NPASS Compound

Structure

NPC474742 OpenBabel07101719242D 26 27 0 0 1 0 0 0 0 0999 V2000 -4.3464 -0.8232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0172 2.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5362 3.0443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9749 -1.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6885 -2.4943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6411 0.1324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1910 2.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9610 0.8654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4227 -2.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4255 -2.1692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7100 2.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9860 -1.2682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2412 -1.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7453 -1.4361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9860 0.6429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8944 -0.4473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7604 0.0527 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7847 1.4838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7018 -0.7124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6913 -0.3127 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3059 1.3760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0415 0.9205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6906 -0.5633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6662 -0.0901 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 -1.6857 1.0499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 8 2 0 0 0 0 7 11 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 12 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 6 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 10 1 1 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 15 21 2 0 0 0 0 16 17 1 0 0 0 0 16 25 1 6 0 0 0 17 20 1 1 0 0 0 17 26 1 0 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	374.286
LogP:	2.399
LogD:	1.63
LogS:	-3.579
# Rotatable Bonds:	5
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.609
Synthetic Accessibility Score:	4.733
Fsp3:	0.55
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:	-4.667
MDCK Permeability:	1.4689095223729964e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.128
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.269
Plasma Protein Binding (PPB):	81.73270416259766%
Volume Distribution (VD):	1.517
Pgp-substrate:	15.824302673339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.583
CYP1A2-substrate:	0.358
CYP2C19-inhibitor:	0.698
CYP2C19-substrate:	0.692
CYP2C9-inhibitor:	0.583
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.245
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.686
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	7.207
Half-life (T1/2):	0.165

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.865
Drug-inuced Liver Injury (DILI):	0.37
AMES Toxicity:	0.118
Rat Oral Acute Toxicity:	0.84
Maximum Recommended Daily Dose:	0.503
Skin Sensitization:	0.922
Carcinogencity:	0.701
Eye Corrosion:	0.167
Eye Irritation:	0.211
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC474742

Natural Product ID:	NPC474742
*Common Name:**	(1S,5S,6R,7S,10S)-5-Angeloyloxy-1-Hydroxy-2-Oxaxantha-3,11-Dien-6,12-Olide
IUPAC Name:	[(3aR,6S,7S,8S,8aR)-7-[(E)-but-2-enoyl]-7-hydroxy-6-methyl-3-methylidene-2-oxo-3a,4,5,6,8,8a-hexahydrocyclohepta[b]furan-8-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	WZMSNQSBWAAHTM-YYACAIMJSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-6-8-15(21)20(24)12(4)9-10-14-13(5)19(23)25-16(14)17(20)26-18(22)11(3)7-2/h6-8,12,14,16-17,24H,5,9-10H2,1-4H3/b8-6+,11-7-/t12-,14+,16+,17-,20+/m0/s1
SMILES:	CC=CC(=O)C1(C(CCC2C(C1OC(=O)C(=CC)C)OC(=O)C2=C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481064
PubChem CID:	44575368
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO21597	Ratibida columnifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579870]
NPO21597	Ratibida columnifera	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
ED50	10

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2049	Cell Line	HT	Homo sapiens	ED50	=	0.4	ug ml-1	PMID[493004]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	0.4	ug ml-1	PMID[493004]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	0.9	ug ml-1	PMID[493004]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.4	ug ml-1	PMID[493004]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[493004]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	1.4	ug ml-1	PMID[493004]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.8	ug ml-1	PMID[493004]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.3	ug ml-1	PMID[493004]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.6	ug ml-1	PMID[493004]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.2	ug ml-1	PMID[493004]

☑ 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 NPC474742 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	230
0.1-0.2	1274
0.2-0.3	4560
0.3-0.4	8478
0.4-0.5	14486
0.5-0.6	8016
0.6-0.7	4065
0.7-0.8	1393
0.8-0.85	155
0.85-0.9	28
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC475945
0.9789	High Similarity	NPC475871
0.9688	High Similarity	NPC474741
0.9684	High Similarity	NPC474747
0.9583	High Similarity	NPC475873
0.9278	High Similarity	NPC149371
0.9175	High Similarity	NPC47880
0.9091	High Similarity	NPC203659
0.9053	High Similarity	NPC475900
0.899	High Similarity	NPC110989
0.8958	High Similarity	NPC476009
0.8889	High Similarity	NPC225353
0.8788	High Similarity	NPC164598
0.8788	High Similarity	NPC472753
0.8788	High Similarity	NPC474339
0.8776	High Similarity	NPC471144
0.8725	High Similarity	NPC26617
0.8713	High Similarity	NPC100487
0.87	High Similarity	NPC472754
0.8692	High Similarity	NPC471145
0.8692	High Similarity	NPC471146
0.8646	High Similarity	NPC469692
0.8646	High Similarity	NPC469645
0.8646	High Similarity	NPC475912
0.8646	High Similarity	NPC476300
0.8632	High Similarity	NPC51004
0.8614	High Similarity	NPC472755
0.86	High Similarity	NPC110443
0.86	High Similarity	NPC133907
0.86	High Similarity	NPC46998
0.86	High Similarity	NPC476270
0.86	High Similarity	NPC128733
0.86	High Similarity	NPC201718
0.86	High Similarity	NPC185141
0.8558	High Similarity	NPC38154
0.8557	High Similarity	NPC121825
0.8544	High Similarity	NPC477513
0.8542	High Similarity	NPC261607
0.8542	High Similarity	NPC30515
0.8542	High Similarity	NPC300312
0.8542	High Similarity	NPC184463
0.8542	High Similarity	NPC111114
0.8529	High Similarity	NPC472756
0.8526	High Similarity	NPC307411
0.85	High Similarity	NPC288876
0.8485	Intermediate Similarity	NPC108475
0.8485	Intermediate Similarity	NPC213947
0.8485	Intermediate Similarity	NPC170143
0.8469	Intermediate Similarity	NPC14961
0.8469	Intermediate Similarity	NPC475659
0.8469	Intermediate Similarity	NPC304886
0.8469	Intermediate Similarity	NPC270013
0.8469	Intermediate Similarity	NPC36954
0.8454	Intermediate Similarity	NPC212486
0.8454	Intermediate Similarity	NPC135776
0.8454	Intermediate Similarity	NPC179746
0.8454	Intermediate Similarity	NPC81419
0.8447	Intermediate Similarity	NPC243998
0.8447	Intermediate Similarity	NPC223450
0.8438	Intermediate Similarity	NPC476004
0.8438	Intermediate Similarity	NPC474761
0.8438	Intermediate Similarity	NPC62815
0.8421	Intermediate Similarity	NPC202672
0.8416	Intermediate Similarity	NPC15993
0.84	Intermediate Similarity	NPC141191
0.8384	Intermediate Similarity	NPC39859
0.8384	Intermediate Similarity	NPC470883
0.8384	Intermediate Similarity	NPC158416
0.8384	Intermediate Similarity	NPC76862
0.8384	Intermediate Similarity	NPC473859
0.8367	Intermediate Similarity	NPC81386
0.8367	Intermediate Similarity	NPC477131
0.8367	Intermediate Similarity	NPC474035
0.8367	Intermediate Similarity	NPC167219
0.8351	Intermediate Similarity	NPC20713
0.8351	Intermediate Similarity	NPC12172
0.8351	Intermediate Similarity	NPC208886
0.8333	Intermediate Similarity	NPC86077
0.8333	Intermediate Similarity	NPC173926
0.8333	Intermediate Similarity	NPC474951
0.8333	Intermediate Similarity	NPC324017
0.8333	Intermediate Similarity	NPC471148
0.8333	Intermediate Similarity	NPC320019
0.8317	Intermediate Similarity	NPC475949
0.8316	Intermediate Similarity	NPC190753
0.8302	Intermediate Similarity	NPC5103
0.8302	Intermediate Similarity	NPC477103
0.83	Intermediate Similarity	NPC40812
0.83	Intermediate Similarity	NPC169205
0.83	Intermediate Similarity	NPC474313
0.8283	Intermediate Similarity	NPC193645
0.8283	Intermediate Similarity	NPC471142
0.8283	Intermediate Similarity	NPC48803
0.8283	Intermediate Similarity	NPC90121
0.8283	Intermediate Similarity	NPC275960
0.8265	Intermediate Similarity	NPC295204
0.8265	Intermediate Similarity	NPC288240
0.8265	Intermediate Similarity	NPC162205
0.8265	Intermediate Similarity	NPC273579
0.8252	Intermediate Similarity	NPC472747
0.8252	Intermediate Similarity	NPC4620
0.8252	Intermediate Similarity	NPC472750
0.8247	Intermediate Similarity	NPC144133
0.8247	Intermediate Similarity	NPC473619
0.8247	Intermediate Similarity	NPC179394
0.8235	Intermediate Similarity	NPC171759
0.8235	Intermediate Similarity	NPC477511
0.8235	Intermediate Similarity	NPC264477
0.8229	Intermediate Similarity	NPC153805
0.8224	Intermediate Similarity	NPC179798
0.8224	Intermediate Similarity	NPC304180
0.8218	Intermediate Similarity	NPC473326
0.8218	Intermediate Similarity	NPC187761
0.8218	Intermediate Similarity	NPC83895
0.8218	Intermediate Similarity	NPC54843
0.8208	Intermediate Similarity	NPC477102
0.82	Intermediate Similarity	NPC17585
0.82	Intermediate Similarity	NPC477921
0.82	Intermediate Similarity	NPC476315
0.82	Intermediate Similarity	NPC185553
0.8182	Intermediate Similarity	NPC469632
0.8182	Intermediate Similarity	NPC190294
0.8173	Intermediate Similarity	NPC475676
0.8173	Intermediate Similarity	NPC472748
0.8173	Intermediate Similarity	NPC477510
0.8173	Intermediate Similarity	NPC220964
0.8173	Intermediate Similarity	NPC471143
0.8163	Intermediate Similarity	NPC150978
0.8163	Intermediate Similarity	NPC74103
0.8163	Intermediate Similarity	NPC284185
0.8163	Intermediate Similarity	NPC473321
0.8163	Intermediate Similarity	NPC70595
0.8163	Intermediate Similarity	NPC133698
0.8163	Intermediate Similarity	NPC123177
0.8148	Intermediate Similarity	NPC66108
0.8144	Intermediate Similarity	NPC295312
0.8144	Intermediate Similarity	NPC32922
0.8144	Intermediate Similarity	NPC474032
0.8137	Intermediate Similarity	NPC477512
0.8131	Intermediate Similarity	NPC257240
0.8125	Intermediate Similarity	NPC231889
0.8125	Intermediate Similarity	NPC248602
0.8125	Intermediate Similarity	NPC160138
0.8125	Intermediate Similarity	NPC179659
0.8113	Intermediate Similarity	NPC475960
0.8105	Intermediate Similarity	NPC21469
0.81	Intermediate Similarity	NPC163228
0.81	Intermediate Similarity	NPC107476
0.81	Intermediate Similarity	NPC474947
0.81	Intermediate Similarity	NPC477922
0.8095	Intermediate Similarity	NPC54737
0.8095	Intermediate Similarity	NPC472749
0.8095	Intermediate Similarity	NPC16313
0.8095	Intermediate Similarity	NPC472751
0.8095	Intermediate Similarity	NPC9303
0.8085	Intermediate Similarity	NPC250315
0.8085	Intermediate Similarity	NPC318468
0.8081	Intermediate Similarity	NPC60386
0.8081	Intermediate Similarity	NPC473273
0.8081	Intermediate Similarity	NPC473263
0.8081	Intermediate Similarity	NPC473234
0.8081	Intermediate Similarity	NPC475302
0.8081	Intermediate Similarity	NPC308656
0.8073	Intermediate Similarity	NPC469496
0.8073	Intermediate Similarity	NPC46269
0.8073	Intermediate Similarity	NPC106395
0.8073	Intermediate Similarity	NPC469454
0.8073	Intermediate Similarity	NPC56448
0.8073	Intermediate Similarity	NPC469463
0.807	Intermediate Similarity	NPC473802
0.8061	Intermediate Similarity	NPC473448
0.8061	Intermediate Similarity	NPC475748
0.8061	Intermediate Similarity	NPC253144
0.8061	Intermediate Similarity	NPC71533
0.8061	Intermediate Similarity	NPC475855
0.8061	Intermediate Similarity	NPC106510
0.8058	Intermediate Similarity	NPC150923
0.8041	Intermediate Similarity	NPC227379
0.8041	Intermediate Similarity	NPC281516
0.8041	Intermediate Similarity	NPC469653
0.8041	Intermediate Similarity	NPC469628
0.8041	Intermediate Similarity	NPC475906
0.8041	Intermediate Similarity	NPC469631
0.8041	Intermediate Similarity	NPC471047
0.8041	Intermediate Similarity	NPC53158
0.8041	Intermediate Similarity	NPC476708
0.8041	Intermediate Similarity	NPC474471
0.8039	Intermediate Similarity	NPC208233
0.8039	Intermediate Similarity	NPC474213
0.8039	Intermediate Similarity	NPC261377
0.8039	Intermediate Similarity	NPC187268
0.8039	Intermediate Similarity	NPC161855
0.8039	Intermediate Similarity	NPC308567
0.8039	Intermediate Similarity	NPC255592
0.8021	Intermediate Similarity	NPC261721
0.8021	Intermediate Similarity	NPC284902
0.802	Intermediate Similarity	NPC31645
0.802	Intermediate Similarity	NPC230800
0.802	Intermediate Similarity	NPC473291
0.802	Intermediate Similarity	NPC476275

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 NPC474742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1848
0.2-0.3	3619
0.3-0.4	2219
0.4-0.5	844
0.5-0.6	292
0.6-0.7	106
0.7-0.8	10
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8725	High Similarity	NPD7899	Clinical (unspecified phase)
0.8283	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.8131	Intermediate Similarity	NPD6371	Approved
0.7732	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5282	Discontinued
0.7624	Intermediate Similarity	NPD7983	Approved
0.7525	Intermediate Similarity	NPD46	Approved
0.7525	Intermediate Similarity	NPD6698	Approved
0.7426	Intermediate Similarity	NPD1695	Approved
0.7358	Intermediate Similarity	NPD4225	Approved
0.7353	Intermediate Similarity	NPD5785	Approved
0.7353	Intermediate Similarity	NPD7838	Discovery
0.7257	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5779	Approved
0.7212	Intermediate Similarity	NPD5778	Approved
0.72	Intermediate Similarity	NPD5363	Approved
0.7129	Intermediate Similarity	NPD5786	Approved
0.7094	Intermediate Similarity	NPD7115	Discovery
0.7059	Intermediate Similarity	NPD6319	Approved
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.7	Intermediate Similarity	NPD8513	Phase 3
0.6991	Remote Similarity	NPD6686	Approved
0.6991	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5369	Approved
0.6909	Remote Similarity	NPD5344	Discontinued
0.69	Remote Similarity	NPD4269	Approved
0.69	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4270	Approved
0.6899	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6053	Discontinued
0.6881	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1694	Approved
0.6838	Remote Similarity	NPD4632	Approved
0.6829	Remote Similarity	NPD7492	Approved
0.6777	Remote Similarity	NPD6054	Approved
0.6774	Remote Similarity	NPD6616	Approved
0.6762	Remote Similarity	NPD6101	Approved
0.6762	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7642	Approved
0.6733	Remote Similarity	NPD5209	Approved
0.6733	Remote Similarity	NPD6435	Approved
0.6721	Remote Similarity	NPD6016	Approved
0.6721	Remote Similarity	NPD6015	Approved
0.672	Remote Similarity	NPD8074	Phase 3
0.672	Remote Similarity	NPD7078	Approved
0.67	Remote Similarity	NPD4252	Approved
0.6697	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6641	Remote Similarity	NPD7260	Phase 2
0.6636	Remote Similarity	NPD6411	Approved
0.6635	Remote Similarity	NPD4249	Approved
0.661	Remote Similarity	NPD8297	Approved
0.6609	Remote Similarity	NPD5697	Approved
0.6581	Remote Similarity	NPD4634	Approved
0.6571	Remote Similarity	NPD4250	Approved
0.6571	Remote Similarity	NPD4251	Approved
0.6569	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6881	Approved
0.6552	Remote Similarity	NPD6899	Approved
0.6535	Remote Similarity	NPD5368	Approved
0.6529	Remote Similarity	NPD6009	Approved
0.6525	Remote Similarity	NPD6649	Approved
0.6525	Remote Similarity	NPD2204	Approved
0.6525	Remote Similarity	NPD6650	Approved
0.6505	Remote Similarity	NPD5362	Discontinued
0.6504	Remote Similarity	NPD6059	Approved
0.6496	Remote Similarity	NPD6012	Approved
0.6496	Remote Similarity	NPD6013	Approved
0.6496	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6014	Approved
0.6484	Remote Similarity	NPD7319	Approved
0.648	Remote Similarity	NPD7829	Approved
0.648	Remote Similarity	NPD8328	Phase 3
0.648	Remote Similarity	NPD7830	Approved
0.6457	Remote Similarity	NPD8293	Discontinued
0.6455	Remote Similarity	NPD5695	Phase 3
0.6452	Remote Similarity	NPD5983	Phase 2
0.6441	Remote Similarity	NPD6883	Approved
0.6441	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7290	Approved
0.6441	Remote Similarity	NPD7102	Approved
0.6429	Remote Similarity	NPD7638	Approved
0.6429	Remote Similarity	NPD5696	Approved
0.641	Remote Similarity	NPD6011	Approved
0.6387	Remote Similarity	NPD8130	Phase 1
0.6387	Remote Similarity	NPD6847	Approved
0.6387	Remote Similarity	NPD6869	Approved
0.6387	Remote Similarity	NPD6617	Approved
0.6379	Remote Similarity	NPD7128	Approved
0.6379	Remote Similarity	NPD5739	Approved
0.6379	Remote Similarity	NPD6402	Approved
0.6379	Remote Similarity	NPD6008	Approved
0.6379	Remote Similarity	NPD6675	Approved
0.6378	Remote Similarity	NPD7507	Approved
0.6378	Remote Similarity	NPD8273	Phase 1
0.6378	Remote Similarity	NPD8451	Approved
0.6373	Remote Similarity	NPD4821	Approved
0.6373	Remote Similarity	NPD4819	Approved
0.6373	Remote Similarity	NPD4822	Approved
0.6373	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4820	Approved
0.6372	Remote Similarity	NPD7639	Approved
0.6372	Remote Similarity	NPD7640	Approved
0.6356	Remote Similarity	NPD6372	Approved
0.6356	Remote Similarity	NPD6373	Approved
0.6349	Remote Similarity	NPD7604	Phase 2
0.6341	Remote Similarity	NPD7641	Discontinued
0.6339	Remote Similarity	NPD6083	Phase 2
0.6339	Remote Similarity	NPD6084	Phase 2
0.6337	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD6845	Suspended
0.6333	Remote Similarity	NPD6882	Approved
0.633	Remote Similarity	NPD7637	Suspended
0.6328	Remote Similarity	NPD8448	Approved
0.6325	Remote Similarity	NPD5701	Approved
0.632	Remote Similarity	NPD8444	Approved
0.632	Remote Similarity	NPD6921	Approved
0.6271	Remote Similarity	NPD7320	Approved
0.627	Remote Similarity	NPD8080	Discontinued
0.6261	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD6336	Discontinued
0.6238	Remote Similarity	NPD4756	Discovery
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6228	Remote Similarity	NPD4696	Approved
0.6226	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6412	Phase 2
0.6186	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD8392	Approved
0.6183	Remote Similarity	NPD8390	Approved
0.6183	Remote Similarity	NPD8391	Approved
0.6182	Remote Similarity	NPD5693	Phase 1
0.6176	Remote Similarity	NPD4271	Approved
0.6176	Remote Similarity	NPD4268	Approved
0.6172	Remote Similarity	NPD8340	Approved
0.6172	Remote Similarity	NPD8342	Approved
0.6172	Remote Similarity	NPD8341	Approved
0.6172	Remote Similarity	NPD8299	Approved
0.6161	Remote Similarity	NPD4629	Approved
0.6161	Remote Similarity	NPD5210	Approved
0.6154	Remote Similarity	NPD5141	Approved
0.6147	Remote Similarity	NPD5370	Suspended
0.6129	Remote Similarity	NPD7500	Approved
0.6129	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6399	Phase 3
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.6106	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5222	Approved
0.6106	Remote Similarity	NPD5221	Approved
0.6105	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD5175	Approved
0.6063	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5956	Approved
0.6058	Remote Similarity	NPD4695	Discontinued
0.6055	Remote Similarity	NPD6672	Approved
0.6055	Remote Similarity	NPD5737	Approved
0.6053	Remote Similarity	NPD5173	Approved
0.6053	Remote Similarity	NPD4755	Approved
0.6048	Remote Similarity	NPD6274	Approved
0.6042	Remote Similarity	NPD7331	Phase 2
0.6038	Remote Similarity	NPD5332	Approved
0.6038	Remote Similarity	NPD5331	Approved
0.6036	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD5223	Approved
0.6032	Remote Similarity	NPD7100	Approved
0.6032	Remote Similarity	NPD7101	Approved
0.6031	Remote Similarity	NPD6033	Approved
0.6	Remote Similarity	NPD8415	Approved
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD3197	Phase 1
0.5984	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD4697	Phase 3
0.5965	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD3573	Approved
0.5956	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6313	Approved
0.5952	Remote Similarity	NPD6314	Approved
0.5952	Remote Similarity	NPD6335	Approved
0.5948	Remote Similarity	NPD4700	Approved
0.5938	Remote Similarity	NPD8268	Approved
0.5938	Remote Similarity	NPD8266	Approved
0.5938	Remote Similarity	NPD7503	Approved
0.5938	Remote Similarity	NPD7341	Phase 2
0.5938	Remote Similarity	NPD8269	Approved
0.5938	Remote Similarity	NPD8267	Approved
0.5929	Remote Similarity	NPD7748	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