NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	564.26
Volume:	539.028
LogP:	2.039
LogD:	1.596
LogS:	-3.343
# Rotatable Bonds:	3
TPSA:	169.05
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	7.546
Fsp3:	0.897
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.317
MDCK Permeability:	0.0001009293191600591
Pgp-inhibitor:	0.994
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.131
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.116
Plasma Protein Binding (PPB):	65.14937591552734%
Volume Distribution (VD):	0.806
Pgp-substrate:	30.424976348876953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.664
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.419
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.228
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	7.115
Half-life (T1/2):	0.218

ADMET: Toxicity

hERG Blockers:	0.328
Human Hepatotoxicity (H-HT):	0.894
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.913
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.124
Carcinogencity:	0.446
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC274678

Natural Product ID:	NPC274678
*Common Name:**	Lunularin
IUPAC Name:	3-[2-(4-hydroxyphenyl)ethyl]phenol
Synonyms:	Lunularin
Standard InCHIKey:	ILEYXPCRQKRNIJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14O2/c15-13-8-6-11(7-9-13)4-5-12-2-1-3-14(16)10-12/h1-3,6-10,15-16H,4-5H2
SMILES:	c1cc(CCc2ccc(cc2)O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445252
PubChem CID:	181511
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[15467233]
NPO12644	Lunularia cruciata	Species	Lunulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO12644	Lunularia cruciata	Species	Lunulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30848895]
NPO9360	Hydrangea macrophylla	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9360	Hydrangea macrophylla	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30750	Morus laevigata	Species	Sulidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9360	Hydrangea macrophylla	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9360	Hydrangea macrophylla	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9360	Hydrangea macrophylla	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12644	Lunularia cruciata	Species	Lunulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21341	Morus macroura	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	4
MIC	5
Others	3

Activity Type	# Activity
Cell Line	3
Organism	8
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1886	Cell Line	J774	Mus musculus	IC50	>	512000.0	nM	PMID[569222]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	200000.0	nM	PMID[569224]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	150000.0	nM	PMID[569224]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	Activity	<	70.0	%	PMID[569220]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	<	70.0	%	PMID[569220]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[569221]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	152200.0	nM	PMID[569222]
NPT27	Others	Unspecified		Ratio IC50	=	3.4	n.a.	PMID[569222]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[569223]

☑ 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 NPC274678 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	328
0.1-0.2	2182
0.2-0.3	6457
0.3-0.4	12434
0.4-0.5	5527
0.5-0.6	9255
0.6-0.7	4779
0.7-0.8	1332
0.8-0.85	238
0.85-0.9	128
0.9-0.95	34
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9663	High Similarity	NPC45040
0.9451	High Similarity	NPC76938
0.9451	High Similarity	NPC128062
0.9451	High Similarity	NPC151715
0.9355	High Similarity	NPC32674
0.9348	High Similarity	NPC32714
0.9348	High Similarity	NPC26244
0.9271	High Similarity	NPC30506
0.9271	High Similarity	NPC471511
0.9255	High Similarity	NPC92730
0.9247	High Similarity	NPC292730
0.9247	High Similarity	NPC216520
0.9247	High Similarity	NPC473388
0.9247	High Similarity	NPC132271
0.9247	High Similarity	NPC82664
0.9175	High Similarity	NPC239291
0.9158	High Similarity	NPC294741
0.9149	High Similarity	NPC225464
0.9121	High Similarity	NPC192
0.9111	High Similarity	NPC27974
0.9082	High Similarity	NPC54765
0.9072	High Similarity	NPC254965
0.9072	High Similarity	NPC327811
0.9062	High Similarity	NPC12221
0.9062	High Similarity	NPC100340
0.9062	High Similarity	NPC143659
0.9053	High Similarity	NPC132078
0.9053	High Similarity	NPC78119
0.9053	High Similarity	NPC51333
0.9053	High Similarity	NPC216468
0.9022	High Similarity	NPC304541
0.9011	High Similarity	NPC123273
0.9011	High Similarity	NPC318325
0.9011	High Similarity	NPC242240
0.9011	High Similarity	NPC258219
0.9	High Similarity	NPC23167
0.8989	High Similarity	NPC175313
0.8969	High Similarity	NPC168829
0.8958	High Similarity	NPC161571
0.8958	High Similarity	NPC275053
0.8958	High Similarity	NPC213730
0.8958	High Similarity	NPC223393
0.8958	High Similarity	NPC248573
0.8947	High Similarity	NPC156313
0.8947	High Similarity	NPC109955
0.8925	High Similarity	NPC162314
0.8925	High Similarity	NPC210497
0.8925	High Similarity	NPC306884
0.8925	High Similarity	NPC94139
0.8925	High Similarity	NPC147284
0.8925	High Similarity	NPC3358
0.8925	High Similarity	NPC55903
0.8925	High Similarity	NPC271440
0.8913	High Similarity	NPC300017
0.8901	High Similarity	NPC25493
0.8901	High Similarity	NPC113460
0.89	High Similarity	NPC95344
0.89	High Similarity	NPC75440
0.89	High Similarity	NPC11554
0.8889	High Similarity	NPC197783
0.8878	High Similarity	NPC102216
0.8878	High Similarity	NPC323810
0.8878	High Similarity	NPC288411
0.8878	High Similarity	NPC241891
0.8876	High Similarity	NPC265146
0.8866	High Similarity	NPC40258
0.8866	High Similarity	NPC7686
0.8866	High Similarity	NPC91461
0.8842	High Similarity	NPC202986
0.883	High Similarity	NPC27323
0.883	High Similarity	NPC316301
0.8817	High Similarity	NPC155908
0.8812	High Similarity	NPC62258
0.8812	High Similarity	NPC228343
0.8812	High Similarity	NPC55617
0.8812	High Similarity	NPC254833
0.8804	High Similarity	NPC177420
0.8804	High Similarity	NPC280347
0.8788	High Similarity	NPC134829
0.8788	High Similarity	NPC292452
0.8788	High Similarity	NPC138942
0.8778	High Similarity	NPC150837
0.8778	High Similarity	NPC248817
0.8776	High Similarity	NPC168393
0.8776	High Similarity	NPC233827
0.8776	High Similarity	NPC135784
0.875	High Similarity	NPC291789
0.875	High Similarity	NPC474073
0.8725	High Similarity	NPC120982
0.8725	High Similarity	NPC226401
0.8725	High Similarity	NPC147634
0.8725	High Similarity	NPC79793
0.8725	High Similarity	NPC174096
0.8723	High Similarity	NPC138117
0.8723	High Similarity	NPC325292
0.8713	High Similarity	NPC233835
0.871	High Similarity	NPC312304
0.871	High Similarity	NPC55561
0.87	High Similarity	NPC248904
0.87	High Similarity	NPC39664
0.87	High Similarity	NPC470700
0.87	High Similarity	NPC39097
0.87	High Similarity	NPC109691
0.87	High Similarity	NPC118286
0.87	High Similarity	NPC302681
0.8696	High Similarity	NPC104216
0.8696	High Similarity	NPC19680
0.8687	High Similarity	NPC119860
0.8687	High Similarity	NPC12987
0.8687	High Similarity	NPC120719
0.8687	High Similarity	NPC261573
0.8687	High Similarity	NPC474603
0.8687	High Similarity	NPC120693
0.8687	High Similarity	NPC8931
0.8681	High Similarity	NPC155393
0.8673	High Similarity	NPC110764
0.8667	High Similarity	NPC124436
0.8646	High Similarity	NPC312132
0.8646	High Similarity	NPC259512
0.8641	High Similarity	NPC179002
0.8641	High Similarity	NPC225679
0.8641	High Similarity	NPC95716
0.8641	High Similarity	NPC165770
0.8641	High Similarity	NPC4493
0.8641	High Similarity	NPC187583
0.8641	High Similarity	NPC476632
0.8641	High Similarity	NPC257430
0.8641	High Similarity	NPC268032
0.8632	High Similarity	NPC245187
0.8627	High Similarity	NPC202647
0.8627	High Similarity	NPC58865
0.8627	High Similarity	NPC314187
0.8617	High Similarity	NPC204210
0.8617	High Similarity	NPC231150
0.8614	High Similarity	NPC54844
0.86	High Similarity	NPC154899
0.86	High Similarity	NPC233396
0.86	High Similarity	NPC246056
0.86	High Similarity	NPC474839
0.8587	High Similarity	NPC307235
0.8587	High Similarity	NPC184169
0.8587	High Similarity	NPC407
0.8586	High Similarity	NPC196479
0.8571	High Similarity	NPC10588
0.8571	High Similarity	NPC129373
0.8571	High Similarity	NPC174911
0.8571	High Similarity	NPC248396
0.8571	High Similarity	NPC48730
0.8571	High Similarity	NPC211885
0.8571	High Similarity	NPC72729
0.8558	High Similarity	NPC46940
0.8558	High Similarity	NPC166995
0.8558	High Similarity	NPC43525
0.8557	High Similarity	NPC77492
0.8557	High Similarity	NPC152097
0.8557	High Similarity	NPC79241
0.8557	High Similarity	NPC6597
0.8557	High Similarity	NPC201967
0.8542	High Similarity	NPC8392
0.8542	High Similarity	NPC107522
0.8542	High Similarity	NPC222146
0.8542	High Similarity	NPC313650
0.8529	High Similarity	NPC262365
0.8529	High Similarity	NPC174981
0.8526	High Similarity	NPC29373
0.8515	High Similarity	NPC188677
0.8515	High Similarity	NPC67250
0.8515	High Similarity	NPC113457
0.8515	High Similarity	NPC135464
0.8515	High Similarity	NPC477814
0.8515	High Similarity	NPC271274
0.8515	High Similarity	NPC92623
0.8511	High Similarity	NPC300478
0.85	High Similarity	NPC238696
0.85	High Similarity	NPC12278
0.8485	Intermediate Similarity	NPC284011
0.8485	Intermediate Similarity	NPC72947
0.8476	Intermediate Similarity	NPC471485
0.8476	Intermediate Similarity	NPC117846
0.8469	Intermediate Similarity	NPC275104
0.8469	Intermediate Similarity	NPC299762
0.8469	Intermediate Similarity	NPC122005
0.8469	Intermediate Similarity	NPC128723
0.8469	Intermediate Similarity	NPC260775
0.8469	Intermediate Similarity	NPC130193
0.8469	Intermediate Similarity	NPC33675
0.8469	Intermediate Similarity	NPC131587
0.8469	Intermediate Similarity	NPC252821
0.8462	Intermediate Similarity	NPC151537
0.8462	Intermediate Similarity	NPC297657
0.8447	Intermediate Similarity	NPC19808
0.8447	Intermediate Similarity	NPC33728
0.8438	Intermediate Similarity	NPC152415
0.8431	Intermediate Similarity	NPC151477
0.8431	Intermediate Similarity	NPC176527
0.8431	Intermediate Similarity	NPC320439
0.8421	Intermediate Similarity	NPC270547
0.8421	Intermediate Similarity	NPC306074
0.8404	Intermediate Similarity	NPC70436
0.8404	Intermediate Similarity	NPC98772

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 NPC274678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	1087
0.2-0.3	1198
0.3-0.4	2868
0.4-0.5	1934
0.5-0.6	1124
0.6-0.7	460
0.7-0.8	109
0.8-0.85	7
0.85-0.9	5
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9348	High Similarity	NPD2859	Approved
0.9348	High Similarity	NPD2860	Approved
0.9255	High Similarity	NPD3020	Approved
0.9239	High Similarity	NPD2934	Approved
0.9239	High Similarity	NPD2933	Approved
0.8958	High Similarity	NPD1242	Phase 1
0.883	High Similarity	NPD1432	Clinical (unspecified phase)
0.8812	High Similarity	NPD3021	Approved
0.8812	High Similarity	NPD3022	Approved
0.8737	High Similarity	NPD844	Approved
0.8667	High Similarity	NPD111	Approved
0.8646	High Similarity	NPD288	Approved
0.8571	High Similarity	NPD289	Clinical (unspecified phase)
0.83	Intermediate Similarity	NPD940	Approved
0.83	Intermediate Similarity	NPD846	Approved
0.8252	Intermediate Similarity	NPD2342	Discontinued
0.8163	Intermediate Similarity	NPD1809	Phase 2
0.8144	Intermediate Similarity	NPD845	Approved
0.8095	Intermediate Similarity	NPD1792	Phase 2
0.8037	Intermediate Similarity	NPD7635	Approved
0.802	Intermediate Similarity	NPD3028	Approved
0.7981	Intermediate Similarity	NPD1445	Approved
0.7981	Intermediate Similarity	NPD1444	Approved
0.7963	Intermediate Similarity	NPD2228	Approved
0.7963	Intermediate Similarity	NPD2229	Approved
0.7963	Intermediate Similarity	NPD2234	Approved
0.7946	Intermediate Similarity	NPD2286	Discontinued
0.7944	Intermediate Similarity	NPD228	Approved
0.7928	Intermediate Similarity	NPD3091	Approved
0.7925	Intermediate Similarity	NPD4750	Phase 3
0.787	Intermediate Similarity	NPD9379	Approved
0.787	Intermediate Similarity	NPD9377	Approved
0.7857	Intermediate Similarity	NPD4093	Discontinued
0.781	Intermediate Similarity	NPD968	Approved
0.7788	Intermediate Similarity	NPD9610	Approved
0.7788	Intermediate Similarity	NPD3019	Approved
0.7788	Intermediate Similarity	NPD2932	Approved
0.7788	Intermediate Similarity	NPD4059	Approved
0.7788	Intermediate Similarity	NPD9608	Approved
0.7692	Intermediate Similarity	NPD9500	Approved
0.7672	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6671	Approved
0.7652	Intermediate Similarity	NPD3092	Approved
0.764	Intermediate Similarity	NPD9087	Approved
0.7636	Intermediate Similarity	NPD5283	Phase 1
0.7632	Intermediate Similarity	NPD1751	Approved
0.7593	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD9088	Approved
0.7479	Intermediate Similarity	NPD6584	Phase 3
0.7478	Intermediate Similarity	NPD4589	Approved
0.7478	Intermediate Similarity	NPD3095	Discontinued
0.7478	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD9273	Approved
0.7458	Intermediate Similarity	NPD5311	Approved
0.7458	Intermediate Similarity	NPD5310	Approved
0.7456	Intermediate Similarity	NPD5303	Approved
0.7456	Intermediate Similarity	NPD1548	Phase 1
0.7456	Intermediate Similarity	NPD5304	Approved
0.7431	Intermediate Similarity	NPD5451	Approved
0.7417	Intermediate Similarity	NPD2861	Phase 2
0.7411	Intermediate Similarity	NPD1793	Approved
0.7411	Intermediate Similarity	NPD9614	Approved
0.7411	Intermediate Similarity	NPD497	Approved
0.7411	Intermediate Similarity	NPD1791	Approved
0.7411	Intermediate Similarity	NPD9618	Approved
0.7395	Intermediate Similarity	NPD3053	Approved
0.7395	Intermediate Similarity	NPD3094	Phase 2
0.7395	Intermediate Similarity	NPD3055	Approved
0.7391	Intermediate Similarity	NPD9294	Approved
0.7355	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD709	Approved
0.7345	Intermediate Similarity	NPD256	Approved
0.7345	Intermediate Similarity	NPD255	Approved
0.7339	Intermediate Similarity	NPD2684	Approved
0.7328	Intermediate Similarity	NPD9381	Approved
0.7328	Intermediate Similarity	NPD9384	Approved
0.7321	Intermediate Similarity	NPD498	Approved
0.7321	Intermediate Similarity	NPD495	Approved
0.7321	Intermediate Similarity	NPD496	Approved
0.7311	Intermediate Similarity	NPD1283	Approved
0.7304	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD3027	Phase 3
0.7288	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5736	Approved
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD475	Phase 2
0.725	Intermediate Similarity	NPD1470	Approved
0.725	Intermediate Similarity	NPD1164	Approved
0.7248	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1651	Approved
0.7236	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5535	Approved
0.7227	Intermediate Similarity	NPD6583	Phase 3
0.7227	Intermediate Similarity	NPD4659	Approved
0.7227	Intermediate Similarity	NPD6582	Phase 2
0.7227	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD1669	Approved
0.7217	Intermediate Similarity	NPD9616	Approved
0.7217	Intermediate Similarity	NPD9613	Approved
0.7217	Intermediate Similarity	NPD9615	Approved
0.7203	Intermediate Similarity	NPD1535	Discovery
0.719	Intermediate Similarity	NPD2195	Approved
0.719	Intermediate Similarity	NPD2194	Approved
0.7188	Intermediate Similarity	NPD9089	Approved
0.7179	Intermediate Similarity	NPD4626	Approved
0.7179	Intermediate Similarity	NPD2668	Approved
0.7179	Intermediate Similarity	NPD2667	Approved
0.717	Intermediate Similarity	NPD1616	Discontinued
0.7168	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD1182	Approved
0.7155	Intermediate Similarity	NPD316	Approved
0.7154	Intermediate Similarity	NPD5156	Approved
0.7154	Intermediate Similarity	NPD5155	Approved
0.7143	Intermediate Similarity	NPD2232	Approved
0.7143	Intermediate Similarity	NPD2561	Approved
0.7143	Intermediate Similarity	NPD2230	Approved
0.7143	Intermediate Similarity	NPD2562	Approved
0.7143	Intermediate Similarity	NPD2233	Approved
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7131	Intermediate Similarity	NPD3637	Approved
0.7131	Intermediate Similarity	NPD3636	Approved
0.7131	Intermediate Similarity	NPD3635	Approved
0.713	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD9568	Approved
0.712	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1613	Approved
0.712	Intermediate Similarity	NPD943	Approved
0.712	Intermediate Similarity	NPD4060	Phase 1
0.7119	Intermediate Similarity	NPD3023	Approved
0.7119	Intermediate Similarity	NPD1983	Approved
0.7119	Intermediate Similarity	NPD1981	Approved
0.7119	Intermediate Similarity	NPD1980	Approved
0.7119	Intermediate Similarity	NPD3026	Approved
0.7119	Intermediate Similarity	NPD3847	Discontinued
0.7119	Intermediate Similarity	NPD3421	Phase 3
0.7107	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4103	Phase 2
0.7094	Intermediate Similarity	NPD3024	Approved
0.7094	Intermediate Similarity	NPD3025	Approved
0.7083	Intermediate Similarity	NPD9093	Approved
0.7083	Intermediate Similarity	NPD9622	Approved
0.7083	Intermediate Similarity	NPD1755	Approved
0.708	Intermediate Similarity	NPD821	Approved
0.708	Intermediate Similarity	NPD7843	Approved
0.7073	Intermediate Similarity	NPD4908	Phase 1
0.7073	Intermediate Similarity	NPD3595	Approved
0.7073	Intermediate Similarity	NPD2605	Approved
0.7073	Intermediate Similarity	NPD2606	Approved
0.7073	Intermediate Similarity	NPD3594	Approved
0.7069	Intermediate Similarity	NPD318	Approved
0.7069	Intermediate Similarity	NPD317	Approved
0.7069	Intermediate Similarity	NPD16	Approved
0.7069	Intermediate Similarity	NPD856	Approved
0.7059	Intermediate Similarity	NPD1281	Approved
0.7049	Intermediate Similarity	NPD258	Approved
0.7049	Intermediate Similarity	NPD4624	Approved
0.7049	Intermediate Similarity	NPD257	Approved
0.7043	Intermediate Similarity	NPD7157	Approved
0.704	Intermediate Similarity	NPD6663	Approved
0.7037	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6516	Phase 2
0.7034	Intermediate Similarity	NPD5846	Approved
0.7025	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4625	Phase 3
0.7016	Intermediate Similarity	NPD7095	Approved
0.7009	Intermediate Similarity	NPD7330	Discontinued
0.7009	Intermediate Similarity	NPD1894	Discontinued
0.7	Intermediate Similarity	NPD2231	Phase 2
0.7	Intermediate Similarity	NPD1840	Phase 2
0.7	Intermediate Similarity	NPD2235	Phase 2
0.6984	Remote Similarity	NPD3061	Approved
0.6984	Remote Similarity	NPD3062	Approved
0.6984	Remote Similarity	NPD1558	Phase 1
0.6984	Remote Similarity	NPD3059	Approved
0.6972	Remote Similarity	NPD1237	Approved
0.696	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.696	Remote Similarity	NPD3764	Approved
0.6949	Remote Similarity	NPD1357	Approved
0.6942	Remote Similarity	NPD4749	Approved
0.6937	Remote Similarity	NPD290	Approved
0.6923	Remote Similarity	NPD5536	Phase 2
0.6917	Remote Similarity	NPD422	Phase 1
0.6911	Remote Similarity	NPD7451	Discontinued
0.6911	Remote Similarity	NPD9620	Approved
0.6911	Remote Similarity	NPD9621	Approved
0.6911	Remote Similarity	NPD9619	Approved
0.6905	Remote Similarity	NPD6405	Approved
0.6905	Remote Similarity	NPD6407	Approved
0.6891	Remote Similarity	NPD17	Approved
0.6881	Remote Similarity	NPD4656	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