NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.11
Volume:	261.435
LogP:	3.019
LogD:	3.211
LogS:	-2.642
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	1.923
Fsp3:	0.2
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:	-4.821
MDCK Permeability:	1.664703268033918e-05
Pgp-inhibitor:	0.108
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.07
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	96.76547241210938%
Volume Distribution (VD):	0.876
Pgp-substrate:	3.2188124656677246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.426
CYP2C19-inhibitor:	0.94
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.754
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.951
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.25

ADMET: Excretion

Clearance (CL):	15.918
Half-life (T1/2):	0.921

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.408
Rat Oral Acute Toxicity:	0.629
Maximum Recommended Daily Dose:	0.172
Skin Sensitization:	0.954
Carcinogencity:	0.181
Eye Corrosion:	0.645
Eye Irritation:	0.976
Respiratory Toxicity:	0.096

Download Data

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

Natural Product: NPC119860

Natural Product ID:	NPC119860
*Common Name:**	4-[3-(4-Hydroxyphenyl)Propyl]Benzene-1,3-Diol
IUPAC Name:	4-[3-(4-hydroxyphenyl)propyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	OKSKNGMIUSMMMM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O3/c16-13-7-4-11(5-8-13)2-1-3-12-6-9-14(17)10-15(12)18/h4-10,16-18H,1-3H2
SMILES:	C(Cc1ccc(cc1)O)Cc1ccc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453448
PubChem CID:	10900865
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]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
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]
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]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]

☑ 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
Individual Protein	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	>	40.0	ug.mL-1	PMID[511265]

☑ 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 NPC119860 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	407
0.1-0.2	2028
0.2-0.3	6934
0.3-0.4	12715
0.4-0.5	4596
0.5-0.6	7622
0.6-0.7	6284
0.7-0.8	1758
0.8-0.85	216
0.85-0.9	104
0.9-0.95	30
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC474839
0.96	High Similarity	NPC61885
0.96	High Similarity	NPC63698
0.9596	High Similarity	NPC248904
0.9412	High Similarity	NPC475018
0.9394	High Similarity	NPC102216
0.9394	High Similarity	NPC30506
0.9381	High Similarity	NPC80027
0.932	High Similarity	NPC225679
0.932	High Similarity	NPC4493
0.932	High Similarity	NPC476632
0.932	High Similarity	NPC165770
0.93	High Similarity	NPC292452
0.9231	High Similarity	NPC166995
0.9231	High Similarity	NPC43525
0.9216	High Similarity	NPC174981
0.92	High Similarity	NPC241891
0.9192	High Similarity	NPC100340
0.9192	High Similarity	NPC143659
0.9167	High Similarity	NPC128062
0.9143	High Similarity	NPC117846
0.9126	High Similarity	NPC33728
0.9126	High Similarity	NPC202647
0.9126	High Similarity	NPC19808
0.9109	High Similarity	NPC134829
0.9091	High Similarity	NPC275053
0.9091	High Similarity	NPC248573
0.9091	High Similarity	NPC161571
0.9057	High Similarity	NPC107240
0.902	High Similarity	NPC39664
0.902	High Similarity	NPC118286
0.902	High Similarity	NPC109691
0.902	High Similarity	NPC39097
0.902	High Similarity	NPC302681
0.902	High Similarity	NPC470700
0.8969	High Similarity	NPC151715
0.8958	High Similarity	NPC45040
0.8952	High Similarity	NPC224527
0.8932	High Similarity	NPC54844
0.8922	High Similarity	NPC246056
0.89	High Similarity	NPC10588
0.8889	High Similarity	NPC54507
0.8889	High Similarity	NPC85292
0.8889	High Similarity	NPC229147
0.8889	High Similarity	NPC291789
0.8878	High Similarity	NPC26244
0.8824	High Similarity	NPC244513
0.8824	High Similarity	NPC218879
0.8824	High Similarity	NPC227458
0.8812	High Similarity	NPC284011
0.8812	High Similarity	NPC72947
0.8807	High Similarity	NPC470760
0.8796	High Similarity	NPC185541
0.8796	High Similarity	NPC464
0.8788	High Similarity	NPC473388
0.8785	High Similarity	NPC261343
0.8774	High Similarity	NPC268032
0.875	High Similarity	NPC158253
0.875	High Similarity	NPC204901
0.875	High Similarity	NPC232523
0.8738	High Similarity	NPC37802
0.8727	High Similarity	NPC144343
0.8727	High Similarity	NPC131118
0.8725	High Similarity	NPC168303
0.8725	High Similarity	NPC242342
0.8725	High Similarity	NPC85479
0.8725	High Similarity	NPC302219
0.8725	High Similarity	NPC106396
0.8725	High Similarity	NPC313030
0.8725	High Similarity	NPC94351
0.8725	High Similarity	NPC53051
0.8725	High Similarity	NPC222522
0.8725	High Similarity	NPC168829
0.8725	High Similarity	NPC71002
0.8725	High Similarity	NPC146798
0.8725	High Similarity	NPC24404
0.8725	High Similarity	NPC249828
0.8716	High Similarity	NPC115808
0.8713	High Similarity	NPC213730
0.8713	High Similarity	NPC166761
0.8687	High Similarity	NPC274678
0.8673	High Similarity	NPC271440
0.8654	High Similarity	NPC201662
0.8654	High Similarity	NPC12640
0.8654	High Similarity	NPC99836
0.8641	High Similarity	NPC288411
0.8636	High Similarity	NPC277588
0.8627	High Similarity	NPC24407
0.8627	High Similarity	NPC7686
0.8627	High Similarity	NPC91461
0.8627	High Similarity	NPC147310
0.8627	High Similarity	NPC40258
0.8627	High Similarity	NPC11280
0.8627	High Similarity	NPC166313
0.8627	High Similarity	NPC137415
0.8627	High Similarity	NPC294186
0.8627	High Similarity	NPC192032
0.8624	High Similarity	NPC808
0.8624	High Similarity	NPC246760
0.8624	High Similarity	NPC84999
0.8614	High Similarity	NPC132078
0.8614	High Similarity	NPC216468
0.8614	High Similarity	NPC78119
0.8614	High Similarity	NPC51333
0.8614	High Similarity	NPC92730
0.8611	High Similarity	NPC23804
0.86	High Similarity	NPC132271
0.86	High Similarity	NPC292730
0.86	High Similarity	NPC216520
0.86	High Similarity	NPC82664
0.8585	High Similarity	NPC186385
0.8585	High Similarity	NPC299568
0.8571	High Similarity	NPC223451
0.8571	High Similarity	NPC176527
0.8571	High Similarity	NPC69006
0.8558	High Similarity	NPC99557
0.8558	High Similarity	NPC219286
0.8558	High Similarity	NPC138942
0.8557	High Similarity	NPC318325
0.8557	High Similarity	NPC123273
0.8557	High Similarity	NPC242240
0.8545	High Similarity	NPC141090
0.8545	High Similarity	NPC150624
0.8544	High Similarity	NPC168393
0.8519	High Similarity	NPC473521
0.8515	High Similarity	NPC225464
0.8505	High Similarity	NPC224870
0.8496	Intermediate Similarity	NPC24125
0.8491	Intermediate Similarity	NPC105727
0.8491	Intermediate Similarity	NPC34864
0.8491	Intermediate Similarity	NPC95344
0.8491	Intermediate Similarity	NPC58427
0.8491	Intermediate Similarity	NPC114392
0.8482	Intermediate Similarity	NPC217174
0.8482	Intermediate Similarity	NPC191866
0.8468	Intermediate Similarity	NPC474933
0.8468	Intermediate Similarity	NPC69261
0.8468	Intermediate Similarity	NPC33270
0.8454	Intermediate Similarity	NPC113460
0.8454	Intermediate Similarity	NPC25493
0.844	Intermediate Similarity	NPC263753
0.8438	Intermediate Similarity	NPC155393
0.8431	Intermediate Similarity	NPC128723
0.8421	Intermediate Similarity	NPC237667
0.8421	Intermediate Similarity	NPC54972
0.8421	Intermediate Similarity	NPC476633
0.8421	Intermediate Similarity	NPC196976
0.8407	Intermediate Similarity	NPC93398
0.8407	Intermediate Similarity	NPC159525
0.8407	Intermediate Similarity	NPC258979
0.8407	Intermediate Similarity	NPC8283
0.8407	Intermediate Similarity	NPC472071
0.84	Intermediate Similarity	NPC76938
0.8396	Intermediate Similarity	NPC305603
0.8396	Intermediate Similarity	NPC61033
0.8393	Intermediate Similarity	NPC190514
0.8393	Intermediate Similarity	NPC74821
0.8384	Intermediate Similarity	NPC204210
0.8381	Intermediate Similarity	NPC154899
0.8381	Intermediate Similarity	NPC233396
0.8378	Intermediate Similarity	NPC203113
0.8367	Intermediate Similarity	NPC280347
0.8367	Intermediate Similarity	NPC177420
0.8367	Intermediate Similarity	NPC258219
0.8364	Intermediate Similarity	NPC22610
0.8364	Intermediate Similarity	NPC473137
0.8364	Intermediate Similarity	NPC276737
0.8351	Intermediate Similarity	NPC407
0.8351	Intermediate Similarity	NPC307235
0.8351	Intermediate Similarity	NPC23167
0.8348	Intermediate Similarity	NPC100099
0.8348	Intermediate Similarity	NPC120172
0.8348	Intermediate Similarity	NPC36016
0.8333	Intermediate Similarity	NPC77492
0.8333	Intermediate Similarity	NPC175313
0.8333	Intermediate Similarity	NPC102639
0.8319	Intermediate Similarity	NPC188814
0.8319	Intermediate Similarity	NPC195262
0.8319	Intermediate Similarity	NPC295259
0.8319	Intermediate Similarity	NPC158222
0.8319	Intermediate Similarity	NPC184302
0.8318	Intermediate Similarity	NPC262365
0.8317	Intermediate Similarity	NPC8392
0.8317	Intermediate Similarity	NPC313650
0.8317	Intermediate Similarity	NPC32714
0.8304	Intermediate Similarity	NPC50521
0.8304	Intermediate Similarity	NPC195466
0.8304	Intermediate Similarity	NPC221549
0.8304	Intermediate Similarity	NPC244816
0.8302	Intermediate Similarity	NPC67250
0.8302	Intermediate Similarity	NPC54765
0.8302	Intermediate Similarity	NPC92623
0.8302	Intermediate Similarity	NPC271274
0.8302	Intermediate Similarity	NPC135464
0.83	Intermediate Similarity	NPC295295
0.8288	Intermediate Similarity	NPC472893
0.8288	Intermediate Similarity	NPC53906
0.8286	Intermediate Similarity	NPC261573
0.8286	Intermediate Similarity	NPC120693
0.8286	Intermediate Similarity	NPC8931

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 NPC119860 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	1043
0.2-0.3	1418
0.3-0.4	2975
0.4-0.5	1830
0.5-0.6	1046
0.6-0.7	372
0.7-0.8	62
0.8-0.85	5
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9588	High Similarity	NPD846	Approved
0.9588	High Similarity	NPD940	Approved
0.9091	High Similarity	NPD1242	Phase 1
0.8878	High Similarity	NPD2860	Approved
0.8878	High Similarity	NPD2859	Approved
0.8776	High Similarity	NPD2934	Approved
0.8776	High Similarity	NPD2933	Approved
0.8614	High Similarity	NPD3020	Approved
0.8585	High Similarity	NPD4750	Phase 3
0.8393	Intermediate Similarity	NPD1548	Phase 1
0.8261	Intermediate Similarity	NPD1610	Phase 2
0.8218	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD1809	Phase 2
0.8137	Intermediate Similarity	NPD844	Approved
0.8119	Intermediate Similarity	NPD845	Approved
0.8041	Intermediate Similarity	NPD111	Approved
0.7934	Intermediate Similarity	NPD4908	Phase 1
0.7917	Intermediate Similarity	NPD9089	Approved
0.7909	Intermediate Similarity	NPD3021	Approved
0.7909	Intermediate Similarity	NPD3022	Approved
0.7885	Intermediate Similarity	NPD288	Approved
0.783	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD9093	Approved
0.7805	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD422	Phase 1
0.7787	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD3028	Approved
0.7642	Intermediate Similarity	NPD9273	Approved
0.7581	Intermediate Similarity	NPD4625	Phase 3
0.7581	Intermediate Similarity	NPD3027	Phase 3
0.7568	Intermediate Similarity	NPD2342	Discontinued
0.7544	Intermediate Similarity	NPD7635	Approved
0.754	Intermediate Similarity	NPD1240	Approved
0.754	Intermediate Similarity	NPD1613	Approved
0.754	Intermediate Similarity	NPD943	Approved
0.754	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD4749	Approved
0.7479	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD2228	Approved
0.7478	Intermediate Similarity	NPD2234	Approved
0.7478	Intermediate Similarity	NPD2229	Approved
0.7458	Intermediate Similarity	NPD5303	Approved
0.7458	Intermediate Similarity	NPD5304	Approved
0.7451	Intermediate Similarity	NPD9094	Approved
0.7434	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD1607	Approved
0.7402	Intermediate Similarity	NPD1555	Discontinued
0.7381	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4589	Approved
0.7323	Intermediate Similarity	NPD6405	Approved
0.7323	Intermediate Similarity	NPD6407	Approved
0.7321	Intermediate Similarity	NPD968	Approved
0.7308	Intermediate Similarity	NPD1510	Phase 2
0.7304	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD9608	Approved
0.7297	Intermediate Similarity	NPD9610	Approved
0.7281	Intermediate Similarity	NPD1792	Phase 2
0.728	Intermediate Similarity	NPD2861	Phase 2
0.7258	Intermediate Similarity	NPD1164	Approved
0.7258	Intermediate Similarity	NPD1129	Approved
0.7258	Intermediate Similarity	NPD1133	Approved
0.7258	Intermediate Similarity	NPD1134	Approved
0.7258	Intermediate Similarity	NPD1135	Approved
0.7258	Intermediate Similarity	NPD1131	Approved
0.7236	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4659	Approved
0.7213	Intermediate Similarity	NPD1201	Approved
0.7203	Intermediate Similarity	NPD6671	Approved
0.72	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1445	Approved
0.7168	Intermediate Similarity	NPD1444	Approved
0.7167	Intermediate Similarity	NPD3091	Approved
0.7154	Intermediate Similarity	NPD2561	Approved
0.7154	Intermediate Similarity	NPD2562	Approved
0.7154	Intermediate Similarity	NPD2568	Approved
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD3018	Phase 2
0.713	Intermediate Similarity	NPD5451	Approved
0.712	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4103	Phase 2
0.7109	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4093	Discontinued
0.7105	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3555	Approved
0.7099	Intermediate Similarity	NPD3554	Approved
0.7099	Intermediate Similarity	NPD3552	Approved
0.7099	Intermediate Similarity	NPD3553	Approved
0.7083	Intermediate Similarity	NPD856	Approved
0.7083	Intermediate Similarity	NPD9087	Approved
0.7083	Intermediate Similarity	NPD16	Approved
0.7073	Intermediate Similarity	NPD3092	Approved
0.7049	Intermediate Similarity	NPD2286	Discontinued
0.7049	Intermediate Similarity	NPD4059	Approved
0.7049	Intermediate Similarity	NPD2932	Approved
0.7049	Intermediate Similarity	NPD3019	Approved
0.7043	Intermediate Similarity	NPD74	Approved
0.7043	Intermediate Similarity	NPD2684	Approved
0.7043	Intermediate Similarity	NPD9266	Approved
0.7037	Intermediate Similarity	NPD3750	Approved
0.7025	Intermediate Similarity	NPD1759	Phase 1
0.7025	Intermediate Similarity	NPD7330	Discontinued
0.7009	Intermediate Similarity	NPD228	Approved
0.7007	Intermediate Similarity	NPD7212	Phase 2
0.7007	Intermediate Similarity	NPD7213	Phase 3
0.7	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2797	Approved
0.6984	Remote Similarity	NPD1470	Approved
0.6984	Remote Similarity	NPD3094	Phase 2
0.697	Remote Similarity	NPD9088	Approved
0.696	Remote Similarity	NPD2982	Phase 2
0.696	Remote Similarity	NPD6583	Phase 3
0.696	Remote Similarity	NPD2983	Phase 2
0.696	Remote Similarity	NPD6582	Phase 2
0.6957	Remote Similarity	NPD9264	Approved
0.6957	Remote Similarity	NPD7447	Phase 1
0.6957	Remote Similarity	NPD9267	Approved
0.6957	Remote Similarity	NPD290	Approved
0.6957	Remote Similarity	NPD9263	Approved
0.6957	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5535	Approved
0.6949	Remote Similarity	NPD9377	Approved
0.6949	Remote Similarity	NPD9379	Approved
0.6942	Remote Similarity	NPD317	Approved
0.6942	Remote Similarity	NPD1758	Phase 1
0.6942	Remote Similarity	NPD318	Approved
0.6935	Remote Similarity	NPD1091	Approved
0.6923	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD255	Approved
0.6917	Remote Similarity	NPD256	Approved
0.6911	Remote Similarity	NPD1751	Approved
0.6891	Remote Similarity	NPD5283	Phase 1
0.6885	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7390	Discontinued
0.688	Remote Similarity	NPD2981	Phase 2
0.687	Remote Similarity	NPD468	Phase 1
0.6869	Remote Similarity	NPD9294	Approved
0.6866	Remote Similarity	NPD5406	Approved
0.6866	Remote Similarity	NPD5404	Approved
0.6866	Remote Similarity	NPD5408	Approved
0.6866	Remote Similarity	NPD6100	Approved
0.6866	Remote Similarity	NPD6099	Approved
0.6866	Remote Similarity	NPD5405	Approved
0.686	Remote Similarity	NPD9493	Approved
0.6855	Remote Similarity	NPD3421	Phase 3
0.6855	Remote Similarity	NPD3847	Discontinued
0.6842	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD497	Approved
0.6829	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5124	Phase 1
0.6807	Remote Similarity	NPD821	Approved
0.6807	Remote Similarity	NPD7843	Approved
0.68	Remote Similarity	NPD1535	Discovery
0.6797	Remote Similarity	NPD858	Approved
0.6797	Remote Similarity	NPD602	Approved
0.6797	Remote Similarity	NPD859	Approved
0.6797	Remote Similarity	NPD599	Approved
0.6797	Remote Similarity	NPD6584	Phase 3
0.6791	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD709	Approved
0.6774	Remote Similarity	NPD9381	Approved
0.6774	Remote Similarity	NPD2667	Approved
0.6774	Remote Similarity	NPD5846	Approved
0.6774	Remote Similarity	NPD6516	Phase 2
0.6774	Remote Similarity	NPD2668	Approved
0.6774	Remote Similarity	NPD3095	Discontinued
0.6774	Remote Similarity	NPD4626	Approved
0.6774	Remote Similarity	NPD9384	Approved
0.6772	Remote Similarity	NPD3225	Approved
0.6772	Remote Similarity	NPD5311	Approved
0.6772	Remote Similarity	NPD5310	Approved
0.6763	Remote Similarity	NPD1511	Approved
0.6754	Remote Similarity	NPD9500	Approved
0.675	Remote Similarity	NPD496	Approved
0.675	Remote Similarity	NPD495	Approved
0.675	Remote Similarity	NPD498	Approved
0.6748	Remote Similarity	NPD9545	Approved
0.6746	Remote Similarity	NPD9269	Phase 2
0.6746	Remote Similarity	NPD1481	Phase 2
0.6742	Remote Similarity	NPD4060	Phase 1
0.6742	Remote Similarity	NPD2238	Phase 2
0.6741	Remote Similarity	NPD2935	Discontinued
0.6741	Remote Similarity	NPD2796	Approved
0.6741	Remote Similarity	NPD1551	Phase 2
0.6721	Remote Similarity	NPD9568	Approved
0.6721	Remote Similarity	NPD405	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1981	Approved
0.672	Remote Similarity	NPD1983	Approved
0.672	Remote Similarity	NPD1980	Approved
0.672	Remote Similarity	NPD3143	Discontinued
0.6719	Remote Similarity	NPD3053	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