NPASS Compound

Structure

NPC181994 OpenBabel07101718182D 30 33 0 0 1 0 0 0 0 0999 V2000 -4.4152 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2812 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1472 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.6910 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 7 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 20 1 0 0 0 0 7 10 2 0 0 0 0 8 15 1 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 20 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 1 0 0 0 13 23 2 0 0 0 0 13 27 1 0 0 0 0 14 22 1 0 0 0 0 15 27 1 1 0 0 0 16 21 1 6 0 0 0 16 29 1 0 0 0 0 17 24 2 0 0 0 0 17 28 1 0 0 0 0 18 25 2 0 0 0 0 18 30 1 0 0 0 0 19 21 1 1 0 0 0 19 22 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 1 0 0 0 21 29 1 1 0 0 0 22 26 1 6 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	411.982
LogP:	3.124
LogD:	2.437
LogS:	-4.599
# Rotatable Bonds:	5
TPSA:	111.66
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	5.637
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.191
MDCK Permeability:	5.4709933465346694e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.752
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.503
Plasma Protein Binding (PPB):	58.74921417236328%
Volume Distribution (VD):	1.671
Pgp-substrate:	19.121976852416992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.275
CYP2C19-inhibitor:	0.143
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.529
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.635
CYP3A4-substrate:	0.686

ADMET: Excretion

Clearance (CL):	5.374
Half-life (T1/2):	0.437

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.918
Drug-inuced Liver Injury (DILI):	0.9
AMES Toxicity:	0.096
Rat Oral Acute Toxicity:	0.244
Maximum Recommended Daily Dose:	0.635
Skin Sensitization:	0.485
Carcinogencity:	0.235
Eye Corrosion:	0.012
Eye Irritation:	0.066
Respiratory Toxicity:	0.426

Download Data

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

Natural Product: NPC181994

Natural Product ID:	NPC181994
*Common Name:**	GNNUZBCUYRDLNT-ROSJVHPRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GNNUZBCUYRDLNT-ROSJVHPRSA-N
Standard InCHI:	InChI=1S/C22H28O8/c1-7-10(2)17(24)28-19-21-16(29-21)8-15(27-13(5)23)12(4)20(21,6)9-14-11(3)18(25)30-22(14,19)26/h7,12,15-16,19,26H,8-9H2,1-6H3/b10-7-/t12-,15-,16+,19+,20+,21-,22-/m0/s1
SMILES:	C/C=C(/C)C(=O)O[C@@H]1[C@@]23[C@@H](C[C@@H]([C@H](C)[C@@]2(C)CC2=C(C)C(=O)O[C@]12O)OC(=O)C)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467819
PubChem CID:	10862710
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
NPO8462	Ligulariopsis shichuana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027747]
NPO8462	Ligulariopsis shichuana	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	13.0	mm	PMID[526041]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	13.0	mm	PMID[526041]

☑ 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 NPC181994 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	226
0.1-0.2	1504
0.2-0.3	4289
0.3-0.4	6948
0.4-0.5	14069
0.5-0.6	8219
0.6-0.7	5521
0.7-0.8	1759
0.8-0.85	134
0.85-0.9	22
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9293	High Similarity	NPC16601
0.902	High Similarity	NPC471938
0.8942	High Similarity	NPC471205
0.8942	High Similarity	NPC122816
0.8932	High Similarity	NPC471937
0.8922	High Similarity	NPC472552
0.8922	High Similarity	NPC109195
0.8922	High Similarity	NPC475038
0.8922	High Similarity	NPC471914
0.8846	High Similarity	NPC51719
0.8824	High Similarity	NPC472554
0.8725	High Similarity	NPC38855
0.87	High Similarity	NPC471915
0.8692	High Similarity	NPC177047
0.8679	High Similarity	NPC38948
0.8654	High Similarity	NPC474822
0.8614	High Similarity	NPC209297
0.8614	High Similarity	NPC475380
0.8614	High Similarity	NPC165632
0.8598	High Similarity	NPC206618
0.8529	High Similarity	NPC205143
0.8529	High Similarity	NPC475446
0.8529	High Similarity	NPC311241
0.8529	High Similarity	NPC199099
0.8505	High Similarity	NPC50124
0.85	High Similarity	NPC110022
0.85	High Similarity	NPC472640
0.85	High Similarity	NPC472641
0.8476	Intermediate Similarity	NPC23584
0.8476	Intermediate Similarity	NPC281378
0.8476	Intermediate Similarity	NPC165608
0.8468	Intermediate Similarity	NPC471816
0.8462	Intermediate Similarity	NPC11974
0.8447	Intermediate Similarity	NPC72647
0.8447	Intermediate Similarity	NPC107806
0.8431	Intermediate Similarity	NPC472995
0.8426	Intermediate Similarity	NPC475586
0.8416	Intermediate Similarity	NPC140277
0.8411	Intermediate Similarity	NPC187435
0.8411	Intermediate Similarity	NPC67321
0.84	Intermediate Similarity	NPC78594
0.8396	Intermediate Similarity	NPC194941
0.8381	Intermediate Similarity	NPC121423
0.8381	Intermediate Similarity	NPC11956
0.8381	Intermediate Similarity	NPC472815
0.8365	Intermediate Similarity	NPC324841
0.835	Intermediate Similarity	NPC100912
0.835	Intermediate Similarity	NPC472998
0.8333	Intermediate Similarity	NPC111273
0.8333	Intermediate Similarity	NPC469583
0.8333	Intermediate Similarity	NPC276110
0.8318	Intermediate Similarity	NPC477090
0.8318	Intermediate Similarity	NPC471206
0.8317	Intermediate Similarity	NPC53555
0.8317	Intermediate Similarity	NPC7349
0.8302	Intermediate Similarity	NPC120009
0.8302	Intermediate Similarity	NPC474575
0.83	Intermediate Similarity	NPC472642
0.8288	Intermediate Similarity	NPC264153
0.8288	Intermediate Similarity	NPC477126
0.8286	Intermediate Similarity	NPC198992
0.8283	Intermediate Similarity	NPC242448
0.8257	Intermediate Similarity	NPC299590
0.8257	Intermediate Similarity	NPC257853
0.8252	Intermediate Similarity	NPC472996
0.8252	Intermediate Similarity	NPC472997
0.8252	Intermediate Similarity	NPC194132
0.8252	Intermediate Similarity	NPC473153
0.8235	Intermediate Similarity	NPC161998
0.8235	Intermediate Similarity	NPC105490
0.823	Intermediate Similarity	NPC13713
0.823	Intermediate Similarity	NPC473968
0.8208	Intermediate Similarity	NPC470972
0.8198	Intermediate Similarity	NPC317460
0.8198	Intermediate Similarity	NPC42658
0.8198	Intermediate Similarity	NPC321272
0.8198	Intermediate Similarity	NPC328074
0.8198	Intermediate Similarity	NPC470025
0.819	Intermediate Similarity	NPC79303
0.819	Intermediate Similarity	NPC271295
0.8173	Intermediate Similarity	NPC120446
0.8165	Intermediate Similarity	NPC306265
0.8165	Intermediate Similarity	NPC475263
0.8155	Intermediate Similarity	NPC472441
0.8148	Intermediate Similarity	NPC239961
0.8148	Intermediate Similarity	NPC470980
0.8142	Intermediate Similarity	NPC470075
0.8137	Intermediate Similarity	NPC472812
0.8131	Intermediate Similarity	NPC61442
0.8131	Intermediate Similarity	NPC45897
0.8125	Intermediate Similarity	NPC470027
0.8108	Intermediate Similarity	NPC474846
0.8108	Intermediate Similarity	NPC469655
0.8108	Intermediate Similarity	NPC17791
0.8108	Intermediate Similarity	NPC469656
0.8108	Intermediate Similarity	NPC470076
0.8095	Intermediate Similarity	NPC278386
0.8095	Intermediate Similarity	NPC124512
0.8095	Intermediate Similarity	NPC159763
0.8091	Intermediate Similarity	NPC322912
0.8083	Intermediate Similarity	NPC104382
0.8077	Intermediate Similarity	NPC134072
0.8077	Intermediate Similarity	NPC234993
0.8073	Intermediate Similarity	NPC319438
0.8073	Intermediate Similarity	NPC473586
0.8058	Intermediate Similarity	NPC57117
0.8056	Intermediate Similarity	NPC283850
0.8056	Intermediate Similarity	NPC161775
0.8056	Intermediate Similarity	NPC473543
0.8053	Intermediate Similarity	NPC216665
0.8053	Intermediate Similarity	NPC43213
0.8039	Intermediate Similarity	NPC472811
0.8037	Intermediate Similarity	NPC214277
0.8037	Intermediate Similarity	NPC162973
0.8037	Intermediate Similarity	NPC58329
0.8037	Intermediate Similarity	NPC476081
0.802	Intermediate Similarity	NPC82876
0.8019	Intermediate Similarity	NPC272223
0.8019	Intermediate Similarity	NPC188968
0.8018	Intermediate Similarity	NPC472215
0.8018	Intermediate Similarity	NPC253906
0.8018	Intermediate Similarity	NPC472214
0.8018	Intermediate Similarity	NPC316708
0.8	Intermediate Similarity	NPC392
0.8	Intermediate Similarity	NPC470850
0.8	Intermediate Similarity	NPC177524
0.8	Intermediate Similarity	NPC88701
0.8	Intermediate Similarity	NPC83287
0.8	Intermediate Similarity	NPC94377
0.8	Intermediate Similarity	NPC219900
0.8	Intermediate Similarity	NPC48548
0.8	Intermediate Similarity	NPC217921
0.8	Intermediate Similarity	NPC473891
0.8	Intermediate Similarity	NPC135015
0.8	Intermediate Similarity	NPC128795
0.8	Intermediate Similarity	NPC473244
0.7982	Intermediate Similarity	NPC88349
0.7982	Intermediate Similarity	NPC82251
0.7982	Intermediate Similarity	NPC218158
0.7982	Intermediate Similarity	NPC81630
0.7982	Intermediate Similarity	NPC234858
0.7982	Intermediate Similarity	NPC154363
0.7982	Intermediate Similarity	NPC85670
0.7982	Intermediate Similarity	NPC471127
0.798	Intermediate Similarity	NPC253604
0.7963	Intermediate Similarity	NPC474124
0.7963	Intermediate Similarity	NPC473523
0.7963	Intermediate Similarity	NPC99510
0.7961	Intermediate Similarity	NPC162615
0.7961	Intermediate Similarity	NPC205034
0.7961	Intermediate Similarity	NPC152778
0.7946	Intermediate Similarity	NPC470026
0.7944	Intermediate Similarity	NPC475617
0.7941	Intermediate Similarity	NPC78973
0.7934	Intermediate Similarity	NPC175186
0.7931	Intermediate Similarity	NPC472667
0.7931	Intermediate Similarity	NPC476529
0.7931	Intermediate Similarity	NPC153085
0.7931	Intermediate Similarity	NPC268326
0.7931	Intermediate Similarity	NPC470914
0.7931	Intermediate Similarity	NPC475775
0.7928	Intermediate Similarity	NPC40728
0.7928	Intermediate Similarity	NPC316974
0.7925	Intermediate Similarity	NPC325229
0.7925	Intermediate Similarity	NPC275086
0.7925	Intermediate Similarity	NPC474440
0.7925	Intermediate Similarity	NPC222303
0.7925	Intermediate Similarity	NPC278673
0.7925	Intermediate Similarity	NPC312325
0.7925	Intermediate Similarity	NPC475068
0.7921	Intermediate Similarity	NPC93411
0.7913	Intermediate Similarity	NPC142066
0.7913	Intermediate Similarity	NPC474418
0.7913	Intermediate Similarity	NPC243196
0.7913	Intermediate Similarity	NPC469684
0.7913	Intermediate Similarity	NPC77319
0.7913	Intermediate Similarity	NPC27507
0.7913	Intermediate Similarity	NPC152615
0.7913	Intermediate Similarity	NPC10721
0.7913	Intermediate Similarity	NPC58662
0.7913	Intermediate Similarity	NPC84987
0.7913	Intermediate Similarity	NPC244402
0.7913	Intermediate Similarity	NPC157376
0.7913	Intermediate Similarity	NPC50305
0.7913	Intermediate Similarity	NPC87250
0.7913	Intermediate Similarity	NPC290693
0.7913	Intermediate Similarity	NPC471353
0.7913	Intermediate Similarity	NPC99728
0.7913	Intermediate Similarity	NPC34390
0.7913	Intermediate Similarity	NPC474483
0.7913	Intermediate Similarity	NPC158344
0.7913	Intermediate Similarity	NPC471355
0.7913	Intermediate Similarity	NPC309034
0.7913	Intermediate Similarity	NPC471354
0.7913	Intermediate Similarity	NPC203862
0.7913	Intermediate Similarity	NPC471351
0.7913	Intermediate Similarity	NPC473852
0.7913	Intermediate Similarity	NPC196429
0.7909	Intermediate Similarity	NPC216636
0.7909	Intermediate Similarity	NPC125423

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 NPC181994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	1689
0.2-0.3	3756
0.3-0.4	2320
0.4-0.5	785
0.5-0.6	290
0.6-0.7	95
0.7-0.8	24
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD5344	Discontinued
0.8257	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD6648	Approved
0.8182	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD4225	Approved
0.8087	Intermediate Similarity	NPD7516	Approved
0.8	Intermediate Similarity	NPD6686	Approved
0.8	Intermediate Similarity	NPD7327	Approved
0.8	Intermediate Similarity	NPD7328	Approved
0.7909	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8296	Approved
0.7647	Intermediate Similarity	NPD8380	Approved
0.7647	Intermediate Similarity	NPD8335	Approved
0.7647	Intermediate Similarity	NPD8379	Approved
0.7647	Intermediate Similarity	NPD8378	Approved
0.7647	Intermediate Similarity	NPD8033	Approved
0.7563	Intermediate Similarity	NPD8377	Approved
0.7563	Intermediate Similarity	NPD8294	Approved
0.7523	Intermediate Similarity	NPD7640	Approved
0.7523	Intermediate Similarity	NPD7639	Approved
0.7458	Intermediate Similarity	NPD7115	Discovery
0.7431	Intermediate Similarity	NPD7638	Approved
0.7429	Intermediate Similarity	NPD7838	Discovery
0.7398	Intermediate Similarity	NPD7507	Approved
0.736	Intermediate Similarity	NPD7319	Approved
0.7355	Intermediate Similarity	NPD7503	Approved
0.7264	Intermediate Similarity	NPD6698	Approved
0.7264	Intermediate Similarity	NPD46	Approved
0.7117	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3168	Discontinued
0.699	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7524	Approved
0.6949	Remote Similarity	NPD6371	Approved
0.693	Remote Similarity	NPD7632	Discontinued
0.6923	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6319	Approved
0.6777	Remote Similarity	NPD8133	Approved
0.6777	Remote Similarity	NPD4632	Approved
0.6752	Remote Similarity	NPD6008	Approved
0.6748	Remote Similarity	NPD6009	Approved
0.6727	Remote Similarity	NPD7637	Suspended
0.6723	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6412	Phase 2
0.6695	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8297	Approved
0.6694	Remote Similarity	NPD6882	Approved
0.6641	Remote Similarity	NPD7492	Approved
0.6612	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6695	Phase 3
0.6589	Remote Similarity	NPD6616	Approved
0.6587	Remote Similarity	NPD6054	Approved
0.6562	Remote Similarity	NPD8328	Phase 3
0.6555	Remote Similarity	NPD5697	Approved
0.6552	Remote Similarity	NPD4159	Approved
0.6538	Remote Similarity	NPD7078	Approved
0.6535	Remote Similarity	NPD8517	Approved
0.6535	Remote Similarity	NPD6015	Approved
0.6535	Remote Similarity	NPD8515	Approved
0.6535	Remote Similarity	NPD8513	Phase 3
0.6535	Remote Similarity	NPD8516	Approved
0.6535	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD6881	Approved
0.65	Remote Similarity	NPD6899	Approved
0.6496	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7736	Approved
0.6484	Remote Similarity	NPD5988	Approved
0.6484	Remote Similarity	NPD6370	Approved
0.6475	Remote Similarity	NPD6650	Approved
0.6475	Remote Similarity	NPD6649	Approved
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6471	Remote Similarity	NPD6402	Approved
0.6471	Remote Similarity	NPD5357	Phase 1
0.646	Remote Similarity	NPD7748	Approved
0.6457	Remote Similarity	NPD6059	Approved
0.6446	Remote Similarity	NPD6014	Approved
0.6446	Remote Similarity	NPD6013	Approved
0.6446	Remote Similarity	NPD6372	Approved
0.6446	Remote Similarity	NPD6373	Approved
0.6446	Remote Similarity	NPD6012	Approved
0.6435	Remote Similarity	NPD7902	Approved
0.6434	Remote Similarity	NPD7604	Phase 2
0.6417	Remote Similarity	NPD5701	Approved
0.6412	Remote Similarity	NPD8293	Discontinued
0.6406	Remote Similarity	NPD6921	Approved
0.6406	Remote Similarity	NPD5983	Phase 2
0.6393	Remote Similarity	NPD7102	Approved
0.6393	Remote Similarity	NPD7290	Approved
0.6393	Remote Similarity	NPD6883	Approved
0.6372	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD7320	Approved
0.6364	Remote Similarity	NPD7750	Discontinued
0.6364	Remote Similarity	NPD6011	Approved
0.6356	Remote Similarity	NPD5211	Phase 2
0.6349	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6847	Approved
0.6341	Remote Similarity	NPD6869	Approved
0.6341	Remote Similarity	NPD6617	Approved
0.6341	Remote Similarity	NPD8130	Phase 1
0.633	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.633	Remote Similarity	NPD1694	Approved
0.6321	Remote Similarity	NPD6930	Phase 2
0.6321	Remote Similarity	NPD6931	Approved
0.6294	Remote Similarity	NPD7625	Phase 1
0.629	Remote Similarity	NPD6053	Discontinued
0.6288	Remote Similarity	NPD8074	Phase 3
0.6283	Remote Similarity	NPD7515	Phase 2
0.6283	Remote Similarity	NPD7983	Approved
0.626	Remote Similarity	NPD4634	Approved
0.625	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD1695	Approved
0.625	Remote Similarity	NPD6051	Approved
0.6228	Remote Similarity	NPD5779	Approved
0.6228	Remote Similarity	NPD5778	Approved
0.6226	Remote Similarity	NPD6929	Approved
0.6212	Remote Similarity	NPD6336	Discontinued
0.6186	Remote Similarity	NPD5286	Approved
0.6186	Remote Similarity	NPD5285	Approved
0.6186	Remote Similarity	NPD4696	Approved
0.6174	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7900	Approved
0.6168	Remote Similarity	NPD7514	Phase 3
0.6168	Remote Similarity	NPD7525	Registered
0.6168	Remote Similarity	NPD7332	Phase 2
0.6154	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD6083	Phase 2
0.6154	Remote Similarity	NPD6084	Phase 2
0.6142	Remote Similarity	NPD6274	Approved
0.614	Remote Similarity	NPD7087	Discontinued
0.6138	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD3618	Phase 1
0.6121	Remote Similarity	NPD5695	Phase 3
0.6121	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6902	Approved
0.6103	Remote Similarity	NPD7260	Phase 2
0.6102	Remote Similarity	NPD5696	Approved
0.6087	Remote Similarity	NPD4202	Approved
0.6083	Remote Similarity	NPD5225	Approved
0.6083	Remote Similarity	NPD5226	Approved
0.6083	Remote Similarity	NPD5224	Approved
0.6083	Remote Similarity	NPD4633	Approved
0.608	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD3573	Approved
0.6066	Remote Similarity	NPD6640	Phase 3
0.6061	Remote Similarity	NPD7830	Approved
0.6061	Remote Similarity	NPD7829	Approved
0.6061	Remote Similarity	NPD6067	Discontinued
0.6061	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5785	Approved
0.605	Remote Similarity	NPD4700	Approved
0.6038	Remote Similarity	NPD6925	Approved
0.6038	Remote Similarity	NPD5776	Phase 2
0.6036	Remote Similarity	NPD6893	Approved
0.6034	Remote Similarity	NPD5282	Discontinued
0.6033	Remote Similarity	NPD5175	Approved
0.6033	Remote Similarity	NPD5174	Approved
0.6	Remote Similarity	NPD8034	Phase 2
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD6033	Approved
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD8035	Phase 2
0.6	Remote Similarity	NPD5693	Phase 1
0.5983	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5330	Approved
0.5982	Remote Similarity	NPD7521	Approved
0.5982	Remote Similarity	NPD6684	Approved
0.5982	Remote Similarity	NPD6409	Approved
0.5982	Remote Similarity	NPD7146	Approved
0.5982	Remote Similarity	NPD4249	Approved
0.5982	Remote Similarity	NPD7334	Approved
0.5981	Remote Similarity	NPD7145	Approved
0.5969	Remote Similarity	NPD6317	Approved
0.5968	Remote Similarity	NPD4730	Approved
0.5968	Remote Similarity	NPD4729	Approved
0.5965	Remote Similarity	NPD5328	Approved
0.5963	Remote Similarity	NPD6898	Phase 1
0.5943	Remote Similarity	NPD6933	Approved
0.594	Remote Similarity	NPD7642	Approved
0.5935	Remote Similarity	NPD4767	Approved
0.5935	Remote Similarity	NPD4768	Approved
0.5932	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5222	Approved
0.5932	Remote Similarity	NPD5221	Approved
0.5929	Remote Similarity	NPD4250	Approved
0.5929	Remote Similarity	NPD4251	Approved
0.5926	Remote Similarity	NPD7645	Phase 2
0.5923	Remote Similarity	NPD6335	Approved
0.5923	Remote Similarity	NPD6313	Approved
0.5923	Remote Similarity	NPD6314	Approved
0.5909	Remote Similarity	NPD3667	Approved
0.5909	Remote Similarity	NPD5209	Approved
0.5893	Remote Similarity	NPD1696	Phase 3
0.5888	Remote Similarity	NPD6932	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