NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	168.08
Volume:	174.125
LogP:	0.723
LogD:	0.87
LogS:	-0.258
# Rotatable Bonds:	3
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.59
Synthetic Accessibility Score:	1.912
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.424
MDCK Permeability:	1.8149310562876053e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.768
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	37.839202880859375%
Volume Distribution (VD):	1.308
Pgp-substrate:	56.513912200927734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.363
CYP1A2-substrate:	0.364
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.72
CYP2D6-inhibitor:	0.191
CYP2D6-substrate:	0.563
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	17.212
Half-life (T1/2):	0.916

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.051
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.698
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.943
Carcinogencity:	0.338
Eye Corrosion:	0.739
Eye Irritation:	0.985
Respiratory Toxicity:	0.082

Download Data

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

Natural Product: NPC110764

Natural Product ID:	NPC110764
*Common Name:**	Hydroxytyrosol
IUPAC Name:	4-(3-hydroxypropyl)benzene-1,2-diol
Synonyms:	Hydroxytyrosol
Standard InCHIKey:	DPTPQXXDBLPEOP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H12O3/c10-5-1-2-7-3-4-8(11)9(12)6-7/h3-4,6,10-12H,1-2,5H2
SMILES:	OCCCc1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485747
PubChem CID:	11217464
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

*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
NPO18994	Mucuna pruriens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30552	Syringa amurensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18994	Mucuna pruriens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16259.1	Syringa reticulata subsp. amurensis	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18994	Mucuna pruriens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18994	Mucuna pruriens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16259.1	Syringa reticulata subsp. amurensis	Subspecies	Oleaceae	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	2
Potency	12

Activity Type	# Activity
Cell Line	1
Individual Protein	10
NON-MOLECULAR	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	22387.2	nM	PMID[465205]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	39810.7	nM	PMID[465205]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	3548.1	nM	PMID[465205]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	50118.7	nM	PMID[465205]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	35481.3	nM	PMID[465205]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[465205]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[465205]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4109.5	nM	PMID[465205]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	>	198310.0	nM	PMID[465206]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	35481.3	nM	PMID[465205]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[465205]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	79432.8	nM	PMID[465205]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	14715.7	nM	PMID[465205]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	8.66	n.a.	PMID[465206]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22910.0	nM	PMID[465206]

☑ 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 NPC110764 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	322
0.1-0.2	1851
0.2-0.3	6602
0.3-0.4	13086
0.4-0.5	5400
0.5-0.6	9221
0.6-0.7	4412
0.7-0.8	1539
0.8-0.85	204
0.85-0.9	37
0.9-0.95	19
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC12278
0.9787	High Similarity	NPC131587
0.9681	High Similarity	NPC109955
0.9307	High Similarity	NPC55617
0.9307	High Similarity	NPC62258
0.9286	High Similarity	NPC196479
0.9263	High Similarity	NPC107522
0.9216	High Similarity	NPC147634
0.9216	High Similarity	NPC79793
0.9216	High Similarity	NPC120982
0.9216	High Similarity	NPC174096
0.9216	High Similarity	NPC226401
0.9192	High Similarity	NPC120719
0.9192	High Similarity	NPC471511
0.9126	High Similarity	NPC187583
0.9126	High Similarity	NPC179002
0.9126	High Similarity	NPC257430
0.91	High Similarity	NPC239291
0.9091	High Similarity	NPC477802
0.9091	High Similarity	NPC477801
0.9082	High Similarity	NPC223393
0.9043	High Similarity	NPC300017
0.901	High Similarity	NPC19149
0.901	High Similarity	NPC477814
0.8952	High Similarity	NPC471485
0.8868	High Similarity	NPC120280
0.8854	High Similarity	NPC325292
0.8854	High Similarity	NPC138117
0.8842	High Similarity	NPC312304
0.8835	High Similarity	NPC233835
0.883	High Similarity	NPC104216
0.8812	High Similarity	NPC79672
0.8812	High Similarity	NPC52087
0.8774	High Similarity	NPC264558
0.8762	High Similarity	NPC156840
0.8762	High Similarity	NPC257124
0.8762	High Similarity	NPC8547
0.8762	High Similarity	NPC78918
0.8762	High Similarity	NPC173746
0.8762	High Similarity	NPC139617
0.875	High Similarity	NPC254833
0.875	High Similarity	NPC228343
0.8704	High Similarity	NPC221049
0.8687	High Similarity	NPC474073
0.8673	High Similarity	NPC274678
0.8673	High Similarity	NPC313650
0.8667	High Similarity	NPC222084
0.8646	High Similarity	NPC300478
0.8641	High Similarity	NPC294902
0.8641	High Similarity	NPC1075
0.8641	High Similarity	NPC1786
0.8632	High Similarity	NPC27974
0.8624	High Similarity	NPC164386
0.8598	High Similarity	NPC148969
0.8585	High Similarity	NPC268032
0.8585	High Similarity	NPC297657
0.8571	High Similarity	NPC246358
0.8571	High Similarity	NPC36108
0.8571	High Similarity	NPC7097
0.8571	High Similarity	NPC233731
0.8558	High Similarity	NPC176527
0.8545	High Similarity	NPC63126
0.8545	High Similarity	NPC255675
0.8526	High Similarity	NPC23167
0.8519	High Similarity	NPC217472
0.8515	High Similarity	NPC130103
0.8515	High Similarity	NPC174911
0.8515	High Similarity	NPC294741
0.8511	High Similarity	NPC175313
0.8505	High Similarity	NPC146422
0.8491	Intermediate Similarity	NPC137685
0.8476	Intermediate Similarity	NPC34864
0.8476	Intermediate Similarity	NPC58427
0.8476	Intermediate Similarity	NPC105727
0.8476	Intermediate Similarity	NPC114392
0.8468	Intermediate Similarity	NPC470214
0.8468	Intermediate Similarity	NPC320987
0.8468	Intermediate Similarity	NPC470215
0.8468	Intermediate Similarity	NPC181969
0.8468	Intermediate Similarity	NPC24474
0.8468	Intermediate Similarity	NPC109371
0.8468	Intermediate Similarity	NPC311595
0.8455	Intermediate Similarity	NPC175799
0.8455	Intermediate Similarity	NPC610
0.8455	Intermediate Similarity	NPC200988
0.8455	Intermediate Similarity	NPC145023
0.8454	Intermediate Similarity	NPC192
0.8438	Intermediate Similarity	NPC113460
0.8438	Intermediate Similarity	NPC25493
0.8431	Intermediate Similarity	NPC471578
0.8431	Intermediate Similarity	NPC101025
0.8426	Intermediate Similarity	NPC95381
0.8421	Intermediate Similarity	NPC197783
0.8416	Intermediate Similarity	NPC51333
0.8416	Intermediate Similarity	NPC128723
0.8416	Intermediate Similarity	NPC132078
0.8416	Intermediate Similarity	NPC78119
0.8416	Intermediate Similarity	NPC216468
0.8411	Intermediate Similarity	NPC195873
0.8411	Intermediate Similarity	NPC226250
0.8404	Intermediate Similarity	NPC265146
0.84	Intermediate Similarity	NPC202986
0.8393	Intermediate Similarity	NPC472071
0.8393	Intermediate Similarity	NPC115627
0.8393	Intermediate Similarity	NPC177475
0.8393	Intermediate Similarity	NPC265454
0.8393	Intermediate Similarity	NPC35071
0.8393	Intermediate Similarity	NPC34634
0.8393	Intermediate Similarity	NPC118522
0.8393	Intermediate Similarity	NPC169207
0.8393	Intermediate Similarity	NPC148615
0.8381	Intermediate Similarity	NPC227894
0.8378	Intermediate Similarity	NPC86198
0.8378	Intermediate Similarity	NPC309434
0.8378	Intermediate Similarity	NPC203124
0.8367	Intermediate Similarity	NPC304541
0.8367	Intermediate Similarity	NPC45040
0.8351	Intermediate Similarity	NPC242240
0.8351	Intermediate Similarity	NPC318325
0.8351	Intermediate Similarity	NPC123273
0.8351	Intermediate Similarity	NPC280347
0.8351	Intermediate Similarity	NPC258219
0.8351	Intermediate Similarity	NPC177420
0.835	Intermediate Similarity	NPC235762
0.835	Intermediate Similarity	NPC471228
0.8349	Intermediate Similarity	NPC261453
0.8349	Intermediate Similarity	NPC142599
0.8349	Intermediate Similarity	NPC328593
0.8349	Intermediate Similarity	NPC33749
0.8333	Intermediate Similarity	NPC213730
0.8319	Intermediate Similarity	NPC207613
0.8317	Intermediate Similarity	NPC32674
0.8317	Intermediate Similarity	NPC88420
0.8316	Intermediate Similarity	NPC248817
0.8316	Intermediate Similarity	NPC150837
0.8304	Intermediate Similarity	NPC70084
0.8304	Intermediate Similarity	NPC141791
0.8304	Intermediate Similarity	NPC263386
0.8304	Intermediate Similarity	NPC477803
0.8288	Intermediate Similarity	NPC293619
0.8283	Intermediate Similarity	NPC162314
0.8283	Intermediate Similarity	NPC3358
0.8283	Intermediate Similarity	NPC94139
0.8283	Intermediate Similarity	NPC306884
0.8283	Intermediate Similarity	NPC147284
0.8283	Intermediate Similarity	NPC210497
0.8283	Intermediate Similarity	NPC55903
0.8273	Intermediate Similarity	NPC233669
0.8273	Intermediate Similarity	NPC4665
0.8273	Intermediate Similarity	NPC474967
0.8269	Intermediate Similarity	NPC475225
0.8269	Intermediate Similarity	NPC323810
0.8265	Intermediate Similarity	NPC47950
0.8265	Intermediate Similarity	NPC55561
0.8252	Intermediate Similarity	NPC40258
0.8252	Intermediate Similarity	NPC7686
0.8252	Intermediate Similarity	NPC91461
0.8246	Intermediate Similarity	NPC324571
0.8246	Intermediate Similarity	NPC54872
0.8246	Intermediate Similarity	NPC184651
0.8246	Intermediate Similarity	NPC113865
0.8246	Intermediate Similarity	NPC476343
0.8246	Intermediate Similarity	NPC473853
0.8246	Intermediate Similarity	NPC262156
0.8246	Intermediate Similarity	NPC290451
0.8246	Intermediate Similarity	NPC470212
0.8246	Intermediate Similarity	NPC266045
0.8246	Intermediate Similarity	NPC312675
0.8246	Intermediate Similarity	NPC127389
0.8246	Intermediate Similarity	NPC470804
0.8246	Intermediate Similarity	NPC343720
0.8229	Intermediate Similarity	NPC155393
0.8224	Intermediate Similarity	NPC473524
0.8224	Intermediate Similarity	NPC71266
0.8214	Intermediate Similarity	NPC470626
0.8214	Intermediate Similarity	NPC275519
0.8211	Intermediate Similarity	NPC124436
0.82	Intermediate Similarity	NPC245187
0.82	Intermediate Similarity	NPC76938
0.82	Intermediate Similarity	NPC128062
0.82	Intermediate Similarity	NPC151715
0.82	Intermediate Similarity	NPC316301
0.82	Intermediate Similarity	NPC27323
0.8198	Intermediate Similarity	NPC61062
0.8198	Intermediate Similarity	NPC299252
0.8198	Intermediate Similarity	NPC277394
0.8198	Intermediate Similarity	NPC281277
0.819	Intermediate Similarity	NPC471350
0.8182	Intermediate Similarity	NPC155908
0.8182	Intermediate Similarity	NPC231150
0.8174	Intermediate Similarity	NPC86900
0.8174	Intermediate Similarity	NPC209567
0.8174	Intermediate Similarity	NPC85488
0.8165	Intermediate Similarity	NPC131530
0.8165	Intermediate Similarity	NPC471179
0.8165	Intermediate Similarity	NPC51698
0.8158	Intermediate Similarity	NPC470848
0.8158	Intermediate Similarity	NPC470414
0.8158	Intermediate Similarity	NPC98305
0.8158	Intermediate Similarity	NPC470849

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 NPC110764 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	1015
0.2-0.3	1783
0.3-0.4	2925
0.4-0.5	1667
0.5-0.6	969
0.6-0.7	360
0.7-0.8	82
0.8-0.85	13
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8762	High Similarity	NPD228	Approved
0.875	High Similarity	NPD3021	Approved
0.875	High Similarity	NPD3022	Approved
0.8505	High Similarity	NPD9379	Approved
0.8505	High Similarity	NPD9377	Approved
0.8393	Intermediate Similarity	NPD9381	Approved
0.8393	Intermediate Similarity	NPD9384	Approved
0.8211	Intermediate Similarity	NPD111	Approved
0.82	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2934	Approved
0.82	Intermediate Similarity	NPD2933	Approved
0.8148	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.8119	Intermediate Similarity	NPD2859	Approved
0.8119	Intermediate Similarity	NPD2860	Approved
0.8119	Intermediate Similarity	NPD844	Approved
0.8103	Intermediate Similarity	NPD9622	Approved
0.8058	Intermediate Similarity	NPD3020	Approved
0.8039	Intermediate Similarity	NPD288	Approved
0.7981	Intermediate Similarity	NPD1242	Phase 1
0.7981	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD9619	Approved
0.7899	Intermediate Similarity	NPD9621	Approved
0.7899	Intermediate Similarity	NPD9620	Approved
0.7736	Intermediate Similarity	NPD940	Approved
0.7736	Intermediate Similarity	NPD846	Approved
0.7727	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD3027	Phase 3
0.7672	Intermediate Similarity	NPD1357	Approved
0.7642	Intermediate Similarity	NPD601	Approved
0.7642	Intermediate Similarity	NPD598	Approved
0.7642	Intermediate Similarity	NPD597	Approved
0.7636	Intermediate Similarity	NPD2684	Approved
0.7627	Intermediate Similarity	NPD3092	Approved
0.7596	Intermediate Similarity	NPD1809	Phase 2
0.7586	Intermediate Similarity	NPD3091	Approved
0.7583	Intermediate Similarity	NPD5311	Approved
0.7583	Intermediate Similarity	NPD5310	Approved
0.7583	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD1132	Approved
0.7581	Intermediate Similarity	NPD1136	Approved
0.7581	Intermediate Similarity	NPD1130	Approved
0.7573	Intermediate Similarity	NPD845	Approved
0.7553	Intermediate Similarity	NPD9294	Approved
0.7544	Intermediate Similarity	NPD9618	Approved
0.7544	Intermediate Similarity	NPD9614	Approved
0.7521	Intermediate Similarity	NPD3053	Approved
0.7521	Intermediate Similarity	NPD3055	Approved
0.752	Intermediate Similarity	NPD3061	Approved
0.752	Intermediate Similarity	NPD3059	Approved
0.752	Intermediate Similarity	NPD1613	Approved
0.752	Intermediate Similarity	NPD3062	Approved
0.752	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD257	Approved
0.7459	Intermediate Similarity	NPD258	Approved
0.7456	Intermediate Similarity	NPD5283	Phase 1
0.7455	Intermediate Similarity	NPD1445	Approved
0.7455	Intermediate Similarity	NPD1444	Approved
0.7431	Intermediate Similarity	NPD9608	Approved
0.7431	Intermediate Similarity	NPD9610	Approved
0.7426	Intermediate Similarity	NPD9094	Approved
0.7417	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD5314	Approved
0.7402	Intermediate Similarity	NPD823	Approved
0.7402	Intermediate Similarity	NPD817	Approved
0.7398	Intermediate Similarity	NPD9494	Approved
0.7398	Intermediate Similarity	NPD9569	Approved
0.7387	Intermediate Similarity	NPD290	Approved
0.7381	Intermediate Similarity	NPD826	Approved
0.7381	Intermediate Similarity	NPD825	Approved
0.7381	Intermediate Similarity	NPD3620	Phase 2
0.7381	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD3094	Phase 2
0.7368	Intermediate Similarity	NPD7843	Approved
0.735	Intermediate Similarity	NPD9616	Approved
0.735	Intermediate Similarity	NPD9613	Approved
0.735	Intermediate Similarity	NPD9615	Approved
0.7339	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9296	Approved
0.7328	Intermediate Similarity	NPD7157	Approved
0.7323	Intermediate Similarity	NPD555	Phase 2
0.7302	Intermediate Similarity	NPD259	Phase 1
0.7302	Intermediate Similarity	NPD2674	Phase 3
0.7297	Intermediate Similarity	NPD968	Approved
0.7288	Intermediate Similarity	NPD316	Approved
0.7258	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4750	Phase 3
0.7257	Intermediate Similarity	NPD1792	Phase 2
0.7234	Intermediate Similarity	NPD9087	Approved
0.7232	Intermediate Similarity	NPD2342	Discontinued
0.7231	Intermediate Similarity	NPD9570	Approved
0.7222	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD317	Approved
0.7203	Intermediate Similarity	NPD318	Approved
0.7203	Intermediate Similarity	NPD856	Approved
0.7203	Intermediate Similarity	NPD16	Approved
0.7182	Intermediate Similarity	NPD9500	Approved
0.7176	Intermediate Similarity	NPD7266	Discontinued
0.7167	Intermediate Similarity	NPD3095	Discontinued
0.7156	Intermediate Similarity	NPD3028	Approved
0.7155	Intermediate Similarity	NPD2234	Approved
0.7155	Intermediate Similarity	NPD2228	Approved
0.7155	Intermediate Similarity	NPD2229	Approved
0.7143	Intermediate Similarity	NPD9537	Phase 1
0.7143	Intermediate Similarity	NPD9536	Phase 1
0.7131	Intermediate Similarity	NPD9269	Phase 2
0.713	Intermediate Similarity	NPD9273	Approved
0.713	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD9495	Approved
0.7113	Intermediate Similarity	NPD9088	Approved
0.7109	Intermediate Similarity	NPD1558	Phase 1
0.7109	Intermediate Similarity	NPD943	Approved
0.7087	Intermediate Similarity	NPD3144	Approved
0.7087	Intermediate Similarity	NPD3145	Approved
0.7069	Intermediate Similarity	NPD7635	Approved
0.7069	Intermediate Similarity	NPD821	Approved
0.7054	Intermediate Similarity	NPD275	Approved
0.7054	Intermediate Similarity	NPD230	Phase 1
0.7054	Intermediate Similarity	NPD274	Approved
0.7049	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6671	Approved
0.7025	Intermediate Similarity	NPD2932	Approved
0.7025	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2286	Discontinued
0.7025	Intermediate Similarity	NPD3019	Approved
0.7025	Intermediate Similarity	NPD4059	Approved
0.7009	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1548	Phase 1
0.6949	Remote Similarity	NPD1793	Approved
0.6949	Remote Similarity	NPD1791	Approved
0.6942	Remote Similarity	NPD4093	Discontinued
0.6937	Remote Similarity	NPD291	Approved
0.6935	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.693	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5536	Phase 2
0.6911	Remote Similarity	NPD3705	Approved
0.6911	Remote Similarity	NPD1610	Phase 2
0.6905	Remote Similarity	NPD6584	Phase 3
0.6894	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD255	Approved
0.6891	Remote Similarity	NPD256	Approved
0.6889	Remote Similarity	NPD8166	Discontinued
0.6887	Remote Similarity	NPD9365	Approved
0.6885	Remote Similarity	NPD5846	Approved
0.6885	Remote Similarity	NPD1751	Approved
0.6885	Remote Similarity	NPD6516	Phase 2
0.6885	Remote Similarity	NPD4626	Approved
0.6864	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.686	Remote Similarity	NPD9545	Approved
0.6855	Remote Similarity	NPD2562	Approved
0.6855	Remote Similarity	NPD2231	Phase 2
0.6855	Remote Similarity	NPD2235	Phase 2
0.6855	Remote Similarity	NPD2561	Approved
0.685	Remote Similarity	NPD2861	Phase 2
0.685	Remote Similarity	NPD5736	Approved
0.6846	Remote Similarity	NPD4060	Phase 1
0.6842	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6190	Approved
0.6838	Remote Similarity	NPD302	Approved
0.6833	Remote Similarity	NPD9568	Approved
0.6833	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD9089	Approved
0.6815	Remote Similarity	NPD3060	Approved
0.6807	Remote Similarity	NPD475	Phase 2
0.6803	Remote Similarity	NPD9268	Approved
0.68	Remote Similarity	NPD4659	Approved
0.6783	Remote Similarity	NPD1358	Approved
0.6769	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD9093	Approved
0.6721	Remote Similarity	NPD1182	Approved
0.6721	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD9295	Approved
0.6696	Remote Similarity	NPD3134	Approved
0.6694	Remote Similarity	NPD3421	Phase 3
0.6694	Remote Similarity	NPD3496	Discontinued
0.6693	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1133	Approved
0.6693	Remote Similarity	NPD1134	Approved
0.6693	Remote Similarity	NPD1135	Approved
0.6693	Remote Similarity	NPD1131	Approved
0.6693	Remote Similarity	NPD1129	Approved
0.6693	Remote Similarity	NPD4103	Phase 2
0.6691	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3645	Discontinued
0.6667	Remote Similarity	NPD2983	Phase 2
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD6582	Phase 2
0.6667	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2982	Phase 2
0.6667	Remote Similarity	NPD5451	Approved
0.6667	Remote Similarity	NPD5735	Approved
0.6667	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6583	Phase 3
0.6667	Remote Similarity	NPD9612	Approved
0.6667	Remote Similarity	NPD9611	Approved
0.6667	Remote Similarity	NPD9609	Approved
0.6641	Remote Similarity	NPD859	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