NPASS Compound

Structure

NPC51015 OpenBabel07101719252D 23 25 0 0 1 0 0 0 0 0999 V2000 1.7321 -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 4.3301 1.5000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 2.5981 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 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 0.8660 1.5000 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 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 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 -1.7321 -1.0000 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 0.5000 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 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 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 10 1 0 0 0 0 6 11 2 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 16 1 1 6 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 2 1 1 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 20 22 2 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.17
Volume:	348.461
LogP:	5.395
LogD:	4.011
LogS:	-5.519
# 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:	2.68
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:	-4.828
MDCK Permeability:	1.3619091077998746e-05
Pgp-inhibitor:	0.733
Pgp-substrate:	0.059
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.437

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.338
Plasma Protein Binding (PPB):	99.9552230834961%
Volume Distribution (VD):	1.232
Pgp-substrate:	0.7799417972564697%

ADMET: Metabolism

CYP1A2-inhibitor:	0.8
CYP1A2-substrate:	0.912
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.929
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.305
CYP2D6-substrate:	0.181
CYP3A4-inhibitor:	0.788
CYP3A4-substrate:	0.846

ADMET: Excretion

Clearance (CL):	2.792
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.458
Drug-inuced Liver Injury (DILI):	0.665
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.065
Carcinogencity:	0.181
Eye Corrosion:	0.003
Eye Irritation:	0.697
Respiratory Toxicity:	0.478

Download Data

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

Natural Product: NPC51015

Natural Product ID:	NPC51015
*Common Name:**	2,6-Bis(1-Phenylethyl)Phenol
IUPAC Name:	2-[(1S)-1-phenylethyl]-6-[(1R)-1-phenylethyl]phenol
Synonyms:	2,6-Bis(1-Phenylethyl)Phenol
Standard InCHIKey:	NYPMHOYLEBBBGY-CALCHBBNSA-N
Standard InCHI:	InChI=1S/C22H22O/c1-16(18-10-5-3-6-11-18)20-14-9-15-21(22(20)23)17(2)19-12-7-4-8-13-19/h3-17,23H,1-2H3/t16-,17+
SMILES:	C[C@H](c1cccc(c1O)[C@@H](c1ccccc1)C)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL398564
PubChem CID:	44445793
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]
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]

☑ 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[493513]

☑ 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 NPC51015 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	307
0.1-0.2	1874
0.2-0.3	4848
0.3-0.4	13398
0.4-0.5	6561
0.5-0.6	10167
0.6-0.7	4476
0.7-0.8	894
0.8-0.85	128
0.85-0.9	41
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9592	High Similarity	NPC271274
0.8958	High Similarity	NPC289769
0.8952	High Similarity	NPC715
0.8911	High Similarity	NPC138942
0.89	High Similarity	NPC168829
0.8878	High Similarity	NPC77492
0.8866	High Similarity	NPC8392
0.8854	High Similarity	NPC271440
0.8846	High Similarity	NPC296683
0.8812	High Similarity	NPC288411
0.8776	High Similarity	NPC473388
0.8762	High Similarity	NPC95716
0.8725	High Similarity	NPC117115
0.8725	High Similarity	NPC99557
0.8725	High Similarity	NPC219286
0.87	High Similarity	NPC225506
0.8692	High Similarity	NPC195922
0.8679	High Similarity	NPC46940
0.8673	High Similarity	NPC144682
0.8673	High Similarity	NPC26244
0.8667	High Similarity	NPC141782
0.8667	High Similarity	NPC13482
0.8654	High Similarity	NPC11554
0.8627	High Similarity	NPC238696
0.86	High Similarity	NPC252821
0.86	High Similarity	NPC122005
0.8586	High Similarity	NPC292730
0.8586	High Similarity	NPC132271
0.8586	High Similarity	NPC82664
0.8586	High Similarity	NPC216520
0.8585	High Similarity	NPC77772
0.8585	High Similarity	NPC260323
0.8585	High Similarity	NPC176279
0.8571	High Similarity	NPC151715
0.8571	High Similarity	NPC152415
0.8571	High Similarity	NPC76938
0.8571	High Similarity	NPC314187
0.8571	High Similarity	NPC58865
0.8571	High Similarity	NPC128062
0.8558	High Similarity	NPC151477
0.8557	High Similarity	NPC204210
0.8557	High Similarity	NPC306074
0.8542	High Similarity	NPC70436
0.8526	High Similarity	NPC307235
0.8526	High Similarity	NPC407
0.8505	High Similarity	NPC250323
0.85	High Similarity	NPC6597
0.85	High Similarity	NPC225464
0.85	High Similarity	NPC79241
0.8485	Intermediate Similarity	NPC32714
0.8476	Intermediate Similarity	NPC63698
0.8476	Intermediate Similarity	NPC262365
0.8476	Intermediate Similarity	NPC61885
0.844	Intermediate Similarity	NPC246760
0.844	Intermediate Similarity	NPC469719
0.844	Intermediate Similarity	NPC84999
0.8431	Intermediate Similarity	NPC12221
0.8426	Intermediate Similarity	NPC322239
0.8421	Intermediate Similarity	NPC155393
0.8416	Intermediate Similarity	NPC92730
0.8416	Intermediate Similarity	NPC128723
0.8411	Intermediate Similarity	NPC470770
0.8411	Intermediate Similarity	NPC266937
0.84	Intermediate Similarity	NPC312132
0.84	Intermediate Similarity	NPC259512
0.8381	Intermediate Similarity	NPC320439
0.8367	Intermediate Similarity	NPC304541
0.8367	Intermediate Similarity	NPC45040
0.8364	Intermediate Similarity	NPC469663
0.8364	Intermediate Similarity	NPC92
0.8351	Intermediate Similarity	NPC258219
0.8351	Intermediate Similarity	NPC242240
0.8351	Intermediate Similarity	NPC123273
0.8351	Intermediate Similarity	NPC280347
0.8351	Intermediate Similarity	NPC318325
0.8351	Intermediate Similarity	NPC177420
0.835	Intermediate Similarity	NPC108497
0.8349	Intermediate Similarity	NPC268160
0.8349	Intermediate Similarity	NPC249270
0.8333	Intermediate Similarity	NPC72729
0.8333	Intermediate Similarity	NPC228425
0.8333	Intermediate Similarity	NPC177962
0.8333	Intermediate Similarity	NPC62867
0.8318	Intermediate Similarity	NPC44732
0.8318	Intermediate Similarity	NPC132720
0.8317	Intermediate Similarity	NPC156313
0.8316	Intermediate Similarity	NPC286904
0.83	Intermediate Similarity	NPC222146
0.8288	Intermediate Similarity	NPC299180
0.8286	Intermediate Similarity	NPC21594
0.8286	Intermediate Similarity	NPC54765
0.8283	Intermediate Similarity	NPC162314
0.8283	Intermediate Similarity	NPC3358
0.8283	Intermediate Similarity	NPC210497
0.8283	Intermediate Similarity	NPC94139
0.8283	Intermediate Similarity	NPC306884
0.8283	Intermediate Similarity	NPC147284
0.8273	Intermediate Similarity	NPC192948
0.8273	Intermediate Similarity	NPC35797
0.8273	Intermediate Similarity	NPC147179
0.8269	Intermediate Similarity	NPC323810
0.8265	Intermediate Similarity	NPC192
0.8265	Intermediate Similarity	NPC55561
0.8257	Intermediate Similarity	NPC35344
0.8257	Intermediate Similarity	NPC141003
0.8252	Intermediate Similarity	NPC252105
0.8247	Intermediate Similarity	NPC113460
0.8247	Intermediate Similarity	NPC25493
0.8241	Intermediate Similarity	NPC224527
0.8241	Intermediate Similarity	NPC322753
0.8241	Intermediate Similarity	NPC308689
0.8241	Intermediate Similarity	NPC225679
0.8241	Intermediate Similarity	NPC151537
0.8241	Intermediate Similarity	NPC476632
0.8241	Intermediate Similarity	NPC165770
0.8241	Intermediate Similarity	NPC4493
0.8235	Intermediate Similarity	NPC78119
0.8235	Intermediate Similarity	NPC51333
0.8235	Intermediate Similarity	NPC132078
0.8235	Intermediate Similarity	NPC299762
0.8235	Intermediate Similarity	NPC216468
0.8235	Intermediate Similarity	NPC33675
0.8208	Intermediate Similarity	NPC228737
0.82	Intermediate Similarity	NPC245187
0.82	Intermediate Similarity	NPC27323
0.82	Intermediate Similarity	NPC316301
0.8198	Intermediate Similarity	NPC471668
0.8198	Intermediate Similarity	NPC477137
0.8198	Intermediate Similarity	NPC261973
0.8198	Intermediate Similarity	NPC38893
0.8198	Intermediate Similarity	NPC308828
0.8198	Intermediate Similarity	NPC219112
0.8198	Intermediate Similarity	NPC141001
0.8198	Intermediate Similarity	NPC308311
0.819	Intermediate Similarity	NPC474839
0.819	Intermediate Similarity	NPC243677
0.8182	Intermediate Similarity	NPC107240
0.8182	Intermediate Similarity	NPC471534
0.8182	Intermediate Similarity	NPC12656
0.8173	Intermediate Similarity	NPC269212
0.8165	Intermediate Similarity	NPC228988
0.8165	Intermediate Similarity	NPC43525
0.8165	Intermediate Similarity	NPC286222
0.8155	Intermediate Similarity	NPC48730
0.8155	Intermediate Similarity	NPC248396
0.8155	Intermediate Similarity	NPC294741
0.8155	Intermediate Similarity	NPC213730
0.8155	Intermediate Similarity	NPC129373
0.8144	Intermediate Similarity	NPC23167
0.8137	Intermediate Similarity	NPC152097
0.8131	Intermediate Similarity	NPC470039
0.8131	Intermediate Similarity	NPC95344
0.8125	Intermediate Similarity	NPC304510
0.8125	Intermediate Similarity	NPC477136
0.8125	Intermediate Similarity	NPC172219
0.8125	Intermediate Similarity	NPC16030
0.8119	Intermediate Similarity	NPC274678
0.8113	Intermediate Similarity	NPC248904
0.8113	Intermediate Similarity	NPC469913
0.81	Intermediate Similarity	NPC55903
0.8095	Intermediate Similarity	NPC475225
0.8095	Intermediate Similarity	NPC119860
0.8091	Intermediate Similarity	NPC117846
0.8091	Intermediate Similarity	NPC321589
0.8091	Intermediate Similarity	NPC317869
0.8077	Intermediate Similarity	NPC91461
0.8077	Intermediate Similarity	NPC7686
0.8077	Intermediate Similarity	NPC40258
0.8061	Intermediate Similarity	NPC19680
0.8061	Intermediate Similarity	NPC27974
0.8058	Intermediate Similarity	NPC260775
0.8056	Intermediate Similarity	NPC33728
0.8056	Intermediate Similarity	NPC19808
0.8056	Intermediate Similarity	NPC254833
0.8056	Intermediate Similarity	NPC228343
0.8053	Intermediate Similarity	NPC471671
0.8053	Intermediate Similarity	NPC469609
0.8041	Intermediate Similarity	NPC197783
0.8019	Intermediate Similarity	NPC303141
0.8019	Intermediate Similarity	NPC154899
0.8019	Intermediate Similarity	NPC47284
0.8019	Intermediate Similarity	NPC233396
0.8018	Intermediate Similarity	NPC473137
0.8017	Intermediate Similarity	NPC71094
0.8	Intermediate Similarity	NPC471228
0.8	Intermediate Similarity	NPC471179
0.8	Intermediate Similarity	NPC135784
0.8	Intermediate Similarity	NPC231150
0.8	Intermediate Similarity	NPC168393
0.8	Intermediate Similarity	NPC235762
0.8	Intermediate Similarity	NPC233827
0.8	Intermediate Similarity	NPC155908
0.7982	Intermediate Similarity	NPC151197
0.7982	Intermediate Similarity	NPC126002
0.7982	Intermediate Similarity	NPC93071
0.7982	Intermediate Similarity	NPC323074
0.7982	Intermediate Similarity	NPC176893
0.7982	Intermediate Similarity	NPC469644
0.7981	Intermediate Similarity	NPC70677
0.7981	Intermediate Similarity	NPC130756

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 NPC51015 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	1047
0.2-0.3	972
0.3-0.4	2949
0.4-0.5	2113
0.5-0.6	1240
0.6-0.7	425
0.7-0.8	57
0.8-0.85	6
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9255	High Similarity	NPD845	Approved
0.8922	High Similarity	NPD2342	Discontinued
0.8788	High Similarity	NPD3020	Approved
0.8673	High Similarity	NPD1809	Phase 2
0.8673	High Similarity	NPD2859	Approved
0.8673	High Similarity	NPD2860	Approved
0.8571	High Similarity	NPD2933	Approved
0.8571	High Similarity	NPD2934	Approved
0.8505	High Similarity	NPD7635	Approved
0.84	Intermediate Similarity	NPD288	Approved
0.83	Intermediate Similarity	NPD844	Approved
0.82	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD3021	Approved
0.8056	Intermediate Similarity	NPD3022	Approved
0.8053	Intermediate Similarity	NPD5303	Approved
0.8053	Intermediate Similarity	NPD5304	Approved
0.7981	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD940	Approved
0.7905	Intermediate Similarity	NPD846	Approved
0.789	Intermediate Similarity	NPD4750	Phase 3
0.7876	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD111	Approved
0.7826	Intermediate Similarity	NPD4093	Discontinued
0.7759	Intermediate Similarity	NPD4589	Approved
0.7748	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD3091	Approved
0.7739	Intermediate Similarity	NPD7330	Discontinued
0.7727	Intermediate Similarity	NPD1792	Phase 2
0.7664	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1444	Approved
0.7615	Intermediate Similarity	NPD1445	Approved
0.7611	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD2229	Approved
0.7611	Intermediate Similarity	NPD2234	Approved
0.7611	Intermediate Similarity	NPD2228	Approved
0.7607	Intermediate Similarity	NPD2286	Discontinued
0.7607	Intermediate Similarity	NPD4059	Approved
0.7607	Intermediate Similarity	NPD3019	Approved
0.7544	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD4908	Phase 1
0.7479	Intermediate Similarity	NPD3092	Approved
0.7478	Intermediate Similarity	NPD6387	Discontinued
0.7477	Intermediate Similarity	NPD3028	Approved
0.7458	Intermediate Similarity	NPD2932	Approved
0.7411	Intermediate Similarity	NPD5451	Approved
0.7333	Intermediate Similarity	NPD1201	Approved
0.7328	Intermediate Similarity	NPD6671	Approved
0.7315	Intermediate Similarity	NPD1242	Phase 1
0.7311	Intermediate Similarity	NPD3095	Discontinued
0.7311	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD4625	Phase 3
0.7265	Intermediate Similarity	NPD7636	Approved
0.7248	Intermediate Similarity	NPD4818	Approved
0.7248	Intermediate Similarity	NPD4817	Approved
0.7241	Intermediate Similarity	NPD497	Approved
0.7236	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3094	Phase 2
0.7236	Intermediate Similarity	NPD2797	Approved
0.7227	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD1138	Approved
0.7213	Intermediate Similarity	NPD6583	Phase 3
0.7213	Intermediate Similarity	NPD6582	Phase 2
0.7209	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1610	Phase 2
0.7182	Intermediate Similarity	NPD4231	Approved
0.7182	Intermediate Similarity	NPD4658	Approved
0.7182	Intermediate Similarity	NPD9500	Approved
0.7182	Intermediate Similarity	NPD4656	Approved
0.7182	Intermediate Similarity	NPD4229	Approved
0.7167	Intermediate Similarity	NPD1751	Approved
0.7155	Intermediate Similarity	NPD498	Approved
0.7155	Intermediate Similarity	NPD495	Approved
0.7155	Intermediate Similarity	NPD496	Approved
0.7143	Intermediate Similarity	NPD5155	Approved
0.7143	Intermediate Similarity	NPD968	Approved
0.7143	Intermediate Similarity	NPD5156	Approved
0.713	Intermediate Similarity	NPD1139	Approved
0.713	Intermediate Similarity	NPD1137	Approved
0.713	Intermediate Similarity	NPD9273	Approved
0.712	Intermediate Similarity	NPD2861	Phase 2
0.712	Intermediate Similarity	NPD5736	Approved
0.7117	Intermediate Similarity	NPD9608	Approved
0.7117	Intermediate Similarity	NPD9610	Approved
0.7109	Intermediate Similarity	NPD4060	Phase 1
0.7107	Intermediate Similarity	NPD3143	Discontinued
0.7107	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1470	Approved
0.7073	Intermediate Similarity	NPD4749	Approved
0.7073	Intermediate Similarity	NPD4659	Approved
0.7069	Intermediate Similarity	NPD5535	Approved
0.7063	Intermediate Similarity	NPD2606	Approved
0.7063	Intermediate Similarity	NPD2605	Approved
0.7053	Intermediate Similarity	NPD9087	Approved
0.7045	Intermediate Similarity	NPD7030	Discontinued
0.704	Intermediate Similarity	NPD6584	Phase 3
0.7027	Intermediate Similarity	NPD3680	Approved
0.7027	Intermediate Similarity	NPD3682	Approved
0.7025	Intermediate Similarity	NPD4626	Approved
0.701	Intermediate Similarity	NPD9294	Approved
0.7009	Intermediate Similarity	NPD5283	Phase 1
0.7	Intermediate Similarity	NPD4097	Suspended
0.7	Intermediate Similarity	NPD1616	Discontinued
0.7	Intermediate Similarity	NPD1548	Phase 1
0.6992	Remote Similarity	NPD2233	Approved
0.6992	Remote Similarity	NPD2232	Approved
0.6992	Remote Similarity	NPD3070	Discontinued
0.6992	Remote Similarity	NPD2230	Approved
0.6984	Remote Similarity	NPD3636	Approved
0.6984	Remote Similarity	NPD3635	Approved
0.6984	Remote Similarity	NPD3637	Approved
0.6975	Remote Similarity	NPD7340	Approved
0.697	Remote Similarity	NPD5404	Approved
0.697	Remote Similarity	NPD5406	Approved
0.697	Remote Similarity	NPD5408	Approved
0.697	Remote Similarity	NPD5405	Approved
0.6967	Remote Similarity	NPD3026	Approved
0.6967	Remote Similarity	NPD3023	Approved
0.696	Remote Similarity	NPD4103	Phase 2
0.696	Remote Similarity	NPD1164	Approved
0.696	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD3268	Approved
0.6949	Remote Similarity	NPD1793	Approved
0.6949	Remote Similarity	NPD5951	Approved
0.6949	Remote Similarity	NPD1791	Approved
0.6942	Remote Similarity	NPD3024	Approved
0.6942	Remote Similarity	NPD3025	Approved
0.693	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3595	Approved
0.6929	Remote Similarity	NPD3594	Approved
0.6905	Remote Similarity	NPD2194	Approved
0.6905	Remote Similarity	NPD2195	Approved
0.6905	Remote Similarity	NPD7451	Discontinued
0.6905	Remote Similarity	NPD2798	Approved
0.6905	Remote Similarity	NPD4624	Approved
0.6899	Remote Similarity	NPD6663	Approved
0.6897	Remote Similarity	NPD4253	Approved
0.6897	Remote Similarity	NPD4254	Approved
0.6891	Remote Similarity	NPD2557	Approved
0.6891	Remote Similarity	NPD709	Approved
0.6889	Remote Similarity	NPD7003	Approved
0.6885	Remote Similarity	NPD2667	Approved
0.6885	Remote Similarity	NPD5846	Approved
0.6885	Remote Similarity	NPD2668	Approved
0.6885	Remote Similarity	NPD6516	Phase 2
0.6875	Remote Similarity	NPD3681	Approved
0.6875	Remote Similarity	NPD3683	Approved
0.687	Remote Similarity	NPD2684	Approved
0.6864	Remote Similarity	NPD1398	Phase 1
0.6861	Remote Similarity	NPD7041	Phase 2
0.6861	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6580	Approved
0.686	Remote Similarity	NPD7741	Discontinued
0.686	Remote Similarity	NPD6581	Approved
0.6852	Remote Similarity	NPD3772	Phase 3
0.685	Remote Similarity	NPD4208	Discontinued
0.6833	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1981	Approved
0.6829	Remote Similarity	NPD1983	Approved
0.6829	Remote Similarity	NPD1980	Approved
0.6822	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6798	Discontinued
0.6814	Remote Similarity	NPD5909	Discontinued
0.6803	Remote Similarity	NPD3444	Approved
0.6803	Remote Similarity	NPD3443	Approved
0.6803	Remote Similarity	NPD3445	Approved
0.6803	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD290	Approved
0.6772	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7477	Discontinued
0.6769	Remote Similarity	NPD6405	Approved
0.6769	Remote Similarity	NPD6407	Approved
0.6768	Remote Similarity	NPD9088	Approved
0.6767	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7725	Approved
0.6746	Remote Similarity	NPD1283	Approved
0.6746	Remote Similarity	NPD6696	Suspended
0.6726	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1929	Approved
0.6726	Remote Similarity	NPD1930	Approved
0.672	Remote Similarity	NPD2562	Approved
0.672	Remote Similarity	NPD2561	Approved
0.6719	Remote Similarity	NPD4212	Discontinued
0.6718	Remote Similarity	NPD6346	Approved
0.6718	Remote Similarity	NPD3620	Phase 2
0.6718	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD2499	Approved
0.6695	Remote Similarity	NPD228	Approved
0.6695	Remote Similarity	NPD2500	Approved
0.6694	Remote Similarity	NPD3847	Discontinued
0.6694	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD3421	Phase 3

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