477563
0.7989	Intermediate Similarity	NPC306843
0.7989	Intermediate Similarity	NPC96603
0.7989	Intermediate Similarity	NPC226708
0.7989	Intermediate Similarity	NPC212794
0.7989	Intermediate Similarity	NPC196447
0.7989	Intermediate Similarity	NPC13504
0.7978	Intermediate Similarity	NPC141440
0.7976	Intermediate Similarity	NPC151895
0.7976	Intermediate Similarity	NPC192768
0.7976	Intermediate Similarity	NPC97221
0.7976	Intermediate Similarity	NPC220858
0.7976	Intermediate Similarity	NPC88249
0.7968	Intermediate Similarity	NPC14622
0.7968	Intermediate Similarity	NPC124302
0.7968	Intermediate Similarity	NPC46744
0.7968	Intermediate Similarity	NPC70290
0.7968	Intermediate Similarity	NPC73020
0.7968	Intermediate Similarity	NPC215098
0.7966	Intermediate Similarity	NPC149090
0.7966	Intermediate Similarity	NPC19520
0.7965	Intermediate Similarity	NPC106786
0.7965	Intermediate Similarity	NPC69360
0.7956	Intermediate Similarity	NPC476575
0.7956	Intermediate Similarity	NPC474650
0.795	Intermediate Similarity	NPC7018
0.7931	Intermediate Similarity	NPC324144
0.7919	Intermediate Similarity	NPC232924
0.7919	Intermediate Similarity	NPC306902
0.7919	Intermediate Similarity	NPC477559
0.7919	Intermediate Similarity	NPC160298
0.7919	Intermediate Similarity	NPC266753
0.7917	Intermediate Similarity	NPC103379
0.7917	Intermediate Similarity	NPC477565
0.791	Intermediate Similarity	NPC6152
0.7907	Intermediate Similarity	NPC475326
0.7907	Intermediate Similarity	NPC148014
0.7907	Intermediate Similarity	NPC315707
0.7907	Intermediate Similarity	NPC65490
0.7907	Intermediate Similarity	NPC40389
0.7907	Intermediate Similarity	NPC78359
0.7904	Intermediate Similarity	NPC476151
0.7898	Intermediate Similarity	NPC12053
0.7898	Intermediate Similarity	NPC306555
0.7898	Intermediate Similarity	NPC81218
0.7898	Intermediate Similarity	NPC145832
0.7898	Intermediate Similarity	NPC474931
0.7898	Intermediate Similarity	NPC158376
0.7898	Intermediate Similarity	NPC117188
0.7898	Intermediate Similarity	NPC205421
0.7895	Intermediate Similarity	NPC127674
0.7895	Intermediate Similarity	NPC276588
0.7895	Intermediate Similarity	NPC54379
0.7895	Intermediate Similarity	NPC328700
0.7895	Intermediate Similarity	NPC2413
0.7895	Intermediate Similarity	NPC202771
0.7895	Intermediate Similarity	NPC2173
0.7895	Intermediate Similarity	NPC76079
0.7895	Intermediate Similarity	NPC110416
0.7895	Intermediate Similarity	NPC193949

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 NPC474325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	545
0.2-0.3	976
0.3-0.4	2210
0.4-0.5	2646
0.5-0.6	1822
0.6-0.7	679
0.7-0.8	113
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8208	Intermediate Similarity	NPD2969	Approved
0.8208	Intermediate Similarity	NPD2970	Approved
0.8161	Intermediate Similarity	NPD4481	Phase 3
0.8155	Intermediate Similarity	NPD4772	Phase 2
0.8155	Intermediate Similarity	NPD4773	Phase 2
0.8092	Intermediate Similarity	NPD6107	Approved
0.8087	Intermediate Similarity	NPD7296	Approved
0.8057	Intermediate Similarity	NPD2489	Approved
0.8057	Intermediate Similarity	NPD27	Approved
0.8046	Intermediate Similarity	NPD3051	Approved
0.8	Intermediate Similarity	NPD7280	Phase 3
0.8	Intermediate Similarity	NPD7281	Phase 3
0.7968	Intermediate Similarity	NPD4420	Approved
0.7956	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6071	Discontinued
0.7907	Intermediate Similarity	NPD2563	Approved
0.7907	Intermediate Similarity	NPD2560	Approved
0.7895	Intermediate Similarity	NPD5006	Approved
0.7895	Intermediate Similarity	NPD5005	Approved
0.7866	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5313	Approved
0.7821	Intermediate Similarity	NPD5312	Approved
0.7811	Intermediate Similarity	NPD3640	Phase 3
0.7811	Intermediate Similarity	NPD3639	Approved
0.7811	Intermediate Similarity	NPD3641	Approved
0.7753	Intermediate Similarity	NPD2898	Approved
0.7725	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7827	Phase 1
0.7705	Intermediate Similarity	NPD7312	Approved
0.7705	Intermediate Similarity	NPD7313	Approved
0.7705	Intermediate Similarity	NPD7310	Approved
0.7705	Intermediate Similarity	NPD7311	Approved
0.7692	Intermediate Similarity	NPD4584	Approved
0.7672	Intermediate Similarity	NPD5582	Discontinued
0.7663	Intermediate Similarity	NPD7309	Approved
0.7644	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD2977	Approved
0.7644	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD2978	Approved
0.7605	Intermediate Similarity	NPD4237	Approved
0.7605	Intermediate Similarity	NPD4236	Phase 3
0.7581	Intermediate Similarity	NPD4663	Approved
0.7579	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4210	Discontinued
0.7553	Intermediate Similarity	NPD2488	Approved
0.7553	Intermediate Similarity	NPD2490	Approved
0.7543	Intermediate Similarity	NPD5773	Approved
0.7543	Intermediate Similarity	NPD5772	Approved
0.7542	Intermediate Similarity	NPD4166	Phase 2
0.754	Intermediate Similarity	NPD7906	Approved
0.7515	Intermediate Similarity	NPD5241	Discontinued
0.7514	Intermediate Similarity	NPD4578	Approved
0.7514	Intermediate Similarity	NPD4577	Approved
0.7473	Intermediate Similarity	NPD8054	Approved
0.7473	Intermediate Similarity	NPD6853	Approved
0.7473	Intermediate Similarity	NPD6851	Approved
0.7473	Intermediate Similarity	NPD8053	Approved
0.7471	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD6297	Approved
0.7444	Intermediate Similarity	NPD4010	Discontinued
0.7419	Intermediate Similarity	NPD2968	Approved
0.7419	Intermediate Similarity	NPD2971	Approved
0.7416	Intermediate Similarity	NPD7833	Phase 2
0.7416	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7831	Phase 2
0.7386	Intermediate Similarity	NPD7298	Approved
0.7384	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6667	Approved
0.7368	Intermediate Similarity	NPD6666	Approved
0.736	Intermediate Similarity	NPD4967	Phase 2
0.736	Intermediate Similarity	NPD4966	Approved
0.736	Intermediate Similarity	NPD4965	Approved
0.7356	Intermediate Similarity	NPD3687	Approved
0.7356	Intermediate Similarity	NPD3686	Approved
0.7354	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3057	Approved
0.7337	Intermediate Similarity	NPD8156	Discontinued
0.7318	Intermediate Similarity	NPD5604	Discontinued
0.7314	Intermediate Similarity	NPD4017	Approved
0.7299	Intermediate Similarity	NPD6031	Approved
0.7299	Intermediate Similarity	NPD6030	Approved
0.7296	Intermediate Similarity	NPD3452	Approved
0.7296	Intermediate Similarity	NPD2494	Approved
0.7296	Intermediate Similarity	NPD2493	Approved
0.7296	Intermediate Similarity	NPD3450	Approved
0.7283	Intermediate Similarity	NPD8252	Approved
0.7283	Intermediate Similarity	NPD8099	Discontinued
0.7283	Intermediate Similarity	NPD8251	Approved
0.7278	Intermediate Similarity	NPD6234	Discontinued
0.7277	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4583	Approved
0.7273	Intermediate Similarity	NPD4582	Approved
0.7268	Intermediate Similarity	NPD2973	Approved
0.7268	Intermediate Similarity	NPD2975	Approved
0.7268	Intermediate Similarity	NPD2974	Approved
0.726	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3533	Approved
0.7259	Intermediate Similarity	NPD2972	Approved
0.7256	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD4107	Approved
0.7245	Intermediate Similarity	NPD4580	Approved
0.7238	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6723	Discontinued
0.7222	Intermediate Similarity	NPD4002	Approved
0.7222	Intermediate Similarity	NPD4004	Approved
0.7212	Intermediate Similarity	NPD6997	Phase 2
0.72	Intermediate Similarity	NPD4727	Phase 1
0.7191	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD37	Approved
0.7189	Intermediate Similarity	NPD7228	Approved
0.7176	Intermediate Similarity	NPD3656	Approved
0.7172	Intermediate Similarity	NPD3448	Approved
0.7172	Intermediate Similarity	NPD2491	Approved
0.7171	Intermediate Similarity	NPD7047	Phase 3
0.7143	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4666	Phase 3
0.7135	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4482	Phase 3
0.712	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4040	Phase 1
0.7098	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3060	Approved
0.7093	Intermediate Similarity	NPD5177	Phase 3
0.7088	Intermediate Similarity	NPD5709	Phase 3
0.7072	Intermediate Similarity	NPD6788	Approved
0.7066	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5676	Approved
0.7059	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5677	Discontinued
0.7049	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2492	Phase 1
0.7039	Intermediate Similarity	NPD6386	Approved
0.7039	Intermediate Similarity	NPD6385	Approved
0.7029	Intermediate Similarity	NPD2420	Approved
0.7029	Intermediate Similarity	NPD2421	Approved
0.7024	Intermediate Similarity	NPD2238	Phase 2
0.7022	Intermediate Similarity	NPD4005	Discontinued
0.7017	Intermediate Similarity	NPD5977	Approved
0.7017	Intermediate Similarity	NPD5978	Approved
0.7011	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7549	Discontinued
0.6995	Remote Similarity	NPD6841	Approved
0.6995	Remote Similarity	NPD4859	Phase 1
0.6995	Remote Similarity	NPD6843	Phase 3
0.6995	Remote Similarity	NPD6842	Approved
0.6994	Remote Similarity	NPD4162	Approved
0.6991	Remote Similarity	NPD6625	Approved
0.6977	Remote Similarity	NPD1375	Discontinued
0.6975	Remote Similarity	NPD3705	Approved
0.6971	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7497	Discontinued
0.6961	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2904	Discontinued
0.6954	Remote Similarity	NPD5754	Discontinued
0.6947	Remote Similarity	NPD7240	Approved
0.6947	Remote Similarity	NPD7038	Approved
0.6947	Remote Similarity	NPD7039	Approved
0.6941	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2653	Approved
0.6935	Remote Similarity	NPD6688	Approved
0.6935	Remote Similarity	NPD6687	Approved
0.6932	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3124	Discontinued
0.6927	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7199	Phase 2
0.6919	Remote Similarity	NPD2161	Phase 2
0.6911	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2122	Discontinued
0.6905	Remote Similarity	NPD5718	Phase 2
0.6897	Remote Similarity	NPD7999	Approved
0.6897	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD1424	Approved
0.6893	Remote Similarity	NPD3536	Discontinued
0.6893	Remote Similarity	NPD4123	Phase 3
0.6886	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3845	Phase 1
0.6864	Remote Similarity	NPD2674	Phase 3
0.6862	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4108	Discontinued
0.686	Remote Similarity	NPD1753	Discontinued
0.6857	Remote Similarity	NPD6331	Phase 2
0.6854	Remote Similarity	NPD6090	Discontinued
0.6851	Remote Similarity	NPD7110	Phase 1
0.6851	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5242	Approved
0.6842	Remote Similarity	NPD3885	Approved
0.6833	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4665	Approved
0.6825	Remote Similarity	NPD4111	Phase 1
0.6824	Remote Similarity	NPD3110	Approved
0.6824	Remote Similarity	NPD3109	Approved
0.6821	Remote Similarity	NPD7291	Discontinued
0.6821	Remote Similarity	NPD1632	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data