NPASS Compound

Structure

NPC474193 OpenBabel07101718222D 30 32 0 0 1 0 0 0 0 0999 V2000 -0.9511 -2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 -0.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3479 1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6764 -5.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8097 -5.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4086 -1.8749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8097 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -3.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8097 -2.6180 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 2.4899 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6709 -5.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8097 -4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0777 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 -3.4271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9437 -3.1180 0.0000 C 0 0 1 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 3.0777 -2.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2587 -5.9586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6758 -4.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0777 -4.2361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 -4.1180 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 13 2 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 23 1 0 0 0 0 16 25 2 0 0 0 0 16 28 1 0 0 0 0 17 26 2 0 0 0 0 17 29 1 0 0 0 0 18 20 1 0 0 0 0 19 24 1 1 0 0 0 20 11 1 6 0 0 0 20 30 1 0 0 0 0 21 24 1 6 0 0 0 21 28 1 0 0 0 0 22 24 1 6 0 0 0 22 29 1 0 0 0 0 23 27 2 0 0 0 0 23 30 1 0 0 0 0 24 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.22
Volume:	434.913
LogP:	4.544
LogD:	3.34
LogS:	-3.598
# Rotatable Bonds:	4
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.589
Synthetic Accessibility Score:	5.353
Fsp3:	0.583
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:	-4.872
MDCK Permeability:	3.1088206014828756e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.242
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.425
Plasma Protein Binding (PPB):	91.21302032470703%
Volume Distribution (VD):	2.046
Pgp-substrate:	11.561338424682617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.441
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.223
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.19
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.495
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	4.992
Half-life (T1/2):	0.516

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.932
Drug-inuced Liver Injury (DILI):	0.569
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.358
Maximum Recommended Daily Dose:	0.84
Skin Sensitization:	0.93
Carcinogencity:	0.592
Eye Corrosion:	0.188
Eye Irritation:	0.044
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: NPC474193

Natural Product ID:	NPC474193
*Common Name:**	Brianthein W
IUPAC Name:	n.a.
Synonyms:	Brianthein W
Standard InCHIKey:	ZJOXMWJKQWLNFX-YBFVYHPSSA-N
Standard InCHI:	InChI=1S/C24H32O6/c1-13-7-9-21(28-16(4)25)24(6)19(14(2)8-10-22(24)29-17(5)26)12-18-15(3)23(27)30-20(18)11-13/h8,11,19-22H,7,9-10,12H2,1-6H3/b13-11-/t19-,20-,21+,22-,24-/m0/s1
SMILES:	C/C/1=C/[C@@H]2OC(=O)C(=C2C[C@@H]2[C@]([C@@H](CC1)OC(=O)C)(C)[C@H](CC=C2C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463328
PubChem CID:	44584195
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640510]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Formosan gorgonian	n.a.	PMID[8984161]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Indonesian Gorgonian	n.a.	PMID[9548870]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.76	ug ml-1	PMID[481556]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[481556]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[481556]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[481556]

☑ 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 NPC474193 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	190
0.1-0.2	1312
0.2-0.3	5474
0.3-0.4	15928
0.4-0.5	8981
0.5-0.6	6939
0.6-0.7	3302
0.7-0.8	533
0.8-0.85	26
0.85-0.9	9
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC12283
0.9506	High Similarity	NPC476600
0.8953	High Similarity	NPC476597
0.8953	High Similarity	NPC476598
0.8889	High Similarity	NPC471218
0.8851	High Similarity	NPC476596
0.8701	High Similarity	NPC222244
0.8701	High Similarity	NPC16349
0.8554	High Similarity	NPC193198
0.8452	Intermediate Similarity	NPC96055
0.8427	Intermediate Similarity	NPC161998
0.8395	Intermediate Similarity	NPC184737
0.8353	Intermediate Similarity	NPC474013
0.8333	Intermediate Similarity	NPC474809
0.8333	Intermediate Similarity	NPC472377
0.8313	Intermediate Similarity	NPC475944
0.8295	Intermediate Similarity	NPC78973
0.8293	Intermediate Similarity	NPC471299
0.8276	Intermediate Similarity	NPC93411
0.8276	Intermediate Similarity	NPC472378
0.8272	Intermediate Similarity	NPC189206
0.8256	Intermediate Similarity	NPC131813
0.8205	Intermediate Similarity	NPC469660
0.8193	Intermediate Similarity	NPC268827
0.8182	Intermediate Similarity	NPC177141
0.8171	Intermediate Similarity	NPC209135
0.8171	Intermediate Similarity	NPC474816
0.8161	Intermediate Similarity	NPC312561
0.814	Intermediate Similarity	NPC472442
0.814	Intermediate Similarity	NPC189311
0.8118	Intermediate Similarity	NPC311070
0.8118	Intermediate Similarity	NPC472440
0.8118	Intermediate Similarity	NPC477124
0.8111	Intermediate Similarity	NPC205034
0.8111	Intermediate Similarity	NPC152778
0.8111	Intermediate Similarity	NPC162615
0.8095	Intermediate Similarity	NPC25554
0.809	Intermediate Similarity	NPC280149
0.809	Intermediate Similarity	NPC232426
0.809	Intermediate Similarity	NPC281942
0.809	Intermediate Similarity	NPC221111
0.8068	Intermediate Similarity	NPC226863
0.8052	Intermediate Similarity	NPC472266
0.8049	Intermediate Similarity	NPC262747
0.8046	Intermediate Similarity	NPC220478
0.8043	Intermediate Similarity	NPC16967
0.8022	Intermediate Similarity	NPC104925
0.8022	Intermediate Similarity	NPC298973
0.8	Intermediate Similarity	NPC200513
0.8	Intermediate Similarity	NPC256112
0.8	Intermediate Similarity	NPC72845
0.8	Intermediate Similarity	NPC141831
0.7978	Intermediate Similarity	NPC470734
0.7976	Intermediate Similarity	NPC469802
0.7955	Intermediate Similarity	NPC102640
0.7952	Intermediate Similarity	NPC471220
0.7935	Intermediate Similarity	NPC276110
0.7931	Intermediate Similarity	NPC471795
0.7931	Intermediate Similarity	NPC30984
0.7912	Intermediate Similarity	NPC475657
0.7912	Intermediate Similarity	NPC139692
0.7912	Intermediate Similarity	NPC53555
0.7912	Intermediate Similarity	NPC472812
0.7907	Intermediate Similarity	NPC42476
0.7901	Intermediate Similarity	NPC474758
0.7889	Intermediate Similarity	NPC182136
0.7889	Intermediate Similarity	NPC273199
0.7889	Intermediate Similarity	NPC469595
0.7889	Intermediate Similarity	NPC310479
0.7889	Intermediate Similarity	NPC212679
0.7889	Intermediate Similarity	NPC220454
0.7882	Intermediate Similarity	NPC471325
0.7882	Intermediate Similarity	NPC170303
0.7875	Intermediate Similarity	NPC257618
0.7865	Intermediate Similarity	NPC69713
0.7865	Intermediate Similarity	NPC472810
0.7865	Intermediate Similarity	NPC471956
0.7865	Intermediate Similarity	NPC472809
0.7857	Intermediate Similarity	NPC242767
0.7857	Intermediate Similarity	NPC325869
0.7849	Intermediate Similarity	NPC209297
0.7849	Intermediate Similarity	NPC475380
0.7849	Intermediate Similarity	NPC165632
0.7841	Intermediate Similarity	NPC102996
0.7841	Intermediate Similarity	NPC471219
0.7831	Intermediate Similarity	NPC54996
0.7826	Intermediate Similarity	NPC166143
0.7826	Intermediate Similarity	NPC470697
0.7826	Intermediate Similarity	NPC148463
0.7826	Intermediate Similarity	NPC120351
0.7826	Intermediate Similarity	NPC140277
0.7826	Intermediate Similarity	NPC469697
0.7826	Intermediate Similarity	NPC471994
0.7826	Intermediate Similarity	NPC191521
0.7816	Intermediate Similarity	NPC474359
0.7816	Intermediate Similarity	NPC149869
0.7816	Intermediate Similarity	NPC30486
0.7816	Intermediate Similarity	NPC31086
0.7816	Intermediate Similarity	NPC474865
0.7816	Intermediate Similarity	NPC318515
0.7812	Intermediate Similarity	NPC472552
0.7802	Intermediate Similarity	NPC472811
0.7802	Intermediate Similarity	NPC329842
0.7802	Intermediate Similarity	NPC473944
0.7791	Intermediate Similarity	NPC471298
0.7791	Intermediate Similarity	NPC35556
0.7791	Intermediate Similarity	NPC178676
0.7791	Intermediate Similarity	NPC323251
0.7789	Intermediate Similarity	NPC474012
0.7789	Intermediate Similarity	NPC476299
0.7778	Intermediate Similarity	NPC50488
0.7778	Intermediate Similarity	NPC474396
0.7778	Intermediate Similarity	NPC5509
0.7778	Intermediate Similarity	NPC284561
0.7778	Intermediate Similarity	NPC174342
0.7766	Intermediate Similarity	NPC100912
0.7766	Intermediate Similarity	NPC311241
0.7766	Intermediate Similarity	NPC110937
0.7766	Intermediate Similarity	NPC475446
0.7766	Intermediate Similarity	NPC53844
0.7766	Intermediate Similarity	NPC73911
0.7765	Intermediate Similarity	NPC233332
0.7753	Intermediate Similarity	NPC166857
0.7742	Intermediate Similarity	NPC474909
0.7742	Intermediate Similarity	NPC281134
0.7738	Intermediate Similarity	NPC474005
0.7732	Intermediate Similarity	NPC23584
0.7727	Intermediate Similarity	NPC65661
0.7727	Intermediate Similarity	NPC35933
0.7717	Intermediate Similarity	NPC115021
0.7717	Intermediate Similarity	NPC7349
0.7711	Intermediate Similarity	NPC27205
0.7708	Intermediate Similarity	NPC472554
0.7701	Intermediate Similarity	NPC30502
0.7701	Intermediate Similarity	NPC471297
0.7701	Intermediate Similarity	NPC49208
0.7701	Intermediate Similarity	NPC22611
0.7701	Intermediate Similarity	NPC222358
0.7701	Intermediate Similarity	NPC23748
0.7692	Intermediate Similarity	NPC469372
0.7692	Intermediate Similarity	NPC471818
0.7684	Intermediate Similarity	NPC107806
0.7684	Intermediate Similarity	NPC72647
0.7684	Intermediate Similarity	NPC474440
0.7667	Intermediate Similarity	NPC474629
0.7667	Intermediate Similarity	NPC477128
0.7667	Intermediate Similarity	NPC106332
0.7667	Intermediate Similarity	NPC473879
0.7667	Intermediate Similarity	NPC472302
0.766	Intermediate Similarity	NPC242848
0.766	Intermediate Similarity	NPC234993
0.766	Intermediate Similarity	NPC260796
0.766	Intermediate Similarity	NPC162346
0.766	Intermediate Similarity	NPC134072
0.766	Intermediate Similarity	NPC473153
0.766	Intermediate Similarity	NPC194132
0.7647	Intermediate Similarity	NPC153987
0.7647	Intermediate Similarity	NPC178277
0.7647	Intermediate Similarity	NPC44083
0.764	Intermediate Similarity	NPC329692
0.764	Intermediate Similarity	NPC286153
0.7634	Intermediate Similarity	NPC38830
0.7634	Intermediate Similarity	NPC477130
0.7634	Intermediate Similarity	NPC105490
0.7634	Intermediate Similarity	NPC477722
0.7634	Intermediate Similarity	NPC57117
0.7634	Intermediate Similarity	NPC470255
0.7634	Intermediate Similarity	NPC477129
0.7634	Intermediate Similarity	NPC53685
0.7629	Intermediate Similarity	NPC183571
0.7629	Intermediate Similarity	NPC476081
0.7629	Intermediate Similarity	NPC11956
0.7619	Intermediate Similarity	NPC316500
0.7619	Intermediate Similarity	NPC473825
0.7619	Intermediate Similarity	NPC41780
0.7619	Intermediate Similarity	NPC187568
0.7614	Intermediate Similarity	NPC126518
0.7614	Intermediate Similarity	NPC471301
0.7614	Intermediate Similarity	NPC475100
0.7614	Intermediate Similarity	NPC159635
0.7609	Intermediate Similarity	NPC177641
0.7609	Intermediate Similarity	NPC472814
0.7609	Intermediate Similarity	NPC124374
0.7609	Intermediate Similarity	NPC234335
0.7609	Intermediate Similarity	NPC177037
0.7604	Intermediate Similarity	NPC38855
0.7604	Intermediate Similarity	NPC227865
0.7604	Intermediate Similarity	NPC470761
0.7604	Intermediate Similarity	NPC473219
0.7582	Intermediate Similarity	NPC314727
0.7582	Intermediate Similarity	NPC288699
0.7582	Intermediate Similarity	NPC246028
0.7582	Intermediate Similarity	NPC73995
0.7582	Intermediate Similarity	NPC261320
0.7582	Intermediate Similarity	NPC293044
0.7579	Intermediate Similarity	NPC84335
0.7579	Intermediate Similarity	NPC69385
0.7579	Intermediate Similarity	NPC51499
0.7579	Intermediate Similarity	NPC38530
0.7579	Intermediate Similarity	NPC202705

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 NPC474193 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1819
0.2-0.3	4009
0.3-0.4	2228
0.4-0.5	576
0.5-0.6	281
0.6-0.7	57
0.7-0.8	5
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
0.8	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4225	Approved
0.7391	Intermediate Similarity	NPD6051	Approved
0.732	Intermediate Similarity	NPD7638	Approved
0.7253	Intermediate Similarity	NPD5330	Approved
0.7253	Intermediate Similarity	NPD7334	Approved
0.7253	Intermediate Similarity	NPD7521	Approved
0.7253	Intermediate Similarity	NPD6684	Approved
0.7253	Intermediate Similarity	NPD6409	Approved
0.7253	Intermediate Similarity	NPD7146	Approved
0.7245	Intermediate Similarity	NPD7639	Approved
0.7245	Intermediate Similarity	NPD7640	Approved
0.7176	Intermediate Similarity	NPD8039	Approved
0.7143	Intermediate Similarity	NPD1694	Approved
0.7125	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6903	Approved
0.7097	Intermediate Similarity	NPD6672	Approved
0.7097	Intermediate Similarity	NPD5737	Approved
0.7	Intermediate Similarity	NPD5209	Approved
0.7	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD6686	Approved
0.6907	Remote Similarity	NPD7748	Approved
0.6907	Remote Similarity	NPD7900	Approved
0.6907	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5693	Phase 1
0.6771	Remote Similarity	NPD46	Approved
0.6771	Remote Similarity	NPD6698	Approved
0.6771	Remote Similarity	NPD5785	Approved
0.6771	Remote Similarity	NPD7838	Discovery
0.6733	Remote Similarity	NPD6648	Approved
0.6727	Remote Similarity	NPD7115	Discovery
0.6701	Remote Similarity	NPD6411	Approved
0.6701	Remote Similarity	NPD7515	Phase 2
0.6701	Remote Similarity	NPD7637	Suspended
0.67	Remote Similarity	NPD7902	Approved
0.67	Remote Similarity	NPD6083	Phase 2
0.67	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6673	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6633	Remote Similarity	NPD5778	Approved
0.6633	Remote Similarity	NPD5779	Approved
0.6602	Remote Similarity	NPD7632	Discontinued
0.6596	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5739	Approved
0.6571	Remote Similarity	NPD7128	Approved
0.6571	Remote Similarity	NPD6675	Approved
0.6571	Remote Similarity	NPD6402	Approved
0.6559	Remote Similarity	NPD7154	Phase 3
0.6542	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6050	Approved
0.6514	Remote Similarity	NPD6053	Discontinued
0.65	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD3668	Phase 3
0.6489	Remote Similarity	NPD4786	Approved
0.6481	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5696	Approved
0.6458	Remote Similarity	NPD3573	Approved
0.6452	Remote Similarity	NPD3667	Approved
0.6449	Remote Similarity	NPD6881	Approved
0.6449	Remote Similarity	NPD7320	Approved
0.6449	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD5692	Phase 3
0.6415	Remote Similarity	NPD6008	Approved
0.6413	Remote Similarity	NPD4820	Approved
0.6413	Remote Similarity	NPD4819	Approved
0.6413	Remote Similarity	NPD4822	Approved
0.6413	Remote Similarity	NPD4821	Approved
0.6404	Remote Similarity	NPD6942	Approved
0.6404	Remote Similarity	NPD8264	Approved
0.6404	Remote Similarity	NPD7339	Approved
0.6392	Remote Similarity	NPD5208	Approved
0.6389	Remote Similarity	NPD6372	Approved
0.6389	Remote Similarity	NPD6373	Approved
0.6383	Remote Similarity	NPD6695	Phase 3
0.6383	Remote Similarity	NPD5362	Discontinued
0.6374	Remote Similarity	NPD4268	Approved
0.6374	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4271	Approved
0.6372	Remote Similarity	NPD7328	Approved
0.6372	Remote Similarity	NPD7327	Approved
0.6364	Remote Similarity	NPD5694	Approved
0.6355	Remote Similarity	NPD5697	Approved
0.6355	Remote Similarity	NPD5701	Approved
0.6354	Remote Similarity	NPD6098	Approved
0.6354	Remote Similarity	NPD3618	Phase 1
0.6348	Remote Similarity	NPD8033	Approved
0.6333	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7102	Approved
0.633	Remote Similarity	NPD7290	Approved
0.633	Remote Similarity	NPD6883	Approved
0.633	Remote Similarity	NPD6371	Approved
0.6327	Remote Similarity	NPD5328	Approved
0.6327	Remote Similarity	NPD1695	Approved
0.6316	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7516	Approved
0.6316	Remote Similarity	NPD3665	Phase 1
0.6316	Remote Similarity	NPD3666	Approved
0.6316	Remote Similarity	NPD3133	Approved
0.6304	Remote Similarity	NPD7645	Phase 2
0.6273	Remote Similarity	NPD6847	Approved
0.6273	Remote Similarity	NPD6649	Approved
0.6273	Remote Similarity	NPD6869	Approved
0.6273	Remote Similarity	NPD6650	Approved
0.6273	Remote Similarity	NPD6617	Approved
0.6273	Remote Similarity	NPD8130	Phase 1
0.6263	Remote Similarity	NPD5207	Approved
0.6261	Remote Similarity	NPD8377	Approved
0.6261	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD5363	Approved
0.6239	Remote Similarity	NPD6012	Approved
0.6239	Remote Similarity	NPD6014	Approved
0.6239	Remote Similarity	NPD6013	Approved
0.6237	Remote Similarity	NPD4695	Discontinued
0.6216	Remote Similarity	NPD6882	Approved
0.6216	Remote Similarity	NPD8297	Approved
0.6211	Remote Similarity	NPD5332	Approved
0.6211	Remote Similarity	NPD5331	Approved
0.6207	Remote Similarity	NPD8378	Approved
0.6207	Remote Similarity	NPD8335	Approved
0.6207	Remote Similarity	NPD8296	Approved
0.6207	Remote Similarity	NPD8380	Approved
0.6207	Remote Similarity	NPD8379	Approved
0.6204	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6079	Approved
0.6186	Remote Similarity	NPD5279	Phase 3
0.617	Remote Similarity	NPD4790	Discontinued
0.6162	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4753	Phase 2
0.6154	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6011	Approved
0.6145	Remote Similarity	NPD4193	Approved
0.6145	Remote Similarity	NPD4191	Approved
0.6145	Remote Similarity	NPD4194	Approved
0.6145	Remote Similarity	NPD4192	Approved
0.6134	Remote Similarity	NPD7507	Approved
0.6129	Remote Similarity	NPD6929	Approved
0.6126	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7750	Discontinued
0.6122	Remote Similarity	NPD7524	Approved
0.6122	Remote Similarity	NPD4251	Approved
0.6122	Remote Similarity	NPD4250	Approved
0.6111	Remote Similarity	NPD6926	Approved
0.6111	Remote Similarity	NPD6924	Approved
0.6105	Remote Similarity	NPD6435	Approved
0.6105	Remote Similarity	NPD4269	Approved
0.6105	Remote Similarity	NPD4270	Approved
0.6082	Remote Similarity	NPD1696	Phase 3
0.6078	Remote Similarity	NPD6001	Approved
0.6078	Remote Similarity	NPD5282	Discontinued
0.6068	Remote Similarity	NPD7503	Approved
0.6064	Remote Similarity	NPD6930	Phase 2
0.6064	Remote Similarity	NPD7525	Registered
0.6064	Remote Similarity	NPD6931	Approved
0.6064	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4755	Approved
0.6055	Remote Similarity	NPD6412	Phase 2
0.604	Remote Similarity	NPD5281	Approved
0.604	Remote Similarity	NPD8034	Phase 2
0.604	Remote Similarity	NPD8035	Phase 2
0.604	Remote Similarity	NPD5284	Approved
0.602	Remote Similarity	NPD4249	Approved
0.602	Remote Similarity	NPD4519	Discontinued
0.602	Remote Similarity	NPD5786	Approved
0.602	Remote Similarity	NPD4623	Approved
0.6019	Remote Similarity	NPD5654	Approved
0.6	Remote Similarity	NPD5369	Approved
0.5984	Remote Similarity	NPD7319	Approved
0.5981	Remote Similarity	NPD5211	Phase 2
0.598	Remote Similarity	NPD4202	Approved
0.5978	Remote Similarity	NPD6933	Approved
0.5962	Remote Similarity	NPD5221	Approved
0.5962	Remote Similarity	NPD7732	Phase 3
0.5962	Remote Similarity	NPD5222	Approved
0.5962	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4697	Phase 3
0.596	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD4195	Approved
0.5943	Remote Similarity	NPD4700	Approved
0.5943	Remote Similarity	NPD5286	Approved
0.5943	Remote Similarity	NPD4696	Approved
0.5943	Remote Similarity	NPD5285	Approved
0.5938	Remote Similarity	NPD4221	Approved
0.5938	Remote Similarity	NPD4223	Phase 3
0.5926	Remote Similarity	NPD6052	Approved
0.5918	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5329	Approved
0.5914	Remote Similarity	NPD6925	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