NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.06
Volume:	171.489
LogP:	0.508
LogD:	0.74
LogS:	-1.164
# Rotatable Bonds:	3
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.524
Synthetic Accessibility Score:	2.211
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.542
MDCK Permeability:	1.8803288185154088e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.249
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.917
30% Bioavailability (F30%):	0.291

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	52.926422119140625%
Volume Distribution (VD):	0.646
Pgp-substrate:	56.23617172241211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.239
CYP1A2-substrate:	0.511
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.827
CYP2D6-inhibitor:	0.344
CYP2D6-substrate:	0.722
CYP3A4-inhibitor:	0.052
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	18.252
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.705
Rat Oral Acute Toxicity:	0.689
Maximum Recommended Daily Dose:	0.059
Skin Sensitization:	0.953
Carcinogencity:	0.265
Eye Corrosion:	0.963
Eye Irritation:	0.987
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC131587

Natural Product ID:	NPC131587
*Common Name:**	4-[(E)-3-Hydroxyprop-1-Enyl]Benzene-1,2-Diol
IUPAC Name:	4-[(E)-3-hydroxyprop-1-enyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	ZCKDCRKBURQZPT-OWOJBTEDSA-N
Standard InCHI:	InChI=1S/C9H10O3/c10-5-1-2-7-3-4-8(11)9(12)6-7/h1-4,6,10-12H,5H2/b2-1+
SMILES:	OC/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1321891
PubChem CID:	5282096
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002754] Cinnamyl alcohols

*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
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1
Potency	4

Activity Type	# Activity
Individual Protein	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	39810.7	nM	PMID[568909]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	15848.9	nM	PMID[568909]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	28183.8	nM	PMID[568909]
NPT2	Others	Unspecified		Inhibition	=	95.2	%	PMID[568910]
NPT2	Others	Unspecified		IC50	=	73900.0	nM	PMID[568910]

☑ 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 NPC131587 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	319
0.1-0.2	2158
0.2-0.3	7960
0.3-0.4	12061
0.4-0.5	5805
0.5-0.6	9013
0.6-0.7	3910
0.7-0.8	1253
0.8-0.85	164
0.85-0.9	37
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC110764
0.9583	High Similarity	NPC12278
0.9468	High Similarity	NPC109955
0.9462	High Similarity	NPC107522
0.9278	High Similarity	NPC477802
0.9278	High Similarity	NPC477801
0.9271	High Similarity	NPC223393
0.9192	High Similarity	NPC19149
0.9109	High Similarity	NPC62258
0.9109	High Similarity	NPC55617
0.9082	High Similarity	NPC196479
0.9022	High Similarity	NPC104216
0.902	High Similarity	NPC147634
0.902	High Similarity	NPC174096
0.902	High Similarity	NPC120982
0.902	High Similarity	NPC226401
0.902	High Similarity	NPC79793
0.899	High Similarity	NPC52087
0.899	High Similarity	NPC79672
0.899	High Similarity	NPC120719
0.899	High Similarity	NPC471511
0.8932	High Similarity	NPC187583
0.8932	High Similarity	NPC78918
0.8932	High Similarity	NPC257430
0.8932	High Similarity	NPC139617
0.8932	High Similarity	NPC179002
0.89	High Similarity	NPC239291
0.883	High Similarity	NPC312304
0.883	High Similarity	NPC300017
0.8812	High Similarity	NPC477814
0.8812	High Similarity	NPC1075
0.8812	High Similarity	NPC1786
0.8812	High Similarity	NPC294902
0.8762	High Similarity	NPC471485
0.8738	High Similarity	NPC233731
0.8738	High Similarity	NPC36108
0.8738	High Similarity	NPC246358
0.8738	High Similarity	NPC7097
0.8725	High Similarity	NPC176527
0.8679	High Similarity	NPC217472
0.8679	High Similarity	NPC120280
0.8646	High Similarity	NPC138117
0.8646	High Similarity	NPC325292
0.8641	High Similarity	NPC233835
0.8641	High Similarity	NPC34864
0.8641	High Similarity	NPC58427
0.8641	High Similarity	NPC114392
0.8641	High Similarity	NPC105727
0.8632	High Similarity	NPC300478
0.86	High Similarity	NPC471578
0.86	High Similarity	NPC101025
0.8587	High Similarity	NPC265146
0.8585	High Similarity	NPC264558
0.8585	High Similarity	NPC95381
0.8571	High Similarity	NPC173746
0.8571	High Similarity	NPC257124
0.8571	High Similarity	NPC156840
0.8571	High Similarity	NPC8547
0.8571	High Similarity	NPC226250
0.8558	High Similarity	NPC228343
0.8558	High Similarity	NPC254833
0.8544	High Similarity	NPC227894
0.8519	High Similarity	NPC221049
0.8505	High Similarity	NPC328593
0.8505	High Similarity	NPC261453
0.8505	High Similarity	NPC33749
0.8495	Intermediate Similarity	NPC248817
0.8495	Intermediate Similarity	NPC175313
0.8495	Intermediate Similarity	NPC150837
0.8485	Intermediate Similarity	NPC474073
0.8476	Intermediate Similarity	NPC222084
0.8469	Intermediate Similarity	NPC274678
0.8469	Intermediate Similarity	NPC313650
0.844	Intermediate Similarity	NPC164386
0.8426	Intermediate Similarity	NPC474967
0.8426	Intermediate Similarity	NPC233669
0.8421	Intermediate Similarity	NPC27974
0.8411	Intermediate Similarity	NPC148969
0.8404	Intermediate Similarity	NPC197783
0.8396	Intermediate Similarity	NPC268032
0.8396	Intermediate Similarity	NPC297657
0.8387	Intermediate Similarity	NPC124436
0.8364	Intermediate Similarity	NPC255675
0.8364	Intermediate Similarity	NPC63126
0.8349	Intermediate Similarity	NPC281277
0.8318	Intermediate Similarity	NPC131530
0.8318	Intermediate Similarity	NPC146422
0.8318	Intermediate Similarity	NPC51698
0.8317	Intermediate Similarity	NPC174911
0.8317	Intermediate Similarity	NPC294741
0.8317	Intermediate Similarity	NPC130103
0.8316	Intermediate Similarity	NPC184169
0.8316	Intermediate Similarity	NPC23167
0.8302	Intermediate Similarity	NPC137685
0.83	Intermediate Similarity	NPC88420
0.8288	Intermediate Similarity	NPC470215
0.8288	Intermediate Similarity	NPC24474
0.8288	Intermediate Similarity	NPC320987
0.8288	Intermediate Similarity	NPC311595
0.8288	Intermediate Similarity	NPC470214
0.8288	Intermediate Similarity	NPC181969
0.8288	Intermediate Similarity	NPC109371
0.8283	Intermediate Similarity	NPC286006
0.8273	Intermediate Similarity	NPC610
0.8273	Intermediate Similarity	NPC200988
0.8273	Intermediate Similarity	NPC175799
0.8273	Intermediate Similarity	NPC65791
0.8273	Intermediate Similarity	NPC145023
0.8273	Intermediate Similarity	NPC39793
0.8247	Intermediate Similarity	NPC192
0.8247	Intermediate Similarity	NPC47950
0.8229	Intermediate Similarity	NPC19680
0.8229	Intermediate Similarity	NPC113460
0.8229	Intermediate Similarity	NPC25493
0.8224	Intermediate Similarity	NPC195873
0.8224	Intermediate Similarity	NPC55300
0.8224	Intermediate Similarity	NPC280382
0.8218	Intermediate Similarity	NPC128723
0.8218	Intermediate Similarity	NPC78119
0.8218	Intermediate Similarity	NPC51333
0.8218	Intermediate Similarity	NPC132078
0.8218	Intermediate Similarity	NPC216468
0.8214	Intermediate Similarity	NPC115627
0.8214	Intermediate Similarity	NPC148615
0.8214	Intermediate Similarity	NPC35071
0.8214	Intermediate Similarity	NPC265454
0.8214	Intermediate Similarity	NPC118522
0.8214	Intermediate Similarity	NPC34634
0.8214	Intermediate Similarity	NPC229401
0.8214	Intermediate Similarity	NPC169207
0.8214	Intermediate Similarity	NPC177475
0.8214	Intermediate Similarity	NPC472071
0.8208	Intermediate Similarity	NPC71266
0.82	Intermediate Similarity	NPC202986
0.8198	Intermediate Similarity	NPC275519
0.8198	Intermediate Similarity	NPC309434
0.8198	Intermediate Similarity	NPC203124
0.8198	Intermediate Similarity	NPC86198
0.8165	Intermediate Similarity	NPC142599
0.8163	Intermediate Similarity	NPC155908
0.8163	Intermediate Similarity	NPC270547
0.8163	Intermediate Similarity	NPC45040
0.8163	Intermediate Similarity	NPC231150
0.8163	Intermediate Similarity	NPC304541
0.8155	Intermediate Similarity	NPC235762
0.8155	Intermediate Similarity	NPC471228
0.8152	Intermediate Similarity	NPC204932
0.8148	Intermediate Similarity	NPC165646
0.8144	Intermediate Similarity	NPC280347
0.8144	Intermediate Similarity	NPC98772
0.8144	Intermediate Similarity	NPC318325
0.8144	Intermediate Similarity	NPC242240
0.8144	Intermediate Similarity	NPC123273
0.8144	Intermediate Similarity	NPC258219
0.8144	Intermediate Similarity	NPC177420
0.8142	Intermediate Similarity	NPC207613
0.8137	Intermediate Similarity	NPC161571
0.8137	Intermediate Similarity	NPC248573
0.8137	Intermediate Similarity	NPC213730
0.8137	Intermediate Similarity	NPC275053
0.8125	Intermediate Similarity	NPC70084
0.8125	Intermediate Similarity	NPC477803
0.8125	Intermediate Similarity	NPC141791
0.8125	Intermediate Similarity	NPC263386
0.8119	Intermediate Similarity	NPC32674
0.8108	Intermediate Similarity	NPC259638
0.8108	Intermediate Similarity	NPC293619
0.81	Intermediate Similarity	NPC257182
0.8091	Intermediate Similarity	NPC278102
0.8091	Intermediate Similarity	NPC4665
0.8081	Intermediate Similarity	NPC181709
0.8081	Intermediate Similarity	NPC29373
0.8081	Intermediate Similarity	NPC162314
0.8081	Intermediate Similarity	NPC306884
0.8081	Intermediate Similarity	NPC94139
0.8081	Intermediate Similarity	NPC147284
0.8081	Intermediate Similarity	NPC55903
0.8081	Intermediate Similarity	NPC3358
0.8081	Intermediate Similarity	NPC210497
0.8077	Intermediate Similarity	NPC475225
0.8077	Intermediate Similarity	NPC323810
0.8077	Intermediate Similarity	NPC12987
0.8077	Intermediate Similarity	NPC474603
0.807	Intermediate Similarity	NPC470212
0.807	Intermediate Similarity	NPC473853
0.807	Intermediate Similarity	NPC54872
0.807	Intermediate Similarity	NPC113865
0.807	Intermediate Similarity	NPC290451
0.807	Intermediate Similarity	NPC262156
0.807	Intermediate Similarity	NPC343720
0.807	Intermediate Similarity	NPC476343
0.807	Intermediate Similarity	NPC266045
0.807	Intermediate Similarity	NPC184651
0.807	Intermediate Similarity	NPC324571
0.807	Intermediate Similarity	NPC312675
0.807	Intermediate Similarity	NPC470804
0.807	Intermediate Similarity	NPC127389
0.8061	Intermediate Similarity	NPC55561
0.8058	Intermediate Similarity	NPC310905
0.8058	Intermediate Similarity	NPC91461

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 NPC131587 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	1055
0.2-0.3	1927
0.3-0.4	2916
0.4-0.5	1621
0.5-0.6	948
0.6-0.7	285
0.7-0.8	70
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD228	Approved
0.8558	High Similarity	NPD3022	Approved
0.8558	High Similarity	NPD3021	Approved
0.8387	Intermediate Similarity	NPD111	Approved
0.8318	Intermediate Similarity	NPD9377	Approved
0.8318	Intermediate Similarity	NPD9379	Approved
0.8214	Intermediate Similarity	NPD9384	Approved
0.8214	Intermediate Similarity	NPD9381	Approved
0.8137	Intermediate Similarity	NPD1242	Phase 1
0.8131	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2934	Approved
0.8	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2933	Approved
0.7931	Intermediate Similarity	NPD9622	Approved
0.7921	Intermediate Similarity	NPD844	Approved
0.7921	Intermediate Similarity	NPD2859	Approved
0.7921	Intermediate Similarity	NPD2860	Approved
0.7864	Intermediate Similarity	NPD3020	Approved
0.7843	Intermediate Similarity	NPD288	Approved
0.7807	Intermediate Similarity	NPD1357	Approved
0.7788	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD9619	Approved
0.7731	Intermediate Similarity	NPD9621	Approved
0.7731	Intermediate Similarity	NPD9620	Approved
0.7627	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD9094	Approved
0.7547	Intermediate Similarity	NPD846	Approved
0.7547	Intermediate Similarity	NPD940	Approved
0.7545	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD3027	Phase 3
0.7527	Intermediate Similarity	NPD9294	Approved
0.7521	Intermediate Similarity	NPD9494	Approved
0.748	Intermediate Similarity	NPD597	Approved
0.748	Intermediate Similarity	NPD601	Approved
0.748	Intermediate Similarity	NPD598	Approved
0.7476	Intermediate Similarity	NPD9296	Approved
0.7458	Intermediate Similarity	NPD3092	Approved
0.7455	Intermediate Similarity	NPD2684	Approved
0.7419	Intermediate Similarity	NPD1130	Approved
0.7419	Intermediate Similarity	NPD1132	Approved
0.7419	Intermediate Similarity	NPD1136	Approved
0.7417	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5310	Approved
0.7417	Intermediate Similarity	NPD5311	Approved
0.7414	Intermediate Similarity	NPD3091	Approved
0.7404	Intermediate Similarity	NPD1809	Phase 2
0.7391	Intermediate Similarity	NPD9087	Approved
0.7379	Intermediate Similarity	NPD845	Approved
0.7368	Intermediate Similarity	NPD9618	Approved
0.7368	Intermediate Similarity	NPD9614	Approved
0.7364	Intermediate Similarity	NPD290	Approved
0.736	Intermediate Similarity	NPD3062	Approved
0.736	Intermediate Similarity	NPD3061	Approved
0.736	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD1613	Approved
0.736	Intermediate Similarity	NPD3059	Approved
0.7355	Intermediate Similarity	NPD3053	Approved
0.7355	Intermediate Similarity	NPD3055	Approved
0.7315	Intermediate Similarity	NPD9500	Approved
0.7295	Intermediate Similarity	NPD257	Approved
0.7295	Intermediate Similarity	NPD258	Approved
0.7281	Intermediate Similarity	NPD5283	Phase 1
0.7273	Intermediate Similarity	NPD1444	Approved
0.7273	Intermediate Similarity	NPD968	Approved
0.7273	Intermediate Similarity	NPD1445	Approved
0.7263	Intermediate Similarity	NPD9088	Approved
0.7248	Intermediate Similarity	NPD9608	Approved
0.7248	Intermediate Similarity	NPD9610	Approved
0.7244	Intermediate Similarity	NPD823	Approved
0.7244	Intermediate Similarity	NPD5314	Approved
0.7244	Intermediate Similarity	NPD817	Approved
0.7236	Intermediate Similarity	NPD9569	Approved
0.7222	Intermediate Similarity	NPD826	Approved
0.7222	Intermediate Similarity	NPD3620	Phase 2
0.7222	Intermediate Similarity	NPD825	Approved
0.7222	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD3094	Phase 2
0.72	Intermediate Similarity	NPD3145	Approved
0.72	Intermediate Similarity	NPD3144	Approved
0.7193	Intermediate Similarity	NPD7843	Approved
0.7179	Intermediate Similarity	NPD9613	Approved
0.7179	Intermediate Similarity	NPD9615	Approved
0.7179	Intermediate Similarity	NPD9616	Approved
0.7177	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD555	Phase 2
0.7155	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD2674	Phase 3
0.7143	Intermediate Similarity	NPD259	Phase 1
0.7119	Intermediate Similarity	NPD316	Approved
0.7107	Intermediate Similarity	NPD9269	Phase 2
0.7103	Intermediate Similarity	NPD9273	Approved
0.7097	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4750	Phase 3
0.708	Intermediate Similarity	NPD1792	Phase 2
0.7077	Intermediate Similarity	NPD9570	Approved
0.7064	Intermediate Similarity	NPD291	Approved
0.7063	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2342	Discontinued
0.7034	Intermediate Similarity	NPD16	Approved
0.7034	Intermediate Similarity	NPD5536	Phase 2
0.7034	Intermediate Similarity	NPD318	Approved
0.7034	Intermediate Similarity	NPD317	Approved
0.7034	Intermediate Similarity	NPD856	Approved
0.7031	Intermediate Similarity	NPD230	Phase 1
0.7023	Intermediate Similarity	NPD7266	Discontinued
0.7019	Intermediate Similarity	NPD9365	Approved
0.7	Intermediate Similarity	NPD3095	Discontinued
0.6984	Remote Similarity	NPD9537	Phase 1
0.6984	Remote Similarity	NPD9536	Phase 1
0.6983	Remote Similarity	NPD2228	Approved
0.6983	Remote Similarity	NPD2229	Approved
0.6983	Remote Similarity	NPD2234	Approved
0.6972	Remote Similarity	NPD3028	Approved
0.697	Remote Similarity	NPD9089	Approved
0.6957	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1558	Phase 1
0.6953	Remote Similarity	NPD943	Approved
0.6944	Remote Similarity	NPD9495	Approved
0.6903	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1358	Approved
0.6899	Remote Similarity	NPD275	Approved
0.6899	Remote Similarity	NPD274	Approved
0.6897	Remote Similarity	NPD7635	Approved
0.6897	Remote Similarity	NPD821	Approved
0.6894	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD9093	Approved
0.6864	Remote Similarity	NPD6671	Approved
0.686	Remote Similarity	NPD3019	Approved
0.686	Remote Similarity	NPD2286	Discontinued
0.686	Remote Similarity	NPD2932	Approved
0.686	Remote Similarity	NPD4059	Approved
0.686	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1548	Phase 1
0.6833	Remote Similarity	NPD9545	Approved
0.6827	Remote Similarity	NPD9295	Approved
0.6815	Remote Similarity	NPD302	Approved
0.6815	Remote Similarity	NPD6190	Approved
0.6814	Remote Similarity	NPD3134	Approved
0.678	Remote Similarity	NPD1791	Approved
0.678	Remote Similarity	NPD1793	Approved
0.6777	Remote Similarity	NPD4093	Discontinued
0.6777	Remote Similarity	NPD9268	Approved
0.6774	Remote Similarity	NPD2982	Phase 2
0.6774	Remote Similarity	NPD2983	Phase 2
0.6774	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1610	Phase 2
0.6748	Remote Similarity	NPD3705	Approved
0.6746	Remote Similarity	NPD6584	Phase 3
0.6742	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD8166	Discontinued
0.6723	Remote Similarity	NPD255	Approved
0.6723	Remote Similarity	NPD256	Approved
0.6721	Remote Similarity	NPD6516	Phase 2
0.6721	Remote Similarity	NPD1751	Approved
0.6721	Remote Similarity	NPD5846	Approved
0.6721	Remote Similarity	NPD4626	Approved
0.6695	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2561	Approved
0.6694	Remote Similarity	NPD2981	Phase 2
0.6694	Remote Similarity	NPD1182	Approved
0.6694	Remote Similarity	NPD2562	Approved
0.6694	Remote Similarity	NPD2235	Phase 2
0.6694	Remote Similarity	NPD2231	Phase 2
0.6693	Remote Similarity	NPD5736	Approved
0.6693	Remote Similarity	NPD2861	Phase 2
0.6692	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD9568	Approved
0.6667	Remote Similarity	NPD3060	Approved
0.6667	Remote Similarity	NPD3421	Phase 3
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.664	Remote Similarity	NPD4659	Approved
0.6639	Remote Similarity	NPD475	Phase 2
0.6637	Remote Similarity	NPD9244	Approved
0.6615	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD1091	Approved
0.6602	Remote Similarity	NPD9073	Approved
0.6585	Remote Similarity	NPD1778	Approved
0.6562	Remote Similarity	NPD3018	Phase 2
0.6557	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD74	Approved
0.6552	Remote Similarity	NPD9266	Approved
0.6547	Remote Similarity	NPD3645	Discontinued
0.6547	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1133	Approved
0.6535	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1129	Approved
0.6535	Remote Similarity	NPD1134	Approved
0.6535	Remote Similarity	NPD1135	Approved
0.6535	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD9250	Approved
0.6535	Remote Similarity	NPD4103	Phase 2
0.6535	Remote Similarity	NPD1131	Approved
0.6532	Remote Similarity	NPD3496	Discontinued
0.6529	Remote Similarity	NPD9493	Approved
0.6525	Remote Similarity	NPD1653	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