NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	392.15
Volume:	389.23
LogP:	0.628
LogD:	0.854
LogS:	-2.491
# Rotatable Bonds:	8
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	5.184
Fsp3:	0.45
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:	-5.224
MDCK Permeability:	7.632219785591587e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.377
Plasma Protein Binding (PPB):	46.757286071777344%
Volume Distribution (VD):	1.052
Pgp-substrate:	39.03355407714844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.175
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.317
CYP2C9-inhibitor:	0.24
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.695
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	3.204
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.763
AMES Toxicity:	0.254
Rat Oral Acute Toxicity:	0.817
Maximum Recommended Daily Dose:	0.87
Skin Sensitization:	0.923
Carcinogencity:	0.483
Eye Corrosion:	0.084
Eye Irritation:	0.552
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC111292

Natural Product ID:	NPC111292
*Common Name:**	Vernodalol
IUPAC Name:	[(4aR,5R,6S,7S,8aR)-8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-1,4a,5,6,7,8-hexahydroisochromen-7-yl] 2-(hydroxymethyl)prop-2-enoate
Synonyms:	Vernodalol
Standard InCHIKey:	FZALQGCQQJLGKE-BBNZOYGDSA-N
Standard InCHI:	InChI=1S/C20H24O8/c1-6-20-7-13(28-17(23)10(2)8-21)14(11(3)18(24)26-5)16(22)15(20)12(4)19(25)27-9-20/h6,13-16,21-22H,1-4,7-9H2,5H3/t13-,14+,15+,16-,20+/m0/s1
SMILES:	COC(=O)C(=C)[C@@H]1[C@@H](OC(=O)C(=C)CO)C[C@]2([C@@H]([C@H]1O)C(=C)C(=O)OC2)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172876
PubChem CID:	442318
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
NPO25254	Vernonia colorata	Species	Asteraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[15043416]
NPO25254	Vernonia colorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO40097	Daucus virgatus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28976194]
NPO25254	Vernonia colorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25254	Vernonia colorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25254	Vernonia colorata	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4.8	ug.mL-1	PMID[534589]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	IC50	=	19000.0	nM	PMID[534590]

☑ 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 NPC111292 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	225
0.1-0.2	1413
0.2-0.3	4255
0.3-0.4	6804
0.4-0.5	13350
0.5-0.6	7970
0.6-0.7	6355
0.7-0.8	2163
0.8-0.85	126
0.85-0.9	31
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC164551
0.9579	High Similarity	NPC242666
0.9263	High Similarity	NPC474395
0.9175	High Similarity	NPC308824
0.9158	High Similarity	NPC284518
0.9158	High Similarity	NPC165528
0.9158	High Similarity	NPC228766
0.899	High Similarity	NPC156681
0.8947	High Similarity	NPC473434
0.8947	High Similarity	NPC471446
0.8947	High Similarity	NPC474841
0.8922	High Similarity	NPC474243
0.8911	High Similarity	NPC78966
0.8911	High Similarity	NPC284732
0.8854	High Similarity	NPC157686
0.8854	High Similarity	NPC259042
0.8824	High Similarity	NPC37628
0.875	High Similarity	NPC24861
0.875	High Similarity	NPC225474
0.875	High Similarity	NPC148000
0.875	High Similarity	NPC469596
0.8687	High Similarity	NPC47024
0.8673	High Similarity	NPC473963
0.8632	High Similarity	NPC153853
0.8586	High Similarity	NPC476807
0.8586	High Similarity	NPC216478
0.8586	High Similarity	NPC476806
0.8571	High Similarity	NPC93245
0.8571	High Similarity	NPC473964
0.8438	Intermediate Similarity	NPC475776
0.8431	Intermediate Similarity	NPC72842
0.8431	Intermediate Similarity	NPC61442
0.8431	Intermediate Similarity	NPC99510
0.8416	Intermediate Similarity	NPC475958
0.8404	Intermediate Similarity	NPC185638
0.8333	Intermediate Similarity	NPC275990
0.8333	Intermediate Similarity	NPC194642
0.8333	Intermediate Similarity	NPC116620
0.83	Intermediate Similarity	NPC136781
0.8286	Intermediate Similarity	NPC476802
0.8286	Intermediate Similarity	NPC89171
0.8283	Intermediate Similarity	NPC217329
0.8283	Intermediate Similarity	NPC90014
0.8269	Intermediate Similarity	NPC295366
0.8265	Intermediate Similarity	NPC199543
0.8252	Intermediate Similarity	NPC96217
0.8235	Intermediate Similarity	NPC236585
0.8235	Intermediate Similarity	NPC46848
0.8218	Intermediate Similarity	NPC474793
0.8218	Intermediate Similarity	NPC316598
0.82	Intermediate Similarity	NPC202833
0.819	Intermediate Similarity	NPC143609
0.8182	Intermediate Similarity	NPC469684
0.8173	Intermediate Similarity	NPC283850
0.8173	Intermediate Similarity	NPC239162
0.8155	Intermediate Similarity	NPC88203
0.8155	Intermediate Similarity	NPC76866
0.8155	Intermediate Similarity	NPC304832
0.8155	Intermediate Similarity	NPC286519
0.8155	Intermediate Similarity	NPC246736
0.8155	Intermediate Similarity	NPC148628
0.8155	Intermediate Similarity	NPC214946
0.8155	Intermediate Similarity	NPC476081
0.8148	Intermediate Similarity	NPC277769
0.8148	Intermediate Similarity	NPC4573
0.8148	Intermediate Similarity	NPC90952
0.8137	Intermediate Similarity	NPC474718
0.8137	Intermediate Similarity	NPC287676
0.8131	Intermediate Similarity	NPC124053
0.8125	Intermediate Similarity	NPC175293
0.8125	Intermediate Similarity	NPC305029
0.8125	Intermediate Similarity	NPC181103
0.8119	Intermediate Similarity	NPC474921
0.8113	Intermediate Similarity	NPC289702
0.8113	Intermediate Similarity	NPC476479
0.8113	Intermediate Similarity	NPC208461
0.8113	Intermediate Similarity	NPC273155
0.8095	Intermediate Similarity	NPC200957
0.8095	Intermediate Similarity	NPC37600
0.8095	Intermediate Similarity	NPC138908
0.8095	Intermediate Similarity	NPC111952
0.8095	Intermediate Similarity	NPC284365
0.8095	Intermediate Similarity	NPC123726
0.8091	Intermediate Similarity	NPC270478
0.8081	Intermediate Similarity	NPC147272
0.8077	Intermediate Similarity	NPC87927
0.8077	Intermediate Similarity	NPC159533
0.8077	Intermediate Similarity	NPC139347
0.8073	Intermediate Similarity	NPC477126
0.8073	Intermediate Similarity	NPC25909
0.8058	Intermediate Similarity	NPC39683
0.8058	Intermediate Similarity	NPC163963
0.8058	Intermediate Similarity	NPC52899
0.8058	Intermediate Similarity	NPC148279
0.8058	Intermediate Similarity	NPC289148
0.8039	Intermediate Similarity	NPC78427
0.8039	Intermediate Similarity	NPC20479
0.8039	Intermediate Similarity	NPC89099
0.8039	Intermediate Similarity	NPC38296
0.8039	Intermediate Similarity	NPC28864
0.8039	Intermediate Similarity	NPC16911
0.8039	Intermediate Similarity	NPC162459
0.8039	Intermediate Similarity	NPC471038
0.8039	Intermediate Similarity	NPC98837
0.8039	Intermediate Similarity	NPC38471
0.8037	Intermediate Similarity	NPC469983
0.8021	Intermediate Similarity	NPC85698
0.802	Intermediate Similarity	NPC234993
0.802	Intermediate Similarity	NPC242848
0.802	Intermediate Similarity	NPC134072
0.8019	Intermediate Similarity	NPC176949
0.8019	Intermediate Similarity	NPC166993
0.8019	Intermediate Similarity	NPC187435
0.8019	Intermediate Similarity	NPC67321
0.8019	Intermediate Similarity	NPC201908
0.8018	Intermediate Similarity	NPC475809
0.8018	Intermediate Similarity	NPC134430
0.8	Intermediate Similarity	NPC146731
0.8	Intermediate Similarity	NPC474558
0.8	Intermediate Similarity	NPC202793
0.8	Intermediate Similarity	NPC84928
0.8	Intermediate Similarity	NPC296950
0.8	Intermediate Similarity	NPC118911
0.8	Intermediate Similarity	NPC469982
0.7982	Intermediate Similarity	NPC476964
0.7982	Intermediate Similarity	NPC269530
0.7982	Intermediate Similarity	NPC476801
0.7981	Intermediate Similarity	NPC170615
0.7981	Intermediate Similarity	NPC475091
0.7981	Intermediate Similarity	NPC478156
0.7981	Intermediate Similarity	NPC474709
0.798	Intermediate Similarity	NPC186363
0.798	Intermediate Similarity	NPC233345
0.7963	Intermediate Similarity	NPC85391
0.7963	Intermediate Similarity	NPC472666
0.7963	Intermediate Similarity	NPC5103
0.7963	Intermediate Similarity	NPC255655
0.7963	Intermediate Similarity	NPC478209
0.7961	Intermediate Similarity	NPC477656
0.7961	Intermediate Similarity	NPC476299
0.7961	Intermediate Similarity	NPC474012
0.7961	Intermediate Similarity	NPC293866
0.7961	Intermediate Similarity	NPC477655
0.7961	Intermediate Similarity	NPC267921
0.7961	Intermediate Similarity	NPC293890
0.7959	Intermediate Similarity	NPC59682
0.7946	Intermediate Similarity	NPC251310
0.7946	Intermediate Similarity	NPC284707
0.7944	Intermediate Similarity	NPC275539
0.7944	Intermediate Similarity	NPC218123
0.7944	Intermediate Similarity	NPC151393
0.7944	Intermediate Similarity	NPC189075
0.7944	Intermediate Similarity	NPC322903
0.7944	Intermediate Similarity	NPC232133
0.7944	Intermediate Similarity	NPC231278
0.7944	Intermediate Similarity	NPC112895
0.7944	Intermediate Similarity	NPC102843
0.7941	Intermediate Similarity	NPC70145
0.7941	Intermediate Similarity	NPC287668
0.7941	Intermediate Similarity	NPC91695
0.7941	Intermediate Similarity	NPC10864
0.7938	Intermediate Similarity	NPC470012
0.7925	Intermediate Similarity	NPC28791
0.7925	Intermediate Similarity	NPC1679
0.7925	Intermediate Similarity	NPC469607
0.7921	Intermediate Similarity	NPC471786
0.7921	Intermediate Similarity	NPC56369
0.7921	Intermediate Similarity	NPC37603
0.7921	Intermediate Similarity	NPC470232
0.7913	Intermediate Similarity	NPC67251
0.7909	Intermediate Similarity	NPC320118
0.7905	Intermediate Similarity	NPC95899
0.7905	Intermediate Similarity	NPC159442
0.7905	Intermediate Similarity	NPC122811
0.7905	Intermediate Similarity	NPC120321
0.7905	Intermediate Similarity	NPC216114
0.7905	Intermediate Similarity	NPC8196
0.789	Intermediate Similarity	NPC471251
0.789	Intermediate Similarity	NPC94650
0.789	Intermediate Similarity	NPC157476
0.789	Intermediate Similarity	NPC213320
0.7885	Intermediate Similarity	NPC471790
0.7885	Intermediate Similarity	NPC471412
0.7885	Intermediate Similarity	NPC253886
0.7885	Intermediate Similarity	NPC14634
0.7885	Intermediate Similarity	NPC121218
0.7879	Intermediate Similarity	NPC158488
0.7876	Intermediate Similarity	NPC473839
0.7876	Intermediate Similarity	NPC77689
0.7876	Intermediate Similarity	NPC476960
0.7876	Intermediate Similarity	NPC211093
0.7876	Intermediate Similarity	NPC473636
0.787	Intermediate Similarity	NPC131903
0.787	Intermediate Similarity	NPC102741
0.787	Intermediate Similarity	NPC42662
0.7864	Intermediate Similarity	NPC26270
0.7864	Intermediate Similarity	NPC23364
0.7864	Intermediate Similarity	NPC477653
0.7864	Intermediate Similarity	NPC469986
0.7857	Intermediate Similarity	NPC53396

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 NPC111292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	1787
0.2-0.3	3581
0.3-0.4	2193
0.4-0.5	869
0.5-0.6	286
0.6-0.7	201
0.7-0.8	20
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8113	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4225	Approved
0.7453	Intermediate Similarity	NPD7640	Approved
0.7453	Intermediate Similarity	NPD7639	Approved
0.7436	Intermediate Similarity	NPD6921	Approved
0.7391	Intermediate Similarity	NPD7115	Discovery
0.7379	Intermediate Similarity	NPD5778	Approved
0.7379	Intermediate Similarity	NPD5779	Approved
0.7358	Intermediate Similarity	NPD7638	Approved
0.7297	Intermediate Similarity	NPD6686	Approved
0.7282	Intermediate Similarity	NPD6411	Approved
0.7238	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6319	Approved
0.7168	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD7319	Approved
0.7105	Intermediate Similarity	NPD6649	Approved
0.7105	Intermediate Similarity	NPD6650	Approved
0.7087	Intermediate Similarity	NPD6101	Approved
0.7087	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5344	Discontinued
0.7054	Intermediate Similarity	NPD5697	Approved
0.7025	Intermediate Similarity	NPD8328	Phase 3
0.7019	Intermediate Similarity	NPD46	Approved
0.7019	Intermediate Similarity	NPD6698	Approved
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8513	Phase 3
0.6991	Remote Similarity	NPD6881	Approved
0.6991	Remote Similarity	NPD6899	Approved
0.6983	Remote Similarity	NPD8133	Approved
0.6952	Remote Similarity	NPD7637	Suspended
0.6952	Remote Similarity	NPD7983	Approved
0.6952	Remote Similarity	NPD8035	Phase 2
0.6952	Remote Similarity	NPD8034	Phase 2
0.6949	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7902	Approved
0.693	Remote Similarity	NPD6013	Approved
0.693	Remote Similarity	NPD6014	Approved
0.693	Remote Similarity	NPD6012	Approved
0.693	Remote Similarity	NPD6372	Approved
0.693	Remote Similarity	NPD6373	Approved
0.6911	Remote Similarity	NPD7507	Approved
0.6903	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8297	Approved
0.6897	Remote Similarity	NPD6882	Approved
0.6887	Remote Similarity	NPD6399	Phase 3
0.687	Remote Similarity	NPD6883	Approved
0.687	Remote Similarity	NPD6371	Approved
0.687	Remote Similarity	NPD7290	Approved
0.687	Remote Similarity	NPD7102	Approved
0.6863	Remote Similarity	NPD1694	Approved
0.6857	Remote Similarity	NPD5785	Approved
0.6847	Remote Similarity	NPD5211	Phase 2
0.6847	Remote Similarity	NPD7632	Discontinued
0.6842	Remote Similarity	NPD6011	Approved
0.6838	Remote Similarity	NPD4632	Approved
0.6829	Remote Similarity	NPD7492	Approved
0.6822	Remote Similarity	NPD5282	Discontinued
0.6822	Remote Similarity	NPD7748	Approved
0.6818	Remote Similarity	NPD6648	Approved
0.6814	Remote Similarity	NPD6008	Approved
0.6814	Remote Similarity	NPD5739	Approved
0.6814	Remote Similarity	NPD6675	Approved
0.6814	Remote Similarity	NPD7128	Approved
0.6814	Remote Similarity	NPD6402	Approved
0.681	Remote Similarity	NPD6617	Approved
0.681	Remote Similarity	NPD6847	Approved
0.681	Remote Similarity	NPD8130	Phase 1
0.681	Remote Similarity	NPD6869	Approved
0.6792	Remote Similarity	NPD7515	Phase 2
0.6783	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6054	Approved
0.6774	Remote Similarity	NPD6616	Approved
0.6754	Remote Similarity	NPD5701	Approved
0.6733	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3573	Approved
0.6727	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5141	Approved
0.6724	Remote Similarity	NPD4634	Approved
0.6721	Remote Similarity	NPD6015	Approved
0.6721	Remote Similarity	NPD6016	Approved
0.672	Remote Similarity	NPD8074	Phase 3
0.672	Remote Similarity	NPD7078	Approved
0.6699	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7839	Suspended
0.6696	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6636	Remote Similarity	NPD6079	Approved
0.6635	Remote Similarity	NPD3618	Phase 1
0.6612	Remote Similarity	NPD7328	Approved
0.6612	Remote Similarity	NPD7327	Approved
0.661	Remote Similarity	NPD6053	Discontinued
0.6609	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5983	Phase 2
0.6557	Remote Similarity	NPD7516	Approved
0.6549	Remote Similarity	NPD4633	Approved
0.6549	Remote Similarity	NPD5226	Approved
0.6549	Remote Similarity	NPD5224	Approved
0.6549	Remote Similarity	NPD5225	Approved
0.6545	Remote Similarity	NPD5222	Approved
0.6545	Remote Similarity	NPD5221	Approved
0.6545	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7838	Discovery
0.6525	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7260	Phase 2
0.6504	Remote Similarity	NPD6059	Approved
0.6491	Remote Similarity	NPD5174	Approved
0.6491	Remote Similarity	NPD5175	Approved
0.6486	Remote Similarity	NPD4755	Approved
0.6486	Remote Similarity	NPD5173	Approved
0.648	Remote Similarity	NPD7604	Phase 2
0.6466	Remote Similarity	NPD6412	Phase 2
0.646	Remote Similarity	NPD5223	Approved
0.6457	Remote Similarity	NPD8293	Discontinued
0.6452	Remote Similarity	NPD8380	Approved
0.6452	Remote Similarity	NPD8296	Approved
0.6452	Remote Similarity	NPD8379	Approved
0.6452	Remote Similarity	NPD8335	Approved
0.6452	Remote Similarity	NPD8033	Approved
0.6452	Remote Similarity	NPD8378	Approved
0.6452	Remote Similarity	NPD7503	Approved
0.6449	Remote Similarity	NPD5328	Approved
0.6446	Remote Similarity	NPD6274	Approved
0.6423	Remote Similarity	NPD7101	Approved
0.6423	Remote Similarity	NPD7100	Approved
0.641	Remote Similarity	NPD4729	Approved
0.641	Remote Similarity	NPD4730	Approved
0.6408	Remote Similarity	NPD3667	Approved
0.6396	Remote Similarity	NPD4697	Phase 3
0.6393	Remote Similarity	NPD6317	Approved
0.6387	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5363	Approved
0.6378	Remote Similarity	NPD6336	Discontinued
0.6372	Remote Similarity	NPD4700	Approved
0.6371	Remote Similarity	NPD8294	Approved
0.6371	Remote Similarity	NPD8377	Approved
0.6341	Remote Similarity	NPD6314	Approved
0.6341	Remote Similarity	NPD6313	Approved
0.6341	Remote Similarity	NPD6335	Approved
0.6339	Remote Similarity	NPD6083	Phase 2
0.6339	Remote Similarity	NPD6084	Phase 2
0.6337	Remote Similarity	NPD6118	Approved
0.6337	Remote Similarity	NPD6115	Approved
0.6337	Remote Similarity	NPD6697	Approved
0.6337	Remote Similarity	NPD6114	Approved
0.6321	Remote Similarity	NPD5786	Approved
0.6321	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6868	Approved
0.6306	Remote Similarity	NPD5695	Phase 3
0.6303	Remote Similarity	NPD5251	Approved
0.6303	Remote Similarity	NPD5250	Approved
0.6303	Remote Similarity	NPD5247	Approved
0.6303	Remote Similarity	NPD5249	Phase 3
0.6303	Remote Similarity	NPD5248	Approved
0.6296	Remote Similarity	NPD1695	Approved
0.6286	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4786	Approved
0.6283	Remote Similarity	NPD5696	Approved
0.6273	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD4270	Approved
0.6239	Remote Similarity	NPD4767	Approved
0.6239	Remote Similarity	NPD4768	Approved
0.6238	Remote Similarity	NPD6116	Phase 1
0.6226	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6695	Phase 3
0.619	Remote Similarity	NPD7154	Phase 3
0.6182	Remote Similarity	NPD5281	Approved
0.6182	Remote Similarity	NPD5284	Approved
0.6174	Remote Similarity	NPD1700	Approved
0.6168	Remote Similarity	NPD7334	Approved
0.6168	Remote Similarity	NPD4249	Approved
0.6168	Remote Similarity	NPD5330	Approved
0.6168	Remote Similarity	NPD7146	Approved
0.6168	Remote Similarity	NPD7521	Approved
0.6168	Remote Similarity	NPD6409	Approved
0.6168	Remote Similarity	NPD6684	Approved
0.6161	Remote Similarity	NPD5210	Approved
0.6161	Remote Similarity	NPD4629	Approved
0.6154	Remote Similarity	NPD5369	Approved
0.6139	Remote Similarity	NPD6117	Approved
0.6134	Remote Similarity	NPD5128	Approved
0.6132	Remote Similarity	NPD3666	Approved
0.6132	Remote Similarity	NPD3665	Phase 1
0.6132	Remote Similarity	NPD3133	Approved
0.6116	Remote Similarity	NPD5217	Approved
0.6116	Remote Similarity	NPD5216	Approved
0.6116	Remote Similarity	NPD5215	Approved
0.6111	Remote Similarity	NPD4251	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