NPASS Compound

Structure

NPC475873 OpenBabel07101719142D 27 28 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 0.2657 3.9121 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 0.6885 -2.4943 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 -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 -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 3 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 -2.9860 -1.2682 0.0000 C 0 0 1 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 -2.4227 -2.0945 0.0000 C 0 0 0 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 -2.9227 -2.9605 0.0000 O 0 0 0 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 10 1 0 0 0 0 4 11 2 0 0 0 0 5 12 1 0 0 0 0 6 8 2 0 0 0 0 7 10 1 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 6 0 0 0 13 9 1 1 0 0 0 13 16 1 0 0 0 0 14 21 2 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 17 1 0 0 0 0 16 26 1 6 0 0 0 17 20 1 1 0 0 0 17 27 1 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.17
Volume:	383.076
LogP:	1.847
LogD:	0.882
LogS:	-2.956
# Rotatable Bonds:	6
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	4.822
Fsp3:	0.6
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:	-4.739
MDCK Permeability:	1.7467697034589946e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.456
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.876
Plasma Protein Binding (PPB):	62.40714645385742%
Volume Distribution (VD):	0.785
Pgp-substrate:	50.39826583862305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.533
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.202
CYP3A4-substrate:	0.294

ADMET: Excretion

Clearance (CL):	7.126
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.713
Drug-inuced Liver Injury (DILI):	0.747
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.421
Maximum Recommended Daily Dose:	0.625
Skin Sensitization:	0.443
Carcinogencity:	0.394
Eye Corrosion:	0.018
Eye Irritation:	0.022
Respiratory Toxicity:	0.855

Download Data

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

Natural Product: NPC475873

Natural Product ID:	NPC475873
*Common Name:**	9-Oxo-Seco-Ratiferolide-5Alpha-O-(2-Methylbutyrate)
IUPAC Name:	[(3aR,6R,7S,8S,8aR)-7-[(E)-but-2-enoyl]-7-hydroxy-6-methyl-3-methylidene-2,5-dioxo-4,6,8,8a-tetrahydro-3aH-cyclohepta[b]furan-8-yl] 2-methylbutanoate
Synonyms:
Standard InCHIKey:	DFGOIVFBKDWNBI-XNGAVGKVSA-N
Standard InCHI:	InChI=1S/C20H26O7/c1-6-8-15(22)20(25)12(5)14(21)9-13-11(4)19(24)26-16(13)17(20)27-18(23)10(3)7-2/h6,8,10,12-13,16-17,25H,4,7,9H2,1-3,5H3/b8-6+/t10?,12-,13+,16+,17-,20+/m0/s1
SMILES:	CCC(C)C(=O)OC1C2C(CC(=O)C(C1(C(=O)C=CC)O)C)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517705
PubChem CID:	44575371
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	7

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	2.3	ug ml-1	PMID[557463]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	1.2	ug ml-1	PMID[557463]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.1	ug ml-1	PMID[557463]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	0.4	ug ml-1	PMID[557463]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.5	ug ml-1	PMID[557463]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.1	ug ml-1	PMID[557463]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.0	ug ml-1	PMID[557463]

☑ 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 NPC475873 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	235
0.1-0.2	1375
0.2-0.3	5006
0.3-0.4	8886
0.4-0.5	14611
0.5-0.6	7858
0.6-0.7	3637
0.7-0.8	983
0.8-0.85	87
0.85-0.9	13
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC474742
0.9485	High Similarity	NPC474747
0.9388	High Similarity	NPC475945
0.9388	High Similarity	NPC475871
0.9293	High Similarity	NPC474741
0.899	High Similarity	NPC47880
0.89	High Similarity	NPC149371
0.8866	High Similarity	NPC475900
0.88	High Similarity	NPC476270
0.8776	High Similarity	NPC476009
0.8725	High Similarity	NPC203659
0.8713	High Similarity	NPC225353
0.8627	High Similarity	NPC110989
0.8544	High Similarity	NPC472756
0.8532	High Similarity	NPC471145
0.8532	High Similarity	NPC471146
0.8469	Intermediate Similarity	NPC469692
0.8469	Intermediate Similarity	NPC469645
0.8431	Intermediate Similarity	NPC472753
0.8431	Intermediate Similarity	NPC164598
0.8431	Intermediate Similarity	NPC133907
0.8431	Intermediate Similarity	NPC185141
0.8431	Intermediate Similarity	NPC110443
0.8431	Intermediate Similarity	NPC128733
0.8431	Intermediate Similarity	NPC474339
0.8431	Intermediate Similarity	NPC46998
0.8431	Intermediate Similarity	NPC15993
0.8416	Intermediate Similarity	NPC471144
0.8384	Intermediate Similarity	NPC121825
0.8381	Intermediate Similarity	NPC26617
0.8367	Intermediate Similarity	NPC184463
0.8365	Intermediate Similarity	NPC100487
0.8351	Intermediate Similarity	NPC307411
0.835	Intermediate Similarity	NPC472754
0.835	Intermediate Similarity	NPC320019
0.835	Intermediate Similarity	NPC324017
0.8283	Intermediate Similarity	NPC475912
0.8283	Intermediate Similarity	NPC212486
0.8283	Intermediate Similarity	NPC476300
0.8269	Intermediate Similarity	NPC472755
0.8265	Intermediate Similarity	NPC51004
0.8252	Intermediate Similarity	NPC201718
0.8247	Intermediate Similarity	NPC202672
0.8235	Intermediate Similarity	NPC54843
0.8224	Intermediate Similarity	NPC38154
0.8218	Intermediate Similarity	NPC76862
0.8218	Intermediate Similarity	NPC158416
0.8218	Intermediate Similarity	NPC31645
0.8218	Intermediate Similarity	NPC476275
0.8218	Intermediate Similarity	NPC39859
0.8218	Intermediate Similarity	NPC470883
0.8208	Intermediate Similarity	NPC477513
0.8182	Intermediate Similarity	NPC208886
0.8182	Intermediate Similarity	NPC300312
0.8182	Intermediate Similarity	NPC111114
0.8182	Intermediate Similarity	NPC30515
0.8182	Intermediate Similarity	NPC261607
0.8182	Intermediate Similarity	NPC12172
0.8165	Intermediate Similarity	NPC66108
0.8163	Intermediate Similarity	NPC173926
0.8163	Intermediate Similarity	NPC474951
0.8155	Intermediate Similarity	NPC288876
0.8144	Intermediate Similarity	NPC190753
0.8137	Intermediate Similarity	NPC474313
0.8137	Intermediate Similarity	NPC169205
0.8137	Intermediate Similarity	NPC170143
0.8137	Intermediate Similarity	NPC213947
0.8137	Intermediate Similarity	NPC323421
0.8137	Intermediate Similarity	NPC328562
0.8137	Intermediate Similarity	NPC108475
0.8119	Intermediate Similarity	NPC14961
0.8119	Intermediate Similarity	NPC474947
0.8119	Intermediate Similarity	NPC36954
0.8119	Intermediate Similarity	NPC304886
0.8119	Intermediate Similarity	NPC48803
0.8119	Intermediate Similarity	NPC270013
0.8119	Intermediate Similarity	NPC275960
0.8119	Intermediate Similarity	NPC475659
0.8119	Intermediate Similarity	NPC193645
0.8119	Intermediate Similarity	NPC90121
0.8113	Intermediate Similarity	NPC243998
0.8113	Intermediate Similarity	NPC223450
0.81	Intermediate Similarity	NPC475302
0.81	Intermediate Similarity	NPC81419
0.81	Intermediate Similarity	NPC179746
0.81	Intermediate Similarity	NPC135776
0.8081	Intermediate Similarity	NPC49342
0.8081	Intermediate Similarity	NPC329857
0.8081	Intermediate Similarity	NPC62815
0.8081	Intermediate Similarity	NPC474761
0.8081	Intermediate Similarity	NPC469718
0.8081	Intermediate Similarity	NPC251385
0.8081	Intermediate Similarity	NPC476004
0.8061	Intermediate Similarity	NPC53158
0.8058	Intermediate Similarity	NPC141191
0.8041	Intermediate Similarity	NPC279859
0.8041	Intermediate Similarity	NPC38576
0.8039	Intermediate Similarity	NPC185553
0.8039	Intermediate Similarity	NPC473859
0.802	Intermediate Similarity	NPC474035
0.802	Intermediate Similarity	NPC167219
0.802	Intermediate Similarity	NPC81386
0.802	Intermediate Similarity	NPC477131
0.802	Intermediate Similarity	NPC190294
0.802	Intermediate Similarity	NPC469632
0.8	Intermediate Similarity	NPC150978
0.8	Intermediate Similarity	NPC123177
0.8	Intermediate Similarity	NPC20713
0.8	Intermediate Similarity	NPC70595
0.8	Intermediate Similarity	NPC471148
0.8	Intermediate Similarity	NPC133698
0.8	Intermediate Similarity	NPC74103
0.8	Intermediate Similarity	NPC86077
0.7982	Intermediate Similarity	NPC477103
0.7982	Intermediate Similarity	NPC5103
0.7981	Intermediate Similarity	NPC475949
0.7961	Intermediate Similarity	NPC40812
0.7959	Intermediate Similarity	NPC248602
0.7946	Intermediate Similarity	NPC270478
0.7946	Intermediate Similarity	NPC54739
0.7941	Intermediate Similarity	NPC163228
0.7941	Intermediate Similarity	NPC471142
0.7925	Intermediate Similarity	NPC475321
0.7925	Intermediate Similarity	NPC472747
0.7925	Intermediate Similarity	NPC472750
0.7925	Intermediate Similarity	NPC4620
0.7921	Intermediate Similarity	NPC60386
0.7921	Intermediate Similarity	NPC288240
0.7921	Intermediate Similarity	NPC473273
0.7921	Intermediate Similarity	NPC162205
0.7921	Intermediate Similarity	NPC308656
0.7921	Intermediate Similarity	NPC473234
0.7921	Intermediate Similarity	NPC295204
0.7921	Intermediate Similarity	NPC273579
0.7921	Intermediate Similarity	NPC473263
0.7909	Intermediate Similarity	NPC304180
0.7909	Intermediate Similarity	NPC179798
0.7905	Intermediate Similarity	NPC264477
0.7905	Intermediate Similarity	NPC171759
0.7905	Intermediate Similarity	NPC477511
0.79	Intermediate Similarity	NPC179394
0.79	Intermediate Similarity	NPC473619
0.79	Intermediate Similarity	NPC253144
0.79	Intermediate Similarity	NPC144133
0.789	Intermediate Similarity	NPC477102
0.7885	Intermediate Similarity	NPC187761
0.7885	Intermediate Similarity	NPC473326
0.7885	Intermediate Similarity	NPC83895
0.7879	Intermediate Similarity	NPC469631
0.7879	Intermediate Similarity	NPC153805
0.7879	Intermediate Similarity	NPC475906
0.7879	Intermediate Similarity	NPC476708
0.7879	Intermediate Similarity	NPC469628
0.7879	Intermediate Similarity	NPC471047
0.7879	Intermediate Similarity	NPC281516
0.7879	Intermediate Similarity	NPC469653
0.7864	Intermediate Similarity	NPC477921
0.7864	Intermediate Similarity	NPC17585
0.7864	Intermediate Similarity	NPC476315
0.7857	Intermediate Similarity	NPC261721
0.785	Intermediate Similarity	NPC471143
0.785	Intermediate Similarity	NPC472748
0.785	Intermediate Similarity	NPC477510
0.785	Intermediate Similarity	NPC475676
0.785	Intermediate Similarity	NPC220964
0.7845	Intermediate Similarity	NPC192309
0.7843	Intermediate Similarity	NPC198853
0.7822	Intermediate Similarity	NPC284185
0.7822	Intermediate Similarity	NPC131209
0.7822	Intermediate Similarity	NPC473321
0.7818	Intermediate Similarity	NPC257240
0.781	Intermediate Similarity	NPC477512
0.78	Intermediate Similarity	NPC295312
0.78	Intermediate Similarity	NPC151770
0.78	Intermediate Similarity	NPC474032
0.78	Intermediate Similarity	NPC32922
0.7798	Intermediate Similarity	NPC475960
0.7788	Intermediate Similarity	NPC471150
0.7778	Intermediate Similarity	NPC160138
0.7778	Intermediate Similarity	NPC186148
0.7778	Intermediate Similarity	NPC179659
0.7778	Intermediate Similarity	NPC16313
0.7778	Intermediate Similarity	NPC473802
0.7778	Intermediate Similarity	NPC9303
0.7778	Intermediate Similarity	NPC118601
0.7778	Intermediate Similarity	NPC1538
0.7778	Intermediate Similarity	NPC54737
0.7778	Intermediate Similarity	NPC472751
0.7778	Intermediate Similarity	NPC231889
0.7778	Intermediate Similarity	NPC42747
0.7778	Intermediate Similarity	NPC472749
0.7768	Intermediate Similarity	NPC469454
0.7768	Intermediate Similarity	NPC469496
0.7768	Intermediate Similarity	NPC106395
0.7768	Intermediate Similarity	NPC469463
0.7768	Intermediate Similarity	NPC46269
0.7768	Intermediate Similarity	NPC56448
0.7767	Intermediate Similarity	NPC474490
0.7767	Intermediate Similarity	NPC107476
0.7767	Intermediate Similarity	NPC477922

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 NPC475873 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	1978
0.2-0.3	3743
0.3-0.4	2080
0.4-0.5	757
0.5-0.6	267
0.6-0.7	96
0.7-0.8	8
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8381	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8119	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6371	Approved
0.7576	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5282	Discontinued
0.7308	Intermediate Similarity	NPD7983	Approved
0.7282	Intermediate Similarity	NPD1695	Approved
0.7212	Intermediate Similarity	NPD6698	Approved
0.7212	Intermediate Similarity	NPD46	Approved
0.7064	Intermediate Similarity	NPD4225	Approved
0.7048	Intermediate Similarity	NPD7838	Discovery
0.7048	Intermediate Similarity	NPD5785	Approved
0.699	Remote Similarity	NPD5786	Approved
0.6983	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6319	Approved
0.6923	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5779	Approved
0.6916	Remote Similarity	NPD5778	Approved
0.6893	Remote Similarity	NPD5363	Approved
0.687	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7115	Discovery
0.6832	Remote Similarity	NPD5369	Approved
0.6765	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8513	Phase 3
0.6748	Remote Similarity	NPD8516	Approved
0.6748	Remote Similarity	NPD8515	Approved
0.6748	Remote Similarity	NPD8517	Approved
0.6724	Remote Similarity	NPD6686	Approved
0.6723	Remote Similarity	NPD4632	Approved
0.672	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6639	Remote Similarity	NPD6053	Discontinued
0.6637	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6614	Remote Similarity	NPD7078	Approved
0.6613	Remote Similarity	NPD6016	Approved
0.6613	Remote Similarity	NPD6015	Approved
0.6607	Remote Similarity	NPD5696	Approved
0.6602	Remote Similarity	NPD4269	Approved
0.6602	Remote Similarity	NPD6435	Approved
0.6602	Remote Similarity	NPD4270	Approved
0.6571	Remote Similarity	NPD1694	Approved
0.6562	Remote Similarity	NPD7736	Approved
0.656	Remote Similarity	NPD5988	Approved
0.656	Remote Similarity	NPD6370	Approved
0.6555	Remote Similarity	NPD6650	Approved
0.6555	Remote Similarity	NPD6649	Approved
0.6514	Remote Similarity	NPD6411	Approved
0.6508	Remote Similarity	NPD7642	Approved
0.65	Remote Similarity	NPD8297	Approved
0.6496	Remote Similarity	NPD5697	Approved
0.6484	Remote Similarity	NPD8074	Phase 3
0.6471	Remote Similarity	NPD4634	Approved
0.6442	Remote Similarity	NPD5209	Approved
0.6441	Remote Similarity	NPD6881	Approved
0.6441	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD7839	Suspended
0.6423	Remote Similarity	NPD6009	Approved
0.6417	Remote Similarity	NPD2204	Approved
0.6408	Remote Similarity	NPD5368	Approved
0.6408	Remote Similarity	NPD4252	Approved
0.6404	Remote Similarity	NPD6648	Approved
0.64	Remote Similarity	NPD6059	Approved
0.6387	Remote Similarity	NPD6012	Approved
0.6387	Remote Similarity	NPD6372	Approved
0.6387	Remote Similarity	NPD6013	Approved
0.6387	Remote Similarity	NPD6373	Approved
0.6387	Remote Similarity	NPD6014	Approved
0.6381	Remote Similarity	NPD6110	Phase 1
0.6381	Remote Similarity	NPD7154	Phase 3
0.6378	Remote Similarity	NPD8328	Phase 3
0.6364	Remote Similarity	NPD6845	Suspended
0.6357	Remote Similarity	NPD8293	Discontinued
0.6355	Remote Similarity	NPD4249	Approved
0.6349	Remote Similarity	NPD8444	Approved
0.6349	Remote Similarity	NPD5983	Phase 2
0.6339	Remote Similarity	NPD5695	Phase 3
0.6339	Remote Similarity	NPD4629	Approved
0.6339	Remote Similarity	NPD5210	Approved
0.6333	Remote Similarity	NPD7290	Approved
0.6333	Remote Similarity	NPD6883	Approved
0.6333	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7102	Approved
0.6303	Remote Similarity	NPD6011	Approved
0.6296	Remote Similarity	NPD4251	Approved
0.6296	Remote Similarity	NPD4250	Approved
0.6286	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6847	Approved
0.6281	Remote Similarity	NPD6869	Approved
0.6281	Remote Similarity	NPD6617	Approved
0.6281	Remote Similarity	NPD8130	Phase 1
0.6271	Remote Similarity	NPD5739	Approved
0.6271	Remote Similarity	NPD6402	Approved
0.6271	Remote Similarity	NPD7128	Approved
0.6271	Remote Similarity	NPD6675	Approved
0.6271	Remote Similarity	NPD6008	Approved
0.626	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD7829	Approved
0.625	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7830	Approved
0.625	Remote Similarity	NPD7604	Phase 2
0.624	Remote Similarity	NPD7641	Discontinued
0.623	Remote Similarity	NPD6882	Approved
0.6228	Remote Similarity	NPD6083	Phase 2
0.6228	Remote Similarity	NPD6084	Phase 2
0.6226	Remote Similarity	NPD5362	Discontinued
0.622	Remote Similarity	NPD6921	Approved
0.6218	Remote Similarity	NPD5701	Approved
0.6174	Remote Similarity	NPD7638	Approved
0.6172	Remote Similarity	NPD8080	Discontinued
0.6167	Remote Similarity	NPD7320	Approved
0.6161	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD8451	Approved
0.6154	Remote Similarity	NPD7507	Approved
0.6154	Remote Similarity	NPD8273	Phase 1
0.6154	Remote Similarity	NPD5211	Phase 2
0.6154	Remote Similarity	NPD6336	Discontinued
0.6121	Remote Similarity	NPD4696	Approved
0.6121	Remote Similarity	NPD7640	Approved
0.6121	Remote Similarity	NPD5285	Approved
0.6121	Remote Similarity	NPD5286	Approved
0.6121	Remote Similarity	NPD7639	Approved
0.6107	Remote Similarity	NPD8448	Approved
0.6095	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4820	Approved
0.6095	Remote Similarity	NPD4822	Approved
0.6095	Remote Similarity	NPD4819	Approved
0.6095	Remote Similarity	NPD4821	Approved
0.6083	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6412	Phase 2
0.6071	Remote Similarity	NPD5693	Phase 1
0.6071	Remote Similarity	NPD7637	Suspended
0.6058	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.605	Remote Similarity	NPD5141	Approved
0.6032	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5225	Approved
0.6017	Remote Similarity	NPD5226	Approved
0.6017	Remote Similarity	NPD4633	Approved
0.6017	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5221	Approved
0.597	Remote Similarity	NPD5956	Approved
0.597	Remote Similarity	NPD8390	Approved
0.597	Remote Similarity	NPD8392	Approved
0.597	Remote Similarity	NPD8391	Approved
0.5969	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD5174	Approved
0.5966	Remote Similarity	NPD5175	Approved
0.5963	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4756	Discovery
0.5954	Remote Similarity	NPD8299	Approved
0.5954	Remote Similarity	NPD8342	Approved
0.5954	Remote Similarity	NPD8340	Approved
0.5954	Remote Similarity	NPD8341	Approved
0.5952	Remote Similarity	NPD6274	Approved
0.5948	Remote Similarity	NPD4755	Approved
0.5948	Remote Similarity	NPD7902	Approved
0.5948	Remote Similarity	NPD5173	Approved
0.5946	Remote Similarity	NPD5737	Approved
0.5946	Remote Similarity	NPD6672	Approved
0.5943	Remote Similarity	NPD4695	Discontinued
0.594	Remote Similarity	NPD6033	Approved
0.5938	Remote Similarity	NPD7100	Approved
0.5938	Remote Similarity	NPD7101	Approved
0.5932	Remote Similarity	NPD5223	Approved
0.5918	Remote Similarity	NPD7331	Phase 2
0.5906	Remote Similarity	NPD6317	Approved
0.5906	Remote Similarity	NPD7500	Approved
0.5905	Remote Similarity	NPD4268	Approved
0.5905	Remote Similarity	NPD4271	Approved
0.5893	Remote Similarity	NPD5370	Suspended
0.5893	Remote Similarity	NPD4753	Phase 2
0.5887	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD3197	Phase 1
0.5859	Remote Similarity	NPD6313	Approved
0.5859	Remote Similarity	NPD6314	Approved
0.5859	Remote Similarity	NPD6335	Approved
0.5856	Remote Similarity	NPD3573	Approved
0.5847	Remote Similarity	NPD4700	Approved
0.5846	Remote Similarity	NPD8268	Approved
0.5846	Remote Similarity	NPD8269	Approved
0.5846	Remote Similarity	NPD8266	Approved
0.5846	Remote Similarity	NPD8267	Approved
0.5827	Remote Similarity	NPD6868	Approved
0.5826	Remote Similarity	NPD7748	Approved
0.5816	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7341	Phase 2
0.5814	Remote Similarity	NPD4522	Approved
0.5797	Remote Similarity	NPD8415	Approved
0.5789	Remote Similarity	NPD5694	Approved
0.5789	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5284	Approved
0.5789	Remote Similarity	NPD6079	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