NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.1
Volume:	273.096
LogP:	0.499
LogD:	0.842
LogS:	-2.462
# Rotatable Bonds:	1
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	5.036
Fsp3:	0.467
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:	-5.09
MDCK Permeability:	2.881831824197434e-05
Pgp-inhibitor:	0.185
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.202
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.889

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	67.4960708618164%
Volume Distribution (VD):	0.951
Pgp-substrate:	31.086978912353516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.425
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.405
CYP2C9-inhibitor:	0.15
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.094
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.848
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	3.583
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.629
Drug-inuced Liver Injury (DILI):	0.201
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.881
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.664
Carcinogencity:	0.23
Eye Corrosion:	0.658
Eye Irritation:	0.582
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC165528

Natural Product ID:	NPC165528
*Common Name:**	Vernolepin
IUPAC Name:	(3aR,4S,5aR,9aR,9bR)-5a-ethenyl-4-hydroxy-3,9-dimethylidene-3a,4,5,6,9a,9b-hexahydrofuro[2,3-f]isochromene-2,8-dione
Synonyms:	Vernolepin
Standard InCHIKey:	IFYQXAXVZGMFNW-MVIRXUPPSA-N
Standard InCHI:	InChI=1S/C15H16O5/c1-4-15-5-9(16)10-7(2)14(18)20-12(10)11(15)8(3)13(17)19-6-15/h4,9-12,16H,1-3,5-6H2/t9-,10+,11+,12-,15+/m0/s1
SMILES:	C=C[C@]12COC(=O)C(=C)[C@@H]2[C@@H]2[C@@H]([C@H](C1)O)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL290210
PubChem CID:	442322
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]
NPO7207	Vernonia esculenta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31511	Vernonia flexuosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7207	Vernonia esculenta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27182	Chrysolaena flexuosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7207	Vernonia esculenta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27182	Chrysolaena flexuosa	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	2
IC50	5
Kd	1
Others	8

Activity Type	# Activity
Cell Line	9
Others	2
Tissue	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3500.0	nM	PMID[494558]
NPT4189	Cell Line	GH3	Rattus norvegicus	IC50	=	5200.0	nM	PMID[494558]
NPT91	Cell Line	KB	Homo sapiens	pED50	=	5.19	n.a.	PMID[494559]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.8	ug ml-1	PMID[494559]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	6.52	umol/L	PMID[494561]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	ID50	=	0.043	uM	PMID[494562]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	16900.0	nM	PMID[494563]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2200.0	nM	PMID[494563]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	1900.0	nM	PMID[494563]
NPT548	Tissue	Ileum	Cavia porcellus	Activity	<	40.0	%	PMID[494560]
NPT548	Tissue	Ileum	Cavia porcellus	Activity	<	20.0	%	PMID[494560]
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	>	50.0	%	PMID[494560]
NPT548	Tissue	Ileum	Cavia porcellus	Kd	=	2454.71	nM	PMID[494560]
NPT35	Others	n.a.		K	=	200.0	/M/s	PMID[494564]
NPT35	Others	n.a.		Drug recovery	=	75.0	%	PMID[494564]

☑ 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 NPC165528 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	205
0.1-0.2	1300
0.2-0.3	4394
0.3-0.4	7509
0.4-0.5	13782
0.5-0.6	6491
0.6-0.7	6700
0.7-0.8	2119
0.8-0.85	136
0.85-0.9	34
0.9-0.95	21
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC228766
0.957	High Similarity	NPC242666
0.9468	High Similarity	NPC164551
0.9348	High Similarity	NPC284518
0.9341	High Similarity	NPC225474
0.9341	High Similarity	NPC148000
0.9341	High Similarity	NPC473434
0.9341	High Similarity	NPC474841
0.9341	High Similarity	NPC471446
0.9341	High Similarity	NPC469596
0.9239	High Similarity	NPC259042
0.9239	High Similarity	NPC157686
0.9158	High Similarity	NPC111292
0.9149	High Similarity	NPC216478
0.914	High Similarity	NPC93245
0.913	High Similarity	NPC24861
0.9053	High Similarity	NPC47024
0.9043	High Similarity	NPC473963
0.9011	High Similarity	NPC153853
0.8958	High Similarity	NPC475958
0.8958	High Similarity	NPC308824
0.8947	High Similarity	NPC476807
0.8947	High Similarity	NPC476806
0.8936	High Similarity	NPC473964
0.8901	High Similarity	NPC116620
0.8842	High Similarity	NPC136781
0.8804	High Similarity	NPC475776
0.8776	High Similarity	NPC156681
0.8696	High Similarity	NPC194642
0.8681	High Similarity	NPC305029
0.8632	High Similarity	NPC90014
0.8586	High Similarity	NPC61442
0.8571	High Similarity	NPC85698
0.8529	High Similarity	NPC474243
0.8515	High Similarity	NPC284732
0.8515	High Similarity	NPC78966
0.8511	High Similarity	NPC186363
0.8511	High Similarity	NPC233345
0.8478	Intermediate Similarity	NPC175293
0.8478	Intermediate Similarity	NPC181103
0.8454	Intermediate Similarity	NPC474395
0.8454	Intermediate Similarity	NPC70145
0.8454	Intermediate Similarity	NPC91695
0.8454	Intermediate Similarity	NPC474921
0.8438	Intermediate Similarity	NPC56369
0.8431	Intermediate Similarity	NPC37628
0.8421	Intermediate Similarity	NPC147272
0.8404	Intermediate Similarity	NPC158488
0.84	Intermediate Similarity	NPC72842
0.837	Intermediate Similarity	NPC477920
0.837	Intermediate Similarity	NPC185638
0.837	Intermediate Similarity	NPC9231
0.8352	Intermediate Similarity	NPC97505
0.8333	Intermediate Similarity	NPC250075
0.83	Intermediate Similarity	NPC476081
0.828	Intermediate Similarity	NPC470012
0.8252	Intermediate Similarity	NPC189075
0.8252	Intermediate Similarity	NPC275539
0.8247	Intermediate Similarity	NPC183012
0.8235	Intermediate Similarity	NPC469607
0.8222	Intermediate Similarity	NPC38642
0.8218	Intermediate Similarity	NPC99510
0.8191	Intermediate Similarity	NPC277771
0.8182	Intermediate Similarity	NPC23364
0.8182	Intermediate Similarity	NPC162459
0.8182	Intermediate Similarity	NPC28864
0.8182	Intermediate Similarity	NPC98837
0.8182	Intermediate Similarity	NPC38296
0.8182	Intermediate Similarity	NPC38471
0.8182	Intermediate Similarity	NPC89099
0.8182	Intermediate Similarity	NPC20479
0.8155	Intermediate Similarity	NPC110496
0.8137	Intermediate Similarity	NPC283850
0.8132	Intermediate Similarity	NPC226988
0.8119	Intermediate Similarity	NPC469606
0.8119	Intermediate Similarity	NPC58329
0.8119	Intermediate Similarity	NPC31058
0.8119	Intermediate Similarity	NPC273005
0.8119	Intermediate Similarity	NPC170615
0.81	Intermediate Similarity	NPC293866
0.8095	Intermediate Similarity	NPC5103
0.8081	Intermediate Similarity	NPC10864
0.8081	Intermediate Similarity	NPC111348
0.8056	Intermediate Similarity	NPC270478
0.8039	Intermediate Similarity	NPC120321
0.8037	Intermediate Similarity	NPC25909
0.8022	Intermediate Similarity	NPC209318
0.8022	Intermediate Similarity	NPC223330
0.802	Intermediate Similarity	NPC471412
0.802	Intermediate Similarity	NPC46848
0.8019	Intermediate Similarity	NPC469655
0.8019	Intermediate Similarity	NPC474846
0.8019	Intermediate Similarity	NPC469656
0.8	Intermediate Similarity	NPC474724
0.8	Intermediate Similarity	NPC474793
0.7982	Intermediate Similarity	NPC469684
0.7981	Intermediate Similarity	NPC187435
0.7981	Intermediate Similarity	NPC67321
0.798	Intermediate Similarity	NPC202833
0.798	Intermediate Similarity	NPC256227
0.798	Intermediate Similarity	NPC234993
0.798	Intermediate Similarity	NPC29410
0.798	Intermediate Similarity	NPC200054
0.798	Intermediate Similarity	NPC134072
0.7979	Intermediate Similarity	NPC6979
0.7961	Intermediate Similarity	NPC296950
0.7961	Intermediate Similarity	NPC477127
0.7961	Intermediate Similarity	NPC258532
0.7959	Intermediate Similarity	NPC66581
0.7959	Intermediate Similarity	NPC57117
0.7957	Intermediate Similarity	NPC470011
0.7944	Intermediate Similarity	NPC12046
0.7944	Intermediate Similarity	NPC194951
0.7941	Intermediate Similarity	NPC214946
0.7941	Intermediate Similarity	NPC304832
0.7941	Intermediate Similarity	NPC88203
0.7941	Intermediate Similarity	NPC76866
0.7941	Intermediate Similarity	NPC148628
0.7941	Intermediate Similarity	NPC162973
0.7941	Intermediate Similarity	NPC275990
0.7941	Intermediate Similarity	NPC246736
0.7941	Intermediate Similarity	NPC286519
0.7938	Intermediate Similarity	NPC72845
0.7925	Intermediate Similarity	NPC472666
0.7925	Intermediate Similarity	NPC124053
0.7925	Intermediate Similarity	NPC478209
0.7921	Intermediate Similarity	NPC471413
0.7921	Intermediate Similarity	NPC477656
0.7921	Intermediate Similarity	NPC267921
0.7921	Intermediate Similarity	NPC287676
0.7921	Intermediate Similarity	NPC477655
0.7917	Intermediate Similarity	NPC73995
0.7909	Intermediate Similarity	NPC284707
0.7905	Intermediate Similarity	NPC476479
0.7905	Intermediate Similarity	NPC476802
0.7905	Intermediate Similarity	NPC89171
0.79	Intermediate Similarity	NPC474343
0.7885	Intermediate Similarity	NPC28791
0.7885	Intermediate Similarity	NPC478208
0.7885	Intermediate Similarity	NPC34768
0.7885	Intermediate Similarity	NPC252296
0.7885	Intermediate Similarity	NPC295366
0.7879	Intermediate Similarity	NPC98639
0.7879	Intermediate Similarity	NPC217329
0.787	Intermediate Similarity	NPC469496
0.787	Intermediate Similarity	NPC157441
0.787	Intermediate Similarity	NPC474271
0.787	Intermediate Similarity	NPC469463
0.787	Intermediate Similarity	NPC469454
0.787	Intermediate Similarity	NPC477126
0.7864	Intermediate Similarity	NPC139347
0.7864	Intermediate Similarity	NPC87927
0.7864	Intermediate Similarity	NPC254202
0.7864	Intermediate Similarity	NPC96217
0.7857	Intermediate Similarity	NPC139692
0.7857	Intermediate Similarity	NPC199543
0.785	Intermediate Similarity	NPC304180
0.785	Intermediate Similarity	NPC179798
0.7849	Intermediate Similarity	NPC194637
0.7843	Intermediate Similarity	NPC39683
0.7843	Intermediate Similarity	NPC253886
0.7843	Intermediate Similarity	NPC148279
0.7843	Intermediate Similarity	NPC52899
0.7843	Intermediate Similarity	NPC236585
0.7843	Intermediate Similarity	NPC163963
0.7843	Intermediate Similarity	NPC289148
0.7843	Intermediate Similarity	NPC121218
0.7835	Intermediate Similarity	NPC152467
0.783	Intermediate Similarity	NPC469370
0.7826	Intermediate Similarity	NPC47635
0.7822	Intermediate Similarity	NPC16911
0.7822	Intermediate Similarity	NPC471038
0.7822	Intermediate Similarity	NPC473155
0.7822	Intermediate Similarity	NPC78427
0.7818	Intermediate Similarity	NPC53396
0.7818	Intermediate Similarity	NPC98249
0.7818	Intermediate Similarity	NPC473590
0.7818	Intermediate Similarity	NPC473968
0.7812	Intermediate Similarity	NPC477302
0.7812	Intermediate Similarity	NPC477128
0.7812	Intermediate Similarity	NPC136879
0.7812	Intermediate Similarity	NPC215831
0.781	Intermediate Similarity	NPC88833
0.781	Intermediate Similarity	NPC184512
0.781	Intermediate Similarity	NPC251824
0.781	Intermediate Similarity	NPC61071
0.781	Intermediate Similarity	NPC143609
0.781	Intermediate Similarity	NPC96333
0.781	Intermediate Similarity	NPC302788
0.781	Intermediate Similarity	NPC86852
0.78	Intermediate Similarity	NPC165632
0.7789	Intermediate Similarity	NPC250981
0.7788	Intermediate Similarity	NPC146731
0.7788	Intermediate Similarity	NPC202793
0.7788	Intermediate Similarity	NPC301787
0.7788	Intermediate Similarity	NPC84928
0.7788	Intermediate Similarity	NPC474558
0.7778	Intermediate Similarity	NPC476964
0.7778	Intermediate Similarity	NPC477130
0.7778	Intermediate Similarity	NPC269530

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 NPC165528 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1649
0.2-0.3	3741
0.3-0.4	2295
0.4-0.5	769
0.5-0.6	270
0.6-0.7	188
0.7-0.8	59
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
0.7736	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD4225	Approved
0.7476	Intermediate Similarity	NPD7638	Approved
0.7404	Intermediate Similarity	NPD7639	Approved
0.7404	Intermediate Similarity	NPD7640	Approved
0.7353	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1694	Approved
0.7248	Intermediate Similarity	NPD6686	Approved
0.7182	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5697	Approved
0.7117	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6881	Approved
0.7091	Intermediate Similarity	NPD6899	Approved
0.7064	Intermediate Similarity	NPD6008	Approved
0.7059	Intermediate Similarity	NPD8034	Phase 2
0.7059	Intermediate Similarity	NPD8035	Phase 2
0.7054	Intermediate Similarity	NPD6649	Approved
0.7054	Intermediate Similarity	NPD6650	Approved
0.7043	Intermediate Similarity	NPD7115	Discovery
0.7027	Intermediate Similarity	NPD6012	Approved
0.7027	Intermediate Similarity	NPD6014	Approved
0.7027	Intermediate Similarity	NPD6013	Approved
0.699	Remote Similarity	NPD6399	Phase 3
0.6964	Remote Similarity	NPD6883	Approved
0.6964	Remote Similarity	NPD7290	Approved
0.6964	Remote Similarity	NPD7102	Approved
0.6949	Remote Similarity	NPD6921	Approved
0.6937	Remote Similarity	NPD6011	Approved
0.693	Remote Similarity	NPD4632	Approved
0.693	Remote Similarity	NPD8133	Approved
0.6909	Remote Similarity	NPD6675	Approved
0.6909	Remote Similarity	NPD7128	Approved
0.6909	Remote Similarity	NPD6402	Approved
0.6909	Remote Similarity	NPD5739	Approved
0.6903	Remote Similarity	NPD8130	Phase 1
0.6903	Remote Similarity	NPD6847	Approved
0.6903	Remote Similarity	NPD6617	Approved
0.6903	Remote Similarity	NPD6869	Approved
0.6893	Remote Similarity	NPD6411	Approved
0.6887	Remote Similarity	NPD7902	Approved
0.6875	Remote Similarity	NPD6372	Approved
0.6875	Remote Similarity	NPD6373	Approved
0.6864	Remote Similarity	NPD6319	Approved
0.686	Remote Similarity	NPD7507	Approved
0.6852	Remote Similarity	NPD5344	Discontinued
0.6847	Remote Similarity	NPD5701	Approved
0.6847	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6882	Approved
0.6842	Remote Similarity	NPD8297	Approved
0.6837	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7319	Approved
0.6827	Remote Similarity	NPD5779	Approved
0.6827	Remote Similarity	NPD5778	Approved
0.68	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6698	Approved
0.6796	Remote Similarity	NPD46	Approved
0.6789	Remote Similarity	NPD7632	Discontinued
0.6789	Remote Similarity	NPD5211	Phase 2
0.6786	Remote Similarity	NPD7320	Approved
0.6777	Remote Similarity	NPD7492	Approved
0.6762	Remote Similarity	NPD5282	Discontinued
0.6762	Remote Similarity	NPD7748	Approved
0.6759	Remote Similarity	NPD5285	Approved
0.6759	Remote Similarity	NPD5286	Approved
0.6759	Remote Similarity	NPD4696	Approved
0.6752	Remote Similarity	NPD6009	Approved
0.6733	Remote Similarity	NPD3618	Phase 1
0.6731	Remote Similarity	NPD6079	Approved
0.6731	Remote Similarity	NPD7515	Phase 2
0.6723	Remote Similarity	NPD6054	Approved
0.6721	Remote Similarity	NPD6616	Approved
0.6699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6101	Approved
0.6699	Remote Similarity	NPD1695	Approved
0.6696	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6636	Remote Similarity	NPD5221	Approved
0.6636	Remote Similarity	NPD5224	Approved
0.6636	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD5222	Approved
0.6636	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5225	Approved
0.6636	Remote Similarity	NPD4633	Approved
0.6634	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7736	Approved
0.6612	Remote Similarity	NPD6370	Approved
0.6612	Remote Similarity	NPD5988	Approved
0.6606	Remote Similarity	NPD6648	Approved
0.6604	Remote Similarity	NPD7900	Approved
0.6604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5174	Approved
0.6577	Remote Similarity	NPD5175	Approved
0.6574	Remote Similarity	NPD4755	Approved
0.6574	Remote Similarity	NPD5173	Approved
0.6571	Remote Similarity	NPD7637	Suspended
0.6557	Remote Similarity	NPD7604	Phase 2
0.6557	Remote Similarity	NPD8328	Phase 3
0.6555	Remote Similarity	NPD7327	Approved
0.6555	Remote Similarity	NPD7328	Approved
0.6549	Remote Similarity	NPD6412	Phase 2
0.6545	Remote Similarity	NPD5223	Approved
0.6538	Remote Similarity	NPD5328	Approved
0.6529	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6274	Approved
0.6522	Remote Similarity	NPD6371	Approved
0.6522	Remote Similarity	NPD4634	Approved
0.65	Remote Similarity	NPD7101	Approved
0.65	Remote Similarity	NPD7100	Approved
0.65	Remote Similarity	NPD7516	Approved
0.65	Remote Similarity	NPD3667	Approved
0.6481	Remote Similarity	NPD4697	Phase 3
0.6476	Remote Similarity	NPD5785	Approved
0.6471	Remote Similarity	NPD6317	Approved
0.6471	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7260	Phase 2
0.6455	Remote Similarity	NPD4700	Approved
0.6452	Remote Similarity	NPD6336	Discontinued
0.6446	Remote Similarity	NPD6059	Approved
0.6429	Remote Similarity	NPD6115	Approved
0.6429	Remote Similarity	NPD6114	Approved
0.6429	Remote Similarity	NPD6697	Approved
0.6429	Remote Similarity	NPD6118	Approved
0.6422	Remote Similarity	NPD6083	Phase 2
0.6422	Remote Similarity	NPD6084	Phase 2
0.6417	Remote Similarity	NPD6313	Approved
0.6417	Remote Similarity	NPD6335	Approved
0.6417	Remote Similarity	NPD6314	Approved
0.6404	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8293	Discontinued
0.64	Remote Similarity	NPD8074	Phase 3
0.6393	Remote Similarity	NPD8380	Approved
0.6393	Remote Similarity	NPD8296	Approved
0.6393	Remote Similarity	NPD8379	Approved
0.6393	Remote Similarity	NPD8335	Approved
0.6393	Remote Similarity	NPD7503	Approved
0.6393	Remote Similarity	NPD8378	Approved
0.6393	Remote Similarity	NPD8033	Approved
0.6389	Remote Similarity	NPD5695	Phase 3
0.6387	Remote Similarity	NPD6868	Approved
0.6373	Remote Similarity	NPD4786	Approved
0.6364	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4202	Approved
0.6348	Remote Similarity	NPD4730	Approved
0.6348	Remote Similarity	NPD4729	Approved
0.6327	Remote Similarity	NPD6116	Phase 1
0.6321	Remote Similarity	NPD7838	Discovery
0.6311	Remote Similarity	NPD8294	Approved
0.6311	Remote Similarity	NPD8377	Approved
0.6262	Remote Similarity	NPD7983	Approved
0.6262	Remote Similarity	NPD5281	Approved
0.6262	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD1700	Approved
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD7146	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD7521	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD7334	Approved
0.625	Remote Similarity	NPD4249	Approved
0.6239	Remote Similarity	NPD5249	Phase 3
0.6239	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5247	Approved
0.6239	Remote Similarity	NPD5251	Approved
0.6239	Remote Similarity	NPD4629	Approved
0.6239	Remote Similarity	NPD5250	Approved
0.6239	Remote Similarity	NPD5248	Approved
0.6239	Remote Similarity	NPD5210	Approved
0.6224	Remote Similarity	NPD6117	Approved
0.6214	Remote Similarity	NPD3665	Phase 1
0.6214	Remote Similarity	NPD3666	Approved
0.6214	Remote Similarity	NPD3133	Approved
0.6214	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5128	Approved
0.619	Remote Similarity	NPD4250	Approved
0.619	Remote Similarity	NPD4251	Approved
0.6186	Remote Similarity	NPD5217	Approved
0.6186	Remote Similarity	NPD5215	Approved
0.6186	Remote Similarity	NPD5216	Approved
0.6176	Remote Similarity	NPD6435	Approved
0.6174	Remote Similarity	NPD4767	Approved
0.6174	Remote Similarity	NPD4768	Approved
0.6154	Remote Similarity	NPD6845	Suspended
0.614	Remote Similarity	NPD4754	Approved
0.6132	Remote Similarity	NPD5737	Approved
0.6132	Remote Similarity	NPD6903	Approved
0.6132	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6672	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