NPASS Compound

Structure

NPC473326 OpenBabel07101718182D 21 24 0 0 1 0 0 0 0 0999 V2000 3.0476 -1.5889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0762 2.7388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8673 2.9096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3442 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3904 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3442 -0.6761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7801 2.6130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9545 2.6130 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3442 0.8768 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7801 0.1003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8673 -0.1963 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9545 0.1003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2570 -0.3796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3237 1.8225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3904 0.8768 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8673 -1.1560 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0335 -0.9437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8036 0.9913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4109 1.8225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2570 0.5802 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 6 2 0 0 0 0 3 7 2 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 5 15 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 3 1 6 0 0 0 8 19 1 0 0 0 0 9 4 1 6 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 6 1 1 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 6 0 0 0 12 15 1 1 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 2 1 6 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.09
Volume:	275.966
LogP:	1.332
LogD:	1.496
LogS:	-2.395
# Rotatable Bonds:	0
TPSA:	92.43
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	6.26
Fsp3:	0.533
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:	-5.151
MDCK Permeability:	2.5493965949863195e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.32
Plasma Protein Binding (PPB):	60.69020080566406%
Volume Distribution (VD):	0.881
Pgp-substrate:	31.560043334960938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.285
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.394
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.115
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.28
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	15.413
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.671
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.696
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.512
Carcinogencity:	0.889
Eye Corrosion:	0.034
Eye Irritation:	0.029
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC473326

Natural Product ID:	NPC473326
*Common Name:**	Elephantol
IUPAC Name:	n.a.
Synonyms:	Elephantol
Standard InCHIKey:	ZEVSGZJPWOWMRR-PEZSEORZSA-N
Standard InCHI:	InChI=1S/C15H16O6/c1-6-10-9(20-13(6)17)4-7-3-8(19-14(7)18)5-15(2)12(21-15)11(10)16/h3,8-12,16H,1,4-5H2,2H3/t8-,9-,10+,11-,12+,15-/m0/s1
SMILES:	CC12CC3C=C(CC4C(C(C1O2)O)C(=C)C(=O)O4)C(=O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400759
PubChem CID:	44444895
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	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	pED50	=	3.91	n.a.	PMID[558214]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	36.0	ug ml-1	PMID[558214]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	123.2	umol/L	PMID[558215]

☑ 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 NPC473326 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	233
0.1-0.2	1321
0.2-0.3	4951
0.3-0.4	9222
0.4-0.5	14609
0.5-0.6	7437
0.6-0.7	3555
0.7-0.8	1140
0.8-0.85	132
0.85-0.9	72
0.9-0.95	24
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9348	High Similarity	NPC303942
0.9348	High Similarity	NPC57405
0.9348	High Similarity	NPC473330
0.9348	High Similarity	NPC473316
0.9263	High Similarity	NPC288876
0.9247	High Similarity	NPC270013
0.9247	High Similarity	NPC14961
0.9239	High Similarity	NPC212486
0.9149	High Similarity	NPC473859
0.9149	High Similarity	NPC279621
0.914	High Similarity	NPC474035
0.914	High Similarity	NPC81386
0.9043	High Similarity	NPC475659
0.9032	High Similarity	NPC475912
0.9032	High Similarity	NPC81419
0.9032	High Similarity	NPC125674
0.9032	High Similarity	NPC228451
0.9032	High Similarity	NPC179746
0.9032	High Similarity	NPC475838
0.9022	High Similarity	NPC312042
0.9022	High Similarity	NPC473619
0.8958	High Similarity	NPC208233
0.8958	High Similarity	NPC474213
0.8947	High Similarity	NPC476315
0.8947	High Similarity	NPC35498
0.8936	High Similarity	NPC474247
0.8936	High Similarity	NPC140543
0.8925	High Similarity	NPC184463
0.8925	High Similarity	NPC208886
0.8925	High Similarity	NPC30515
0.8925	High Similarity	NPC473321
0.8925	High Similarity	NPC12172
0.8913	High Similarity	NPC166919
0.8913	High Similarity	NPC151770
0.89	High Similarity	NPC477513
0.8842	High Similarity	NPC36954
0.8842	High Similarity	NPC471141
0.883	High Similarity	NPC295204
0.883	High Similarity	NPC288240
0.883	High Similarity	NPC273579
0.883	High Similarity	NPC162205
0.883	High Similarity	NPC476300
0.8817	High Similarity	NPC51004
0.8804	High Similarity	NPC202672
0.8804	High Similarity	NPC473715
0.88	High Similarity	NPC243998
0.8776	High Similarity	NPC164598
0.8776	High Similarity	NPC476270
0.8776	High Similarity	NPC474339
0.8763	High Similarity	NPC471144
0.8763	High Similarity	NPC279561
0.875	High Similarity	NPC230800
0.8737	High Similarity	NPC476267
0.8723	High Similarity	NPC70251
0.8723	High Similarity	NPC475881
0.871	High Similarity	NPC295312
0.871	High Similarity	NPC474032
0.871	High Similarity	NPC307411
0.8696	High Similarity	NPC475703
0.8696	High Similarity	NPC231889
0.8687	High Similarity	NPC471148
0.8687	High Similarity	NPC149371
0.8681	High Similarity	NPC319795
0.8681	High Similarity	NPC50362
0.8681	High Similarity	NPC38468
0.8673	High Similarity	NPC475949
0.8646	High Similarity	NPC471142
0.8617	High Similarity	NPC474761
0.8617	High Similarity	NPC476004
0.8617	High Similarity	NPC475748
0.8617	High Similarity	NPC251385
0.8617	High Similarity	NPC475855
0.8617	High Similarity	NPC49342
0.8614	High Similarity	NPC223450
0.8587	High Similarity	NPC50637
0.8586	High Similarity	NPC201718
0.8586	High Similarity	NPC47880
0.8586	High Similarity	NPC473332
0.8571	High Similarity	NPC187268
0.8557	High Similarity	NPC477921
0.8542	High Similarity	NPC471147
0.8515	High Similarity	NPC474741
0.8515	High Similarity	NPC100487
0.8495	Intermediate Similarity	NPC186148
0.8454	Intermediate Similarity	NPC477922
0.8431	Intermediate Similarity	NPC54737
0.8421	Intermediate Similarity	NPC144133
0.8421	Intermediate Similarity	NPC179394
0.8416	Intermediate Similarity	NPC475945
0.8416	Intermediate Similarity	NPC475871
0.8404	Intermediate Similarity	NPC281516
0.8404	Intermediate Similarity	NPC177629
0.8404	Intermediate Similarity	NPC58219
0.84	Intermediate Similarity	NPC264477
0.84	Intermediate Similarity	NPC477511
0.8387	Intermediate Similarity	NPC284902
0.8387	Intermediate Similarity	NPC475461
0.8387	Intermediate Similarity	NPC305475
0.8387	Intermediate Similarity	NPC112685
0.837	Intermediate Similarity	NPC114979
0.837	Intermediate Similarity	NPC191476
0.8367	Intermediate Similarity	NPC17585
0.8365	Intermediate Similarity	NPC38154
0.8333	Intermediate Similarity	NPC203659
0.8317	Intermediate Similarity	NPC474747
0.8317	Intermediate Similarity	NPC86077
0.8317	Intermediate Similarity	NPC324017
0.8317	Intermediate Similarity	NPC320019
0.8316	Intermediate Similarity	NPC92974
0.8316	Intermediate Similarity	NPC473564
0.8316	Intermediate Similarity	NPC477011
0.8298	Intermediate Similarity	NPC160138
0.8298	Intermediate Similarity	NPC5130
0.828	Intermediate Similarity	NPC255307
0.828	Intermediate Similarity	NPC21469
0.828	Intermediate Similarity	NPC304509
0.828	Intermediate Similarity	NPC47958
0.828	Intermediate Similarity	NPC149725
0.8265	Intermediate Similarity	NPC304886
0.8265	Intermediate Similarity	NPC107476
0.8261	Intermediate Similarity	NPC272814
0.8247	Intermediate Similarity	NPC135776
0.8235	Intermediate Similarity	NPC110989
0.8229	Intermediate Similarity	NPC473448
0.8229	Intermediate Similarity	NPC62815
0.8218	Intermediate Similarity	NPC185141
0.8218	Intermediate Similarity	NPC15993
0.8218	Intermediate Similarity	NPC133907
0.8218	Intermediate Similarity	NPC474742
0.8218	Intermediate Similarity	NPC46998
0.8218	Intermediate Similarity	NPC128733
0.8218	Intermediate Similarity	NPC110443
0.8218	Intermediate Similarity	NPC150923
0.8211	Intermediate Similarity	NPC89001
0.8211	Intermediate Similarity	NPC40376
0.8211	Intermediate Similarity	NPC153805
0.8211	Intermediate Similarity	NPC233551
0.8211	Intermediate Similarity	NPC21208
0.8211	Intermediate Similarity	NPC280621
0.8211	Intermediate Similarity	NPC20339
0.8211	Intermediate Similarity	NPC48338
0.82	Intermediate Similarity	NPC222303
0.8191	Intermediate Similarity	NPC470242
0.8191	Intermediate Similarity	NPC114694
0.8191	Intermediate Similarity	NPC475581
0.8191	Intermediate Similarity	NPC240695
0.8191	Intermediate Similarity	NPC231096
0.8191	Intermediate Similarity	NPC142117
0.8191	Intermediate Similarity	NPC171174
0.8191	Intermediate Similarity	NPC232555
0.8191	Intermediate Similarity	NPC107717
0.8191	Intermediate Similarity	NPC150755
0.8191	Intermediate Similarity	NPC62118
0.819	Intermediate Similarity	NPC139838
0.819	Intermediate Similarity	NPC59489
0.8172	Intermediate Similarity	NPC141193
0.8172	Intermediate Similarity	NPC96259
0.8163	Intermediate Similarity	NPC71589
0.8163	Intermediate Similarity	NPC474338
0.8163	Intermediate Similarity	NPC190294
0.8163	Intermediate Similarity	NPC477131
0.8155	Intermediate Similarity	NPC477510
0.8155	Intermediate Similarity	NPC471143
0.8152	Intermediate Similarity	NPC229825
0.8144	Intermediate Similarity	NPC158061
0.8144	Intermediate Similarity	NPC131209
0.8137	Intermediate Similarity	NPC225353
0.8125	Intermediate Similarity	NPC280612
0.8125	Intermediate Similarity	NPC477017
0.8125	Intermediate Similarity	NPC477016
0.8119	Intermediate Similarity	NPC70865
0.8119	Intermediate Similarity	NPC477512
0.8119	Intermediate Similarity	NPC471381
0.8119	Intermediate Similarity	NPC475053
0.8105	Intermediate Similarity	NPC178215
0.8105	Intermediate Similarity	NPC248602
0.8105	Intermediate Similarity	NPC190753
0.81	Intermediate Similarity	NPC471140
0.81	Intermediate Similarity	NPC40812
0.8095	Intermediate Similarity	NPC475960
0.8085	Intermediate Similarity	NPC1083
0.8085	Intermediate Similarity	NPC215364
0.8085	Intermediate Similarity	NPC231009
0.8085	Intermediate Similarity	NPC132496
0.8085	Intermediate Similarity	NPC473651
0.8085	Intermediate Similarity	NPC100921
0.8085	Intermediate Similarity	NPC107986
0.8085	Intermediate Similarity	NPC120398
0.8085	Intermediate Similarity	NPC66346
0.8085	Intermediate Similarity	NPC103284
0.8085	Intermediate Similarity	NPC471567
0.8085	Intermediate Similarity	NPC473478
0.8085	Intermediate Similarity	NPC223871
0.8085	Intermediate Similarity	NPC137033
0.8085	Intermediate Similarity	NPC477018
0.8085	Intermediate Similarity	NPC82795
0.8085	Intermediate Similarity	NPC286338
0.8085	Intermediate Similarity	NPC473669
0.8085	Intermediate Similarity	NPC283085
0.8085	Intermediate Similarity	NPC110710

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 NPC473326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1934
0.2-0.3	3747
0.3-0.4	2207
0.4-0.5	695
0.5-0.6	289
0.6-0.7	58
0.7-0.8	9
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8681	High Similarity	NPD1733	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD46	Approved
0.8229	Intermediate Similarity	NPD6698	Approved
0.7857	Intermediate Similarity	NPD7838	Discovery
0.783	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1695	Approved
0.7723	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD6371	Approved
0.7426	Intermediate Similarity	NPD7983	Approved
0.7273	Intermediate Similarity	NPD6686	Approved
0.7196	Intermediate Similarity	NPD5344	Discontinued
0.708	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6053	Discontinued
0.7009	Intermediate Similarity	NPD4225	Approved
0.7009	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5282	Discontinued
0.6789	Remote Similarity	NPD6648	Approved
0.678	Remote Similarity	NPD7115	Discovery
0.6765	Remote Similarity	NPD4249	Approved
0.6748	Remote Similarity	NPD7507	Approved
0.6721	Remote Similarity	NPD7642	Approved
0.6699	Remote Similarity	NPD4251	Approved
0.6699	Remote Similarity	NPD4250	Approved
0.6698	Remote Similarity	NPD5779	Approved
0.6698	Remote Similarity	NPD5778	Approved
0.6694	Remote Similarity	NPD8515	Approved
0.6694	Remote Similarity	NPD8516	Approved
0.6694	Remote Similarity	NPD8517	Approved
0.6694	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD5785	Approved
0.6637	Remote Similarity	NPD6008	Approved
0.6634	Remote Similarity	NPD7154	Phase 3
0.6587	Remote Similarity	NPD7319	Approved
0.6585	Remote Similarity	NPD7829	Approved
0.6585	Remote Similarity	NPD7830	Approved
0.6579	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6435	Approved
0.6535	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD1694	Approved
0.6505	Remote Similarity	NPD5363	Approved
0.6505	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5362	Discontinued
0.6442	Remote Similarity	NPD5786	Approved
0.6429	Remote Similarity	NPD8074	Phase 3
0.6413	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7638	Approved
0.6387	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7839	Suspended
0.6341	Remote Similarity	NPD6319	Approved
0.6339	Remote Similarity	NPD7640	Approved
0.6339	Remote Similarity	NPD7639	Approved
0.6337	Remote Similarity	NPD5368	Approved
0.6337	Remote Similarity	NPD4822	Approved
0.6337	Remote Similarity	NPD4820	Approved
0.6337	Remote Similarity	NPD4821	Approved
0.6337	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4819	Approved
0.6311	Remote Similarity	NPD7641	Discontinued
0.6275	Remote Similarity	NPD5369	Approved
0.627	Remote Similarity	NPD7492	Approved
0.6262	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6101	Approved
0.6239	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8451	Approved
0.622	Remote Similarity	NPD6616	Approved
0.622	Remote Similarity	NPD8273	Phase 1
0.6218	Remote Similarity	NPD2204	Approved
0.6214	Remote Similarity	NPD4270	Approved
0.6214	Remote Similarity	NPD4269	Approved
0.621	Remote Similarity	NPD6054	Approved
0.6179	Remote Similarity	NPD7328	Approved
0.6179	Remote Similarity	NPD7327	Approved
0.6172	Remote Similarity	NPD8448	Approved
0.6172	Remote Similarity	NPD7078	Approved
0.6167	Remote Similarity	NPD8297	Approved
0.616	Remote Similarity	NPD6015	Approved
0.616	Remote Similarity	NPD6016	Approved
0.616	Remote Similarity	NPD8033	Approved
0.6154	Remote Similarity	NPD6110	Phase 1
0.6154	Remote Similarity	NPD5697	Approved
0.6154	Remote Similarity	NPD6412	Phase 2
0.6147	Remote Similarity	NPD6411	Approved
0.6139	Remote Similarity	NPD4271	Approved
0.6139	Remote Similarity	NPD4268	Approved
0.6129	Remote Similarity	NPD7516	Approved
0.6124	Remote Similarity	NPD7736	Approved
0.6111	Remote Similarity	NPD6370	Approved
0.6111	Remote Similarity	NPD5988	Approved
0.6107	Remote Similarity	NPD7260	Phase 2
0.6102	Remote Similarity	NPD6899	Approved
0.6102	Remote Similarity	NPD6881	Approved
0.6102	Remote Similarity	NPD7320	Approved
0.6098	Remote Similarity	NPD6009	Approved
0.6095	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6649	Approved
0.6083	Remote Similarity	NPD6650	Approved
0.608	Remote Similarity	NPD8294	Approved
0.608	Remote Similarity	NPD8377	Approved
0.608	Remote Similarity	NPD6059	Approved
0.6068	Remote Similarity	NPD5739	Approved
0.6068	Remote Similarity	NPD6675	Approved
0.6068	Remote Similarity	NPD6402	Approved
0.6068	Remote Similarity	NPD7128	Approved
0.6063	Remote Similarity	NPD7604	Phase 2
0.6061	Remote Similarity	NPD6845	Suspended
0.6058	Remote Similarity	NPD5209	Approved
0.605	Remote Similarity	NPD6373	Approved
0.605	Remote Similarity	NPD6014	Approved
0.605	Remote Similarity	NPD6372	Approved
0.605	Remote Similarity	NPD6013	Approved
0.605	Remote Similarity	NPD6012	Approved
0.6047	Remote Similarity	NPD8293	Discontinued
0.6032	Remote Similarity	NPD5983	Phase 2
0.6032	Remote Similarity	NPD8378	Approved
0.6032	Remote Similarity	NPD8379	Approved
0.6032	Remote Similarity	NPD8296	Approved
0.6032	Remote Similarity	NPD8380	Approved
0.6032	Remote Similarity	NPD8444	Approved
0.6032	Remote Similarity	NPD8335	Approved
0.6031	Remote Similarity	NPD8392	Approved
0.6031	Remote Similarity	NPD8390	Approved
0.6031	Remote Similarity	NPD8391	Approved
0.6019	Remote Similarity	NPD4252	Approved
0.6017	Remote Similarity	NPD5701	Approved
0.6016	Remote Similarity	NPD8342	Approved
0.6016	Remote Similarity	NPD8341	Approved
0.6016	Remote Similarity	NPD8299	Approved
0.6016	Remote Similarity	NPD8340	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD5331	Approved
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD5332	Approved
0.6	Remote Similarity	NPD6883	Approved
0.5984	Remote Similarity	NPD8080	Discontinued
0.598	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6011	Approved
0.5962	Remote Similarity	NPD4790	Discontinued
0.595	Remote Similarity	NPD8130	Phase 1
0.595	Remote Similarity	NPD6869	Approved
0.595	Remote Similarity	NPD6617	Approved
0.595	Remote Similarity	NPD6847	Approved
0.5946	Remote Similarity	NPD6399	Phase 3
0.5938	Remote Similarity	NPD8328	Phase 3
0.5906	Remote Similarity	NPD7503	Approved
0.5905	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6882	Approved
0.5877	Remote Similarity	NPD6083	Phase 2
0.5877	Remote Similarity	NPD6084	Phase 2
0.5868	Remote Similarity	NPD4634	Approved
0.5856	Remote Similarity	NPD7637	Suspended
0.5854	Remote Similarity	NPD8133	Approved
0.5846	Remote Similarity	NPD6336	Discontinued
0.5841	Remote Similarity	NPD5695	Phase 3
0.584	Remote Similarity	NPD7505	Discontinued
0.5833	Remote Similarity	NPD7331	Phase 2
0.5826	Remote Similarity	NPD5696	Approved
0.5812	Remote Similarity	NPD5211	Phase 2
0.5812	Remote Similarity	NPD7632	Discontinued
0.5781	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD8269	Approved
0.5781	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD8267	Approved
0.5781	Remote Similarity	NPD8268	Approved
0.5781	Remote Similarity	NPD8266	Approved
0.578	Remote Similarity	NPD7524	Approved
0.5776	Remote Similarity	NPD5285	Approved
0.5776	Remote Similarity	NPD5286	Approved
0.5776	Remote Similarity	NPD4696	Approved
0.5773	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.576	Remote Similarity	NPD6274	Approved
0.5739	Remote Similarity	NPD7902	Approved
0.5739	Remote Similarity	NPD4755	Approved
0.5738	Remote Similarity	NPD6421	Discontinued
0.5738	Remote Similarity	NPD2067	Discontinued
0.5729	Remote Similarity	NPD7341	Phase 2
0.5728	Remote Similarity	NPD4756	Discovery
0.5714	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7500	Approved
0.5702	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6422	Discontinued
0.5686	Remote Similarity	NPD8039	Approved
0.5678	Remote Similarity	NPD5224	Approved
0.5678	Remote Similarity	NPD5225	Approved
0.5678	Remote Similarity	NPD4633	Approved
0.5678	Remote Similarity	NPD5226	Approved
0.5676	Remote Similarity	NPD5370	Suspended
0.5659	Remote Similarity	NPD6921	Approved
0.5656	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD4700	Approved
0.5639	Remote Similarity	NPD6033	Approved
0.563	Remote Similarity	NPD5175	Approved
0.563	Remote Similarity	NPD5174	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