NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.13
Volume:	278.731
LogP:	3.462
LogD:	3.56
LogS:	-3.221
# Rotatable Bonds:	4
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.885
Synthetic Accessibility Score:	2.014
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.812
MDCK Permeability:	2.0125147784710862e-05
Pgp-inhibitor:	0.154
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.659

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.146
Plasma Protein Binding (PPB):	97.63031768798828%
Volume Distribution (VD):	1.256
Pgp-substrate:	1.9857823848724365%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.941
CYP2C19-substrate:	0.222
CYP2C9-inhibitor:	0.689
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.945
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.653
CYP3A4-substrate:	0.463

ADMET: Excretion

Clearance (CL):	13.156
Half-life (T1/2):	0.862

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.294
Skin Sensitization:	0.935
Carcinogencity:	0.118
Eye Corrosion:	0.354
Eye Irritation:	0.976
Respiratory Toxicity:	0.188

Download Data

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

Natural Product: NPC190514

Natural Product ID:	NPC190514
*Common Name:**	Stilbostemin D
IUPAC Name:	5-[2-(2-methoxyphenyl)ethyl]-2-methylbenzene-1,3-diol
Synonyms:
Standard InCHIKey:	LLRJCKLNDNKRTF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18O3/c1-11-14(17)9-12(10-15(11)18)7-8-13-5-3-4-6-16(13)19-2/h3-6,9-10,17-18H,7-8H2,1-2H3
SMILES:	Cc1c(cc(CCc2ccccc2OC)cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462852
PubChem CID:	15222503
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	Leaves, rhizomes, and roots	southeast Thailand near Chonburi	2000-Feb, 2001-Jan	PMID[12088422]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	slowly dried tubers	Bangkok, Thailand	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	n.a.	Southeast Thailand near Chonburi, Khao Khieo, close to the Chanthathen waterfall and Sri Racha	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679323]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679323]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[16643052]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	Roots; Stems; Tubers	n.a.	n.a.	PMID[16872143]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[18452334]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21902195]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21902195]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	root	n.a.	PMID[21902195]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12104	Stemona cf. pierrei	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10580	Herba glechomae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12104	Stemona cf. pierrei	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	leaf and root	n.a.	n.a.	Database[Title]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25902	Glechoma grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10316	Glechoma longituba	Species	Lamiaceae	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
EC50	5
IC50	1
MIC	5
Others	6

Activity Type	# Activity
Organism	15
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3821	Organism	Alternaria citri	Alternaria citri	EC50	=	19.0	ug.mL-1	PMID[448252]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC50	=	57.0	ug.mL-1	PMID[448252]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	3.0	ug.mL-1	PMID[448252]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	EC50	=	11.0	ug.mL-1	PMID[448252]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC50	=	17.0	ug.mL-1	PMID[448252]
NPT3821	Organism	Alternaria citri	Alternaria citri	EC90	>	200.0	ug ml-1	PMID[448252]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC90	>	200.0	ug ml-1	PMID[448252]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	152.0	ug ml-1	PMID[448252]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	EC90	>	200.0	ug ml-1	PMID[448252]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC90	>	200.0	ug ml-1	PMID[448252]
NPT3821	Organism	Alternaria citri	Alternaria citri	MIC	>	200.0	ug.mL-1	PMID[448252]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	MIC	>	200.0	ug.mL-1	PMID[448252]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	100.0	ug.mL-1	PMID[448252]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	>	200.0	ug.mL-1	PMID[448252]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	>	200.0	ug.mL-1	PMID[448252]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[448253]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[448253]

☑ 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 NPC190514 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	330
0.1-0.2	1832
0.2-0.3	5066
0.3-0.4	13712
0.4-0.5	4091
0.5-0.6	5046
0.6-0.7	8282
0.7-0.8	3469
0.8-0.85	563
0.85-0.9	242
0.9-0.95	53
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.991	High Similarity	NPC184302
0.973	High Similarity	NPC33270
0.973	High Similarity	NPC69261
0.9727	High Similarity	NPC808
0.964	High Similarity	NPC150624
0.9565	High Similarity	NPC18128
0.9565	High Similarity	NPC77789
0.955	High Similarity	NPC53906
0.9459	High Similarity	NPC22610
0.9459	High Similarity	NPC276737
0.9381	High Similarity	NPC474933
0.9381	High Similarity	NPC219070
0.9381	High Similarity	NPC470759
0.9381	High Similarity	NPC127894
0.9381	High Similarity	NPC244816
0.9381	High Similarity	NPC50521
0.9381	High Similarity	NPC221549
0.9381	High Similarity	NPC15860
0.9322	High Similarity	NPC105031
0.931	High Similarity	NPC476633
0.9292	High Similarity	NPC54507
0.9292	High Similarity	NPC114064
0.9292	High Similarity	NPC141090
0.9292	High Similarity	NPC85292
0.9292	High Similarity	NPC229147
0.9224	High Similarity	NPC218753
0.9224	High Similarity	NPC102639
0.9204	High Similarity	NPC185541
0.9204	High Similarity	NPC464
0.9204	High Similarity	NPC167934
0.9182	High Similarity	NPC19808
0.9182	High Similarity	NPC33728
0.9167	High Similarity	NPC473221
0.9167	High Similarity	NPC236760
0.913	High Similarity	NPC131118
0.9123	High Similarity	NPC203113
0.9115	High Similarity	NPC180508
0.9115	High Similarity	NPC228287
0.9099	High Similarity	NPC2682
0.9099	High Similarity	NPC94045
0.9099	High Similarity	NPC168657
0.9091	High Similarity	NPC174981
0.9083	High Similarity	NPC170485
0.9083	High Similarity	NPC82299
0.9076	High Similarity	NPC270030
0.9052	High Similarity	NPC137294
0.9052	High Similarity	NPC85895
0.9043	High Similarity	NPC195466
0.9018	High Similarity	NPC90520
0.9018	High Similarity	NPC224527
0.9018	High Similarity	NPC296920
0.9008	High Similarity	NPC46978
0.9	High Similarity	NPC113495
0.9	High Similarity	NPC131397
0.9	High Similarity	NPC476254
0.9	High Similarity	NPC105925
0.8992	High Similarity	NPC121115
0.8983	High Similarity	NPC212965
0.8983	High Similarity	NPC75713
0.8966	High Similarity	NPC63010
0.8938	High Similarity	NPC280606
0.8938	High Similarity	NPC166995
0.8934	High Similarity	NPC215300
0.8917	High Similarity	NPC138248
0.8917	High Similarity	NPC228503
0.8908	High Similarity	NPC120638
0.8871	High Similarity	NPC471517
0.8871	High Similarity	NPC472590
0.887	High Similarity	NPC232165
0.8862	High Similarity	NPC16577
0.8862	High Similarity	NPC222108
0.8862	High Similarity	NPC96719
0.886	High Similarity	NPC261343
0.886	High Similarity	NPC117846
0.8852	High Similarity	NPC293054
0.8852	High Similarity	NPC53781
0.8852	High Similarity	NPC236791
0.8852	High Similarity	NPC82679
0.8852	High Similarity	NPC324112
0.8852	High Similarity	NPC74817
0.8852	High Similarity	NPC246620
0.8852	High Similarity	NPC159968
0.8852	High Similarity	NPC124452
0.8852	High Similarity	NPC282000
0.8852	High Similarity	NPC169474
0.8843	High Similarity	NPC278955
0.8843	High Similarity	NPC105718
0.8843	High Similarity	NPC234400
0.8843	High Similarity	NPC60885
0.8833	High Similarity	NPC282496
0.8833	High Similarity	NPC95168
0.8833	High Similarity	NPC474160
0.8833	High Similarity	NPC233526
0.8833	High Similarity	NPC96940
0.8833	High Similarity	NPC136319
0.8829	High Similarity	NPC204901
0.8829	High Similarity	NPC158253
0.8829	High Similarity	NPC232523
0.8829	High Similarity	NPC35543
0.8818	High Similarity	NPC37802
0.88	High Similarity	NPC218884
0.878	High Similarity	NPC266691
0.878	High Similarity	NPC38017
0.877	High Similarity	NPC18924
0.877	High Similarity	NPC214406
0.877	High Similarity	NPC78974
0.877	High Similarity	NPC223953
0.877	High Similarity	NPC28730
0.877	High Similarity	NPC44748
0.877	High Similarity	NPC103823
0.877	High Similarity	NPC223136
0.8761	High Similarity	NPC303521
0.875	High Similarity	NPC75440
0.875	High Similarity	NPC245115
0.875	High Similarity	NPC36016
0.875	High Similarity	NPC100099
0.875	High Similarity	NPC41562
0.8739	High Similarity	NPC12640
0.8739	High Similarity	NPC277798
0.8739	High Similarity	NPC100108
0.8739	High Similarity	NPC201662
0.8739	High Similarity	NPC164576
0.8739	High Similarity	NPC99836
0.873	High Similarity	NPC469610
0.873	High Similarity	NPC269528
0.8729	High Similarity	NPC121866
0.8727	High Similarity	NPC218879
0.8727	High Similarity	NPC241891
0.8727	High Similarity	NPC244513
0.8727	High Similarity	NPC102216
0.8727	High Similarity	NPC227458
0.872	High Similarity	NPC282508
0.872	High Similarity	NPC8899
0.871	High Similarity	NPC190144
0.871	High Similarity	NPC212015
0.871	High Similarity	NPC471518
0.871	High Similarity	NPC472797
0.871	High Similarity	NPC471519
0.8707	High Similarity	NPC246760
0.8707	High Similarity	NPC84999
0.8699	High Similarity	NPC252131
0.8696	High Similarity	NPC23804
0.8689	High Similarity	NPC203133
0.8689	High Similarity	NPC475169
0.8689	High Similarity	NPC17943
0.8689	High Similarity	NPC82483
0.8689	High Similarity	NPC472093
0.8689	High Similarity	NPC57490
0.8689	High Similarity	NPC251855
0.8689	High Similarity	NPC298757
0.8689	High Similarity	NPC265483
0.8689	High Similarity	NPC233410
0.8689	High Similarity	NPC116907
0.8689	High Similarity	NPC117214
0.8689	High Similarity	NPC208950
0.8689	High Similarity	NPC221077
0.8689	High Similarity	NPC293801
0.8689	High Similarity	NPC193544
0.8689	High Similarity	NPC299584
0.8684	High Similarity	NPC225679
0.8684	High Similarity	NPC165770
0.8684	High Similarity	NPC4493
0.8684	High Similarity	NPC255068
0.8684	High Similarity	NPC476632
0.8678	High Similarity	NPC76465
0.8678	High Similarity	NPC197757
0.8678	High Similarity	NPC38761
0.8678	High Similarity	NPC228922
0.8678	High Similarity	NPC261992
0.8673	High Similarity	NPC299568
0.8673	High Similarity	NPC82016
0.8673	High Similarity	NPC186385
0.8667	High Similarity	NPC54972
0.8661	High Similarity	NPC103967
0.8655	High Similarity	NPC474565
0.8651	High Similarity	NPC469611
0.8649	High Similarity	NPC134829
0.864	High Similarity	NPC254000
0.864	High Similarity	NPC192687
0.864	High Similarity	NPC126836
0.864	High Similarity	NPC234488
0.864	High Similarity	NPC51840
0.864	High Similarity	NPC224157
0.864	High Similarity	NPC299221
0.864	High Similarity	NPC311680
0.8629	High Similarity	NPC154866
0.8629	High Similarity	NPC38604
0.8629	High Similarity	NPC211179
0.8629	High Similarity	NPC28765
0.8618	High Similarity	NPC230479
0.8618	High Similarity	NPC283049
0.8618	High Similarity	NPC26879
0.8618	High Similarity	NPC50315
0.8609	High Similarity	NPC43525
0.8607	High Similarity	NPC106914
0.8607	High Similarity	NPC246648
0.8607	High Similarity	NPC197351
0.8607	High Similarity	NPC134195
0.8607	High Similarity	NPC86502
0.8607	High Similarity	NPC140521

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 NPC190514 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	1065
0.2-0.3	1446
0.3-0.4	2726
0.4-0.5	1773
0.5-0.6	1066
0.6-0.7	636
0.7-0.8	99
0.8-0.85	12
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8862	High Similarity	NPD4625	Phase 3
0.8833	High Similarity	NPD4749	Approved
0.8673	High Similarity	NPD4750	Phase 3
0.8618	High Similarity	NPD6917	Clinical (unspecified phase)
0.8512	High Similarity	NPD1610	Phase 2
0.8492	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD1548	Phase 1
0.848	Intermediate Similarity	NPD4908	Phase 1
0.8413	Intermediate Similarity	NPD3027	Phase 3
0.8346	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6671	Approved
0.8214	Intermediate Similarity	NPD940	Approved
0.8214	Intermediate Similarity	NPD846	Approved
0.8189	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1242	Phase 1
0.811	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD844	Approved
0.808	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1613	Approved
0.8077	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD6099	Approved
0.8045	Intermediate Similarity	NPD6100	Approved
0.7969	Intermediate Similarity	NPD2861	Phase 2
0.7969	Intermediate Similarity	NPD3018	Phase 2
0.7955	Intermediate Similarity	NPD1607	Approved
0.792	Intermediate Similarity	NPD422	Phase 1
0.7903	Intermediate Similarity	NPD4626	Approved
0.7857	Intermediate Similarity	NPD288	Approved
0.7803	Intermediate Similarity	NPD1240	Approved
0.7795	Intermediate Similarity	NPD2983	Phase 2
0.7795	Intermediate Similarity	NPD2982	Phase 2
0.7786	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD968	Approved
0.7769	Intermediate Similarity	NPD5283	Phase 1
0.7768	Intermediate Similarity	NPD2860	Approved
0.7768	Intermediate Similarity	NPD2859	Approved
0.775	Intermediate Similarity	NPD228	Approved
0.7734	Intermediate Similarity	NPD6696	Suspended
0.7719	Intermediate Similarity	NPD3020	Approved
0.7717	Intermediate Similarity	NPD2233	Approved
0.7717	Intermediate Similarity	NPD2230	Approved
0.7717	Intermediate Similarity	NPD2232	Approved
0.7717	Intermediate Similarity	NPD2981	Phase 2
0.7687	Intermediate Similarity	NPD4097	Suspended
0.7686	Intermediate Similarity	NPD7635	Approved
0.7681	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD2933	Approved
0.7679	Intermediate Similarity	NPD2934	Approved
0.7669	Intermediate Similarity	NPD2238	Phase 2
0.7642	Intermediate Similarity	NPD709	Approved
0.7619	Intermediate Similarity	NPD1778	Approved
0.7615	Intermediate Similarity	NPD6584	Phase 3
0.7583	Intermediate Similarity	NPD5451	Approved
0.7574	Intermediate Similarity	NPD1510	Phase 2
0.7563	Intermediate Similarity	NPD2342	Discontinued
0.7563	Intermediate Similarity	NPD290	Approved
0.7554	Intermediate Similarity	NPD3892	Phase 2
0.754	Intermediate Similarity	NPD1651	Approved
0.754	Intermediate Similarity	NPD5691	Approved
0.7538	Intermediate Similarity	NPD2797	Approved
0.7537	Intermediate Similarity	NPD4060	Phase 1
0.7518	Intermediate Similarity	NPD2935	Discontinued
0.7518	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD2684	Approved
0.75	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD1398	Phase 1
0.7465	Intermediate Similarity	NPD7447	Phase 1
0.7465	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD1283	Approved
0.7442	Intermediate Similarity	NPD1608	Approved
0.744	Intermediate Similarity	NPD7340	Approved
0.7438	Intermediate Similarity	NPD3021	Approved
0.7438	Intermediate Similarity	NPD3022	Approved
0.7422	Intermediate Similarity	NPD3496	Discontinued
0.7394	Intermediate Similarity	NPD7212	Phase 2
0.7394	Intermediate Similarity	NPD7213	Phase 3
0.7385	Intermediate Similarity	NPD6582	Phase 2
0.7385	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD6583	Phase 3
0.7364	Intermediate Similarity	NPD1091	Approved
0.7364	Intermediate Similarity	NPD1611	Approved
0.736	Intermediate Similarity	NPD2557	Approved
0.7348	Intermediate Similarity	NPD4624	Approved
0.7344	Intermediate Similarity	NPD2668	Approved
0.7344	Intermediate Similarity	NPD2667	Approved
0.7343	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3540	Phase 1
0.7338	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2235	Phase 2
0.7308	Intermediate Similarity	NPD2231	Phase 2
0.7305	Intermediate Similarity	NPD3750	Approved
0.7297	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD3847	Discontinued
0.7286	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1549	Phase 2
0.7281	Intermediate Similarity	NPD845	Approved
0.7266	Intermediate Similarity	NPD3445	Approved
0.7266	Intermediate Similarity	NPD2796	Approved
0.7266	Intermediate Similarity	NPD3539	Phase 1
0.7266	Intermediate Similarity	NPD3444	Approved
0.7266	Intermediate Similarity	NPD3443	Approved
0.7259	Intermediate Similarity	NPD3268	Approved
0.7258	Intermediate Similarity	NPD5535	Approved
0.7258	Intermediate Similarity	NPD7843	Approved
0.7252	Intermediate Similarity	NPD1669	Approved
0.7239	Intermediate Similarity	NPD600	Approved
0.7239	Intermediate Similarity	NPD596	Approved
0.7234	Intermediate Similarity	NPD5177	Phase 3
0.7231	Intermediate Similarity	NPD1281	Approved
0.723	Intermediate Similarity	NPD1934	Approved
0.7226	Intermediate Similarity	NPD5124	Phase 1
0.7226	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7157	Approved
0.7222	Intermediate Similarity	NPD6387	Discontinued
0.7217	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5762	Approved
0.7214	Intermediate Similarity	NPD5763	Approved
0.7209	Intermediate Similarity	NPD17	Approved
0.7197	Intermediate Similarity	NPD3225	Approved
0.7194	Intermediate Similarity	NPD4308	Phase 3
0.7194	Intermediate Similarity	NPD7033	Discontinued
0.719	Intermediate Similarity	NPD6232	Discontinued
0.7183	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2801	Approved
0.7171	Intermediate Similarity	NPD6746	Phase 2
0.7153	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1511	Approved
0.7153	Intermediate Similarity	NPD3620	Phase 2
0.7132	Intermediate Similarity	NPD5585	Approved
0.7132	Intermediate Similarity	NPD3049	Approved
0.7121	Intermediate Similarity	NPD5327	Phase 3
0.712	Intermediate Similarity	NPD1138	Approved
0.712	Intermediate Similarity	NPD821	Approved
0.7114	Intermediate Similarity	NPD37	Approved
0.7109	Intermediate Similarity	NPD5536	Phase 2
0.7103	Intermediate Similarity	NPD2532	Approved
0.7103	Intermediate Similarity	NPD2533	Approved
0.7103	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2534	Approved
0.7101	Intermediate Similarity	NPD5735	Approved
0.7095	Intermediate Similarity	NPD4380	Phase 2
0.709	Intermediate Similarity	NPD3690	Phase 2
0.709	Intermediate Similarity	NPD2798	Approved
0.709	Intermediate Similarity	NPD3691	Phase 2
0.7086	Intermediate Similarity	NPD3882	Suspended
0.708	Intermediate Similarity	NPD840	Approved
0.708	Intermediate Similarity	NPD9295	Approved
0.708	Intermediate Similarity	NPD839	Approved
0.7077	Intermediate Similarity	NPD6516	Phase 2
0.7077	Intermediate Similarity	NPD5846	Approved
0.7068	Intermediate Similarity	NPD8651	Approved
0.7068	Intermediate Similarity	NPD2922	Phase 1
0.7067	Intermediate Similarity	NPD7819	Suspended
0.7063	Intermediate Similarity	NPD7466	Approved
0.7059	Intermediate Similarity	NPD7095	Approved
0.7055	Intermediate Similarity	NPD1512	Approved
0.7054	Intermediate Similarity	NPD3091	Approved
0.7051	Intermediate Similarity	NPD7473	Discontinued
0.7045	Intermediate Similarity	NPD3972	Approved
0.704	Intermediate Similarity	NPD1137	Approved
0.704	Intermediate Similarity	NPD1139	Approved
0.7037	Intermediate Similarity	NPD1712	Approved
0.7034	Intermediate Similarity	NPD4357	Discontinued
0.7034	Intermediate Similarity	NPD7041	Phase 2
0.7034	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3596	Phase 2
0.7029	Intermediate Similarity	NPD4140	Approved
0.7029	Intermediate Similarity	NPD1558	Phase 1
0.7021	Intermediate Similarity	NPD6032	Approved
0.702	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD1792	Phase 2
0.7015	Intermediate Similarity	NPD1203	Approved
0.7014	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6959	Discontinued
0.7009	Intermediate Similarity	NPD1809	Phase 2
0.7007	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD4536	Approved
0.7	Intermediate Similarity	NPD4538	Approved
0.7	Intermediate Similarity	NPD2200	Suspended
0.7	Intermediate Similarity	NPD1357	Approved
0.7	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6234	Discontinued
0.6993	Remote Similarity	NPD3060	Approved
0.698	Remote Similarity	NPD6599	Discontinued
0.6978	Remote Similarity	NPD6355	Discontinued
0.6974	Remote Similarity	NPD4965	Approved
0.6974	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4967	Phase 2
0.6974	Remote Similarity	NPD7768	Phase 2
0.6974	Remote Similarity	NPD4966	Approved
0.697	Remote Similarity	NPD1201	Approved
0.697	Remote Similarity	NPD3092	Approved
0.6966	Remote Similarity	NPD7124	Phase 2
0.6963	Remote Similarity	NPD7905	Discontinued
0.6957	Remote Similarity	NPD7477	Discontinued
0.695	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3748	Approved
0.6947	Remote Similarity	NPD2554	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