NPASS Compound

Structure

NPC471914 OpenBabel07101718182D 26 29 0 0 1 0 0 0 0 0999 V2000 1.7565 4.6487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4308 2.7154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5974 3.4028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5937 2.2320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2680 1.2654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2680 0.2987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0822 4.6487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7565 -0.1846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9194 4.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4308 1.7487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.5641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4308 -0.1846 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9194 1.2654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7565 1.7487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9194 3.1987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5682 0.7820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5937 1.2654 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5937 0.2987 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9194 0.2987 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7550 4.1654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0822 2.7154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5349 0.7820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3125 -0.5844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7565 2.7154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5937 -0.6680 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 9 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 20 1 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 1 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 18 1 1 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 17 1 1 0 0 0 14 24 1 0 0 0 0 15 21 2 0 0 0 0 15 24 1 0 0 0 0 16 22 2 0 0 0 0 16 26 1 0 0 0 0 17 18 1 1 0 0 0 18 8 1 6 0 0 0 18 25 1 0 0 0 0 19 23 1 1 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.15
Volume:	353.94
LogP:	1.648
LogD:	1.582
LogS:	-3.883
# Rotatable Bonds:	4
TPSA:	105.59
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	5.848
Fsp3:	0.684
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:	-5.277
MDCK Permeability:	6.702631071675569e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.141
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.098
30% Bioavailability (F30%):	0.801

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.728
Plasma Protein Binding (PPB):	22.409345626831055%
Volume Distribution (VD):	0.52
Pgp-substrate:	71.20079040527344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.886
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.552
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.666
CYP3A4-substrate:	0.492

ADMET: Excretion

Clearance (CL):	7.582
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.521
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.667
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.92
Carcinogencity:	0.541
Eye Corrosion:	0.975
Eye Irritation:	0.591
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC471914

Natural Product ID:	NPC471914
*Common Name:**	XOQQMHWZRICZPV-XBCTYBCVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XOQQMHWZRICZPV-XBCTYBCVSA-N
Standard InCHI:	InChI=1S/C19H24O7/c1-9(7-20)15(21)24-14-13-11(3)16(22)26-19(13,23)8-18-12(25-18)6-5-10(2)17(14,18)4/h10,12,14,20,23H,1,5-8H2,2-4H3/t10-,12+,14+,17-,18+,19-/m0/s1
SMILES:	CC1CCC2C3(C1(C(C4=C(C(=O)OC4(C3)O)C)OC(=O)C(=C)CO)C)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3297828
PubChem CID:	90682796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24913558]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26428	Ligularia sagitta	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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	7.25	ug.mL-1	PMID[536048]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	7.25	ug.mL-1	PMID[536048]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	15.5	ug.mL-1	PMID[536048]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	7.25	ug.mL-1	PMID[536048]
NPT1286	Organism	Pectobacterium carotovorum	Pectobacterium carotovorum	MIC	=	7.25	ug.mL-1	PMID[536048]

☑ 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 NPC471914 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	1518
0.2-0.3	4520
0.3-0.4	7601
0.4-0.5	14044
0.5-0.6	7291
0.6-0.7	5798
0.7-0.8	1599
0.8-0.85	82
0.85-0.9	21
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC471938
0.9792	High Similarity	NPC471937
0.9375	High Similarity	NPC16601
0.9362	High Similarity	NPC111273
0.9362	High Similarity	NPC471915
0.9149	High Similarity	NPC472640
0.9149	High Similarity	NPC472641
0.899	High Similarity	NPC109195
0.899	High Similarity	NPC475038
0.8936	High Similarity	NPC472642
0.8922	High Similarity	NPC181994
0.8866	High Similarity	NPC165632
0.8842	High Similarity	NPC78594
0.86	High Similarity	NPC324841
0.8586	High Similarity	NPC287668
0.8571	High Similarity	NPC472441
0.8571	High Similarity	NPC276110
0.8557	High Similarity	NPC110022
0.8526	High Similarity	NPC242448
0.8485	Intermediate Similarity	NPC134072
0.8485	Intermediate Similarity	NPC234993
0.8485	Intermediate Similarity	NPC242848
0.8485	Intermediate Similarity	NPC209297
0.8485	Intermediate Similarity	NPC475380
0.8469	Intermediate Similarity	NPC105490
0.8462	Intermediate Similarity	NPC471205
0.8416	Intermediate Similarity	NPC38855
0.8404	Intermediate Similarity	NPC253604
0.84	Intermediate Similarity	NPC311241
0.84	Intermediate Similarity	NPC475446
0.8381	Intermediate Similarity	NPC38948
0.8367	Intermediate Similarity	NPC7349
0.8367	Intermediate Similarity	NPC472812
0.8365	Intermediate Similarity	NPC81630
0.835	Intermediate Similarity	NPC474822
0.835	Intermediate Similarity	NPC45897
0.835	Intermediate Similarity	NPC120009
0.8317	Intermediate Similarity	NPC107806
0.8317	Intermediate Similarity	NPC72647
0.8317	Intermediate Similarity	NPC275086
0.8317	Intermediate Similarity	NPC325229
0.8317	Intermediate Similarity	NPC278673
0.8316	Intermediate Similarity	NPC131813
0.8302	Intermediate Similarity	NPC206618
0.8298	Intermediate Similarity	NPC32223
0.8286	Intermediate Similarity	NPC475074
0.8283	Intermediate Similarity	NPC161998
0.8283	Intermediate Similarity	NPC140277
0.8283	Intermediate Similarity	NPC57117
0.8265	Intermediate Similarity	NPC472811
0.8252	Intermediate Similarity	NPC121423
0.8252	Intermediate Similarity	NPC472815
0.8252	Intermediate Similarity	NPC476081
0.8241	Intermediate Similarity	NPC42658
0.8218	Intermediate Similarity	NPC51499
0.8218	Intermediate Similarity	NPC205143
0.8218	Intermediate Similarity	NPC475709
0.8218	Intermediate Similarity	NPC100912
0.819	Intermediate Similarity	NPC51719
0.819	Intermediate Similarity	NPC477090
0.819	Intermediate Similarity	NPC218158
0.8182	Intermediate Similarity	NPC152778
0.8182	Intermediate Similarity	NPC139692
0.8182	Intermediate Similarity	NPC162615
0.8182	Intermediate Similarity	NPC205034
0.8165	Intermediate Similarity	NPC264153
0.8163	Intermediate Similarity	NPC78973
0.8155	Intermediate Similarity	NPC11974
0.8155	Intermediate Similarity	NPC471412
0.8144	Intermediate Similarity	NPC472809
0.8144	Intermediate Similarity	NPC93411
0.8144	Intermediate Similarity	NPC472810
0.8137	Intermediate Similarity	NPC159763
0.8137	Intermediate Similarity	NPC124512
0.8137	Intermediate Similarity	NPC278386
0.8137	Intermediate Similarity	NPC474440
0.8131	Intermediate Similarity	NPC322912
0.8131	Intermediate Similarity	NPC31522
0.8119	Intermediate Similarity	NPC194132
0.8119	Intermediate Similarity	NPC202833
0.8113	Intermediate Similarity	NPC67321
0.8113	Intermediate Similarity	NPC122816
0.8113	Intermediate Similarity	NPC187435
0.8095	Intermediate Similarity	NPC161775
0.8081	Intermediate Similarity	NPC473675
0.8081	Intermediate Similarity	NPC472814
0.8081	Intermediate Similarity	NPC177037
0.8081	Intermediate Similarity	NPC329842
0.8081	Intermediate Similarity	NPC72845
0.8077	Intermediate Similarity	NPC472552
0.8077	Intermediate Similarity	NPC162973
0.8077	Intermediate Similarity	NPC58329
0.8058	Intermediate Similarity	NPC47024
0.8058	Intermediate Similarity	NPC471413
0.8058	Intermediate Similarity	NPC476767
0.8056	Intermediate Similarity	NPC472666
0.8056	Intermediate Similarity	NPC177047
0.8039	Intermediate Similarity	NPC73911
0.8039	Intermediate Similarity	NPC199099
0.8037	Intermediate Similarity	NPC300614
0.8037	Intermediate Similarity	NPC476765
0.8037	Intermediate Similarity	NPC102843
0.8037	Intermediate Similarity	NPC90946
0.8019	Intermediate Similarity	NPC34768
0.8018	Intermediate Similarity	NPC470075
0.8018	Intermediate Similarity	NPC471816
0.8	Intermediate Similarity	NPC10232
0.8	Intermediate Similarity	NPC189588
0.8	Intermediate Similarity	NPC159533
0.8	Intermediate Similarity	NPC187302
0.8	Intermediate Similarity	NPC53555
0.8	Intermediate Similarity	NPC97487
0.8	Intermediate Similarity	NPC196471
0.8	Intermediate Similarity	NPC165608
0.8	Intermediate Similarity	NPC120321
0.8	Intermediate Similarity	NPC311070
0.8	Intermediate Similarity	NPC281378
0.7981	Intermediate Similarity	NPC198992
0.7981	Intermediate Similarity	NPC472554
0.798	Intermediate Similarity	NPC182136
0.798	Intermediate Similarity	NPC209816
0.798	Intermediate Similarity	NPC310479
0.7963	Intermediate Similarity	NPC299590
0.7963	Intermediate Similarity	NPC475030
0.7963	Intermediate Similarity	NPC474243
0.7961	Intermediate Similarity	NPC218107
0.7961	Intermediate Similarity	NPC473154
0.7961	Intermediate Similarity	NPC316598
0.7959	Intermediate Similarity	NPC291665
0.7946	Intermediate Similarity	NPC474483
0.7946	Intermediate Similarity	NPC469684
0.7944	Intermediate Similarity	NPC319438
0.7941	Intermediate Similarity	NPC473153
0.7941	Intermediate Similarity	NPC16967
0.7921	Intermediate Similarity	NPC470255
0.7921	Intermediate Similarity	NPC191521
0.7917	Intermediate Similarity	NPC102048
0.7909	Intermediate Similarity	NPC90952
0.79	Intermediate Similarity	NPC124374
0.79	Intermediate Similarity	NPC249034
0.79	Intermediate Similarity	NPC158061
0.789	Intermediate Similarity	NPC235014
0.789	Intermediate Similarity	NPC476766
0.7885	Intermediate Similarity	NPC474012
0.7885	Intermediate Similarity	NPC477716
0.7885	Intermediate Similarity	NPC476299
0.7885	Intermediate Similarity	NPC477721
0.7885	Intermediate Similarity	NPC251680
0.7881	Intermediate Similarity	NPC476859
0.7879	Intermediate Similarity	NPC314727
0.7879	Intermediate Similarity	NPC474396
0.7879	Intermediate Similarity	NPC470734
0.7879	Intermediate Similarity	NPC50488
0.7872	Intermediate Similarity	NPC10636
0.787	Intermediate Similarity	NPC322903
0.787	Intermediate Similarity	NPC325054
0.787	Intermediate Similarity	NPC306265
0.787	Intermediate Similarity	NPC470024
0.7864	Intermediate Similarity	NPC477718
0.7864	Intermediate Similarity	NPC473244
0.7864	Intermediate Similarity	NPC136781
0.7864	Intermediate Similarity	NPC477719
0.7864	Intermediate Similarity	NPC473963
0.7857	Intermediate Similarity	NPC166857
0.785	Intermediate Similarity	NPC471206
0.785	Intermediate Similarity	NPC119855
0.785	Intermediate Similarity	NPC220217
0.785	Intermediate Similarity	NPC472818
0.785	Intermediate Similarity	NPC85670
0.785	Intermediate Similarity	NPC239961
0.7843	Intermediate Similarity	NPC259042
0.7843	Intermediate Similarity	NPC476519
0.7843	Intermediate Similarity	NPC157686
0.7843	Intermediate Similarity	NPC37603
0.7843	Intermediate Similarity	NPC471786
0.7838	Intermediate Similarity	NPC171126
0.7838	Intermediate Similarity	NPC477126
0.783	Intermediate Similarity	NPC471208
0.783	Intermediate Similarity	NPC160583
0.783	Intermediate Similarity	NPC472821
0.783	Intermediate Similarity	NPC291154
0.783	Intermediate Similarity	NPC23584
0.7826	Intermediate Similarity	NPC67569
0.7822	Intermediate Similarity	NPC99653
0.7822	Intermediate Similarity	NPC115021
0.7818	Intermediate Similarity	NPC474846
0.7818	Intermediate Similarity	NPC469655
0.7818	Intermediate Similarity	NPC469656
0.7818	Intermediate Similarity	NPC470076
0.7812	Intermediate Similarity	NPC79945
0.781	Intermediate Similarity	NPC247701
0.781	Intermediate Similarity	NPC477717
0.781	Intermediate Similarity	NPC475958
0.781	Intermediate Similarity	NPC25177
0.781	Intermediate Similarity	NPC295110
0.781	Intermediate Similarity	NPC268829
0.781	Intermediate Similarity	NPC222875
0.78	Intermediate Similarity	NPC220216
0.78	Intermediate Similarity	NPC51486
0.78	Intermediate Similarity	NPC280149

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 NPC471914 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1767
0.2-0.3	3840
0.3-0.4	2257
0.4-0.5	698
0.5-0.6	251
0.6-0.7	139
0.7-0.8	19
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8137	Intermediate Similarity	NPD4225	Approved
0.7963	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7640	Approved
0.7885	Intermediate Similarity	NPD7639	Approved
0.781	Intermediate Similarity	NPD5344	Discontinued
0.7788	Intermediate Similarity	NPD7638	Approved
0.7727	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6686	Approved
0.7565	Intermediate Similarity	NPD7327	Approved
0.7565	Intermediate Similarity	NPD7328	Approved
0.7547	Intermediate Similarity	NPD6648	Approved
0.75	Intermediate Similarity	NPD7516	Approved
0.7478	Intermediate Similarity	NPD7115	Discovery
0.7455	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7632	Discontinued
0.7377	Intermediate Similarity	NPD7319	Approved
0.7373	Intermediate Similarity	NPD8296	Approved
0.7373	Intermediate Similarity	NPD8380	Approved
0.7373	Intermediate Similarity	NPD8379	Approved
0.7373	Intermediate Similarity	NPD8335	Approved
0.7373	Intermediate Similarity	NPD8378	Approved
0.7288	Intermediate Similarity	NPD8294	Approved
0.7288	Intermediate Similarity	NPD8377	Approved
0.7227	Intermediate Similarity	NPD8033	Approved
0.7212	Intermediate Similarity	NPD7637	Suspended
0.7172	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7507	Approved
0.7083	Intermediate Similarity	NPD7503	Approved
0.703	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6371	Approved
0.6952	Remote Similarity	NPD7838	Discovery
0.6911	Remote Similarity	NPD7492	Approved
0.6863	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6054	Approved
0.686	Remote Similarity	NPD6319	Approved
0.6855	Remote Similarity	NPD6616	Approved
0.6842	Remote Similarity	NPD5697	Approved
0.6838	Remote Similarity	NPD6882	Approved
0.6818	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6016	Approved
0.6803	Remote Similarity	NPD6015	Approved
0.68	Remote Similarity	NPD7078	Approved
0.6792	Remote Similarity	NPD6698	Approved
0.6792	Remote Similarity	NPD46	Approved
0.6783	Remote Similarity	NPD6881	Approved
0.6783	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6899	Approved
0.6765	Remote Similarity	NPD6695	Phase 3
0.6754	Remote Similarity	NPD6008	Approved
0.6754	Remote Similarity	NPD6675	Approved
0.6754	Remote Similarity	NPD7128	Approved
0.6754	Remote Similarity	NPD5739	Approved
0.6754	Remote Similarity	NPD6402	Approved
0.675	Remote Similarity	NPD6009	Approved
0.6748	Remote Similarity	NPD6370	Approved
0.6748	Remote Similarity	NPD5988	Approved
0.6746	Remote Similarity	NPD7736	Approved
0.6724	Remote Similarity	NPD6014	Approved
0.6724	Remote Similarity	NPD6012	Approved
0.6724	Remote Similarity	NPD6013	Approved
0.6721	Remote Similarity	NPD6059	Approved
0.6696	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6639	Remote Similarity	NPD4632	Approved
0.6639	Remote Similarity	NPD8133	Approved
0.6638	Remote Similarity	NPD6011	Approved
0.6638	Remote Similarity	NPD7320	Approved
0.6637	Remote Similarity	NPD5211	Phase 2
0.661	Remote Similarity	NPD8130	Phase 1
0.661	Remote Similarity	NPD6617	Approved
0.661	Remote Similarity	NPD6649	Approved
0.661	Remote Similarity	NPD6650	Approved
0.661	Remote Similarity	NPD6847	Approved
0.661	Remote Similarity	NPD6869	Approved
0.6606	Remote Similarity	NPD7748	Approved
0.6581	Remote Similarity	NPD6372	Approved
0.6581	Remote Similarity	NPD6373	Approved
0.6577	Remote Similarity	NPD7902	Approved
0.6574	Remote Similarity	NPD7515	Phase 2
0.656	Remote Similarity	NPD8328	Phase 3
0.6555	Remote Similarity	NPD8297	Approved
0.6552	Remote Similarity	NPD6412	Phase 2
0.6545	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4634	Approved
0.6522	Remote Similarity	NPD5141	Approved
0.6509	Remote Similarity	NPD7524	Approved
0.6509	Remote Similarity	NPD7750	Discontinued
0.6481	Remote Similarity	NPD5785	Approved
0.6481	Remote Similarity	NPD3168	Discontinued
0.6476	Remote Similarity	NPD1694	Approved
0.6471	Remote Similarity	NPD6930	Phase 2
0.6471	Remote Similarity	NPD6931	Approved
0.6471	Remote Similarity	NPD7525	Registered
0.646	Remote Similarity	NPD4696	Approved
0.646	Remote Similarity	NPD5285	Approved
0.646	Remote Similarity	NPD5286	Approved
0.6441	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD4755	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6417	Remote Similarity	NPD6053	Discontinued
0.6415	Remote Similarity	NPD3618	Phase 1
0.641	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5983	Phase 2
0.64	Remote Similarity	NPD8515	Approved
0.64	Remote Similarity	NPD8513	Phase 3
0.64	Remote Similarity	NPD8516	Approved
0.64	Remote Similarity	NPD8517	Approved
0.6393	Remote Similarity	NPD6274	Approved
0.6389	Remote Similarity	NPD6051	Approved
0.6373	Remote Similarity	NPD6929	Approved
0.6364	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD4202	Approved
0.6348	Remote Similarity	NPD5224	Approved
0.6348	Remote Similarity	NPD5225	Approved
0.6348	Remote Similarity	NPD5226	Approved
0.6348	Remote Similarity	NPD4633	Approved
0.6346	Remote Similarity	NPD5209	Approved
0.6341	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4700	Approved
0.6311	Remote Similarity	NPD7332	Phase 2
0.6311	Remote Similarity	NPD7514	Phase 3
0.6306	Remote Similarity	NPD5282	Discontinued
0.6306	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7900	Approved
0.6293	Remote Similarity	NPD5175	Approved
0.6293	Remote Similarity	NPD5174	Approved
0.6273	Remote Similarity	NPD8034	Phase 2
0.6273	Remote Similarity	NPD6411	Approved
0.6273	Remote Similarity	NPD8035	Phase 2
0.6273	Remote Similarity	NPD6079	Approved
0.6273	Remote Similarity	NPD7087	Discontinued
0.6262	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4159	Approved
0.6261	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD6902	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.624	Remote Similarity	NPD7100	Approved
0.624	Remote Similarity	NPD7101	Approved
0.6239	Remote Similarity	NPD1695	Approved
0.6239	Remote Similarity	NPD5328	Approved
0.6231	Remote Similarity	NPD6033	Approved
0.6228	Remote Similarity	NPD5696	Approved
0.6214	Remote Similarity	NPD7645	Phase 2
0.6211	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6317	Approved
0.6204	Remote Similarity	NPD3573	Approved
0.6204	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD6336	Discontinued
0.6198	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5221	Approved
0.6195	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5222	Approved
0.6176	Remote Similarity	NPD5776	Phase 2
0.6176	Remote Similarity	NPD6925	Approved
0.6168	Remote Similarity	NPD6893	Approved
0.6168	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6313	Approved
0.616	Remote Similarity	NPD6335	Approved
0.616	Remote Similarity	NPD6314	Approved
0.6154	Remote Similarity	NPD8074	Phase 3
0.6142	Remote Similarity	NPD6921	Approved
0.614	Remote Similarity	NPD5173	Approved
0.6126	Remote Similarity	NPD7983	Approved
0.6126	Remote Similarity	NPD5693	Phase 1
0.6117	Remote Similarity	NPD7145	Approved
0.6111	Remote Similarity	NPD6409	Approved
0.6111	Remote Similarity	NPD7146	Approved
0.6111	Remote Similarity	NPD7334	Approved
0.6111	Remote Similarity	NPD4249	Approved
0.6111	Remote Similarity	NPD5330	Approved
0.6111	Remote Similarity	NPD6684	Approved
0.6111	Remote Similarity	NPD7521	Approved
0.6106	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6898	Phase 1
0.6091	Remote Similarity	NPD6101	Approved
0.6091	Remote Similarity	NPD4753	Phase 2
0.6091	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD4729	Approved
0.6083	Remote Similarity	NPD5128	Approved
0.6083	Remote Similarity	NPD4730	Approved
0.6075	Remote Similarity	NPD3133	Approved
0.6075	Remote Similarity	NPD3665	Phase 1
0.6075	Remote Similarity	NPD3666	Approved
0.6055	Remote Similarity	NPD4251	Approved
0.6055	Remote Similarity	NPD4250	Approved
0.6053	Remote Similarity	NPD7839	Suspended
0.6053	Remote Similarity	NPD4697	Phase 3
0.605	Remote Similarity	NPD4768	Approved
0.605	Remote Similarity	NPD4767	Approved
0.6047	Remote Similarity	NPD6067	Discontinued
0.6038	Remote Similarity	NPD3667	Approved
0.6019	Remote Similarity	NPD6082	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