NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.13
Volume:	278.731
LogP:	3.545
LogD:	3.509
LogS:	-3.13
# Rotatable Bonds:	5
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.865
Synthetic Accessibility Score:	1.829
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:	-4.79
MDCK Permeability:	1.606055229785852e-05
Pgp-inhibitor:	0.076
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	97.96849060058594%
Volume Distribution (VD):	0.973
Pgp-substrate:	1.605013370513916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.961
CYP2C19-substrate:	0.105
CYP2C9-inhibitor:	0.826
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.962
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.684
CYP3A4-substrate:	0.445

ADMET: Excretion

Clearance (CL):	12.66
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.202
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.301
Skin Sensitization:	0.948
Carcinogencity:	0.142
Eye Corrosion:	0.457
Eye Irritation:	0.98
Respiratory Toxicity:	0.259

Download Data

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

Natural Product: NPC229147

Natural Product ID:	NPC229147
*Common Name:**	Broussonin A
IUPAC Name:	2-[3-(4-hydroxyphenyl)propyl]-5-methoxyphenol
Synonyms:
Standard InCHIKey:	MSNVBURPCQDLEP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18O3/c1-19-15-10-7-13(16(18)11-15)4-2-3-12-5-8-14(17)9-6-12/h5-11,17-18H,2-4H2,1H3
SMILES:	COc1ccc(CCCc2ccc(cc2)O)c(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465879
PubChem CID:	5315502
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[11575957]
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]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19046886]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20493686]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO33390	broussonetia kanzinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22450131]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917310]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16111	Broussonetia kazinoki	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]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16111	Broussonetia kazinoki	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[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	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	2
IC50	5
Others	4

Activity Type	# Activity
Cell Line	1
Individual Protein	9
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	30000.0	nM	PMID[527322]
NPT520	Cell Line	3T3-L1	Mus musculus	IC50	=	74500.0	nM	PMID[527323]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	IC50	=	8100.0	nM	PMID[527324]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	RBA	=	0.394	%	PMID[527324]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	RBA	=	0.069	%	PMID[527324]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	IC50	=	1800.0	nM	PMID[527324]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	EC50	=	1590.0	nM	PMID[527324]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	EC50	=	530.0	nM	PMID[527324]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	50.7	%	PMID[527325]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	=	98700.0	nM	PMID[527325]
NPT2	Others	Unspecified		Ratio IC50	=	5.71	n.a.	PMID[527324]

☑ 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 NPC229147 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	313
0.1-0.2	1799
0.2-0.3	5237
0.3-0.4	13660
0.4-0.5	3943
0.5-0.6	4989
0.6-0.7	7709
0.7-0.8	4056
0.8-0.85	647
0.85-0.9	262
0.9-0.95	73
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC54507
1.0	High Similarity	NPC85292
0.9907	High Similarity	NPC464
0.9907	High Similarity	NPC185541
0.9818	High Similarity	NPC131118
0.955	High Similarity	NPC33270
0.955	High Similarity	NPC474933
0.955	High Similarity	NPC69261
0.9474	High Similarity	NPC476633
0.9459	High Similarity	NPC150624
0.9459	High Similarity	NPC141090
0.9391	High Similarity	NPC100099
0.9391	High Similarity	NPC36016
0.9386	High Similarity	NPC102639
0.9381	High Similarity	NPC184302
0.9369	High Similarity	NPC53906
0.9369	High Similarity	NPC808
0.931	High Similarity	NPC474160
0.931	High Similarity	NPC38761
0.931	High Similarity	NPC76465
0.9304	High Similarity	NPC54972
0.9292	High Similarity	NPC190514
0.9286	High Similarity	NPC203113
0.9279	High Similarity	NPC276737
0.9279	High Similarity	NPC228287
0.9279	High Similarity	NPC180508
0.9279	High Similarity	NPC22610
0.9231	High Similarity	NPC197351
0.9231	High Similarity	NPC134195
0.9231	High Similarity	NPC106914
0.9231	High Similarity	NPC246648
0.9231	High Similarity	NPC86502
0.9211	High Similarity	NPC295259
0.9204	High Similarity	NPC50521
0.9204	High Similarity	NPC195466
0.9204	High Similarity	NPC221549
0.9204	High Similarity	NPC15860
0.9204	High Similarity	NPC219070
0.9204	High Similarity	NPC470759
0.9204	High Similarity	NPC244816
0.9204	High Similarity	NPC127894
0.9153	High Similarity	NPC105925
0.9153	High Similarity	NPC285040
0.9153	High Similarity	NPC113495
0.9153	High Similarity	NPC103420
0.9153	High Similarity	NPC188022
0.9153	High Similarity	NPC105031
0.9153	High Similarity	NPC102540
0.9153	High Similarity	NPC17809
0.913	High Similarity	NPC8283
0.913	High Similarity	NPC258979
0.913	High Similarity	NPC93398
0.9123	High Similarity	NPC74821
0.9115	High Similarity	NPC114064
0.9099	High Similarity	NPC280606
0.9076	High Similarity	NPC276212
0.9076	High Similarity	NPC230479
0.9076	High Similarity	NPC283049
0.9076	High Similarity	NPC26879
0.9076	High Similarity	NPC170485
0.9076	High Similarity	NPC50315
0.9074	High Similarity	NPC113457
0.906	High Similarity	NPC18128
0.906	High Similarity	NPC77789
0.9027	High Similarity	NPC167934
0.9009	High Similarity	NPC90520
0.9009	High Similarity	NPC296920
0.9	High Similarity	NPC246620
0.9	High Similarity	NPC74817
0.9	High Similarity	NPC473221
0.9	High Similarity	NPC324112
0.9	High Similarity	NPC159968
0.9	High Similarity	NPC124452
0.9	High Similarity	NPC149796
0.9	High Similarity	NPC236791
0.9	High Similarity	NPC293054
0.9	High Similarity	NPC282000
0.9	High Similarity	NPC82679
0.9	High Similarity	NPC169474
0.8992	High Similarity	NPC60885
0.8992	High Similarity	NPC234400
0.8983	High Similarity	NPC136319
0.8983	High Similarity	NPC282496
0.8983	High Similarity	NPC233526
0.8981	High Similarity	NPC474839
0.8974	High Similarity	NPC193364
0.8926	High Similarity	NPC274717
0.8926	High Similarity	NPC222572
0.8926	High Similarity	NPC53986
0.8926	High Similarity	NPC87224
0.8926	High Similarity	NPC38664
0.8919	High Similarity	NPC94045
0.8919	High Similarity	NPC2682
0.8919	High Similarity	NPC168657
0.8917	High Similarity	NPC103823
0.8917	High Similarity	NPC18924
0.8917	High Similarity	NPC28730
0.8917	High Similarity	NPC44748
0.8917	High Similarity	NPC82299
0.8917	High Similarity	NPC223953
0.8917	High Similarity	NPC78974
0.8917	High Similarity	NPC214406
0.8917	High Similarity	NPC223136
0.8909	High Similarity	NPC63698
0.8909	High Similarity	NPC61885
0.8908	High Similarity	NPC270030
0.8908	High Similarity	NPC228503
0.8908	High Similarity	NPC138248
0.8908	High Similarity	NPC159132
0.8889	High Similarity	NPC119860
0.8879	High Similarity	NPC172253
0.8879	High Similarity	NPC59561
0.8852	High Similarity	NPC471519
0.8852	High Similarity	NPC190144
0.8852	High Similarity	NPC93962
0.8852	High Similarity	NPC134360
0.8852	High Similarity	NPC471518
0.885	High Similarity	NPC141003
0.885	High Similarity	NPC35344
0.8843	High Similarity	NPC46978
0.8833	High Similarity	NPC208950
0.8833	High Similarity	NPC203133
0.8833	High Similarity	NPC278955
0.8833	High Similarity	NPC82483
0.8833	High Similarity	NPC251855
0.8833	High Similarity	NPC265483
0.8833	High Similarity	NPC17943
0.8833	High Similarity	NPC233410
0.8833	High Similarity	NPC57490
0.8833	High Similarity	NPC475169
0.8833	High Similarity	NPC116907
0.8833	High Similarity	NPC472093
0.8833	High Similarity	NPC298757
0.8833	High Similarity	NPC221077
0.8833	High Similarity	NPC105718
0.8833	High Similarity	NPC117214
0.8833	High Similarity	NPC299584
0.8833	High Similarity	NPC193544
0.8829	High Similarity	NPC82016
0.8814	High Similarity	NPC75713
0.8814	High Similarity	NPC97432
0.8814	High Similarity	NPC190454
0.878	High Similarity	NPC51840
0.878	High Similarity	NPC299221
0.878	High Similarity	NPC224157
0.878	High Similarity	NPC234488
0.878	High Similarity	NPC311680
0.878	High Similarity	NPC254000
0.878	High Similarity	NPC192687
0.878	High Similarity	NPC126836
0.877	High Similarity	NPC28765
0.877	High Similarity	NPC215300
0.877	High Similarity	NPC47283
0.877	High Similarity	NPC219923
0.877	High Similarity	NPC39064
0.877	High Similarity	NPC154866
0.875	High Similarity	NPC475018
0.8739	High Similarity	NPC41562
0.8739	High Similarity	NPC201959
0.8739	High Similarity	NPC74137
0.8739	High Similarity	NPC75440
0.8729	High Similarity	NPC166759
0.8729	High Similarity	NPC218753
0.871	High Similarity	NPC162801
0.871	High Similarity	NPC150011
0.871	High Similarity	NPC118114
0.871	High Similarity	NPC268917
0.871	High Similarity	NPC129106
0.871	High Similarity	NPC280653
0.871	High Similarity	NPC12875
0.871	High Similarity	NPC196765
0.871	High Similarity	NPC129784
0.871	High Similarity	NPC207892
0.871	High Similarity	NPC211413
0.871	High Similarity	NPC236014
0.871	High Similarity	NPC17343
0.871	High Similarity	NPC244888
0.871	High Similarity	NPC68205
0.871	High Similarity	NPC474356
0.871	High Similarity	NPC118683
0.871	High Similarity	NPC282508
0.871	High Similarity	NPC471517
0.871	High Similarity	NPC164804
0.871	High Similarity	NPC476166
0.871	High Similarity	NPC103799
0.871	High Similarity	NPC473309
0.871	High Similarity	NPC293203
0.871	High Similarity	NPC15543
0.871	High Similarity	NPC164574
0.871	High Similarity	NPC300875
0.871	High Similarity	NPC12275
0.871	High Similarity	NPC206224
0.871	High Similarity	NPC45715
0.871	High Similarity	NPC228369
0.8699	High Similarity	NPC469951
0.8699	High Similarity	NPC212015
0.8699	High Similarity	NPC10225
0.8699	High Similarity	NPC469963
0.8699	High Similarity	NPC58164
0.8689	High Similarity	NPC252131

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 NPC229147 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	1056
0.2-0.3	1472
0.3-0.4	2711
0.4-0.5	1774
0.5-0.6	1040
0.6-0.7	636
0.7-0.8	127
0.8-0.85	14
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9123	High Similarity	NPD1548	Phase 1
0.8974	High Similarity	NPD1610	Phase 2
0.8926	High Similarity	NPD4908	Phase 1
0.878	High Similarity	NPD4907	Clinical (unspecified phase)
0.8704	High Similarity	NPD940	Approved
0.8704	High Similarity	NPD846	Approved
0.8548	High Similarity	NPD3027	Phase 3
0.85	High Similarity	NPD422	Phase 1
0.84	Intermediate Similarity	NPD4625	Phase 3
0.8361	Intermediate Similarity	NPD4749	Approved
0.8346	Intermediate Similarity	NPD1240	Approved
0.8333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.832	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8241	Intermediate Similarity	NPD2860	Approved
0.8241	Intermediate Similarity	NPD2859	Approved
0.824	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1607	Approved
0.8203	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8203	Intermediate Similarity	NPD1613	Approved
0.816	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD2934	Approved
0.8148	Intermediate Similarity	NPD2933	Approved
0.8108	Intermediate Similarity	NPD1242	Phase 1
0.8095	Intermediate Similarity	NPD2861	Phase 2
0.8095	Intermediate Similarity	NPD3018	Phase 2
0.8065	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD3020	Approved
0.8017	Intermediate Similarity	NPD5451	Approved
0.8017	Intermediate Similarity	NPD4750	Phase 3
0.7955	Intermediate Similarity	NPD1510	Phase 2
0.7931	Intermediate Similarity	NPD2684	Approved
0.792	Intermediate Similarity	NPD2983	Phase 2
0.792	Intermediate Similarity	NPD2982	Phase 2
0.7917	Intermediate Similarity	NPD6671	Approved
0.7913	Intermediate Similarity	NPD968	Approved
0.7883	Intermediate Similarity	NPD7212	Phase 2
0.7883	Intermediate Similarity	NPD7213	Phase 3
0.784	Intermediate Similarity	NPD2981	Phase 2
0.7836	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7447	Phase 1
0.7778	Intermediate Similarity	NPD6582	Phase 2
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.7778	Intermediate Similarity	NPD6583	Phase 3
0.775	Intermediate Similarity	NPD5283	Phase 1
0.7731	Intermediate Similarity	NPD228	Approved
0.7727	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5124	Phase 1
0.7692	Intermediate Similarity	NPD290	Approved
0.768	Intermediate Similarity	NPD3847	Discontinued
0.7667	Intermediate Similarity	NPD5535	Approved
0.7667	Intermediate Similarity	NPD7843	Approved
0.7664	Intermediate Similarity	NPD3750	Approved
0.7656	Intermediate Similarity	NPD2797	Approved
0.763	Intermediate Similarity	NPD6100	Approved
0.763	Intermediate Similarity	NPD2796	Approved
0.763	Intermediate Similarity	NPD6099	Approved
0.7619	Intermediate Similarity	NPD1091	Approved
0.76	Intermediate Similarity	NPD2668	Approved
0.76	Intermediate Similarity	NPD2667	Approved
0.76	Intermediate Similarity	NPD4626	Approved
0.7597	Intermediate Similarity	NPD6584	Phase 3
0.7571	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD821	Approved
0.7519	Intermediate Similarity	NPD2238	Phase 2
0.7519	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7157	Approved
0.748	Intermediate Similarity	NPD2557	Approved
0.746	Intermediate Similarity	NPD6516	Phase 2
0.746	Intermediate Similarity	NPD5846	Approved
0.7445	Intermediate Similarity	NPD3540	Phase 1
0.7442	Intermediate Similarity	NPD8651	Approved
0.7442	Intermediate Similarity	NPD3225	Approved
0.7434	Intermediate Similarity	NPD1809	Phase 2
0.7434	Intermediate Similarity	NPD844	Approved
0.7431	Intermediate Similarity	NPD4380	Phase 2
0.7426	Intermediate Similarity	NPD7033	Discontinued
0.7422	Intermediate Similarity	NPD2233	Approved
0.7422	Intermediate Similarity	NPD2232	Approved
0.7422	Intermediate Similarity	NPD2230	Approved
0.7419	Intermediate Similarity	NPD3596	Phase 2
0.7417	Intermediate Similarity	NPD3022	Approved
0.7417	Intermediate Similarity	NPD3021	Approved
0.7411	Intermediate Similarity	NPD845	Approved
0.741	Intermediate Similarity	NPD3892	Phase 2
0.741	Intermediate Similarity	NPD7466	Approved
0.7407	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4097	Suspended
0.7397	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7411	Suspended
0.7379	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD6799	Approved
0.7372	Intermediate Similarity	NPD1551	Phase 2
0.7372	Intermediate Similarity	NPD3539	Phase 1
0.7368	Intermediate Similarity	NPD6798	Discontinued
0.7368	Intermediate Similarity	NPD3268	Approved
0.7364	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6387	Discontinued
0.7339	Intermediate Similarity	NPD709	Approved
0.7338	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1652	Phase 2
0.7329	Intermediate Similarity	NPD1934	Approved
0.7328	Intermediate Similarity	NPD3690	Phase 2
0.7328	Intermediate Similarity	NPD3691	Phase 2
0.7315	Intermediate Similarity	NPD111	Approved
0.7311	Intermediate Similarity	NPD3134	Approved
0.7308	Intermediate Similarity	NPD6696	Suspended
0.7302	Intermediate Similarity	NPD1894	Discontinued
0.7302	Intermediate Similarity	NPD6580	Approved
0.7302	Intermediate Similarity	NPD6581	Approved
0.7299	Intermediate Similarity	NPD3748	Approved
0.7297	Intermediate Similarity	NPD7768	Phase 2
0.7287	Intermediate Similarity	NPD1608	Approved
0.7286	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2801	Approved
0.7279	Intermediate Similarity	NPD3052	Approved
0.7279	Intermediate Similarity	NPD3054	Approved
0.7279	Intermediate Similarity	NPD6651	Approved
0.7254	Intermediate Similarity	NPD1511	Approved
0.7248	Intermediate Similarity	NPD7075	Discontinued
0.7244	Intermediate Similarity	NPD1651	Approved
0.7244	Intermediate Similarity	NPD3049	Approved
0.7244	Intermediate Similarity	NPD3445	Approved
0.7244	Intermediate Similarity	NPD5691	Approved
0.7244	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3443	Approved
0.7244	Intermediate Similarity	NPD3444	Approved
0.7239	Intermediate Similarity	NPD1296	Phase 2
0.7236	Intermediate Similarity	NPD1138	Approved
0.7231	Intermediate Similarity	NPD1669	Approved
0.7226	Intermediate Similarity	NPD4538	Approved
0.7226	Intermediate Similarity	NPD2200	Suspended
0.7226	Intermediate Similarity	NPD4536	Approved
0.7226	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD288	Approved
0.7209	Intermediate Similarity	NPD1535	Discovery
0.7207	Intermediate Similarity	NPD9295	Approved
0.7206	Intermediate Similarity	NPD6355	Discontinued
0.7197	Intermediate Similarity	NPD4624	Approved
0.7192	Intermediate Similarity	NPD6599	Discontinued
0.7188	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1778	Approved
0.7183	Intermediate Similarity	NPD6667	Approved
0.7183	Intermediate Similarity	NPD6666	Approved
0.7181	Intermediate Similarity	NPD3882	Suspended
0.7179	Intermediate Similarity	NPD3028	Approved
0.7179	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1283	Approved
0.7162	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7819	Suspended
0.7154	Intermediate Similarity	NPD1137	Approved
0.7154	Intermediate Similarity	NPD1481	Phase 2
0.7154	Intermediate Similarity	NPD1139	Approved
0.7154	Intermediate Similarity	NPD3972	Approved
0.7153	Intermediate Similarity	NPD1512	Approved
0.7133	Intermediate Similarity	NPD4357	Discontinued
0.7133	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1558	Phase 1
0.7132	Intermediate Similarity	NPD3496	Discontinued
0.7121	Intermediate Similarity	NPD1203	Approved
0.7113	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1358	Approved
0.7101	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3685	Discontinued
0.7097	Intermediate Similarity	NPD7635	Approved
0.7095	Intermediate Similarity	NPD6801	Discontinued
0.7095	Intermediate Similarity	NPD37	Approved
0.7087	Intermediate Similarity	NPD5536	Phase 2
0.708	Intermediate Similarity	NPD4340	Discontinued
0.7068	Intermediate Similarity	NPD2798	Approved
0.7067	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7124	Phase 2
0.7059	Intermediate Similarity	NPD6405	Approved
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7059	Intermediate Similarity	NPD6232	Discontinued
0.7059	Intermediate Similarity	NPD7477	Discontinued
0.7059	Intermediate Similarity	NPD6407	Approved
0.7054	Intermediate Similarity	NPD17	Approved
0.7054	Intermediate Similarity	NPD2556	Approved
0.7054	Intermediate Similarity	NPD2554	Approved
0.705	Intermediate Similarity	NPD5960	Phase 3
0.705	Intermediate Similarity	NPD5588	Approved
0.7045	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4628	Phase 3
0.704	Intermediate Similarity	NPD2228	Approved
0.704	Intermediate Similarity	NPD2229	Approved
0.704	Intermediate Similarity	NPD2234	Approved
0.704	Intermediate Similarity	NPD1241	Discontinued
0.7037	Intermediate Similarity	NPD7095	Approved
0.7037	Intermediate Similarity	NPD5163	Phase 2
0.7037	Intermediate Similarity	NPD9089	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