NPASS Compound

Structure

NPC189130 OpenBabel07101718182D 25 27 0 0 0 0 0 0 0 0999 V2000 -5.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9781 1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4781 1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4781 1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4781 1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9781 1.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 1.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 -2.3794 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 19 2 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 13 16 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.12
Volume:	349.03
LogP:	4.182
LogD:	3.088
LogS:	-3.706
# Rotatable Bonds:	3
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	2.761
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.074
MDCK Permeability:	2.455088178976439e-05
Pgp-inhibitor:	0.635
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	100.22686004638672%
Volume Distribution (VD):	0.58
Pgp-substrate:	0.955407440662384%

ADMET: Metabolism

CYP1A2-inhibitor:	0.921
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.761
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.721
CYP2C9-substrate:	0.431
CYP2D6-inhibitor:	0.68
CYP2D6-substrate:	0.273
CYP3A4-inhibitor:	0.408
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	11.937
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.449
Drug-inuced Liver Injury (DILI):	0.533
AMES Toxicity:	0.535
Rat Oral Acute Toxicity:	0.642
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.908
Carcinogencity:	0.631
Eye Corrosion:	0.003
Eye Irritation:	0.924
Respiratory Toxicity:	0.325

Download Data

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

Natural Product: NPC189130

Natural Product ID:	NPC189130
*Common Name:**	Broussoaurone A
IUPAC Name:	(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-5-(3-methylbut-2-enyl)-1-benzofuran-3-one
Synonyms:
Standard InCHIKey:	NYCBUBKYUALZIH-UWVJOHFNSA-N
Standard InCHI:	InChI=1S/C20H18O5/c1-11(2)3-5-13-9-14-18(10-16(13)22)25-19(20(14)24)8-12-4-6-15(21)17(23)7-12/h3-4,6-10,21-23H,5H2,1-2H3/b19-8-
SMILES:	CC(=CCc1cc2c(cc1O)O/C(=Cc1ccc(c(c1)O)O)/C2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463019
PubChem CID:	15298907
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001631] Aurone flavonoids

*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
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/0031-9422(95)00135-T]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[17405024]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Wood	n.a.	n.a.	PMID[23113717]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[27908762]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	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	4

Activity Type	# Activity
NON-MOLECULAR	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	93.7	%	PMID[454303]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	89.5	%	PMID[454303]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[454303]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15400.0	nM	PMID[454303]
NPT2	Others	Unspecified		IC50	=	22.7	ug.mL-1	PMID[454303]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1200.0	nM	PMID[454304]

☑ 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 NPC189130 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	418
0.1-0.2	1732
0.2-0.3	4522
0.3-0.4	11117
0.4-0.5	6664
0.5-0.6	3610
0.6-0.7	5006
0.7-0.8	5614
0.8-0.85	2350
0.85-0.9	1482
0.9-0.95	176
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9589	High Similarity	NPC140840
0.9589	High Similarity	NPC86847
0.9533	High Similarity	NPC133392
0.953	High Similarity	NPC37684
0.953	High Similarity	NPC63187
0.953	High Similarity	NPC157784
0.953	High Similarity	NPC304954
0.9524	High Similarity	NPC19545
0.9481	High Similarity	NPC472582
0.9463	High Similarity	NPC304295
0.9463	High Similarity	NPC205046
0.9463	High Similarity	NPC59162
0.9463	High Similarity	NPC154345
0.9396	High Similarity	NPC88804
0.9396	High Similarity	NPC260582
0.9396	High Similarity	NPC3825
0.9346	High Similarity	NPC195832
0.9342	High Similarity	NPC3980
0.9338	High Similarity	NPC227337
0.9338	High Similarity	NPC49402
0.9338	High Similarity	NPC70433
0.9338	High Similarity	NPC273462
0.9338	High Similarity	NPC33051
0.9333	High Similarity	NPC260895
0.929	High Similarity	NPC272722
0.9286	High Similarity	NPC328102
0.9281	High Similarity	NPC237418
0.9281	High Similarity	NPC273843
0.9276	High Similarity	NPC234255
0.9276	High Similarity	NPC168247
0.9276	High Similarity	NPC117992
0.9276	High Similarity	NPC230149
0.9276	High Similarity	NPC472280
0.9276	High Similarity	NPC152951
0.9276	High Similarity	NPC57674
0.9272	High Similarity	NPC237994
0.9267	High Similarity	NPC286342
0.9267	High Similarity	NPC149127
0.9267	High Similarity	NPC188871
0.9226	High Similarity	NPC231758
0.9226	High Similarity	NPC187354
0.9221	High Similarity	NPC22192
0.9216	High Similarity	NPC472455
0.9216	High Similarity	NPC282307
0.9216	High Similarity	NPC170026
0.9216	High Similarity	NPC265511
0.9216	High Similarity	NPC471500
0.9216	High Similarity	NPC475799
0.9216	High Similarity	NPC13779
0.9211	High Similarity	NPC179126
0.9211	High Similarity	NPC270620
0.9211	High Similarity	NPC78326
0.9211	High Similarity	NPC192083
0.9211	High Similarity	NPC236223
0.9211	High Similarity	NPC213896
0.9211	High Similarity	NPC170492
0.92	High Similarity	NPC270465
0.92	High Similarity	NPC171916
0.92	High Similarity	NPC38545
0.92	High Similarity	NPC87125
0.9195	High Similarity	NPC51443
0.9195	High Similarity	NPC74881
0.9184	High Similarity	NPC471417
0.9172	High Similarity	NPC36320
0.9161	High Similarity	NPC246478
0.9161	High Similarity	NPC472624
0.9161	High Similarity	NPC476283
0.9161	High Similarity	NPC287328
0.9161	High Similarity	NPC282009
0.9156	High Similarity	NPC187745
0.9156	High Similarity	NPC161960
0.9156	High Similarity	NPC471479
0.9156	High Similarity	NPC304008
0.9156	High Similarity	NPC471515
0.9156	High Similarity	NPC291508
0.9156	High Similarity	NPC218313
0.9156	High Similarity	NPC67876
0.9156	High Similarity	NPC474681
0.915	High Similarity	NPC321779
0.915	High Similarity	NPC80534
0.915	High Similarity	NPC56786
0.915	High Similarity	NPC256925
0.915	High Similarity	NPC113906
0.9145	High Similarity	NPC471982
0.9145	High Similarity	NPC82325
0.9145	High Similarity	NPC279989
0.9145	High Similarity	NPC55205
0.9145	High Similarity	NPC106976
0.9145	High Similarity	NPC249570
0.9139	High Similarity	NPC472279
0.9133	High Similarity	NPC203077
0.9133	High Similarity	NPC238279
0.9133	High Similarity	NPC166036
0.9128	High Similarity	NPC179271
0.9128	High Similarity	NPC20791
0.9122	High Similarity	NPC105213
0.9116	High Similarity	NPC301178
0.9116	High Similarity	NPC284556
0.9108	High Similarity	NPC124038
0.9103	High Similarity	NPC471499
0.9097	High Similarity	NPC184755
0.9097	High Similarity	NPC185258
0.9097	High Similarity	NPC204879
0.9097	High Similarity	NPC172770
0.9097	High Similarity	NPC74178
0.9091	High Similarity	NPC291878
0.9091	High Similarity	NPC195796
0.9091	High Similarity	NPC472461
0.9091	High Similarity	NPC276444
0.9091	High Similarity	NPC115853
0.9091	High Similarity	NPC35038
0.9091	High Similarity	NPC471985
0.9091	High Similarity	NPC68093
0.9091	High Similarity	NPC138243
0.9091	High Similarity	NPC6633
0.9091	High Similarity	NPC470600
0.9091	High Similarity	NPC133970
0.9091	High Similarity	NPC278778
0.9091	High Similarity	NPC5322
0.9091	High Similarity	NPC191146
0.9085	High Similarity	NPC74924
0.9085	High Similarity	NPC298692
0.9085	High Similarity	NPC58382
0.9085	High Similarity	NPC475895
0.9085	High Similarity	NPC476631
0.9085	High Similarity	NPC162351
0.9085	High Similarity	NPC141212
0.9079	High Similarity	NPC252933
0.9079	High Similarity	NPC256406
0.9079	High Similarity	NPC125062
0.9079	High Similarity	NPC200740
0.9079	High Similarity	NPC54394
0.9079	High Similarity	NPC236769
0.9073	High Similarity	NPC105512
0.9067	High Similarity	NPC95864
0.9067	High Similarity	NPC108406
0.9067	High Similarity	NPC117463
0.906	High Similarity	NPC157133
0.906	High Similarity	NPC70136
0.9054	High Similarity	NPC287722
0.9051	High Similarity	NPC300053
0.9051	High Similarity	NPC108433
0.9051	High Similarity	NPC472277
0.9051	High Similarity	NPC45449
0.9045	High Similarity	NPC81679
0.9045	High Similarity	NPC472635
0.9045	High Similarity	NPC78332
0.9038	High Similarity	NPC28241
0.9038	High Similarity	NPC476980
0.9038	High Similarity	NPC470326
0.9032	High Similarity	NPC27337
0.9032	High Similarity	NPC472598
0.9032	High Similarity	NPC36852
0.9032	High Similarity	NPC218871
0.9032	High Similarity	NPC474055
0.9032	High Similarity	NPC52889
0.9032	High Similarity	NPC476630
0.9032	High Similarity	NPC262286
0.9032	High Similarity	NPC203891
0.9032	High Similarity	NPC79053
0.9032	High Similarity	NPC78225
0.9032	High Similarity	NPC101830
0.9032	High Similarity	NPC52530
0.9032	High Similarity	NPC471209
0.9032	High Similarity	NPC219867
0.9032	High Similarity	NPC110070
0.9032	High Similarity	NPC136674
0.9032	High Similarity	NPC180011
0.9026	High Similarity	NPC45849
0.9026	High Similarity	NPC200761
0.9026	High Similarity	NPC200246
0.9026	High Similarity	NPC214138
0.9026	High Similarity	NPC470327
0.9026	High Similarity	NPC477503
0.902	High Similarity	NPC60972
0.902	High Similarity	NPC477231
0.902	High Similarity	NPC123886
0.902	High Similarity	NPC472912
0.902	High Similarity	NPC39732
0.902	High Similarity	NPC324233
0.902	High Similarity	NPC323626
0.902	High Similarity	NPC257648
0.9013	High Similarity	NPC230713
0.9013	High Similarity	NPC78335
0.9013	High Similarity	NPC50728
0.9013	High Similarity	NPC166753
0.9013	High Similarity	NPC29231
0.9013	High Similarity	NPC472421
0.9007	High Similarity	NPC272721
0.9007	High Similarity	NPC43669
0.9007	High Similarity	NPC3036
0.9007	High Similarity	NPC196277
0.9	High Similarity	NPC5820
0.9	High Similarity	NPC165456
0.9	High Similarity	NPC210826
0.9	High Similarity	NPC306488
0.9	High Similarity	NPC169749
0.9	High Similarity	NPC178343
0.8994	High Similarity	NPC235610
0.8994	High Similarity	NPC277480

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 NPC189130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	991
0.2-0.3	1682
0.3-0.4	2663
0.4-0.5	1795
0.5-0.6	1036
0.6-0.7	423
0.7-0.8	137
0.8-0.85	27
0.85-0.9	16
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.947	High Similarity	NPD3882	Suspended
0.9211	High Similarity	NPD2393	Clinical (unspecified phase)
0.9128	High Similarity	NPD1512	Approved
0.8993	High Similarity	NPD1511	Approved
0.8933	High Similarity	NPD4378	Clinical (unspecified phase)
0.8896	High Similarity	NPD1934	Approved
0.8839	High Similarity	NPD2801	Approved
0.879	High Similarity	NPD7075	Discontinued
0.8718	High Similarity	NPD7096	Clinical (unspecified phase)
0.8696	High Similarity	NPD6167	Clinical (unspecified phase)
0.8696	High Similarity	NPD6168	Clinical (unspecified phase)
0.8696	High Similarity	NPD6166	Phase 2
0.8662	High Similarity	NPD3817	Phase 2
0.8618	High Similarity	NPD6799	Approved
0.8589	High Similarity	NPD3818	Discontinued
0.8562	High Similarity	NPD7410	Clinical (unspecified phase)
0.8535	High Similarity	NPD6801	Discontinued
0.85	High Similarity	NPD919	Approved
0.8447	Intermediate Similarity	NPD5494	Approved
0.8435	Intermediate Similarity	NPD943	Approved
0.8435	Intermediate Similarity	NPD1240	Approved
0.8434	Intermediate Similarity	NPD6797	Phase 2
0.8411	Intermediate Similarity	NPD1549	Phase 2
0.8408	Intermediate Similarity	NPD6599	Discontinued
0.8408	Intermediate Similarity	NPD4380	Phase 2
0.8395	Intermediate Similarity	NPD1247	Approved
0.8383	Intermediate Similarity	NPD7251	Discontinued
0.8365	Intermediate Similarity	NPD7819	Suspended
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1510	Phase 2
0.8322	Intermediate Similarity	NPD1607	Approved
0.8293	Intermediate Similarity	NPD3926	Phase 2
0.8278	Intermediate Similarity	NPD2796	Approved
0.8263	Intermediate Similarity	NPD7074	Phase 3
0.8261	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7411	Suspended
0.8235	Intermediate Similarity	NPD2800	Approved
0.8225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7808	Phase 3
0.8204	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7054	Approved
0.8199	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7472	Approved
0.8121	Intermediate Similarity	NPD6232	Discontinued
0.8117	Intermediate Similarity	NPD1243	Approved
0.8098	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7473	Discontinued
0.8059	Intermediate Similarity	NPD6559	Discontinued
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3749	Approved
0.7987	Intermediate Similarity	NPD2344	Approved
0.7987	Intermediate Similarity	NPD5403	Approved
0.7975	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7975	Intermediate Similarity	NPD5402	Approved
0.7974	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6959	Discontinued
0.7949	Intermediate Similarity	NPD3750	Approved
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7768	Phase 2
0.7917	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1465	Phase 2
0.7885	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD5844	Phase 1
0.7875	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD920	Approved
0.7862	Intermediate Similarity	NPD5401	Approved
0.7857	Intermediate Similarity	NPD2799	Discontinued
0.7848	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1551	Phase 2
0.78	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2309	Approved
0.7778	Intermediate Similarity	NPD230	Phase 1
0.7751	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6651	Approved
0.7701	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5953	Discontinued
0.7669	Intermediate Similarity	NPD3226	Approved
0.7662	Intermediate Similarity	NPD447	Suspended
0.7643	Intermediate Similarity	NPD1471	Phase 3
0.7628	Intermediate Similarity	NPD3748	Approved
0.761	Intermediate Similarity	NPD4628	Phase 3
0.76	Intermediate Similarity	NPD1203	Approved
0.7597	Intermediate Similarity	NPD1613	Approved
0.7597	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2313	Discontinued
0.758	Intermediate Similarity	NPD6100	Approved
0.758	Intermediate Similarity	NPD6099	Approved
0.7578	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7286	Phase 2
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7390	Discontinued
0.7467	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6190	Approved
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.74	Intermediate Similarity	NPD9717	Approved
0.7399	Intermediate Similarity	NPD2403	Approved
0.7386	Intermediate Similarity	NPD9494	Approved
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.7378	Intermediate Similarity	NPD5049	Phase 3
0.7372	Intermediate Similarity	NPD4060	Phase 1
0.7355	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2354	Approved
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD8434	Phase 2
0.733	Intermediate Similarity	NPD1729	Discontinued
0.7329	Intermediate Similarity	NPD2654	Approved
0.7325	Intermediate Similarity	NPD6355	Discontinued
0.7325	Intermediate Similarity	NPD1933	Approved
0.732	Intermediate Similarity	NPD2798	Approved
0.729	Intermediate Similarity	NPD4625	Phase 3
0.7285	Intermediate Similarity	NPD9269	Phase 2
0.7285	Intermediate Similarity	NPD1608	Approved
0.7283	Intermediate Similarity	NPD3787	Discontinued
0.7244	Intermediate Similarity	NPD411	Approved
0.7244	Intermediate Similarity	NPD6798	Discontinued
0.7244	Intermediate Similarity	NPD3268	Approved
0.7243	Intermediate Similarity	NPD4361	Phase 2
0.7243	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2296	Approved
0.7226	Intermediate Similarity	NPD4908	Phase 1
0.7219	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7219	Intermediate Similarity	NPD37	Approved
0.7216	Intermediate Similarity	NPD2163	Approved
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4965	Approved
0.7193	Intermediate Similarity	NPD4966	Approved
0.7193	Intermediate Similarity	NPD4967	Phase 2
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7188	Intermediate Similarity	NPD7033	Discontinued
0.7184	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD5405	Approved
0.7143	Intermediate Similarity	NPD5404	Approved
0.7134	Intermediate Similarity	NPD3764	Approved
0.7119	Intermediate Similarity	NPD7228	Approved
0.7108	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1201	Approved
0.7105	Intermediate Similarity	NPD1610	Phase 2
0.7099	Intermediate Similarity	NPD2353	Approved
0.7099	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4360	Phase 2
0.7097	Intermediate Similarity	NPD4363	Phase 3
0.709	Intermediate Similarity	NPD6779	Approved
0.709	Intermediate Similarity	NPD6780	Approved
0.709	Intermediate Similarity	NPD6782	Approved
0.709	Intermediate Similarity	NPD6777	Approved
0.709	Intermediate Similarity	NPD6776	Approved
0.709	Intermediate Similarity	NPD6778	Approved
0.709	Intermediate Similarity	NPD6781	Approved
0.7086	Intermediate Similarity	NPD17	Approved
0.7083	Intermediate Similarity	NPD1653	Approved
0.7072	Intermediate Similarity	NPD8313	Approved
0.7072	Intermediate Similarity	NPD8312	Approved
0.707	Intermediate Similarity	NPD7095	Approved
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7067	Intermediate Similarity	NPD1548	Phase 1
0.7065	Intermediate Similarity	NPD4287	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7048	Intermediate Similarity	NPD4357	Discontinued
0.7045	Intermediate Similarity	NPD5242	Approved
0.7041	Intermediate Similarity	NPD7458	Discontinued
0.7041	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4288	Approved
0.7032	Intermediate Similarity	NPD1164	Approved
0.703	Intermediate Similarity	NPD3887	Approved
0.7022	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD9268	Approved
0.7013	Intermediate Similarity	NPD4749	Approved
0.7006	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5536	Phase 2
0.6981	Remote Similarity	NPD6233	Phase 2
0.6968	Remote Similarity	NPD3225	Approved
0.6961	Remote Similarity	NPD3658	Clinical (unspecified phase)

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