NPASS Compound

Structure

NPC475895 OpenBabel07101718292D 34 35 0 0 0 0 0 0 0 0999 V2000 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 9 1 0 0 0 0 6 15 2 0 0 0 0 7 10 2 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 24 1 0 0 0 0 12 19 2 0 0 0 0 12 26 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 14 25 2 0 0 0 0 16 27 2 0 0 0 0 16 32 1 0 0 0 0 17 28 2 0 0 0 0 17 33 1 0 0 0 0 18 29 2 0 0 0 0 18 34 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 23 2 0 0 0 0 22 30 2 0 0 0 0 23 31 1 0 0 0 0 24 26 2 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.16
Volume:	479.823
LogP:	4.62
LogD:	2.585
LogS:	-4.529
# Rotatable Bonds:	11
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	2.802
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.901
MDCK Permeability:	2.0866697013843805e-05
Pgp-inhibitor:	0.403
Pgp-substrate:	0.947
Human Intestinal Absorption (HIA):	0.097
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	90.92762756347656%
Volume Distribution (VD):	0.474
Pgp-substrate:	12.312105178833008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.785
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.93
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.871
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.298
CYP2D6-substrate:	0.269
CYP3A4-inhibitor:	0.369
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	1.151
Half-life (T1/2):	0.545

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.012
Drug-inuced Liver Injury (DILI):	0.677
AMES Toxicity:	0.137
Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.711
Skin Sensitization:	0.955
Carcinogencity:	0.182
Eye Corrosion:	0.005
Eye Irritation:	0.871
Respiratory Toxicity:	0.544

Download Data

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

Natural Product: NPC475895

Natural Product ID:	NPC475895
*Common Name:**	Broussochalcone Triacetate
IUPAC Name:	[2-acetyloxy-4-[(E)-3-[4-acetyloxy-2-hydroxy-5-(3-methylbut-2-enyl)phenyl]-3-oxoprop-1-enyl]phenyl] acetate
Synonyms:	Broussochalcone Triacetate
Standard InCHIKey:	OSMAHDXNHPCYBB-JXMROGBWSA-N
Standard InCHI:	InChI=1S/C26H26O8/c1-15(2)6-9-20-13-21(23(31)14-25(20)33-17(4)28)22(30)10-7-19-8-11-24(32-16(3)27)26(12-19)34-18(5)29/h6-8,10-14,31H,9H2,1-5H3/b10-7+
SMILES:	CC(=CCC1=CC(=C(C=C1OC(=O)C)O)C(=O)C=CC2=CC(=C(C=C2)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518101
PubChem CID:	44566814
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003509] 3-prenylated chalcones

*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	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
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]
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]
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	Fruit	n.a.	n.a.	Database[FooDB]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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[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]
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	1
Others	6

Activity Type	# Activity
NON-MOLECULAR	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	9.6	%	PMID[514216]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	88.4	%	PMID[514216]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	23.1	%	PMID[514216]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	82.1	%	PMID[514216]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	9.3	%	PMID[514216]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[514216]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	91700.0	nM	PMID[514216]

☑ 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 NPC475895 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	384
0.1-0.2	1727
0.2-0.3	4398
0.3-0.4	10128
0.4-0.5	7651
0.5-0.6	3470
0.6-0.7	4968
0.7-0.8	5351
0.8-0.85	3136
0.85-0.9	1378
0.9-0.95	104
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
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
0.9329	High Similarity	NPC474648
0.9281	High Similarity	NPC222689
0.9281	High Similarity	NPC108456
0.9281	High Similarity	NPC35598
0.9276	High Similarity	NPC168247
0.9276	High Similarity	NPC234255
0.9276	High Similarity	NPC117992
0.9276	High Similarity	NPC472280
0.9276	High Similarity	NPC152951
0.9276	High Similarity	NPC230149
0.9276	High Similarity	NPC57674
0.9272	High Similarity	NPC237994
0.9272	High Similarity	NPC199773
0.9262	High Similarity	NPC183236
0.9231	High Similarity	NPC474350
0.9221	High Similarity	NPC83763
0.9221	High Similarity	NPC168616
0.9216	High Similarity	NPC472455
0.9205	High Similarity	NPC154345
0.9184	High Similarity	NPC119663
0.9167	High Similarity	NPC8300
0.9161	High Similarity	NPC292415
0.9156	High Similarity	NPC476981
0.9156	High Similarity	NPC474681
0.9156	High Similarity	NPC187745
0.9156	High Similarity	NPC291508
0.9156	High Similarity	NPC161960
0.9156	High Similarity	NPC304008
0.9156	High Similarity	NPC218313
0.915	High Similarity	NPC256925
0.915	High Similarity	NPC226025
0.9145	High Similarity	NPC471982
0.9145	High Similarity	NPC289968
0.9139	High Similarity	NPC472279
0.9139	High Similarity	NPC3825
0.9139	High Similarity	NPC88804
0.9133	High Similarity	NPC195202
0.9128	High Similarity	NPC154217
0.9119	High Similarity	NPC99613
0.9119	High Similarity	NPC49487
0.9108	High Similarity	NPC234004
0.9108	High Similarity	NPC300984
0.9103	High Similarity	NPC103201
0.9103	High Similarity	NPC349525
0.9103	High Similarity	NPC303565
0.9103	High Similarity	NPC473106
0.9103	High Similarity	NPC94155
0.9097	High Similarity	NPC184755
0.9097	High Similarity	NPC74178
0.9097	High Similarity	NPC204879
0.9091	High Similarity	NPC68093
0.9091	High Similarity	NPC291878
0.9091	High Similarity	NPC195796
0.9091	High Similarity	NPC472456
0.9091	High Similarity	NPC115853
0.9091	High Similarity	NPC471985
0.9091	High Similarity	NPC138243
0.9091	High Similarity	NPC6633
0.9091	High Similarity	NPC133970
0.9091	High Similarity	NPC278778
0.9091	High Similarity	NPC470600
0.9091	High Similarity	NPC54928
0.9091	High Similarity	NPC5322
0.9091	High Similarity	NPC35038
0.9091	High Similarity	NPC191146
0.9085	High Similarity	NPC298802
0.9085	High Similarity	NPC189130
0.9079	High Similarity	NPC474663
0.9079	High Similarity	NPC256406
0.9079	High Similarity	NPC308451
0.9079	High Similarity	NPC198615
0.9067	High Similarity	NPC62536
0.9067	High Similarity	NPC12200
0.9067	High Similarity	NPC33265
0.906	High Similarity	NPC287275
0.906	High Similarity	NPC157133
0.906	High Similarity	NPC196137
0.906	High Similarity	NPC1886
0.9057	High Similarity	NPC234331
0.9054	High Similarity	NPC36181
0.9051	High Similarity	NPC85057
0.9051	High Similarity	NPC130920
0.9045	High Similarity	NPC471745
0.9045	High Similarity	NPC93739
0.9038	High Similarity	NPC476980
0.9032	High Similarity	NPC473272
0.9032	High Similarity	NPC27337
0.9032	High Similarity	NPC472598
0.9032	High Similarity	NPC474055
0.9032	High Similarity	NPC52889
0.9032	High Similarity	NPC284820
0.9032	High Similarity	NPC262286
0.9032	High Similarity	NPC78225
0.9032	High Similarity	NPC219867
0.9032	High Similarity	NPC36852
0.9032	High Similarity	NPC136674
0.9032	High Similarity	NPC180011
0.9026	High Similarity	NPC45849
0.9026	High Similarity	NPC200761
0.9026	High Similarity	NPC255807
0.9026	High Similarity	NPC31018
0.9026	High Similarity	NPC200246
0.9026	High Similarity	NPC471800
0.9026	High Similarity	NPC470327
0.9026	High Similarity	NPC286052
0.9026	High Similarity	NPC477503
0.902	High Similarity	NPC157784
0.902	High Similarity	NPC37684
0.902	High Similarity	NPC60972
0.902	High Similarity	NPC477231
0.902	High Similarity	NPC63187
0.902	High Similarity	NPC39732
0.902	High Similarity	NPC472912
0.902	High Similarity	NPC257648
0.9013	High Similarity	NPC338131
0.9013	High Similarity	NPC177839
0.9013	High Similarity	NPC50728
0.9013	High Similarity	NPC219330
0.9013	High Similarity	NPC29056
0.9013	High Similarity	NPC166753
0.9013	High Similarity	NPC29231
0.9007	High Similarity	NPC105415
0.9007	High Similarity	NPC272721
0.9007	High Similarity	NPC43669
0.9007	High Similarity	NPC107636
0.9007	High Similarity	NPC196277
0.9006	High Similarity	NPC475669
0.9006	High Similarity	NPC158226
0.9	High Similarity	NPC470322
0.9	High Similarity	NPC12377
0.9	High Similarity	NPC181388
0.8994	High Similarity	NPC20216
0.8994	High Similarity	NPC29160
0.8994	High Similarity	NPC207575
0.8994	High Similarity	NPC13481
0.8993	High Similarity	NPC94794
0.8993	High Similarity	NPC196459
0.8993	High Similarity	NPC112791
0.8993	High Similarity	NPC470296
0.8993	High Similarity	NPC188632
0.8993	High Similarity	NPC87609
0.8987	High Similarity	NPC156082
0.8987	High Similarity	NPC284007
0.8981	High Similarity	NPC472634
0.8981	High Similarity	NPC471499
0.8981	High Similarity	NPC234644
0.8981	High Similarity	NPC26326
0.8981	High Similarity	NPC258331
0.8981	High Similarity	NPC259456
0.8981	High Similarity	NPC167678
0.8981	High Similarity	NPC29876
0.8981	High Similarity	NPC112418
0.8981	High Similarity	NPC266314
0.8974	High Similarity	NPC187792
0.8974	High Similarity	NPC235448
0.8968	High Similarity	NPC170026
0.8968	High Similarity	NPC209614
0.8968	High Similarity	NPC470328
0.8968	High Similarity	NPC474983
0.8968	High Similarity	NPC472626
0.8968	High Similarity	NPC472907
0.8968	High Similarity	NPC282307
0.8961	High Similarity	NPC280937
0.8961	High Similarity	NPC213896
0.8961	High Similarity	NPC469550
0.8961	High Similarity	NPC192083
0.8961	High Similarity	NPC18727
0.8961	High Similarity	NPC472915
0.8961	High Similarity	NPC472905
0.8961	High Similarity	NPC170492
0.8961	High Similarity	NPC186507
0.8954	High Similarity	NPC149614
0.8954	High Similarity	NPC76376
0.8954	High Similarity	NPC117579
0.8954	High Similarity	NPC205046
0.8954	High Similarity	NPC236769
0.8954	High Similarity	NPC226973
0.8954	High Similarity	NPC31363
0.8954	High Similarity	NPC133856
0.8954	High Similarity	NPC208043
0.8954	High Similarity	NPC472535
0.8954	High Similarity	NPC304295
0.8954	High Similarity	NPC474170
0.8954	High Similarity	NPC59162
0.8954	High Similarity	NPC474388
0.8951	High Similarity	NPC181523
0.8947	High Similarity	NPC159103
0.8947	High Similarity	NPC287101
0.8947	High Similarity	NPC6923
0.8947	High Similarity	NPC328119
0.8947	High Similarity	NPC38545
0.8947	High Similarity	NPC171916
0.8947	High Similarity	NPC233267
0.8947	High Similarity	NPC177298
0.8947	High Similarity	NPC223579

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 NPC475895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	1005
0.2-0.3	1741
0.3-0.4	2572
0.4-0.5	1775
0.5-0.6	1067
0.6-0.7	447
0.7-0.8	138
0.8-0.85	46
0.85-0.9	21
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8961	High Similarity	NPD2393	Clinical (unspecified phase)
0.891	High Similarity	NPD7075	Discontinued
0.8903	High Similarity	NPD3817	Phase 2
0.8896	High Similarity	NPD1934	Approved
0.8846	High Similarity	NPD3882	Suspended
0.8839	High Similarity	NPD2801	Approved
0.8839	High Similarity	NPD7819	Suspended
0.8805	High Similarity	NPD6232	Discontinued
0.8758	High Similarity	NPD7473	Discontinued
0.8742	High Similarity	NPD1511	Approved
0.8718	High Similarity	NPD7096	Clinical (unspecified phase)
0.871	High Similarity	NPD7411	Suspended
0.8684	High Similarity	NPD7410	Clinical (unspecified phase)
0.8684	High Similarity	NPD4378	Clinical (unspecified phase)
0.8654	High Similarity	NPD6801	Discontinued
0.8627	High Similarity	NPD1512	Approved
0.8618	High Similarity	NPD6799	Approved
0.8616	High Similarity	NPD919	Approved
0.8608	High Similarity	NPD4868	Clinical (unspecified phase)
0.8589	High Similarity	NPD3818	Discontinued
0.858	High Similarity	NPD6166	Phase 2
0.858	High Similarity	NPD6168	Clinical (unspecified phase)
0.858	High Similarity	NPD6167	Clinical (unspecified phase)
0.8537	High Similarity	NPD5844	Phase 1
0.8526	High Similarity	NPD4380	Phase 2
0.8485	Intermediate Similarity	NPD7074	Phase 3
0.8481	Intermediate Similarity	NPD1465	Phase 2
0.8447	Intermediate Similarity	NPD5494	Approved
0.8435	Intermediate Similarity	NPD1240	Approved
0.8424	Intermediate Similarity	NPD7054	Approved
0.8411	Intermediate Similarity	NPD1549	Phase 2
0.8408	Intermediate Similarity	NPD6599	Discontinued
0.84	Intermediate Similarity	NPD2935	Discontinued
0.8378	Intermediate Similarity	NPD447	Suspended
0.8373	Intermediate Similarity	NPD7472	Approved
0.8355	Intermediate Similarity	NPD1243	Approved
0.8354	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1510	Phase 2
0.8333	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1607	Approved
0.8313	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD3750	Approved
0.8289	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD2796	Approved
0.8261	Intermediate Similarity	NPD7768	Phase 2
0.8235	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD3226	Approved
0.8225	Intermediate Similarity	NPD7808	Phase 3
0.8214	Intermediate Similarity	NPD6797	Phase 2
0.8212	Intermediate Similarity	NPD2799	Discontinued
0.821	Intermediate Similarity	NPD3749	Approved
0.8188	Intermediate Similarity	NPD943	Approved
0.8182	Intermediate Similarity	NPD3926	Phase 2
0.8166	Intermediate Similarity	NPD6559	Discontinued
0.8166	Intermediate Similarity	NPD7251	Discontinued
0.8158	Intermediate Similarity	NPD1551	Phase 2
0.8107	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD5953	Discontinued
0.8101	Intermediate Similarity	NPD920	Approved
0.8101	Intermediate Similarity	NPD5403	Approved
0.8095	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD2532	Approved
0.8089	Intermediate Similarity	NPD2533	Approved
0.8089	Intermediate Similarity	NPD2534	Approved
0.8086	Intermediate Similarity	NPD5402	Approved
0.8082	Intermediate Similarity	NPD1203	Approved
0.8077	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6959	Discontinued
0.8061	Intermediate Similarity	NPD1247	Approved
0.8054	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2800	Approved
0.7975	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5401	Approved
0.7974	Intermediate Similarity	NPD3748	Approved
0.7949	Intermediate Similarity	NPD4628	Phase 3
0.7933	Intermediate Similarity	NPD2313	Discontinued
0.7919	Intermediate Similarity	NPD6832	Phase 2
0.7911	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD230	Phase 1
0.7895	Intermediate Similarity	NPD1933	Approved
0.7882	Intermediate Similarity	NPD7286	Phase 2
0.7877	Intermediate Similarity	NPD9717	Approved
0.7871	Intermediate Similarity	NPD2346	Discontinued
0.7844	Intermediate Similarity	NPD7199	Phase 2
0.7843	Intermediate Similarity	NPD6651	Approved
0.7841	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2344	Approved
0.7751	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD411	Approved
0.7697	Intermediate Similarity	NPD3268	Approved
0.7687	Intermediate Similarity	NPD422	Phase 1
0.7682	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD37	Approved
0.7635	Intermediate Similarity	NPD1608	Approved
0.7628	Intermediate Similarity	NPD4308	Phase 3
0.7619	Intermediate Similarity	NPD6234	Discontinued
0.7616	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1653	Approved
0.7605	Intermediate Similarity	NPD4967	Phase 2
0.7605	Intermediate Similarity	NPD4965	Approved
0.7605	Intermediate Similarity	NPD4966	Approved
0.76	Intermediate Similarity	NPD2797	Approved
0.7582	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6099	Approved
0.758	Intermediate Similarity	NPD6100	Approved
0.7578	Intermediate Similarity	NPD7390	Discontinued
0.7562	Intermediate Similarity	NPD2309	Approved
0.7556	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5242	Approved
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.7516	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD5710	Approved
0.7484	Intermediate Similarity	NPD1613	Approved
0.7484	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD5406	Approved
0.7468	Intermediate Similarity	NPD5404	Approved
0.7468	Intermediate Similarity	NPD5408	Approved
0.7467	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8313	Approved
0.7458	Intermediate Similarity	NPD8312	Approved
0.7455	Intermediate Similarity	NPD7458	Discontinued
0.7453	Intermediate Similarity	NPD6190	Approved
0.7434	Intermediate Similarity	NPD2798	Approved
0.7432	Intermediate Similarity	NPD17	Approved
0.7417	Intermediate Similarity	NPD3225	Approved
0.7405	Intermediate Similarity	NPD7033	Discontinued
0.74	Intermediate Similarity	NPD9269	Phase 2
0.7386	Intermediate Similarity	NPD9494	Approved
0.7378	Intermediate Similarity	NPD5049	Phase 3
0.7372	Intermediate Similarity	NPD4060	Phase 1
0.7372	Intermediate Similarity	NPD4307	Phase 2
0.7368	Intermediate Similarity	NPD3267	Approved
0.7368	Intermediate Similarity	NPD1164	Approved
0.7368	Intermediate Similarity	NPD3266	Approved
0.7365	Intermediate Similarity	NPD9268	Approved
0.7365	Intermediate Similarity	NPD6385	Approved
0.7365	Intermediate Similarity	NPD6386	Approved
0.7355	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1296	Phase 2
0.7349	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2354	Approved
0.7337	Intermediate Similarity	NPD4288	Approved
0.7337	Intermediate Similarity	NPD5353	Approved
0.7333	Intermediate Similarity	NPD8434	Phase 2
0.7326	Intermediate Similarity	NPD8127	Discontinued
0.7325	Intermediate Similarity	NPD5124	Phase 1
0.7325	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7228	Approved
0.7297	Intermediate Similarity	NPD9545	Approved
0.729	Intermediate Similarity	NPD4625	Phase 3
0.7283	Intermediate Similarity	NPD7229	Phase 3
0.7279	Intermediate Similarity	NPD9493	Approved
0.7273	Intermediate Similarity	NPD3018	Phase 2
0.7262	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4287	Approved
0.7247	Intermediate Similarity	NPD7685	Pre-registration
0.7244	Intermediate Similarity	NPD3764	Approved
0.7244	Intermediate Similarity	NPD6798	Discontinued
0.724	Intermediate Similarity	NPD8151	Discontinued
0.7238	Intermediate Similarity	NPD8150	Discontinued
0.723	Intermediate Similarity	NPD5536	Phase 2
0.7226	Intermediate Similarity	NPD4908	Phase 1
0.7219	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3751	Discontinued
0.7215	Intermediate Similarity	NPD6355	Discontinued
0.7208	Intermediate Similarity	NPD1019	Discontinued
0.7205	Intermediate Similarity	NPD2353	Approved
0.7205	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7003	Approved
0.7178	Intermediate Similarity	NPD4110	Phase 3
0.7169	Intermediate Similarity	NPD6273	Approved
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7152	Intermediate Similarity	NPD4357	Discontinued
0.7151	Intermediate Similarity	NPD6971	Discontinued
0.7151	Intermediate Similarity	NPD7039	Approved
0.7151	Intermediate Similarity	NPD7038	Approved
0.7143	Intermediate Similarity	NPD1470	Approved
0.7135	Intermediate Similarity	NPD1729	Discontinued
0.7135	Intermediate Similarity	NPD7584	Approved
0.7134	Intermediate Similarity	NPD3887	Approved
0.7124	Intermediate Similarity	NPD2982	Phase 2
0.7124	Intermediate Similarity	NPD2983	Phase 2
0.7119	Intermediate Similarity	NPD7177	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