NPASS Compound

Structure

CID271274 OpenBabel06191716072D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.17
Volume:	348.461
LogP:	5.706
LogD:	4.278
LogS:	-6.108
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.656
Synthetic Accessibility Score:	2.707
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.86
MDCK Permeability:	9.779611900739837e-06
Pgp-inhibitor:	0.933
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.122

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.463
Plasma Protein Binding (PPB):	99.51719665527344%
Volume Distribution (VD):	1.395
Pgp-substrate:	0.7575228214263916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.656
CYP1A2-substrate:	0.891
CYP2C19-inhibitor:	0.924
CYP2C19-substrate:	0.692
CYP2C9-inhibitor:	0.824
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.301
CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.844

ADMET: Excretion

Clearance (CL):	4.229
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.344
AMES Toxicity:	0.388
Rat Oral Acute Toxicity:	0.335
Maximum Recommended Daily Dose:	0.869
Skin Sensitization:	0.049
Carcinogencity:	0.161
Eye Corrosion:	0.003
Eye Irritation:	0.806
Respiratory Toxicity:	0.108

Download Data

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

Natural Product: NPC271274

Natural Product ID:	NPC271274
*Common Name:**	2,4-Bis(1-Phenylethyl)Phenol
IUPAC Name:	2,4-bis(1-phenylethyl)phenol
Synonyms:	2,4-Bis(1-Phenylethyl)Phenol
Standard InCHIKey:	RCFAHSGZAAFQJH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H22O/c1-16(18-9-5-3-6-10-18)20-13-14-22(23)21(15-20)17(2)19-11-7-4-8-12-19/h3-17,23H,1-2H3
SMILES:	CC(c1ccc(c(c1)C(c1ccccc1)C)O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252313
PubChem CID:	102877
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	fruit	Lanyu Island, Taitung County, Taiwan	n.a.	PMID[10395498]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822293]
NPO7191	Mimosa pudica	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[26661932]
NPO7191	Mimosa pudica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7191	Mimosa pudica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7191	Mimosa pudica	Species	Fabaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2740	Cell Line	Neutrophils		IC50	>	100000.0	nM	PMID[464485]

☑ 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 NPC271274 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	346
0.1-0.2	1940
0.2-0.3	4794
0.3-0.4	12987
0.4-0.5	5982
0.5-0.6	9468
0.6-0.7	5608
0.7-0.8	1320
0.8-0.85	166
0.85-0.9	68
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9592	High Similarity	NPC51015
0.9333	High Similarity	NPC715
0.9307	High Similarity	NPC138942
0.93	High Similarity	NPC168829
0.9286	High Similarity	NPC77492
0.9231	High Similarity	NPC296683
0.9208	High Similarity	NPC288411
0.9143	High Similarity	NPC95716
0.91	High Similarity	NPC225506
0.9082	High Similarity	NPC8392
0.9065	High Similarity	NPC195922
0.9057	High Similarity	NPC46940
0.9048	High Similarity	NPC13482
0.9048	High Similarity	NPC141782
0.9038	High Similarity	NPC11554
0.9	High Similarity	NPC252821
0.9	High Similarity	NPC122005
0.899	High Similarity	NPC473388
0.899	High Similarity	NPC292730
0.899	High Similarity	NPC216520
0.899	High Similarity	NPC82664
0.899	High Similarity	NPC132271
0.8962	High Similarity	NPC176279
0.8962	High Similarity	NPC260323
0.8952	High Similarity	NPC58865
0.8952	High Similarity	NPC314187
0.8942	High Similarity	NPC151477
0.89	High Similarity	NPC225464
0.8889	High Similarity	NPC26244
0.8879	High Similarity	NPC250323
0.8857	High Similarity	NPC262365
0.8812	High Similarity	NPC92730
0.8796	High Similarity	NPC322239
0.8788	High Similarity	NPC151715
0.8788	High Similarity	NPC128062
0.8776	High Similarity	NPC204210
0.8776	High Similarity	NPC304541
0.875	High Similarity	NPC117115
0.875	High Similarity	NPC219286
0.875	High Similarity	NPC99557
0.8716	High Similarity	NPC268160
0.8704	High Similarity	NPC228425
0.87	High Similarity	NPC144682
0.8692	High Similarity	NPC44732
0.8687	High Similarity	NPC271440
0.8679	High Similarity	NPC61885
0.8679	High Similarity	NPC63698
0.8667	High Similarity	NPC21594
0.8667	High Similarity	NPC54765
0.8649	High Similarity	NPC299180
0.8636	High Similarity	NPC35797
0.8636	High Similarity	NPC147179
0.8636	High Similarity	NPC192948
0.8627	High Similarity	NPC128723
0.8624	High Similarity	NPC141003
0.8624	High Similarity	NPC35344
0.8611	High Similarity	NPC165770
0.8611	High Similarity	NPC4493
0.8611	High Similarity	NPC476632
0.8611	High Similarity	NPC308689
0.8611	High Similarity	NPC322753
0.8611	High Similarity	NPC225679
0.8611	High Similarity	NPC151537
0.8611	High Similarity	NPC77772
0.86	High Similarity	NPC76938
0.86	High Similarity	NPC316301
0.86	High Similarity	NPC27323
0.86	High Similarity	NPC289769
0.86	High Similarity	NPC152415
0.8586	High Similarity	NPC45040
0.8571	High Similarity	NPC318325
0.8571	High Similarity	NPC258219
0.8571	High Similarity	NPC280347
0.8571	High Similarity	NPC123273
0.8571	High Similarity	NPC70436
0.8571	High Similarity	NPC242240
0.8571	High Similarity	NPC177420
0.8559	High Similarity	NPC471668
0.8559	High Similarity	NPC308311
0.8559	High Similarity	NPC308828
0.8559	High Similarity	NPC477137
0.8559	High Similarity	NPC219112
0.8559	High Similarity	NPC38893
0.8559	High Similarity	NPC261973
0.8545	High Similarity	NPC12656
0.8545	High Similarity	NPC107240
0.8532	High Similarity	NPC228988
0.8532	High Similarity	NPC43525
0.8532	High Similarity	NPC286222
0.8529	High Similarity	NPC79241
0.8529	High Similarity	NPC6597
0.8515	High Similarity	NPC32714
0.8515	High Similarity	NPC274678
0.8505	High Similarity	NPC95344
0.8491	Intermediate Similarity	NPC248904
0.8485	Intermediate Similarity	NPC55561
0.8482	Intermediate Similarity	NPC477136
0.8482	Intermediate Similarity	NPC16030
0.8482	Intermediate Similarity	NPC304510
0.8482	Intermediate Similarity	NPC172219
0.8476	Intermediate Similarity	NPC238696
0.8469	Intermediate Similarity	NPC25493
0.8469	Intermediate Similarity	NPC113460
0.8468	Intermediate Similarity	NPC84999
0.8468	Intermediate Similarity	NPC246760
0.8462	Intermediate Similarity	NPC12221
0.8455	Intermediate Similarity	NPC321589
0.8455	Intermediate Similarity	NPC117846
0.8447	Intermediate Similarity	NPC216468
0.8447	Intermediate Similarity	NPC78119
0.8447	Intermediate Similarity	NPC132078
0.8447	Intermediate Similarity	NPC51333
0.844	Intermediate Similarity	NPC470770
0.844	Intermediate Similarity	NPC266937
0.8431	Intermediate Similarity	NPC259512
0.8431	Intermediate Similarity	NPC312132
0.8426	Intermediate Similarity	NPC228343
0.8426	Intermediate Similarity	NPC254833
0.8411	Intermediate Similarity	NPC228737
0.8411	Intermediate Similarity	NPC320439
0.8407	Intermediate Similarity	NPC469609
0.8407	Intermediate Similarity	NPC471671
0.84	Intermediate Similarity	NPC155908
0.84	Intermediate Similarity	NPC306074
0.8396	Intermediate Similarity	NPC474839
0.8393	Intermediate Similarity	NPC92
0.8393	Intermediate Similarity	NPC469663
0.8393	Intermediate Similarity	NPC141001
0.8381	Intermediate Similarity	NPC108497
0.8378	Intermediate Similarity	NPC473137
0.8378	Intermediate Similarity	NPC249270
0.8367	Intermediate Similarity	NPC23167
0.8367	Intermediate Similarity	NPC407
0.8367	Intermediate Similarity	NPC307235
0.8365	Intermediate Similarity	NPC213730
0.8365	Intermediate Similarity	NPC211885
0.8365	Intermediate Similarity	NPC72729
0.8364	Intermediate Similarity	NPC62867
0.8364	Intermediate Similarity	NPC177962
0.835	Intermediate Similarity	NPC32674
0.835	Intermediate Similarity	NPC156313
0.8349	Intermediate Similarity	NPC132720
0.8333	Intermediate Similarity	NPC176893
0.8333	Intermediate Similarity	NPC222146
0.8333	Intermediate Similarity	NPC469644
0.8333	Intermediate Similarity	NPC126002
0.8333	Intermediate Similarity	NPC93071
0.8333	Intermediate Similarity	NPC201959
0.8333	Intermediate Similarity	NPC151197
0.8317	Intermediate Similarity	NPC306884
0.8317	Intermediate Similarity	NPC94139
0.8317	Intermediate Similarity	NPC147284
0.8317	Intermediate Similarity	NPC162314
0.8317	Intermediate Similarity	NPC210497
0.8317	Intermediate Similarity	NPC3358
0.8304	Intermediate Similarity	NPC469719
0.8302	Intermediate Similarity	NPC119860
0.8302	Intermediate Similarity	NPC323810
0.83	Intermediate Similarity	NPC192
0.8288	Intermediate Similarity	NPC317869
0.8286	Intermediate Similarity	NPC91461
0.8286	Intermediate Similarity	NPC7686
0.8286	Intermediate Similarity	NPC252105
0.8286	Intermediate Similarity	NPC40258
0.8273	Intermediate Similarity	NPC224527
0.8269	Intermediate Similarity	NPC299762
0.8269	Intermediate Similarity	NPC33675
0.8265	Intermediate Similarity	NPC197783
0.8265	Intermediate Similarity	NPC155393
0.8261	Intermediate Similarity	NPC135467
0.8261	Intermediate Similarity	NPC69006
0.8261	Intermediate Similarity	NPC103916
0.8261	Intermediate Similarity	NPC260832
0.8235	Intermediate Similarity	NPC245187
0.8224	Intermediate Similarity	NPC303141
0.8224	Intermediate Similarity	NPC243677
0.8224	Intermediate Similarity	NPC154899
0.8224	Intermediate Similarity	NPC239291
0.8224	Intermediate Similarity	NPC233396
0.8214	Intermediate Similarity	NPC471534
0.8208	Intermediate Similarity	NPC135784
0.8208	Intermediate Similarity	NPC269212
0.8205	Intermediate Similarity	NPC71094
0.8205	Intermediate Similarity	NPC176208
0.82	Intermediate Similarity	NPC98772
0.8198	Intermediate Similarity	NPC166995
0.8198	Intermediate Similarity	NPC471179
0.819	Intermediate Similarity	NPC248396
0.819	Intermediate Similarity	NPC48730
0.819	Intermediate Similarity	NPC259703
0.819	Intermediate Similarity	NPC32322
0.819	Intermediate Similarity	NPC129373
0.819	Intermediate Similarity	NPC294741
0.8182	Intermediate Similarity	NPC184169
0.8173	Intermediate Similarity	NPC152097
0.8165	Intermediate Similarity	NPC470039
0.8163	Intermediate Similarity	NPC248817
0.8163	Intermediate Similarity	NPC286904
0.8163	Intermediate Similarity	NPC175313
0.8158	Intermediate Similarity	NPC25648

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 NPC271274 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	1040
0.2-0.3	1024
0.3-0.4	2926
0.4-0.5	2009
0.5-0.6	1225
0.6-0.7	476
0.7-0.8	70
0.8-0.85	7
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9192	High Similarity	NPD3020	Approved
0.8889	High Similarity	NPD2859	Approved
0.8889	High Similarity	NPD2860	Approved
0.8878	High Similarity	NPD845	Approved
0.8788	High Similarity	NPD2934	Approved
0.8788	High Similarity	NPD2933	Approved
0.8762	High Similarity	NPD2342	Discontinued
0.87	High Similarity	NPD1809	Phase 2
0.86	High Similarity	NPD1432	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD288	Approved
0.8426	Intermediate Similarity	NPD3022	Approved
0.8426	Intermediate Similarity	NPD3021	Approved
0.8364	Intermediate Similarity	NPD7635	Approved
0.8333	Intermediate Similarity	NPD844	Approved
0.8246	Intermediate Similarity	NPD5303	Approved
0.8246	Intermediate Similarity	NPD5304	Approved
0.8174	Intermediate Similarity	NPD4093	Discontinued
0.8113	Intermediate Similarity	NPD940	Approved
0.8113	Intermediate Similarity	NPD846	Approved
0.8103	Intermediate Similarity	NPD4589	Approved
0.8087	Intermediate Similarity	NPD3091	Approved
0.8061	Intermediate Similarity	NPD111	Approved
0.8019	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD2228	Approved
0.7965	Intermediate Similarity	NPD2229	Approved
0.7965	Intermediate Similarity	NPD2234	Approved
0.7949	Intermediate Similarity	NPD2286	Discontinued
0.7949	Intermediate Similarity	NPD3019	Approved
0.7949	Intermediate Similarity	NPD4059	Approved
0.7928	Intermediate Similarity	NPD4750	Phase 3
0.7815	Intermediate Similarity	NPD3092	Approved
0.7805	Intermediate Similarity	NPD4908	Phase 1
0.7797	Intermediate Similarity	NPD2932	Approved
0.7788	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD1792	Phase 2
0.7759	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD3028	Approved
0.7685	Intermediate Similarity	NPD1242	Phase 1
0.7658	Intermediate Similarity	NPD1445	Approved
0.7658	Intermediate Similarity	NPD1444	Approved
0.7652	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3095	Discontinued
0.7611	Intermediate Similarity	NPD5451	Approved
0.7561	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3094	Phase 2
0.7545	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1751	Approved
0.7479	Intermediate Similarity	NPD7330	Discontinued
0.746	Intermediate Similarity	NPD5156	Approved
0.746	Intermediate Similarity	NPD5155	Approved
0.744	Intermediate Similarity	NPD5736	Approved
0.744	Intermediate Similarity	NPD2861	Phase 2
0.7436	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD4060	Phase 1
0.7398	Intermediate Similarity	NPD6583	Phase 3
0.7398	Intermediate Similarity	NPD6582	Phase 2
0.7381	Intermediate Similarity	NPD2606	Approved
0.7381	Intermediate Similarity	NPD2605	Approved
0.7377	Intermediate Similarity	NPD1201	Approved
0.7373	Intermediate Similarity	NPD6671	Approved
0.736	Intermediate Similarity	NPD6584	Phase 3
0.7355	Intermediate Similarity	NPD4626	Approved
0.735	Intermediate Similarity	NPD5283	Phase 1
0.735	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD4625	Phase 3
0.7321	Intermediate Similarity	NPD9610	Approved
0.7321	Intermediate Similarity	NPD9608	Approved
0.7308	Intermediate Similarity	NPD4097	Suspended
0.7302	Intermediate Similarity	NPD3635	Approved
0.7302	Intermediate Similarity	NPD3637	Approved
0.7302	Intermediate Similarity	NPD3636	Approved
0.7295	Intermediate Similarity	NPD3023	Approved
0.7295	Intermediate Similarity	NPD3026	Approved
0.7288	Intermediate Similarity	NPD497	Approved
0.728	Intermediate Similarity	NPD1164	Approved
0.7273	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3024	Approved
0.7273	Intermediate Similarity	NPD3025	Approved
0.7273	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5535	Approved
0.7258	Intermediate Similarity	NPD4659	Approved
0.7244	Intermediate Similarity	NPD3594	Approved
0.7244	Intermediate Similarity	NPD3595	Approved
0.7236	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD9500	Approved
0.7227	Intermediate Similarity	NPD6387	Discontinued
0.7222	Intermediate Similarity	NPD2194	Approved
0.7222	Intermediate Similarity	NPD4624	Approved
0.7222	Intermediate Similarity	NPD2195	Approved
0.7213	Intermediate Similarity	NPD2667	Approved
0.7213	Intermediate Similarity	NPD2668	Approved
0.7209	Intermediate Similarity	NPD6663	Approved
0.7203	Intermediate Similarity	NPD495	Approved
0.7203	Intermediate Similarity	NPD498	Approved
0.7203	Intermediate Similarity	NPD496	Approved
0.719	Intermediate Similarity	NPD1548	Phase 1
0.7185	Intermediate Similarity	NPD7003	Approved
0.7154	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3143	Discontinued
0.7153	Intermediate Similarity	NPD7041	Phase 2
0.7153	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD5405	Approved
0.7143	Intermediate Similarity	NPD4103	Phase 2
0.7143	Intermediate Similarity	NPD5404	Approved
0.7121	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4749	Approved
0.7087	Intermediate Similarity	NPD7451	Discontinued
0.7077	Intermediate Similarity	NPD6407	Approved
0.7077	Intermediate Similarity	NPD6405	Approved
0.7073	Intermediate Similarity	NPD6516	Phase 2
0.7073	Intermediate Similarity	NPD5846	Approved
0.7069	Intermediate Similarity	NPD2684	Approved
0.7063	Intermediate Similarity	NPD1283	Approved
0.7049	Intermediate Similarity	NPD6581	Approved
0.7049	Intermediate Similarity	NPD6580	Approved
0.7043	Intermediate Similarity	NPD968	Approved
0.704	Intermediate Similarity	NPD2232	Approved
0.704	Intermediate Similarity	NPD2233	Approved
0.704	Intermediate Similarity	NPD2230	Approved
0.704	Intermediate Similarity	NPD3070	Discontinued
0.7034	Intermediate Similarity	NPD228	Approved
0.7027	Intermediate Similarity	NPD9273	Approved
0.7025	Intermediate Similarity	NPD7636	Approved
0.7023	Intermediate Similarity	NPD3620	Phase 2
0.7023	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1793	Approved
0.7	Intermediate Similarity	NPD1791	Approved
0.7	Intermediate Similarity	NPD475	Phase 2
0.7	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD3764	Approved
0.6992	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1651	Approved
0.6992	Remote Similarity	NPD5691	Approved
0.6991	Remote Similarity	NPD4818	Approved
0.6991	Remote Similarity	NPD4817	Approved
0.6984	Remote Similarity	NPD5327	Phase 3
0.6984	Remote Similarity	NPD1669	Approved
0.6975	Remote Similarity	NPD1138	Approved
0.6953	Remote Similarity	NPD2798	Approved
0.6942	Remote Similarity	NPD709	Approved
0.6942	Remote Similarity	NPD7157	Approved
0.694	Remote Similarity	NPD2799	Discontinued
0.694	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7743	Approved
0.694	Remote Similarity	NPD7742	Approved
0.694	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9087	Approved
0.693	Remote Similarity	NPD4656	Approved
0.693	Remote Similarity	NPD4231	Approved
0.693	Remote Similarity	NPD4658	Approved
0.693	Remote Similarity	NPD4229	Approved
0.6929	Remote Similarity	NPD8651	Approved
0.6923	Remote Similarity	NPD7095	Approved
0.6912	Remote Similarity	NPD7037	Approved
0.6906	Remote Similarity	NPD7390	Discontinued
0.6906	Remote Similarity	NPD2420	Approved
0.6906	Remote Similarity	NPD2421	Approved
0.6905	Remote Similarity	NPD2562	Approved
0.6905	Remote Similarity	NPD2561	Approved
0.6903	Remote Similarity	NPD1616	Discontinued
0.6899	Remote Similarity	NPD4208	Discontinued
0.6894	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4140	Approved
0.6891	Remote Similarity	NPD1139	Approved
0.6891	Remote Similarity	NPD1137	Approved
0.6889	Remote Similarity	NPD2935	Discontinued
0.6885	Remote Similarity	NPD7340	Approved
0.688	Remote Similarity	NPD3847	Discontinued
0.688	Remote Similarity	NPD1981	Approved
0.688	Remote Similarity	NPD3421	Phase 3
0.688	Remote Similarity	NPD1980	Approved
0.688	Remote Similarity	NPD1983	Approved
0.6875	Remote Similarity	NPD1131	Approved
0.6875	Remote Similarity	NPD3053	Approved
0.6875	Remote Similarity	NPD1133	Approved
0.6875	Remote Similarity	NPD1129	Approved
0.6875	Remote Similarity	NPD1135	Approved
0.6875	Remote Similarity	NPD3055	Approved
0.6875	Remote Similarity	NPD1134	Approved
0.687	Remote Similarity	NPD3268	Approved
0.687	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3552	Approved
0.6866	Remote Similarity	NPD3553	Approved
0.6866	Remote Similarity	NPD3554	Approved
0.6866	Remote Similarity	NPD3555	Approved
0.6864	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7421	Clinical (unspecified phase)

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