NPASS Compound

Structure

NPC471140 OpenBabel07101719132D 30 33 0 0 1 0 0 0 0 0999 V2000 3.5886 2.2217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7925 4.4147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7416 2.3813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8671 0.6782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6371 4.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4549 1.2009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7542 0.5700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2674 2.9845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3835 1.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1627 2.4275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6509 2.1231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1297 4.2187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2702 3.1979 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.4484 1.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4509 3.4559 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1875 2.7265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8165 0.4714 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5132 3.3573 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8304 4.8496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6371 3.1979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4536 3.6693 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 0.9429 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3819 1.2882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7318 5.7873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6371 2.2550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0962 2.2952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6469 4.3782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8205 3.6693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2702 4.1407 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 11 1 0 0 0 0 2 12 2 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 21 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 17 1 0 0 0 0 8 11 2 0 0 0 0 9 16 1 0 0 0 0 9 22 1 0 0 0 0 10 26 1 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 13 29 1 0 0 0 0 14 23 2 0 0 0 0 14 26 1 0 0 0 0 15 8 1 6 0 0 0 15 18 1 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 28 1 1 0 0 0 17 22 1 1 0 0 0 17 30 1 0 0 0 0 18 12 1 1 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 10 1 1 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	411.982
LogP:	2.14
LogD:	2.219
LogS:	-3.931
# Rotatable Bonds:	6
TPSA:	103.96
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.224
Synthetic Accessibility Score:	5.421
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.272
MDCK Permeability:	6.253937317524105e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.168
Plasma Protein Binding (PPB):	80.83501434326172%
Volume Distribution (VD):	1.368
Pgp-substrate:	19.888126373291016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.667
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.515
CYP3A4-substrate:	0.404

ADMET: Excretion

Clearance (CL):	5.071
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.383
Drug-inuced Liver Injury (DILI):	0.821
AMES Toxicity:	0.859
Rat Oral Acute Toxicity:	0.534
Maximum Recommended Daily Dose:	0.351
Skin Sensitization:	0.391
Carcinogencity:	0.08
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.605

Download Data

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

Natural Product: NPC471140

Natural Product ID:	NPC471140
*Common Name:**	FAUMCPFTDXKTHJ-MVVKUPJXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FAUMCPFTDXKTHJ-MVVKUPJXSA-N
Standard InCHI:	InChI=1S/C22H28O8/c1-11-6-7-17-22(30-17,10-26-14(4)23)9-16(28-20(25)21(5)13(3)29-21)18-12(2)19(24)27-15(18)8-11/h8,13,15-18H,2,6-7,9-10H2,1,3-5H3/b11-8+/t13?,15-,16-,17-,18+,21?,22+/m1/s1
SMILES:	CC(=O)OC[C@]12C[C@@H](OC(=O)C3(C)OC3C)[C@@H]3[C@@H](/C=C(/CC[C@H]2O1)C)OC(=O)C3=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380317
PubChem CID:	73354913
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO27591	Viguiera hypargyrea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO27591	Viguiera hypargyrea	Species	Asteraceae	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	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	12161.86	nM	PMID[503184]
NPT27	Others	Unspecified		IC50	=	25490.0	nM	PMID[503184]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	12160.0	nM	PMID[503184]

☑ 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 NPC471140 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	279
0.1-0.2	1780
0.2-0.3	6136
0.3-0.4	13585
0.4-0.5	11951
0.5-0.6	6056
0.6-0.7	2288
0.7-0.8	468
0.8-0.85	109
0.85-0.9	31
0.9-0.95	8
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC477511
0.9677	High Similarity	NPC264477
0.9375	High Similarity	NPC471143
0.9375	High Similarity	NPC477510
0.9368	High Similarity	NPC471148
0.9362	High Similarity	NPC477512
0.9247	High Similarity	NPC17585
0.9239	High Similarity	NPC471147
0.9184	High Similarity	NPC477513
0.9062	High Similarity	NPC474339
0.9062	High Similarity	NPC164598
0.9	High Similarity	NPC266957
0.8889	High Similarity	NPC50637
0.8854	High Similarity	NPC208233
0.8842	High Similarity	NPC35498
0.8817	High Similarity	NPC20713
0.8804	High Similarity	NPC151770
0.8763	High Similarity	NPC475949
0.8737	High Similarity	NPC475659
0.871	High Similarity	NPC475748
0.8687	High Similarity	NPC19239
0.8687	High Similarity	NPC474166
0.8646	High Similarity	NPC279621
0.8646	High Similarity	NPC473859
0.8646	High Similarity	NPC230800
0.8632	High Similarity	NPC140543
0.8632	High Similarity	NPC473316
0.8632	High Similarity	NPC473330
0.8602	High Similarity	NPC475971
0.8602	High Similarity	NPC166919
0.8587	High Similarity	NPC231889
0.8586	High Similarity	NPC149371
0.8571	High Similarity	NPC288876
0.8544	High Similarity	NPC473975
0.8544	High Similarity	NPC473843
0.8544	High Similarity	NPC473594
0.8544	High Similarity	NPC474586
0.8526	High Similarity	NPC165383
0.8515	High Similarity	NPC9303
0.8515	High Similarity	NPC475802
0.8515	High Similarity	NPC16313
0.8485	Intermediate Similarity	NPC201718
0.8485	Intermediate Similarity	NPC47880
0.8469	Intermediate Similarity	NPC471144
0.8462	Intermediate Similarity	NPC194619
0.8438	Intermediate Similarity	NPC476267
0.8438	Intermediate Similarity	NPC474247
0.8431	Intermediate Similarity	NPC324327
0.8431	Intermediate Similarity	NPC72813
0.8431	Intermediate Similarity	NPC475510
0.8431	Intermediate Similarity	NPC326994
0.8431	Intermediate Similarity	NPC475587
0.8431	Intermediate Similarity	NPC194620
0.8431	Intermediate Similarity	NPC474421
0.837	Intermediate Similarity	NPC38468
0.837	Intermediate Similarity	NPC319795
0.837	Intermediate Similarity	NPC50362
0.8351	Intermediate Similarity	NPC471141
0.835	Intermediate Similarity	NPC14862
0.835	Intermediate Similarity	NPC233379
0.835	Intermediate Similarity	NPC473595
0.835	Intermediate Similarity	NPC473939
0.835	Intermediate Similarity	NPC327286
0.835	Intermediate Similarity	NPC474664
0.835	Intermediate Similarity	NPC55972
0.835	Intermediate Similarity	NPC169888
0.8333	Intermediate Similarity	NPC125674
0.8333	Intermediate Similarity	NPC475838
0.8333	Intermediate Similarity	NPC141810
0.8333	Intermediate Similarity	NPC228451
0.8316	Intermediate Similarity	NPC329857
0.8316	Intermediate Similarity	NPC469718
0.8283	Intermediate Similarity	NPC279561
0.828	Intermediate Similarity	NPC204048
0.8269	Intermediate Similarity	NPC475922
0.8269	Intermediate Similarity	NPC15218
0.8265	Intermediate Similarity	NPC476275
0.8265	Intermediate Similarity	NPC476315
0.8247	Intermediate Similarity	NPC57405
0.8247	Intermediate Similarity	NPC303942
0.8235	Intermediate Similarity	NPC474741
0.819	Intermediate Similarity	NPC115257
0.819	Intermediate Similarity	NPC161816
0.819	Intermediate Similarity	NPC281624
0.8163	Intermediate Similarity	NPC14961
0.8163	Intermediate Similarity	NPC270013
0.8163	Intermediate Similarity	NPC471142
0.8163	Intermediate Similarity	NPC474947
0.8152	Intermediate Similarity	NPC128429
0.8152	Intermediate Similarity	NPC272814
0.8152	Intermediate Similarity	NPC474703
0.8148	Intermediate Similarity	NPC474333
0.8144	Intermediate Similarity	NPC212486
0.8144	Intermediate Similarity	NPC476300
0.8137	Intermediate Similarity	NPC4620
0.8125	Intermediate Similarity	NPC251385
0.8125	Intermediate Similarity	NPC49342
0.8125	Intermediate Similarity	NPC312042
0.8119	Intermediate Similarity	NPC476270
0.8113	Intermediate Similarity	NPC475495
0.8111	Intermediate Similarity	NPC617
0.8105	Intermediate Similarity	NPC475902
0.8105	Intermediate Similarity	NPC287089
0.81	Intermediate Similarity	NPC474213
0.81	Intermediate Similarity	NPC473326
0.8077	Intermediate Similarity	NPC469558
0.8077	Intermediate Similarity	NPC474716
0.8073	Intermediate Similarity	NPC296822
0.8065	Intermediate Similarity	NPC470238
0.8065	Intermediate Similarity	NPC138647
0.8061	Intermediate Similarity	NPC81386
0.8061	Intermediate Similarity	NPC474035
0.8058	Intermediate Similarity	NPC220964
0.8058	Intermediate Similarity	NPC475676
0.8037	Intermediate Similarity	NPC473522
0.8037	Intermediate Similarity	NPC477093
0.8037	Intermediate Similarity	NPC475277
0.8037	Intermediate Similarity	NPC473877
0.8	Intermediate Similarity	NPC5130
0.8	Intermediate Similarity	NPC475703
0.798	Intermediate Similarity	NPC36954
0.7979	Intermediate Similarity	NPC474547
0.7961	Intermediate Similarity	NPC475871
0.7961	Intermediate Similarity	NPC472755
0.7961	Intermediate Similarity	NPC475945
0.7959	Intermediate Similarity	NPC475912
0.7959	Intermediate Similarity	NPC475302
0.7957	Intermediate Similarity	NPC170286
0.7957	Intermediate Similarity	NPC318468
0.7941	Intermediate Similarity	NPC474742
0.7941	Intermediate Similarity	NPC15993
0.7941	Intermediate Similarity	NPC473332
0.7938	Intermediate Similarity	NPC475855
0.7938	Intermediate Similarity	NPC51004
0.7938	Intermediate Similarity	NPC474232
0.7938	Intermediate Similarity	NPC179394
0.7938	Intermediate Similarity	NPC144133
0.7905	Intermediate Similarity	NPC26617
0.79	Intermediate Similarity	NPC470883
0.79	Intermediate Similarity	NPC39859
0.79	Intermediate Similarity	NPC76862
0.79	Intermediate Similarity	NPC172998
0.79	Intermediate Similarity	NPC301596
0.79	Intermediate Similarity	NPC158416
0.79	Intermediate Similarity	NPC299396
0.7895	Intermediate Similarity	NPC279859
0.7895	Intermediate Similarity	NPC38576
0.7889	Intermediate Similarity	NPC141789
0.7889	Intermediate Similarity	NPC476028
0.7889	Intermediate Similarity	NPC171204
0.7885	Intermediate Similarity	NPC472756
0.7879	Intermediate Similarity	NPC121825
0.7879	Intermediate Similarity	NPC190294
0.7864	Intermediate Similarity	NPC474747
0.7864	Intermediate Similarity	NPC183571
0.7864	Intermediate Similarity	NPC320019
0.7864	Intermediate Similarity	NPC472754
0.7864	Intermediate Similarity	NPC324017
0.7857	Intermediate Similarity	NPC30515
0.7857	Intermediate Similarity	NPC70251
0.7857	Intermediate Similarity	NPC184463
0.7857	Intermediate Similarity	NPC158061
0.7857	Intermediate Similarity	NPC475881
0.7843	Intermediate Similarity	NPC469551
0.7835	Intermediate Similarity	NPC307411
0.7835	Intermediate Similarity	NPC474032
0.783	Intermediate Similarity	NPC94377
0.7826	Intermediate Similarity	NPC474739
0.781	Intermediate Similarity	NPC44004
0.78	Intermediate Similarity	NPC477922
0.78	Intermediate Similarity	NPC234339
0.78	Intermediate Similarity	NPC273197
0.7789	Intermediate Similarity	NPC255307
0.7788	Intermediate Similarity	NPC69171
0.7788	Intermediate Similarity	NPC474165
0.7778	Intermediate Similarity	NPC179746
0.7778	Intermediate Similarity	NPC469692
0.7778	Intermediate Similarity	NPC469645
0.7778	Intermediate Similarity	NPC81419
0.7778	Intermediate Similarity	NPC235906
0.7767	Intermediate Similarity	NPC133907
0.7767	Intermediate Similarity	NPC185141
0.7767	Intermediate Similarity	NPC472753
0.7767	Intermediate Similarity	NPC46998
0.7767	Intermediate Similarity	NPC128733
0.7767	Intermediate Similarity	NPC110443
0.7766	Intermediate Similarity	NPC475947
0.7757	Intermediate Similarity	NPC42662
0.7757	Intermediate Similarity	NPC38154
0.7755	Intermediate Similarity	NPC62815
0.7755	Intermediate Similarity	NPC473619
0.7748	Intermediate Similarity	NPC475305
0.7748	Intermediate Similarity	NPC471146
0.7745	Intermediate Similarity	NPC161855
0.7742	Intermediate Similarity	NPC281949
0.7742	Intermediate Similarity	NPC25684
0.7742	Intermediate Similarity	NPC301477
0.7742	Intermediate Similarity	NPC207188
0.7732	Intermediate Similarity	NPC471047
0.7732	Intermediate Similarity	NPC476805

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 NPC471140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	2405
0.2-0.3	3881
0.3-0.4	1797
0.4-0.5	582
0.5-0.6	204
0.6-0.7	23
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.837	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD1695	Approved
0.7576	Intermediate Similarity	NPD6698	Approved
0.7576	Intermediate Similarity	NPD46	Approved
0.7228	Intermediate Similarity	NPD7838	Discovery
0.7207	Intermediate Similarity	NPD6371	Approved
0.6991	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7983	Approved
0.6937	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5282	Discontinued
0.6852	Remote Similarity	NPD6648	Approved
0.6792	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5344	Discontinued
0.6754	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4225	Approved
0.6579	Remote Similarity	NPD6686	Approved
0.6522	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5209	Approved
0.6436	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7115	Discovery
0.6415	Remote Similarity	NPD5785	Approved
0.6408	Remote Similarity	NPD1694	Approved
0.6341	Remote Similarity	NPD8513	Phase 3
0.6341	Remote Similarity	NPD8515	Approved
0.6341	Remote Similarity	NPD8516	Approved
0.6341	Remote Similarity	NPD8517	Approved
0.6296	Remote Similarity	NPD5779	Approved
0.6296	Remote Similarity	NPD5778	Approved
0.6288	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6008	Approved
0.626	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD5363	Approved
0.624	Remote Similarity	NPD7642	Approved
0.6214	Remote Similarity	NPD7154	Phase 3
0.619	Remote Similarity	NPD4249	Approved
0.6176	Remote Similarity	NPD5369	Approved
0.6142	Remote Similarity	NPD8273	Phase 1
0.6132	Remote Similarity	NPD4250	Approved
0.6132	Remote Similarity	NPD4251	Approved
0.6126	Remote Similarity	NPD7839	Suspended
0.6117	Remote Similarity	NPD4269	Approved
0.6117	Remote Similarity	NPD4270	Approved
0.6111	Remote Similarity	NPD7830	Approved
0.6111	Remote Similarity	NPD7829	Approved
0.6094	Remote Similarity	NPD8074	Phase 3
0.6083	Remote Similarity	NPD6053	Discontinued
0.6063	Remote Similarity	NPD7492	Approved
0.6055	Remote Similarity	NPD5693	Phase 1
0.605	Remote Similarity	NPD2067	Discontinued
0.6038	Remote Similarity	NPD5786	Approved
0.6017	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD2204	Approved
0.6	Remote Similarity	NPD6054	Approved
0.5969	Remote Similarity	NPD7078	Approved
0.5952	Remote Similarity	NPD6016	Approved
0.5952	Remote Similarity	NPD6015	Approved
0.595	Remote Similarity	NPD8297	Approved
0.5943	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6672	Approved
0.5926	Remote Similarity	NPD5737	Approved
0.5923	Remote Similarity	NPD7736	Approved
0.5922	Remote Similarity	NPD4252	Approved
0.5922	Remote Similarity	NPD4820	Approved
0.5922	Remote Similarity	NPD4822	Approved
0.5922	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4821	Approved
0.5922	Remote Similarity	NPD4819	Approved
0.5909	Remote Similarity	NPD7260	Phase 2
0.5906	Remote Similarity	NPD5988	Approved
0.5906	Remote Similarity	NPD6370	Approved
0.5905	Remote Similarity	NPD5362	Discontinued
0.59	Remote Similarity	NPD8039	Approved
0.5893	Remote Similarity	NPD5695	Phase 3
0.5891	Remote Similarity	NPD8451	Approved
0.5878	Remote Similarity	NPD7319	Approved
0.5877	Remote Similarity	NPD5696	Approved
0.5877	Remote Similarity	NPD7638	Approved
0.5873	Remote Similarity	NPD6059	Approved
0.5872	Remote Similarity	NPD6101	Approved
0.5872	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6650	Approved
0.5868	Remote Similarity	NPD6649	Approved
0.5859	Remote Similarity	NPD8328	Phase 3
0.5846	Remote Similarity	NPD8293	Discontinued
0.5846	Remote Similarity	NPD8448	Approved
0.5833	Remote Similarity	NPD6372	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.5826	Remote Similarity	NPD7639	Approved
0.5826	Remote Similarity	NPD7640	Approved
0.5818	Remote Similarity	NPD3168	Discontinued
0.581	Remote Similarity	NPD6435	Approved
0.5798	Remote Similarity	NPD5697	Approved
0.5789	Remote Similarity	NPD6083	Phase 2
0.5789	Remote Similarity	NPD6084	Phase 2
0.5784	Remote Similarity	NPD4756	Discovery
0.5781	Remote Similarity	NPD8080	Discontinued
0.5772	Remote Similarity	NPD4632	Approved
0.5769	Remote Similarity	NPD7507	Approved
0.5766	Remote Similarity	NPD6411	Approved
0.5766	Remote Similarity	NPD7637	Suspended
0.576	Remote Similarity	NPD7500	Approved
0.576	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.576	Remote Similarity	NPD6009	Approved
0.5755	Remote Similarity	NPD6110	Phase 1
0.575	Remote Similarity	NPD6899	Approved
0.575	Remote Similarity	NPD6881	Approved
0.5746	Remote Similarity	NPD6845	Suspended
0.5736	Remote Similarity	NPD7604	Phase 2
0.5728	Remote Similarity	NPD4271	Approved
0.5728	Remote Similarity	NPD4268	Approved
0.5727	Remote Similarity	NPD6673	Approved
0.5727	Remote Similarity	NPD6080	Approved
0.5727	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD8392	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5714	Remote Similarity	NPD8391	Approved
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD8390	Approved
0.5714	Remote Similarity	NPD6402	Approved
0.5703	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD5983	Phase 2
0.5703	Remote Similarity	NPD8444	Approved
0.5702	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD6012	Approved
0.5702	Remote Similarity	NPD6014	Approved
0.5692	Remote Similarity	NPD8299	Approved
0.5692	Remote Similarity	NPD8342	Approved
0.5692	Remote Similarity	NPD8341	Approved
0.5692	Remote Similarity	NPD8340	Approved
0.5691	Remote Similarity	NPD6882	Approved
0.5676	Remote Similarity	NPD5692	Phase 3
0.5667	Remote Similarity	NPD5701	Approved
0.566	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6883	Approved
0.5656	Remote Similarity	NPD7102	Approved
0.5656	Remote Similarity	NPD7290	Approved
0.5625	Remote Similarity	NPD6050	Approved
0.5625	Remote Similarity	NPD5694	Approved
0.562	Remote Similarity	NPD6011	Approved
0.562	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.562	Remote Similarity	NPD7320	Approved
0.5619	Remote Similarity	NPD5368	Approved
0.5614	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.561	Remote Similarity	NPD8130	Phase 1
0.561	Remote Similarity	NPD6869	Approved
0.561	Remote Similarity	NPD6847	Approved
0.561	Remote Similarity	NPD6617	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