NPASS Compound

Structure

CID51887 OpenBabel06191715392D 31 33 0 0 1 0 0 0 0 0999 V2000 -5.1962 3.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 3 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 4 14 1 0 0 0 0 5 10 1 0 0 0 0 5 13 2 0 0 0 0 6 8 1 0 0 0 0 6 15 2 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 11 20 1 0 0 0 0 12 19 2 0 0 0 0 12 31 1 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 16 26 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 19 24 1 0 0 0 0 20 27 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 21 25 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 30 2 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	101.03
Volume:	101.973
LogP:	2.47
LogD:	1.116
LogS:	-1.901
# Rotatable Bonds:	2
TPSA:	12.36
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	3.682
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.388
MDCK Permeability:	3.323728378745727e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.223
Plasma Protein Binding (PPB):	12.830678939819336%
Volume Distribution (VD):	1.528
Pgp-substrate:	87.34134674072266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.382
CYP1A2-substrate:	0.509
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.676
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.646
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	7.537
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.057
Drug-inuced Liver Injury (DILI):	0.224
AMES Toxicity:	0.343
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.125
Skin Sensitization:	0.88
Carcinogencity:	0.39
Eye Corrosion:	0.991
Eye Irritation:	0.99
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC51887

Natural Product ID:	NPC51887
*Common Name:**	Erysenegalensein E
IUPAC Name:	5,7-dihydroxy-8-(2-hydroxy-3-methylbut-3-enyl)-3-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one
Synonyms:	Erysenegalensein E
Standard InCHIKey:	ZXSXDAJQZZFAON-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O6/c1-13(2)5-10-17-22(28)18(11-20(27)14(3)4)25-21(23(17)29)24(30)19(12-31-25)15-6-8-16(26)9-7-15/h5-9,12,20,26-29H,3,10-11H2,1-2,4H3
SMILES:	CC(=CCc1c(O)c(CC(C(=C)C)O)c2c(c1O)c(=O)c(co2)c1ccc(cc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557493
PubChem CID:	15478903
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(99)00103-X]
NPO14905	Erythrina variegata	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10869220]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19969457]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21314138]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO14905	Erythrina variegata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14905	Erythrina variegata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14905	Erythrina variegata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14905	Erythrina variegata	Species	Fabaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	18400.0	nM	PMID[540274]

☑ 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 NPC51887 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	394
0.1-0.2	1518
0.2-0.3	3697
0.3-0.4	9104
0.4-0.5	9591
0.5-0.6	3738
0.6-0.7	5503
0.7-0.8	4632
0.8-0.85	2321
0.85-0.9	1672
0.9-0.95	444
0.95-1	83

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC117836
1.0	High Similarity	NPC475705
1.0	High Similarity	NPC476178
0.9854	High Similarity	NPC321980
0.9854	High Similarity	NPC469404
0.9854	High Similarity	NPC470087
0.9786	High Similarity	NPC222298
0.9786	High Similarity	NPC51070
0.9781	High Similarity	NPC215311
0.9781	High Similarity	NPC204985
0.9781	High Similarity	NPC172250
0.9781	High Similarity	NPC80962
0.9781	High Similarity	NPC326109
0.9781	High Similarity	NPC219917
0.9781	High Similarity	NPC259166
0.9781	High Similarity	NPC144118
0.9781	High Similarity	NPC213659
0.9781	High Similarity	NPC48624
0.9712	High Similarity	NPC245482
0.9712	High Similarity	NPC301751
0.971	High Similarity	NPC55832
0.971	High Similarity	NPC52789
0.971	High Similarity	NPC26051
0.971	High Similarity	NPC268204
0.971	High Similarity	NPC470089
0.9708	High Similarity	NPC470211
0.9708	High Similarity	NPC295384
0.9708	High Similarity	NPC283429
0.9643	High Similarity	NPC224714
0.964	High Similarity	NPC148545
0.9638	High Similarity	NPC253822
0.9638	High Similarity	NPC101366
0.958	High Similarity	NPC61258
0.9577	High Similarity	NPC168085
0.9574	High Similarity	NPC316769
0.9574	High Similarity	NPC472629
0.9562	High Similarity	NPC116632
0.9562	High Similarity	NPC303644
0.9562	High Similarity	NPC162680
0.9562	High Similarity	NPC7013
0.9562	High Similarity	NPC209560
0.9562	High Similarity	NPC181124
0.9562	High Similarity	NPC294409
0.951	High Similarity	NPC89442
0.951	High Similarity	NPC5173
0.951	High Similarity	NPC317492
0.9504	High Similarity	NPC124780
0.9504	High Similarity	NPC476055
0.9504	High Similarity	NPC87486
0.9504	High Similarity	NPC470890
0.9493	High Similarity	NPC279668
0.9493	High Similarity	NPC21350
0.9493	High Similarity	NPC309154
0.9493	High Similarity	NPC278323
0.9493	High Similarity	NPC55162
0.9493	High Similarity	NPC90665
0.9493	High Similarity	NPC12175
0.9489	High Similarity	NPC477244
0.9489	High Similarity	NPC150399
0.9489	High Similarity	NPC98115
0.9489	High Similarity	NPC274109
0.9489	High Similarity	NPC477242
0.9489	High Similarity	NPC249606
0.9489	High Similarity	NPC1486
0.9489	High Similarity	NPC66349
0.9489	High Similarity	NPC12165
0.9489	High Similarity	NPC186838
0.9489	High Similarity	NPC168105
0.9489	High Similarity	NPC477243
0.9489	High Similarity	NPC41461
0.9489	High Similarity	NPC25287
0.9448	High Similarity	NPC324233
0.9448	High Similarity	NPC323626
0.9444	High Similarity	NPC124478
0.9444	High Similarity	NPC177308
0.9444	High Similarity	NPC37348
0.9441	High Similarity	NPC6511
0.9433	High Similarity	NPC175504
0.9433	High Similarity	NPC310130
0.9433	High Similarity	NPC169591
0.9433	High Similarity	NPC257097
0.9433	High Similarity	NPC68104
0.9433	High Similarity	NPC150408
0.9433	High Similarity	NPC164980
0.9433	High Similarity	NPC221432
0.9433	High Similarity	NPC149026
0.9433	High Similarity	NPC143896
0.9433	High Similarity	NPC91560
0.9433	High Similarity	NPC75049
0.9433	High Similarity	NPC39329
0.9429	High Similarity	NPC110969
0.9424	High Similarity	NPC201541
0.9424	High Similarity	NPC477956
0.942	High Similarity	NPC472419
0.942	High Similarity	NPC317119
0.942	High Similarity	NPC153979
0.9416	High Similarity	NPC131039
0.9416	High Similarity	NPC156092
0.9416	High Similarity	NPC84699
0.9416	High Similarity	NPC13575
0.9416	High Similarity	NPC234560
0.9416	High Similarity	NPC39426
0.9384	High Similarity	NPC7989
0.9384	High Similarity	NPC223701
0.9384	High Similarity	NPC472583
0.9379	High Similarity	NPC472422
0.9379	High Similarity	NPC472420
0.9379	High Similarity	NPC471676
0.9379	High Similarity	NPC244577
0.9379	High Similarity	NPC263384
0.9375	High Similarity	NPC470461
0.9371	High Similarity	NPC237635
0.9371	High Similarity	NPC473077
0.9371	High Similarity	NPC296998
0.9371	High Similarity	NPC23728
0.9371	High Similarity	NPC79469
0.9371	High Similarity	NPC24673
0.9371	High Similarity	NPC201731
0.9371	High Similarity	NPC97716
0.9371	High Similarity	NPC104406
0.9371	High Similarity	NPC110303
0.9366	High Similarity	NPC236766
0.9366	High Similarity	NPC197252
0.9366	High Similarity	NPC319752
0.9366	High Similarity	NPC311741
0.9366	High Similarity	NPC273538
0.9366	High Similarity	NPC209040
0.9366	High Similarity	NPC473013
0.9366	High Similarity	NPC216538
0.9366	High Similarity	NPC473015
0.9366	High Similarity	NPC234629
0.9362	High Similarity	NPC161506
0.9362	High Similarity	NPC227579
0.9362	High Similarity	NPC324436
0.9362	High Similarity	NPC177354
0.9362	High Similarity	NPC32739
0.9362	High Similarity	NPC328164
0.9362	High Similarity	NPC66515
0.9362	High Similarity	NPC194432
0.9362	High Similarity	NPC306829
0.9362	High Similarity	NPC265040
0.9362	High Similarity	NPC226636
0.9362	High Similarity	NPC148757
0.9362	High Similarity	NPC125855
0.9362	High Similarity	NPC296917
0.9362	High Similarity	NPC228504
0.9362	High Similarity	NPC324134
0.9362	High Similarity	NPC166934
0.9362	High Similarity	NPC182852
0.9362	High Similarity	NPC220998
0.9362	High Similarity	NPC37496
0.9362	High Similarity	NPC64915
0.9362	High Similarity	NPC167624
0.9362	High Similarity	NPC107572
0.9362	High Similarity	NPC10937
0.9362	High Similarity	NPC40833
0.9362	High Similarity	NPC76338
0.9362	High Similarity	NPC223500
0.9362	High Similarity	NPC11561
0.9362	High Similarity	NPC76372
0.9362	High Similarity	NPC1089
0.9362	High Similarity	NPC78
0.9362	High Similarity	NPC166482
0.9357	High Similarity	NPC261227
0.9357	High Similarity	NPC159275
0.9357	High Similarity	NPC270883
0.9357	High Similarity	NPC172986
0.9357	High Similarity	NPC11056
0.9357	High Similarity	NPC241100
0.9353	High Similarity	NPC243528
0.9353	High Similarity	NPC251681
0.9353	High Similarity	NPC471620
0.9348	High Similarity	NPC87545
0.9348	High Similarity	NPC235428
0.9343	High Similarity	NPC164136
0.9343	High Similarity	NPC103842
0.9343	High Similarity	NPC286336
0.932	High Similarity	NPC470681
0.9315	High Similarity	NPC35567
0.9315	High Similarity	NPC56232
0.9315	High Similarity	NPC31627
0.9315	High Similarity	NPC171651
0.9315	High Similarity	NPC150123
0.9315	High Similarity	NPC327269
0.9315	High Similarity	NPC243171
0.9315	High Similarity	NPC161881
0.9315	High Similarity	NPC10807
0.9315	High Similarity	NPC244583
0.9315	High Similarity	NPC476238
0.9315	High Similarity	NPC285623
0.931	High Similarity	NPC321896
0.931	High Similarity	NPC476185
0.931	High Similarity	NPC472633
0.931	High Similarity	NPC474735
0.9306	High Similarity	NPC132592
0.9306	High Similarity	NPC39195
0.9306	High Similarity	NPC266572
0.9306	High Similarity	NPC160821
0.9306	High Similarity	NPC470460
0.9301	High Similarity	NPC111786

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 NPC51887 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	931
0.2-0.3	1559
0.3-0.4	2590
0.4-0.5	1994
0.5-0.6	1134
0.6-0.7	406
0.7-0.8	122
0.8-0.85	44
0.85-0.9	21
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9444	High Similarity	NPD4380	Phase 2
0.9416	High Similarity	NPD1510	Phase 2
0.9366	High Similarity	NPD4378	Clinical (unspecified phase)
0.9124	High Similarity	NPD1240	Approved
0.9078	High Similarity	NPD1549	Phase 2
0.9071	High Similarity	NPD2796	Approved
0.9007	High Similarity	NPD1550	Clinical (unspecified phase)
0.9007	High Similarity	NPD1552	Clinical (unspecified phase)
0.8993	High Similarity	NPD1607	Approved
0.8993	High Similarity	NPD2393	Clinical (unspecified phase)
0.8966	High Similarity	NPD7410	Clinical (unspecified phase)
0.8816	High Similarity	NPD7075	Discontinued
0.8816	High Similarity	NPD4381	Clinical (unspecified phase)
0.8808	High Similarity	NPD8443	Clinical (unspecified phase)
0.88	High Similarity	NPD6801	Discontinued
0.8742	High Similarity	NPD7096	Clinical (unspecified phase)
0.8733	High Similarity	NPD7411	Suspended
0.8675	High Similarity	NPD1934	Approved
0.8618	High Similarity	NPD7819	Suspended
0.8553	High Similarity	NPD7804	Clinical (unspecified phase)
0.8542	High Similarity	NPD2935	Discontinued
0.8514	High Similarity	NPD1511	Approved
0.8497	Intermediate Similarity	NPD2801	Approved
0.8435	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6959	Discontinued
0.84	Intermediate Similarity	NPD1512	Approved
0.8389	Intermediate Similarity	NPD6799	Approved
0.8387	Intermediate Similarity	NPD7768	Phase 2
0.8375	Intermediate Similarity	NPD3818	Discontinued
0.8367	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD6166	Phase 2
0.8365	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6651	Approved
0.8311	Intermediate Similarity	NPD3750	Approved
0.8299	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD3882	Suspended
0.8243	Intermediate Similarity	NPD2800	Approved
0.8239	Intermediate Similarity	NPD6232	Discontinued
0.8228	Intermediate Similarity	NPD5494	Approved
0.8224	Intermediate Similarity	NPD920	Approved
0.8224	Intermediate Similarity	NPD5403	Approved
0.8212	Intermediate Similarity	NPD2533	Approved
0.8212	Intermediate Similarity	NPD2534	Approved
0.8212	Intermediate Similarity	NPD2532	Approved
0.821	Intermediate Similarity	NPD7054	Approved
0.8205	Intermediate Similarity	NPD3817	Phase 2
0.8199	Intermediate Similarity	NPD7473	Discontinued
0.8182	Intermediate Similarity	NPD6599	Discontinued
0.8171	Intermediate Similarity	NPD6559	Discontinued
0.8163	Intermediate Similarity	NPD1551	Phase 2
0.816	Intermediate Similarity	NPD7074	Phase 3
0.816	Intermediate Similarity	NPD7472	Approved
0.8121	Intermediate Similarity	NPD1243	Approved
0.8121	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6797	Phase 2
0.8095	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD5401	Approved
0.8092	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD5402	Approved
0.8079	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7251	Discontinued
0.8056	Intermediate Similarity	NPD2313	Discontinued
0.8056	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD2798	Approved
0.8012	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD5953	Discontinued
0.7988	Intermediate Similarity	NPD7286	Phase 2
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD3749	Approved
0.7973	Intermediate Similarity	NPD2799	Discontinued
0.7973	Intermediate Similarity	NPD3748	Approved
0.7947	Intermediate Similarity	NPD4628	Phase 3
0.7945	Intermediate Similarity	NPD943	Approved
0.7908	Intermediate Similarity	NPD7390	Discontinued
0.7904	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2344	Approved
0.7861	Intermediate Similarity	NPD4360	Phase 2
0.7861	Intermediate Similarity	NPD4363	Phase 3
0.7852	Intermediate Similarity	NPD7033	Discontinued
0.7808	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3226	Approved
0.773	Intermediate Similarity	NPD1247	Approved
0.7716	Intermediate Similarity	NPD919	Approved
0.7708	Intermediate Similarity	NPD1203	Approved
0.7679	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4908	Phase 1
0.7671	Intermediate Similarity	NPD6832	Phase 2
0.767	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2309	Approved
0.7658	Intermediate Similarity	NPD7458	Discontinued
0.7651	Intermediate Similarity	NPD5124	Phase 1
0.7651	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2654	Approved
0.7644	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1548	Phase 1
0.7632	Intermediate Similarity	NPD2346	Discontinued
0.7622	Intermediate Similarity	NPD3972	Approved
0.7619	Intermediate Similarity	NPD3027	Phase 3
0.7614	Intermediate Similarity	NPD4361	Phase 2
0.7614	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5710	Approved
0.7576	Intermediate Similarity	NPD5711	Approved
0.7568	Intermediate Similarity	NPD3268	Approved
0.7566	Intermediate Similarity	NPD6099	Approved
0.7566	Intermediate Similarity	NPD6100	Approved
0.7562	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7533	Intermediate Similarity	NPD230	Phase 1
0.7518	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD9493	Approved
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7486	Intermediate Similarity	NPD7584	Approved
0.7484	Intermediate Similarity	NPD7003	Approved
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1613	Approved
0.7467	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2797	Approved
0.7466	Intermediate Similarity	NPD1164	Approved
0.7466	Intermediate Similarity	NPD1470	Approved
0.7451	Intermediate Similarity	NPD5408	Approved
0.7451	Intermediate Similarity	NPD5406	Approved
0.7451	Intermediate Similarity	NPD5404	Approved
0.7451	Intermediate Similarity	NPD5405	Approved
0.7438	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD422	Phase 1
0.7431	Intermediate Similarity	NPD1201	Approved
0.7425	Intermediate Similarity	NPD3926	Phase 2
0.7417	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1729	Discontinued
0.7407	Intermediate Similarity	NPD6844	Discontinued
0.7407	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1465	Phase 2
0.7348	Intermediate Similarity	NPD6781	Approved
0.7348	Intermediate Similarity	NPD6779	Approved
0.7348	Intermediate Similarity	NPD6777	Approved
0.7348	Intermediate Similarity	NPD6778	Approved
0.7348	Intermediate Similarity	NPD6782	Approved
0.7348	Intermediate Similarity	NPD6780	Approved
0.7348	Intermediate Similarity	NPD6776	Approved
0.7341	Intermediate Similarity	NPD8313	Approved
0.7341	Intermediate Similarity	NPD8312	Approved
0.7333	Intermediate Similarity	NPD3764	Approved
0.733	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4288	Approved
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.729	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3225	Approved
0.7279	Intermediate Similarity	NPD1876	Approved
0.7273	Intermediate Similarity	NPD4967	Phase 2
0.7273	Intermediate Similarity	NPD4965	Approved
0.7273	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD4625	Phase 3
0.7262	Intermediate Similarity	NPD7229	Phase 3
0.7256	Intermediate Similarity	NPD5761	Phase 2
0.7256	Intermediate Similarity	NPD5760	Phase 2
0.7253	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2424	Discontinued
0.7239	Intermediate Similarity	NPD5890	Approved
0.7239	Intermediate Similarity	NPD5889	Approved
0.7237	Intermediate Similarity	NPD4307	Phase 2
0.7233	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3266	Approved
0.723	Intermediate Similarity	NPD3267	Approved
0.7228	Intermediate Similarity	NPD7696	Phase 3
0.7228	Intermediate Similarity	NPD7698	Approved
0.7228	Intermediate Similarity	NPD7697	Approved
0.7228	Intermediate Similarity	NPD7435	Discontinued
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6798	Discontinued
0.7219	Intermediate Similarity	NPD8151	Discontinued
0.7216	Intermediate Similarity	NPD8150	Discontinued
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.7215	Intermediate Similarity	NPD6190	Approved
0.72	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1652	Phase 2
0.7193	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD447	Suspended
0.719	Intermediate Similarity	NPD1933	Approved
0.7189	Intermediate Similarity	NPD7871	Phase 2
0.7189	Intermediate Similarity	NPD7870	Phase 2
0.7188	Intermediate Similarity	NPD4661	Approved
0.7188	Intermediate Similarity	NPD4662	Approved
0.7186	Intermediate Similarity	NPD6234	Discontinued
0.7181	Intermediate Similarity	NPD1019	Discontinued
0.7179	Intermediate Similarity	NPD6005	Phase 3
0.7179	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6002	Phase 3
0.7179	Intermediate Similarity	NPD6004	Phase 3
0.7179	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3823	Discontinued
0.7163	Intermediate Similarity	NPD1241	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