NPASS Compound

Structure

NPC55561 OpenBabel07101719152D 21 21 0 0 0 0 0 0 0 0999 V2000 -8.6603 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 -3.4641 -3.0000 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 -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 -0.8660 -1.5000 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 -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 -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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 20 2 0 0 0 0 18 20 1 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	344.164
LogP:	7.292
LogD:	4.929
LogS:	-4.869
# Rotatable Bonds:	12
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.348
Synthetic Accessibility Score:	2.017
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.878
MDCK Permeability:	1.2817050446756184e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	99.95262145996094%
Volume Distribution (VD):	3.135
Pgp-substrate:	0.4616398811340332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.659
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.704
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.307
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.848
CYP2D6-substrate:	0.726
CYP3A4-inhibitor:	0.536
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	3.56
Half-life (T1/2):	0.512

ADMET: Toxicity

hERG Blockers:	0.236
Human Hepatotoxicity (H-HT):	0.023
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.17
Skin Sensitization:	0.961
Carcinogencity:	0.037
Eye Corrosion:	0.975
Eye Irritation:	0.972
Respiratory Toxicity:	0.31

Download Data

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

Natural Product: NPC55561

Natural Product ID:	NPC55561
*Common Name:**	Obliquol A
IUPAC Name:	4-[(E)-tetradec-4-enyl]phenol
Synonyms:
Standard InCHIKey:	UHBRTPHHYOTILN-ZHACJKMWSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-19-15-17-20(21)18-16-19/h10-11,15-18,21H,2-9,12-14H2,1H3/b11-10+
SMILES:	CCCCCCCCC/C=C/CCCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449875
PubChem CID:	25113691
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO22658	Piper obliquum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18276144]
NPO22658	Piper obliquum	Species	Piperaceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	5.0	ug.mL-1	PMID[501731]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	2.5	ug.mL-1	PMID[501731]

☑ 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 NPC55561 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	232
0.1-0.2	2038
0.2-0.3	6818
0.3-0.4	12470
0.4-0.5	6781
0.5-0.6	9155
0.6-0.7	3962
0.7-0.8	912
0.8-0.85	202
0.85-0.9	80
0.9-0.95	32
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC177420
0.9882	High Similarity	NPC280347
0.9765	High Similarity	NPC113460
0.9765	High Similarity	NPC25493
0.9651	High Similarity	NPC123273
0.9651	High Similarity	NPC242240
0.9651	High Similarity	NPC318325
0.9647	High Similarity	NPC23167
0.9529	High Similarity	NPC197783
0.9425	High Similarity	NPC98772
0.9425	High Similarity	NPC258219
0.9419	High Similarity	NPC184169
0.9412	High Similarity	NPC248817
0.9412	High Similarity	NPC175313
0.9333	High Similarity	NPC26244
0.9326	High Similarity	NPC162314
0.9326	High Similarity	NPC3358
0.9326	High Similarity	NPC147284
0.9326	High Similarity	NPC94139
0.9326	High Similarity	NPC210497
0.9326	High Similarity	NPC306884
0.9294	High Similarity	NPC124436
0.9294	High Similarity	NPC265146
0.9231	High Similarity	NPC473388
0.9222	High Similarity	NPC151715
0.9222	High Similarity	NPC27323
0.9222	High Similarity	NPC316301
0.9213	High Similarity	NPC270547
0.9213	High Similarity	NPC304541
0.9195	High Similarity	NPC407
0.9195	High Similarity	NPC307235
0.9111	High Similarity	NPC138117
0.9111	High Similarity	NPC325292
0.9101	High Similarity	NPC300017
0.9101	High Similarity	NPC192
0.9091	High Similarity	NPC27974
0.908	High Similarity	NPC155393
0.9	High Similarity	NPC204210
0.9	High Similarity	NPC45040
0.9	High Similarity	NPC155908
0.8966	High Similarity	NPC286904
0.8947	High Similarity	NPC196479
0.8936	High Similarity	NPC225506
0.8925	High Similarity	NPC225464
0.8925	High Similarity	NPC77492
0.8913	High Similarity	NPC313650
0.8913	High Similarity	NPC8392
0.8913	High Similarity	NPC32714
0.8876	High Similarity	NPC104216
0.883	High Similarity	NPC252821
0.883	High Similarity	NPC92730
0.883	High Similarity	NPC132078
0.883	High Similarity	NPC128723
0.883	High Similarity	NPC78119
0.883	High Similarity	NPC216468
0.883	High Similarity	NPC51333
0.883	High Similarity	NPC260775
0.883	High Similarity	NPC122005
0.8817	High Similarity	NPC292730
0.8817	High Similarity	NPC82664
0.8817	High Similarity	NPC132271
0.8817	High Similarity	NPC216520
0.8804	High Similarity	NPC128062
0.8804	High Similarity	NPC152415
0.8804	High Similarity	NPC76938
0.8791	High Similarity	NPC306074
0.8778	High Similarity	NPC70436
0.875	High Similarity	NPC150837
0.8737	High Similarity	NPC48730
0.8737	High Similarity	NPC213730
0.8737	High Similarity	NPC70677
0.8737	High Similarity	NPC130756
0.8737	High Similarity	NPC129373
0.8737	High Similarity	NPC12931
0.8737	High Similarity	NPC248396
0.8723	High Similarity	NPC152097
0.8723	High Similarity	NPC260000
0.871	High Similarity	NPC144682
0.871	High Similarity	NPC274678
0.8696	High Similarity	NPC181709
0.8696	High Similarity	NPC55903
0.8681	High Similarity	NPC300478
0.8646	High Similarity	NPC91461
0.8646	High Similarity	NPC7686
0.8646	High Similarity	NPC252105
0.8646	High Similarity	NPC40258
0.8632	High Similarity	NPC280869
0.8632	High Similarity	NPC80027
0.8617	High Similarity	NPC202986
0.8602	High Similarity	NPC289769
0.8602	High Similarity	NPC245187
0.8587	High Similarity	NPC231150
0.8571	High Similarity	NPC233396
0.8571	High Similarity	NPC154899
0.8571	High Similarity	NPC138942
0.8557	High Similarity	NPC249828
0.8557	High Similarity	NPC168303
0.8557	High Similarity	NPC71002
0.8557	High Similarity	NPC53051
0.8557	High Similarity	NPC106396
0.8557	High Similarity	NPC242342
0.8557	High Similarity	NPC94351
0.8557	High Similarity	NPC302219
0.8557	High Similarity	NPC222522
0.8557	High Similarity	NPC146798
0.8557	High Similarity	NPC313030
0.8557	High Similarity	NPC85479
0.8557	High Similarity	NPC24404
0.8557	High Similarity	NPC168829
0.8542	High Similarity	NPC166761
0.8542	High Similarity	NPC211885
0.8526	High Similarity	NPC109955
0.8526	High Similarity	NPC475078
0.8526	High Similarity	NPC107619
0.8526	High Similarity	NPC79241
0.8526	High Similarity	NPC474073
0.8526	High Similarity	NPC6597
0.8526	High Similarity	NPC201967
0.8526	High Similarity	NPC32674
0.8511	High Similarity	NPC222146
0.85	High Similarity	NPC31274
0.8495	Intermediate Similarity	NPC271440
0.8485	Intermediate Similarity	NPC477814
0.8485	Intermediate Similarity	NPC92623
0.8485	Intermediate Similarity	NPC271274
0.8485	Intermediate Similarity	NPC135464
0.8485	Intermediate Similarity	NPC113457
0.8469	Intermediate Similarity	NPC261573
0.8469	Intermediate Similarity	NPC288411
0.8469	Intermediate Similarity	NPC8931
0.8469	Intermediate Similarity	NPC120693
0.8462	Intermediate Similarity	NPC19680
0.8454	Intermediate Similarity	NPC192032
0.8454	Intermediate Similarity	NPC11280
0.8454	Intermediate Similarity	NPC147310
0.8454	Intermediate Similarity	NPC80800
0.8454	Intermediate Similarity	NPC137415
0.8454	Intermediate Similarity	NPC472585
0.8454	Intermediate Similarity	NPC72947
0.8454	Intermediate Similarity	NPC477685
0.8454	Intermediate Similarity	NPC284011
0.8454	Intermediate Similarity	NPC471578
0.8454	Intermediate Similarity	NPC101025
0.8454	Intermediate Similarity	NPC166313
0.8454	Intermediate Similarity	NPC294186
0.8454	Intermediate Similarity	NPC24407
0.8438	Intermediate Similarity	NPC33675
0.8438	Intermediate Similarity	NPC130193
0.8438	Intermediate Similarity	NPC245561
0.8438	Intermediate Similarity	NPC299762
0.8421	Intermediate Similarity	NPC312132
0.8421	Intermediate Similarity	NPC259512
0.8416	Intermediate Similarity	NPC258056
0.8404	Intermediate Similarity	NPC32977
0.8404	Intermediate Similarity	NPC81010
0.84	Intermediate Similarity	NPC142297
0.8384	Intermediate Similarity	NPC99557
0.8384	Intermediate Similarity	NPC243677
0.8384	Intermediate Similarity	NPC474839
0.8384	Intermediate Similarity	NPC219286
0.8384	Intermediate Similarity	NPC303141
0.8367	Intermediate Similarity	NPC62351
0.8367	Intermediate Similarity	NPC108497
0.8367	Intermediate Similarity	NPC135784
0.8351	Intermediate Similarity	NPC52472
0.8351	Intermediate Similarity	NPC155847
0.8351	Intermediate Similarity	NPC72729
0.8351	Intermediate Similarity	NPC289381
0.8351	Intermediate Similarity	NPC10588
0.8351	Intermediate Similarity	NPC294741
0.8333	Intermediate Similarity	NPC474149
0.8333	Intermediate Similarity	NPC296683
0.8317	Intermediate Similarity	NPC61885
0.8317	Intermediate Similarity	NPC317305
0.8317	Intermediate Similarity	NPC11554
0.8317	Intermediate Similarity	NPC63698
0.8316	Intermediate Similarity	NPC286006
0.8316	Intermediate Similarity	NPC107522
0.83	Intermediate Similarity	NPC188677
0.83	Intermediate Similarity	NPC231705
0.83	Intermediate Similarity	NPC70843
0.83	Intermediate Similarity	NPC29989
0.83	Intermediate Similarity	NPC69332
0.83	Intermediate Similarity	NPC95178
0.83	Intermediate Similarity	NPC155072
0.8298	Intermediate Similarity	NPC29373
0.8283	Intermediate Similarity	NPC120719
0.8283	Intermediate Similarity	NPC119860
0.828	Intermediate Similarity	NPC151764
0.828	Intermediate Similarity	NPC47950
0.828	Intermediate Similarity	NPC312304
0.8265	Intermediate Similarity	NPC110764
0.8265	Intermediate Similarity	NPC51015
0.8247	Intermediate Similarity	NPC100870
0.8247	Intermediate Similarity	NPC125732
0.8247	Intermediate Similarity	NPC171843
0.8235	Intermediate Similarity	NPC228343
0.8235	Intermediate Similarity	NPC254833
0.8218	Intermediate Similarity	NPC151477
0.8218	Intermediate Similarity	NPC228737

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 NPC55561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	1118
0.2-0.3	1306
0.3-0.4	2893
0.4-0.5	1959
0.5-0.6	1087
0.6-0.7	444
0.7-0.8	78
0.8-0.85	9
0.85-0.9	6
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9438	High Similarity	NPD2933	Approved
0.9438	High Similarity	NPD2934	Approved
0.9333	High Similarity	NPD2860	Approved
0.9333	High Similarity	NPD2859	Approved
0.9294	High Similarity	NPD111	Approved
0.9222	High Similarity	NPD1432	Clinical (unspecified phase)
0.9032	High Similarity	NPD3020	Approved
0.871	High Similarity	NPD844	Approved
0.871	High Similarity	NPD1809	Phase 2
0.8696	High Similarity	NPD845	Approved
0.8646	High Similarity	NPD846	Approved
0.8646	High Similarity	NPD940	Approved
0.8421	Intermediate Similarity	NPD288	Approved
0.8283	Intermediate Similarity	NPD9608	Approved
0.8283	Intermediate Similarity	NPD9610	Approved
0.8235	Intermediate Similarity	NPD3021	Approved
0.8235	Intermediate Similarity	NPD3022	Approved
0.8163	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD3028	Approved
0.8	Intermediate Similarity	NPD9087	Approved
0.798	Intermediate Similarity	NPD1242	Phase 1
0.7941	Intermediate Similarity	NPD1444	Approved
0.7941	Intermediate Similarity	NPD1445	Approved
0.7925	Intermediate Similarity	NPD2234	Approved
0.7925	Intermediate Similarity	NPD2229	Approved
0.7925	Intermediate Similarity	NPD2228	Approved
0.7905	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD2684	Approved
0.7757	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD228	Approved
0.7727	Intermediate Similarity	NPD9294	Approved
0.7714	Intermediate Similarity	NPD4750	Phase 3
0.7714	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1792	Phase 2
0.7664	Intermediate Similarity	NPD7843	Approved
0.7664	Intermediate Similarity	NPD7635	Approved
0.764	Intermediate Similarity	NPD9088	Approved
0.7615	Intermediate Similarity	NPD6671	Approved
0.76	Intermediate Similarity	NPD9273	Approved
0.7568	Intermediate Similarity	NPD3091	Approved
0.7568	Intermediate Similarity	NPD5303	Approved
0.7568	Intermediate Similarity	NPD5304	Approved
0.7524	Intermediate Similarity	NPD2342	Discontinued
0.75	Intermediate Similarity	NPD4093	Discontinued
0.75	Intermediate Similarity	NPD9377	Approved
0.75	Intermediate Similarity	NPD9379	Approved
0.75	Intermediate Similarity	NPD821	Approved
0.7477	Intermediate Similarity	NPD856	Approved
0.7477	Intermediate Similarity	NPD16	Approved
0.7476	Intermediate Similarity	NPD9500	Approved
0.7455	Intermediate Similarity	NPD7157	Approved
0.7455	Intermediate Similarity	NPD255	Approved
0.7455	Intermediate Similarity	NPD256	Approved
0.7434	Intermediate Similarity	NPD4589	Approved
0.7434	Intermediate Similarity	NPD3019	Approved
0.7434	Intermediate Similarity	NPD4059	Approved
0.7434	Intermediate Similarity	NPD2932	Approved
0.7434	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD968	Approved
0.7383	Intermediate Similarity	NPD5451	Approved
0.7364	Intermediate Similarity	NPD1793	Approved
0.7364	Intermediate Similarity	NPD1791	Approved
0.7358	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD318	Approved
0.7321	Intermediate Similarity	NPD317	Approved
0.7312	Intermediate Similarity	NPD9089	Approved
0.7304	Intermediate Similarity	NPD3092	Approved
0.7281	Intermediate Similarity	NPD1751	Approved
0.7264	Intermediate Similarity	NPD3134	Approved
0.7257	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2561	Approved
0.7241	Intermediate Similarity	NPD2562	Approved
0.7232	Intermediate Similarity	NPD9568	Approved
0.7217	Intermediate Similarity	NPD3421	Phase 3
0.7212	Intermediate Similarity	NPD4818	Approved
0.7212	Intermediate Similarity	NPD4817	Approved
0.7207	Intermediate Similarity	NPD475	Phase 2
0.7207	Intermediate Similarity	NPD9618	Approved
0.7207	Intermediate Similarity	NPD9614	Approved
0.7204	Intermediate Similarity	NPD9093	Approved
0.7196	Intermediate Similarity	NPD290	Approved
0.7193	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5535	Approved
0.7179	Intermediate Similarity	NPD4659	Approved
0.7179	Intermediate Similarity	NPD6582	Phase 2
0.7179	Intermediate Similarity	NPD6583	Phase 3
0.7179	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9295	Approved
0.7143	Intermediate Similarity	NPD7451	Discontinued
0.713	Intermediate Similarity	NPD4626	Approved
0.713	Intermediate Similarity	NPD2286	Discontinued
0.713	Intermediate Similarity	NPD2667	Approved
0.713	Intermediate Similarity	NPD3095	Discontinued
0.713	Intermediate Similarity	NPD2668	Approved
0.7119	Intermediate Similarity	NPD5311	Approved
0.7119	Intermediate Similarity	NPD5310	Approved
0.7117	Intermediate Similarity	NPD5283	Phase 1
0.7105	Intermediate Similarity	NPD1548	Phase 1
0.7105	Intermediate Similarity	NPD7330	Discontinued
0.7105	Intermediate Similarity	NPD9545	Approved
0.7083	Intermediate Similarity	NPD5736	Approved
0.7083	Intermediate Similarity	NPD9073	Approved
0.708	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3847	Discontinued
0.7069	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3143	Discontinued
0.7059	Intermediate Similarity	NPD4103	Phase 2
0.7059	Intermediate Similarity	NPD3053	Approved
0.7059	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3094	Phase 2
0.7059	Intermediate Similarity	NPD3055	Approved
0.7054	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1358	Approved
0.7018	Intermediate Similarity	NPD9616	Approved
0.7018	Intermediate Similarity	NPD9615	Approved
0.7018	Intermediate Similarity	NPD9613	Approved
0.7009	Intermediate Similarity	NPD422	Phase 1
0.7	Intermediate Similarity	NPD2195	Approved
0.7	Intermediate Similarity	NPD2194	Approved
0.7	Intermediate Similarity	NPD6584	Phase 3
0.6983	Remote Similarity	NPD9384	Approved
0.6983	Remote Similarity	NPD9381	Approved
0.6981	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD74	Approved
0.6972	Remote Similarity	NPD9266	Approved
0.6957	Remote Similarity	NPD316	Approved
0.6957	Remote Similarity	NPD1759	Phase 1
0.6949	Remote Similarity	NPD3070	Discontinued
0.6942	Remote Similarity	NPD3637	Approved
0.6942	Remote Similarity	NPD3635	Approved
0.6942	Remote Similarity	NPD3636	Approved
0.693	Remote Similarity	NPD3596	Phase 2
0.693	Remote Similarity	NPD9493	Approved
0.693	Remote Similarity	NPD7636	Approved
0.6923	Remote Similarity	NPD9609	Approved
0.6923	Remote Similarity	NPD9611	Approved
0.6923	Remote Similarity	NPD9612	Approved
0.6917	Remote Similarity	NPD1129	Approved
0.6917	Remote Similarity	NPD1133	Approved
0.6917	Remote Similarity	NPD1134	Approved
0.6917	Remote Similarity	NPD1131	Approved
0.6917	Remote Similarity	NPD1135	Approved
0.6897	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1357	Approved
0.6891	Remote Similarity	NPD3685	Discontinued
0.6891	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD9622	Approved
0.6887	Remote Similarity	NPD855	Approved
0.6887	Remote Similarity	NPD854	Approved
0.6885	Remote Similarity	NPD4908	Phase 1
0.6885	Remote Similarity	NPD2605	Approved
0.6885	Remote Similarity	NPD2606	Approved
0.6881	Remote Similarity	NPD9263	Approved
0.6881	Remote Similarity	NPD9264	Approved
0.6881	Remote Similarity	NPD9267	Approved
0.687	Remote Similarity	NPD1758	Phase 1
0.6869	Remote Similarity	NPD9094	Approved
0.6864	Remote Similarity	NPD1535	Discovery
0.6864	Remote Similarity	NPD1610	Phase 2
0.6855	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6663	Approved
0.6838	Remote Similarity	NPD5846	Approved
0.6838	Remote Similarity	NPD6516	Phase 2
0.6833	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5155	Approved
0.6829	Remote Similarity	NPD5156	Approved
0.6829	Remote Similarity	NPD3136	Phase 2
0.6829	Remote Similarity	NPD3027	Phase 3
0.6822	Remote Similarity	NPD3680	Approved
0.6822	Remote Similarity	NPD4656	Approved
0.6822	Remote Similarity	NPD3682	Approved
0.6822	Remote Similarity	NPD3681	Approved
0.6822	Remote Similarity	NPD4231	Approved
0.6822	Remote Similarity	NPD4229	Approved
0.6822	Remote Similarity	NPD4658	Approved
0.6822	Remote Similarity	NPD3683	Approved
0.6814	Remote Similarity	NPD1241	Discontinued
0.681	Remote Similarity	NPD1894	Discontinued
0.681	Remote Similarity	NPD6580	Approved
0.681	Remote Similarity	NPD6581	Approved
0.6807	Remote Similarity	NPD1481	Phase 2
0.6807	Remote Similarity	NPD2233	Approved
0.6807	Remote Similarity	NPD2232	Approved
0.6807	Remote Similarity	NPD2230	Approved
0.6803	Remote Similarity	NPD2861	Phase 2
0.6796	Remote Similarity	NPD9296	Approved
0.6792	Remote Similarity	NPD1616	Discontinued
0.6783	Remote Similarity	NPD405	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3023	Approved
0.678	Remote Similarity	NPD3496	Discontinued
0.678	Remote Similarity	NPD3026	Approved
0.678	Remote Similarity	NPD1981	Approved
0.678	Remote Similarity	NPD1983	Approved
0.678	Remote Similarity	NPD1980	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