NPASS Compound

Structure

NPC476267 OpenBabel07101719512D 24 27 0 0 1 0 0 0 0 0999 V2000 -3.4149 -3.9019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3174 -2.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6401 -0.7774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7165 -3.7650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7671 -1.7230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6334 -0.9430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1170 -2.9850 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4005 -2.3399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2004 -3.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7671 -2.6871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6334 -3.4671 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2001 -1.7230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2004 -0.9430 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2001 -2.6871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6837 -2.2050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2580 -2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7165 -0.6451 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2001 -1.3969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6477 -2.2050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2240 -1.8381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6840 -2.9850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1749 -2.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1170 -1.4251 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 2 8 1 0 0 0 0 3 17 1 0 0 0 0 4 9 2 0 0 0 0 5 10 1 0 0 0 0 5 13 1 0 0 0 0 6 17 1 0 0 0 0 7 1 1 1 0 0 0 7 14 1 0 0 0 0 7 15 1 0 0 0 0 8 18 2 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 21 1 6 0 0 0 11 4 1 6 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 6 1 1 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 1 0 0 0 13 24 1 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.12
Volume:	319.348
LogP:	2.102
LogD:	1.8
LogS:	-3.177
# Rotatable Bonds:	2
TPSA:	98.5
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.62
Synthetic Accessibility Score:	5.988
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.895
MDCK Permeability:	7.582338730571792e-05
Pgp-inhibitor:	0.165
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22
Plasma Protein Binding (PPB):	49.327598571777344%
Volume Distribution (VD):	0.638
Pgp-substrate:	44.29841232299805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.107
CYP3A4-substrate:	0.45

ADMET: Excretion

Clearance (CL):	12.728
Half-life (T1/2):	0.329

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.683
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.132
Rat Oral Acute Toxicity:	0.872
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.481
Carcinogencity:	0.861
Eye Corrosion:	0.016
Eye Irritation:	0.024
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC476267

Natural Product ID:	NPC476267
*Common Name:**	ALQWQVLQHXAWBI-RZGXMFIVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ALQWQVLQHXAWBI-RZGXMFIVSA-N
Standard InCHI:	InChI=1S/C17H20O7/c1-7-14-11-4-9(16(20)22-11)10(21-8(2)18)5-13-17(3,24-13)6-12(14)23-15(7)19/h4,7,10-14H,5-6H2,1-3H3/t7-,10+,11-,12+,13+,14+,17+/m1/s1
SMILES:	CC1C2C(CC3(C(O3)CC(C4=CC2OC4=O)OC(=O)C)C)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559846
PubChem CID:	45267061
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO24708	Mikania micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19267453]
NPO24708	Mikania micrantha	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
IC50	3
Others	5

Activity Type	# Activity
Cell Line	1
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	TC50	=	186.0	uM	PMID[554488]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	IC50	=	61900.0	nM	PMID[554488]
NPT27	Others	Unspecified		TC50	=	186.0	uM	PMID[554488]
NPT27	Others	Unspecified		TI	=	3.0	n.a.	PMID[554488]
NPT336	Organism	Human parainfluenza virus 3	Human parainfluenza virus 3	IC50	=	186300.0	nM	PMID[554488]
NPT27	Others	Unspecified		TI	=	1.0	n.a.	PMID[554488]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	186000.0	nM	PMID[554488]

☑ 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 NPC476267 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	253
0.1-0.2	1590
0.2-0.3	5945
0.3-0.4	11744
0.4-0.5	12707
0.5-0.6	6416
0.6-0.7	3042
0.7-0.8	865
0.8-0.85	86
0.85-0.9	38
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC140543
0.9655	High Similarity	NPC312042
0.9348	High Similarity	NPC208233
0.9333	High Similarity	NPC473330
0.9333	High Similarity	NPC473316
0.9318	High Similarity	NPC166919
0.913	High Similarity	NPC35498
0.9091	High Similarity	NPC475703
0.8977	High Similarity	NPC50637
0.8913	High Similarity	NPC471147
0.8889	High Similarity	NPC151770
0.8842	High Similarity	NPC288876
0.8817	High Similarity	NPC475659
0.875	High Similarity	NPC264477
0.875	High Similarity	NPC477511
0.8737	High Similarity	NPC473326
0.8737	High Similarity	NPC279561
0.8723	High Similarity	NPC230800
0.8723	High Similarity	NPC473859
0.8723	High Similarity	NPC17585
0.8696	High Similarity	NPC20713
0.8667	High Similarity	NPC231889
0.8636	High Similarity	NPC272814
0.8602	High Similarity	NPC475838
0.8602	High Similarity	NPC125674
0.8602	High Similarity	NPC228451
0.8587	High Similarity	NPC62815
0.8587	High Similarity	NPC475748
0.8556	High Similarity	NPC284902
0.8511	High Similarity	NPC474247
0.8485	Intermediate Similarity	NPC471143
0.8485	Intermediate Similarity	NPC477510
0.8478	Intermediate Similarity	NPC475971
0.8454	Intermediate Similarity	NPC477512
0.8444	Intermediate Similarity	NPC38468
0.8444	Intermediate Similarity	NPC474547
0.8444	Intermediate Similarity	NPC50362
0.8444	Intermediate Similarity	NPC319795
0.8438	Intermediate Similarity	NPC471140
0.8409	Intermediate Similarity	NPC141810
0.8387	Intermediate Similarity	NPC251385
0.8387	Intermediate Similarity	NPC49342
0.837	Intermediate Similarity	NPC475902
0.837	Intermediate Similarity	NPC469653
0.837	Intermediate Similarity	NPC475906
0.837	Intermediate Similarity	NPC471047
0.837	Intermediate Similarity	NPC469631
0.837	Intermediate Similarity	NPC469628
0.8367	Intermediate Similarity	NPC474339
0.8367	Intermediate Similarity	NPC164598
0.8333	Intermediate Similarity	NPC476275
0.8333	Intermediate Similarity	NPC279621
0.8317	Intermediate Similarity	NPC477513
0.8316	Intermediate Similarity	NPC57405
0.8316	Intermediate Similarity	NPC303942
0.83	Intermediate Similarity	NPC474741
0.8298	Intermediate Similarity	NPC284185
0.8283	Intermediate Similarity	NPC149371
0.828	Intermediate Similarity	NPC295312
0.8242	Intermediate Similarity	NPC215364
0.8229	Intermediate Similarity	NPC471142
0.8229	Intermediate Similarity	NPC14961
0.8229	Intermediate Similarity	NPC471141
0.8229	Intermediate Similarity	NPC270013
0.8222	Intermediate Similarity	NPC475947
0.8222	Intermediate Similarity	NPC170377
0.8211	Intermediate Similarity	NPC212486
0.8202	Intermediate Similarity	NPC207188
0.8191	Intermediate Similarity	NPC253144
0.8191	Intermediate Similarity	NPC475855
0.8191	Intermediate Similarity	NPC144133
0.8191	Intermediate Similarity	NPC179394
0.8191	Intermediate Similarity	NPC329857
0.8191	Intermediate Similarity	NPC469718
0.8182	Intermediate Similarity	NPC47880
0.8182	Intermediate Similarity	NPC201718
0.8182	Intermediate Similarity	NPC617
0.8163	Intermediate Similarity	NPC471144
0.8161	Intermediate Similarity	NPC474760
0.8152	Intermediate Similarity	NPC204048
0.8144	Intermediate Similarity	NPC476315
0.8132	Intermediate Similarity	NPC138647
0.8132	Intermediate Similarity	NPC470238
0.8125	Intermediate Similarity	NPC81386
0.8125	Intermediate Similarity	NPC477131
0.8125	Intermediate Similarity	NPC474035
0.8105	Intermediate Similarity	NPC300312
0.8105	Intermediate Similarity	NPC111114
0.8105	Intermediate Similarity	NPC150978
0.8105	Intermediate Similarity	NPC261607
0.8105	Intermediate Similarity	NPC74103
0.8105	Intermediate Similarity	NPC70595
0.8105	Intermediate Similarity	NPC123177
0.81	Intermediate Similarity	NPC471148
0.809	Intermediate Similarity	NPC474510
0.8085	Intermediate Similarity	NPC78008
0.8085	Intermediate Similarity	NPC4986
0.8081	Intermediate Similarity	NPC475949
0.8065	Intermediate Similarity	NPC160138
0.8065	Intermediate Similarity	NPC5130
0.8065	Intermediate Similarity	NPC266957
0.8061	Intermediate Similarity	NPC471462
0.8041	Intermediate Similarity	NPC477922
0.8041	Intermediate Similarity	NPC304886
0.8041	Intermediate Similarity	NPC474947
0.8039	Intermediate Similarity	NPC243998
0.8039	Intermediate Similarity	NPC223450
0.8022	Intermediate Similarity	NPC318468
0.8022	Intermediate Similarity	NPC475989
0.8021	Intermediate Similarity	NPC476300
0.8021	Intermediate Similarity	NPC135776
0.8021	Intermediate Similarity	NPC179746
0.8021	Intermediate Similarity	NPC81419
0.8021	Intermediate Similarity	NPC475912
0.8021	Intermediate Similarity	NPC165383
0.802	Intermediate Similarity	NPC475871
0.802	Intermediate Similarity	NPC475945
0.802	Intermediate Similarity	NPC110989
0.8	Intermediate Similarity	NPC474742
0.8	Intermediate Similarity	NPC473619
0.8	Intermediate Similarity	NPC80875
0.8	Intermediate Similarity	NPC51004
0.798	Intermediate Similarity	NPC474213
0.7979	Intermediate Similarity	NPC202672
0.7979	Intermediate Similarity	NPC476805
0.7979	Intermediate Similarity	NPC224652
0.7978	Intermediate Similarity	NPC270126
0.7959	Intermediate Similarity	NPC301596
0.7959	Intermediate Similarity	NPC477921
0.7959	Intermediate Similarity	NPC299396
0.7959	Intermediate Similarity	NPC172998
0.7957	Intermediate Similarity	NPC107787
0.7957	Intermediate Similarity	NPC475461
0.7957	Intermediate Similarity	NPC305475
0.7957	Intermediate Similarity	NPC261253
0.7957	Intermediate Similarity	NPC122502
0.7957	Intermediate Similarity	NPC474045
0.7957	Intermediate Similarity	NPC64153
0.7957	Intermediate Similarity	NPC469676
0.7955	Intermediate Similarity	NPC141789
0.7955	Intermediate Similarity	NPC171204
0.7955	Intermediate Similarity	NPC476028
0.7941	Intermediate Similarity	NPC203659
0.7941	Intermediate Similarity	NPC100487
0.7938	Intermediate Similarity	NPC469632
0.7938	Intermediate Similarity	NPC474338
0.7921	Intermediate Similarity	NPC474747
0.7921	Intermediate Similarity	NPC225353
0.7917	Intermediate Similarity	NPC208886
0.7917	Intermediate Similarity	NPC184463
0.7917	Intermediate Similarity	NPC133698
0.7917	Intermediate Similarity	NPC30515
0.7917	Intermediate Similarity	NPC473321
0.7917	Intermediate Similarity	NPC12172
0.7912	Intermediate Similarity	NPC173609
0.79	Intermediate Similarity	NPC469551
0.7895	Intermediate Similarity	NPC474032
0.7895	Intermediate Similarity	NPC307411
0.7889	Intermediate Similarity	NPC281132
0.7889	Intermediate Similarity	NPC223904
0.7879	Intermediate Similarity	NPC213947
0.7879	Intermediate Similarity	NPC108475
0.7879	Intermediate Similarity	NPC170143
0.7865	Intermediate Similarity	NPC128276
0.7857	Intermediate Similarity	NPC67584
0.7857	Intermediate Similarity	NPC273197
0.7857	Intermediate Similarity	NPC234339
0.7857	Intermediate Similarity	NPC36954
0.7849	Intermediate Similarity	NPC78089
0.7849	Intermediate Similarity	NPC235792
0.7849	Intermediate Similarity	NPC255307
0.7849	Intermediate Similarity	NPC470755
0.7843	Intermediate Similarity	NPC19239
0.7843	Intermediate Similarity	NPC474166
0.7841	Intermediate Similarity	NPC235906
0.7841	Intermediate Similarity	NPC123360
0.7835	Intermediate Similarity	NPC475302
0.7835	Intermediate Similarity	NPC295204
0.7835	Intermediate Similarity	NPC273579
0.7835	Intermediate Similarity	NPC288240
0.7835	Intermediate Similarity	NPC162205
0.7835	Intermediate Similarity	NPC475657
0.7826	Intermediate Similarity	NPC474472
0.7826	Intermediate Similarity	NPC474703
0.7826	Intermediate Similarity	NPC53867
0.7826	Intermediate Similarity	NPC257358
0.7822	Intermediate Similarity	NPC476270
0.7822	Intermediate Similarity	NPC171759
0.7812	Intermediate Similarity	NPC469368
0.7812	Intermediate Similarity	NPC473448
0.7812	Intermediate Similarity	NPC71533
0.7812	Intermediate Similarity	NPC106510
0.781	Intermediate Similarity	NPC38154
0.7802	Intermediate Similarity	NPC25684
0.7802	Intermediate Similarity	NPC471325
0.7802	Intermediate Similarity	NPC301477
0.7802	Intermediate Similarity	NPC281949
0.78	Intermediate Similarity	NPC54843
0.78	Intermediate Similarity	NPC141191
0.78	Intermediate Similarity	NPC221615

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 NPC476267 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	2188
0.2-0.3	4014
0.3-0.4	1845
0.4-0.5	545
0.5-0.6	270
0.6-0.7	49
0.7-0.8	4
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8444	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD1695	Approved
0.7677	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6698	Approved
0.7273	Intermediate Similarity	NPD46	Approved
0.7248	Intermediate Similarity	NPD6371	Approved
0.7158	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5282	Discontinued
0.7037	Intermediate Similarity	NPD6008	Approved
0.6979	Remote Similarity	NPD5209	Approved
0.6939	Remote Similarity	NPD1694	Approved
0.6931	Remote Similarity	NPD7838	Discovery
0.6897	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7983	Approved
0.6818	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6053	Discontinued
0.6796	Remote Similarity	NPD5779	Approved
0.6796	Remote Similarity	NPD5778	Approved
0.6765	Remote Similarity	NPD5785	Approved
0.6757	Remote Similarity	NPD6686	Approved
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4225	Approved
0.66	Remote Similarity	NPD5363	Approved
0.6574	Remote Similarity	NPD6648	Approved
0.6549	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4249	Approved
0.6535	Remote Similarity	NPD5786	Approved
0.6514	Remote Similarity	NPD5344	Discontinued
0.6471	Remote Similarity	NPD4250	Approved
0.6471	Remote Similarity	NPD4251	Approved
0.6465	Remote Similarity	NPD6435	Approved
0.6441	Remote Similarity	NPD7115	Discovery
0.6436	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7319	Approved
0.6364	Remote Similarity	NPD8513	Phase 3
0.6364	Remote Similarity	NPD8516	Approved
0.6364	Remote Similarity	NPD5369	Approved
0.6364	Remote Similarity	NPD8517	Approved
0.6364	Remote Similarity	NPD8515	Approved
0.6346	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6101	Approved
0.633	Remote Similarity	NPD7638	Approved
0.633	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4269	Approved
0.63	Remote Similarity	NPD4270	Approved
0.6296	Remote Similarity	NPD7839	Suspended
0.6293	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7507	Approved
0.6273	Remote Similarity	NPD7639	Approved
0.6273	Remote Similarity	NPD7640	Approved
0.6263	Remote Similarity	NPD5368	Approved
0.626	Remote Similarity	NPD7642	Approved
0.6238	Remote Similarity	NPD5362	Discontinued
0.6238	Remote Similarity	NPD7154	Phase 3
0.6226	Remote Similarity	NPD6411	Approved
0.621	Remote Similarity	NPD7492	Approved
0.6204	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6616	Approved
0.6148	Remote Similarity	NPD6054	Approved
0.6148	Remote Similarity	NPD6319	Approved
0.6129	Remote Similarity	NPD7830	Approved
0.6129	Remote Similarity	NPD7829	Approved
0.6111	Remote Similarity	NPD8074	Phase 3
0.6111	Remote Similarity	NPD7078	Approved
0.61	Remote Similarity	NPD4819	Approved
0.61	Remote Similarity	NPD4252	Approved
0.61	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4822	Approved
0.61	Remote Similarity	NPD4820	Approved
0.61	Remote Similarity	NPD4821	Approved
0.6098	Remote Similarity	NPD6016	Approved
0.6098	Remote Similarity	NPD6015	Approved
0.6095	Remote Similarity	NPD6903	Approved
0.6087	Remote Similarity	NPD5697	Approved
0.6082	Remote Similarity	NPD8039	Approved
0.6075	Remote Similarity	NPD5693	Phase 1
0.6063	Remote Similarity	NPD7736	Approved
0.6058	Remote Similarity	NPD6684	Approved
0.6058	Remote Similarity	NPD7146	Approved
0.6058	Remote Similarity	NPD6409	Approved
0.6058	Remote Similarity	NPD7334	Approved
0.6058	Remote Similarity	NPD5330	Approved
0.6058	Remote Similarity	NPD7521	Approved
0.6048	Remote Similarity	NPD6370	Approved
0.6048	Remote Similarity	NPD5988	Approved
0.6034	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6881	Approved
0.6034	Remote Similarity	NPD7320	Approved
0.6034	Remote Similarity	NPD6899	Approved
0.6017	Remote Similarity	NPD6650	Approved
0.6017	Remote Similarity	NPD2204	Approved
0.6017	Remote Similarity	NPD6649	Approved
0.6016	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.5984	Remote Similarity	NPD8293	Discontinued
0.5983	Remote Similarity	NPD6014	Approved
0.5983	Remote Similarity	NPD6372	Approved
0.5983	Remote Similarity	NPD6012	Approved
0.5983	Remote Similarity	NPD6013	Approved
0.5983	Remote Similarity	NPD6373	Approved
0.5981	Remote Similarity	NPD5207	Approved
0.598	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6001	Approved
0.5963	Remote Similarity	NPD7900	Approved
0.5963	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD5701	Approved
0.5943	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6672	Approved
0.5943	Remote Similarity	NPD5737	Approved
0.5932	Remote Similarity	NPD7290	Approved
0.5932	Remote Similarity	NPD6883	Approved
0.5932	Remote Similarity	NPD7102	Approved
0.5926	Remote Similarity	NPD7637	Suspended
0.5917	Remote Similarity	NPD4632	Approved
0.5909	Remote Similarity	NPD5695	Phase 3
0.59	Remote Similarity	NPD4268	Approved
0.59	Remote Similarity	NPD4271	Approved
0.59	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6011	Approved
0.5893	Remote Similarity	NPD5696	Approved
0.5882	Remote Similarity	NPD8130	Phase 1
0.5882	Remote Similarity	NPD6847	Approved
0.5882	Remote Similarity	NPD6869	Approved
0.5882	Remote Similarity	NPD6617	Approved
0.5872	Remote Similarity	NPD6399	Phase 3
0.5833	Remote Similarity	NPD6882	Approved
0.5833	Remote Similarity	NPD8297	Approved
0.5804	Remote Similarity	NPD7902	Approved
0.5804	Remote Similarity	NPD6083	Phase 2
0.5804	Remote Similarity	NPD6084	Phase 2
0.5802	Remote Similarity	NPD7260	Phase 2
0.5798	Remote Similarity	NPD4634	Approved
0.5781	Remote Similarity	NPD8273	Phase 1
0.5781	Remote Similarity	NPD8451	Approved
0.5772	Remote Similarity	NPD6009	Approved
0.5769	Remote Similarity	NPD5332	Approved
0.5769	Remote Similarity	NPD5331	Approved
0.5758	Remote Similarity	NPD6845	Suspended
0.5748	Remote Similarity	NPD7604	Phase 2
0.5748	Remote Similarity	NPD8328	Phase 3
0.5745	Remote Similarity	NPD7331	Phase 2
0.5741	Remote Similarity	NPD6080	Approved
0.5741	Remote Similarity	NPD6904	Approved
0.5741	Remote Similarity	NPD6673	Approved
0.5741	Remote Similarity	NPD6051	Approved
0.5739	Remote Similarity	NPD7632	Discontinued
0.5739	Remote Similarity	NPD5211	Phase 2
0.5736	Remote Similarity	NPD8448	Approved
0.5728	Remote Similarity	NPD4790	Discontinued
0.5726	Remote Similarity	NPD7328	Approved
0.5726	Remote Similarity	NPD7327	Approved
0.5714	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5983	Phase 2
0.5702	Remote Similarity	NPD5285	Approved
0.5702	Remote Similarity	NPD5286	Approved
0.5702	Remote Similarity	NPD4696	Approved
0.5692	Remote Similarity	NPD8337	Approved
0.5692	Remote Similarity	NPD8336	Approved
0.5691	Remote Similarity	NPD6274	Approved
0.5688	Remote Similarity	NPD5692	Phase 3
0.568	Remote Similarity	NPD7516	Approved
0.5678	Remote Similarity	NPD6412	Phase 2
0.5676	Remote Similarity	NPD7748	Approved
0.5667	Remote Similarity	NPD2067	Discontinued
0.5664	Remote Similarity	NPD4755	Approved
0.5648	Remote Similarity	NPD5208	Approved
0.5641	Remote Similarity	NPD5141	Approved
0.5638	Remote Similarity	NPD7341	Phase 2
0.5638	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD5694	Approved
0.5636	Remote Similarity	NPD5284	Approved
0.5636	Remote Similarity	NPD5281	Approved
0.5636	Remote Similarity	NPD6050	Approved
0.5635	Remote Similarity	NPD8377	Approved
0.5635	Remote Similarity	NPD8294	Approved
0.5625	Remote Similarity	NPD229	Approved
0.562	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6110	Phase 1
0.5607	Remote Similarity	NPD6422	Discontinued
0.5607	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD8391	Approved
0.5606	Remote Similarity	NPD8390	Approved
0.5606	Remote Similarity	NPD8392	Approved
0.5603	Remote Similarity	NPD5226	Approved
0.5603	Remote Similarity	NPD4633	Approved
0.5603	Remote Similarity	NPD5225	Approved
0.5603	Remote Similarity	NPD5224	Approved
0.56	Remote Similarity	NPD7641	Discontinued

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