NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.18
Volume:	313.089
LogP:	3.484
LogD:	3.506
LogS:	-3.089
# Rotatable Bonds:	6
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.757
Synthetic Accessibility Score:	3.586
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.507
MDCK Permeability:	2.8543316147988662e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	99.04013061523438%
Volume Distribution (VD):	1.272
Pgp-substrate:	1.9127593040466309%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.388
CYP2C19-substrate:	0.246
CYP2C9-inhibitor:	0.449
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.852
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	6.892
Half-life (T1/2):	0.881

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.868
Skin Sensitization:	0.947
Carcinogencity:	0.349
Eye Corrosion:	0.044
Eye Irritation:	0.815
Respiratory Toxicity:	0.223

Download Data

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

Natural Product: NPC270547

Natural Product ID:	NPC270547
*Common Name:**	13-Hydroxyisobakuchiol
IUPAC Name:	4-[(1E,3S,5E)-3-ethenyl-7-hydroxy-3,7-dimethylocta-1,5-dienyl]phenol
Synonyms:
Standard InCHIKey:	KGYDEXUROYEYFL-CEAFDCLWSA-N
Standard InCHI:	InChI=1S/C18H24O2/c1-5-18(4,13-6-12-17(2,3)20)14-11-15-7-9-16(19)10-8-15/h5-12,14,19-20H,1,13H2,2-4H3/b12-6+,14-11+/t18-/m1/s1
SMILES:	C=C[C@@](/C=C/c1ccc(cc1)O)(C/C=C/C(O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577256
PubChem CID:	15818784
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18359631]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[25710081]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3069958]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[8759164]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[458792]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[458792]

☑ 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 NPC270547 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	201
0.1-0.2	2010
0.2-0.3	6308
0.3-0.4	13007
0.4-0.5	7624
0.5-0.6	9289
0.6-0.7	3307
0.7-0.8	739
0.8-0.85	138
0.85-0.9	51
0.9-0.95	20
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC98772
0.9535	High Similarity	NPC184169
0.9318	High Similarity	NPC177420
0.9318	High Similarity	NPC280347
0.9302	High Similarity	NPC248817
0.9213	High Similarity	NPC55561
0.9205	High Similarity	NPC113460
0.9205	High Similarity	NPC25493
0.9195	High Similarity	NPC197783
0.9186	High Similarity	NPC124436
0.9186	High Similarity	NPC265146
0.9149	High Similarity	NPC471578
0.9149	High Similarity	NPC101025
0.9121	High Similarity	NPC316301
0.9121	High Similarity	NPC27323
0.9111	High Similarity	NPC155908
0.9101	High Similarity	NPC242240
0.9101	High Similarity	NPC123273
0.9101	High Similarity	NPC318325
0.9091	High Similarity	NPC23167
0.908	High Similarity	NPC175313
0.9053	High Similarity	NPC62351
0.9022	High Similarity	NPC26244
0.8989	High Similarity	NPC104216
0.8947	High Similarity	NPC472585
0.8936	High Similarity	NPC92730
0.8925	High Similarity	NPC473388
0.8913	High Similarity	NPC151715
0.8889	High Similarity	NPC258219
0.8842	High Similarity	NPC225506
0.883	High Similarity	NPC225464
0.8804	High Similarity	NPC138117
0.8804	High Similarity	NPC325292
0.8804	High Similarity	NPC181709
0.8791	High Similarity	NPC300017
0.8737	High Similarity	NPC122005
0.8737	High Similarity	NPC252821
0.8723	High Similarity	NPC292730
0.8723	High Similarity	NPC132271
0.8723	High Similarity	NPC216520
0.8723	High Similarity	NPC82664
0.871	High Similarity	NPC152415
0.8696	High Similarity	NPC306074
0.8696	High Similarity	NPC204210
0.8696	High Similarity	NPC45040
0.8696	High Similarity	NPC304541
0.8667	High Similarity	NPC307235
0.8667	High Similarity	NPC407
0.8652	High Similarity	NPC286904
0.8652	High Similarity	NPC150837
0.8632	High Similarity	NPC475078
0.8632	High Similarity	NPC201967
0.8617	High Similarity	NPC313650
0.8617	High Similarity	NPC144682
0.8602	High Similarity	NPC3358
0.8602	High Similarity	NPC55903
0.8602	High Similarity	NPC306884
0.8602	High Similarity	NPC147284
0.8602	High Similarity	NPC162314
0.8602	High Similarity	NPC210497
0.8602	High Similarity	NPC94139
0.8587	High Similarity	NPC300478
0.8587	High Similarity	NPC192
0.8586	High Similarity	NPC477814
0.8571	High Similarity	NPC27974
0.8556	High Similarity	NPC155393
0.8542	High Similarity	NPC128723
0.8542	High Similarity	NPC216468
0.8542	High Similarity	NPC130193
0.8542	High Similarity	NPC132078
0.8542	High Similarity	NPC51333
0.8542	High Similarity	NPC78119
0.8511	High Similarity	NPC32977
0.8511	High Similarity	NPC128062
0.8511	High Similarity	NPC289769
0.8511	High Similarity	NPC81010
0.8478	Intermediate Similarity	NPC70436
0.8469	Intermediate Similarity	NPC196479
0.8454	Intermediate Similarity	NPC211885
0.8454	Intermediate Similarity	NPC213730
0.8438	Intermediate Similarity	NPC260000
0.8438	Intermediate Similarity	NPC152097
0.8438	Intermediate Similarity	NPC77492
0.8421	Intermediate Similarity	NPC222146
0.8421	Intermediate Similarity	NPC274678
0.8421	Intermediate Similarity	NPC8392
0.8421	Intermediate Similarity	NPC286006
0.8421	Intermediate Similarity	NPC107522
0.84	Intermediate Similarity	NPC53740
0.8384	Intermediate Similarity	NPC120719
0.837	Intermediate Similarity	NPC19680
0.8367	Intermediate Similarity	NPC7686
0.8367	Intermediate Similarity	NPC252105
0.8367	Intermediate Similarity	NPC80800
0.8367	Intermediate Similarity	NPC91461
0.8367	Intermediate Similarity	NPC40258
0.8351	Intermediate Similarity	NPC80027
0.8351	Intermediate Similarity	NPC33675
0.8351	Intermediate Similarity	NPC299762
0.8351	Intermediate Similarity	NPC171843
0.8351	Intermediate Similarity	NPC280869
0.8351	Intermediate Similarity	NPC260775
0.8316	Intermediate Similarity	NPC76938
0.8316	Intermediate Similarity	NPC471581
0.83	Intermediate Similarity	NPC154899
0.83	Intermediate Similarity	NPC47284
0.83	Intermediate Similarity	NPC219286
0.83	Intermediate Similarity	NPC99557
0.83	Intermediate Similarity	NPC233396
0.83	Intermediate Similarity	NPC138942
0.8298	Intermediate Similarity	NPC231150
0.8283	Intermediate Similarity	NPC168829
0.8283	Intermediate Similarity	NPC108497
0.8283	Intermediate Similarity	NPC68269
0.8265	Intermediate Similarity	NPC130756
0.8265	Intermediate Similarity	NPC129373
0.8265	Intermediate Similarity	NPC12931
0.8265	Intermediate Similarity	NPC166761
0.8265	Intermediate Similarity	NPC72729
0.8265	Intermediate Similarity	NPC48730
0.8265	Intermediate Similarity	NPC253746
0.8265	Intermediate Similarity	NPC248396
0.8265	Intermediate Similarity	NPC70677
0.8252	Intermediate Similarity	NPC222905
0.8247	Intermediate Similarity	NPC109955
0.8247	Intermediate Similarity	NPC107619
0.8247	Intermediate Similarity	NPC474073
0.8235	Intermediate Similarity	NPC470039
0.8229	Intermediate Similarity	NPC32714
0.8218	Intermediate Similarity	NPC155072
0.8218	Intermediate Similarity	NPC113457
0.8218	Intermediate Similarity	NPC231705
0.8218	Intermediate Similarity	NPC135464
0.8218	Intermediate Similarity	NPC92623
0.8218	Intermediate Similarity	NPC310456
0.8211	Intermediate Similarity	NPC29373
0.82	Intermediate Similarity	NPC261573
0.82	Intermediate Similarity	NPC120693
0.82	Intermediate Similarity	NPC8931
0.82	Intermediate Similarity	NPC288411
0.8191	Intermediate Similarity	NPC151764
0.8191	Intermediate Similarity	NPC47950
0.8191	Intermediate Similarity	NPC312304
0.8173	Intermediate Similarity	NPC139946
0.8163	Intermediate Similarity	NPC131587
0.8163	Intermediate Similarity	NPC245561
0.8163	Intermediate Similarity	NPC275104
0.8144	Intermediate Similarity	NPC202986
0.8137	Intermediate Similarity	NPC320439
0.8137	Intermediate Similarity	NPC142297
0.8125	Intermediate Similarity	NPC245187
0.8119	Intermediate Similarity	NPC303141
0.8119	Intermediate Similarity	NPC474839
0.8119	Intermediate Similarity	NPC243677
0.81	Intermediate Similarity	NPC24404
0.81	Intermediate Similarity	NPC302219
0.81	Intermediate Similarity	NPC222522
0.81	Intermediate Similarity	NPC94351
0.81	Intermediate Similarity	NPC71002
0.81	Intermediate Similarity	NPC269212
0.81	Intermediate Similarity	NPC168303
0.81	Intermediate Similarity	NPC313030
0.81	Intermediate Similarity	NPC53051
0.81	Intermediate Similarity	NPC178902
0.81	Intermediate Similarity	NPC242342
0.81	Intermediate Similarity	NPC85479
0.81	Intermediate Similarity	NPC106396
0.81	Intermediate Similarity	NPC146798
0.81	Intermediate Similarity	NPC304638
0.81	Intermediate Similarity	NPC249828
0.81	Intermediate Similarity	NPC135784
0.81	Intermediate Similarity	NPC192596
0.8095	Intermediate Similarity	NPC228425
0.8081	Intermediate Similarity	NPC223393
0.8081	Intermediate Similarity	NPC10588
0.8081	Intermediate Similarity	NPC52472
0.8081	Intermediate Similarity	NPC248573
0.8081	Intermediate Similarity	NPC161571
0.8081	Intermediate Similarity	NPC294741
0.8081	Intermediate Similarity	NPC155847
0.8081	Intermediate Similarity	NPC289381
0.8081	Intermediate Similarity	NPC275053
0.8077	Intermediate Similarity	NPC13482
0.8061	Intermediate Similarity	NPC32674
0.8061	Intermediate Similarity	NPC6597
0.8061	Intermediate Similarity	NPC79241
0.8058	Intermediate Similarity	NPC11554
0.8058	Intermediate Similarity	NPC317305
0.8058	Intermediate Similarity	NPC201959
0.8058	Intermediate Similarity	NPC306295
0.8058	Intermediate Similarity	NPC61885
0.8058	Intermediate Similarity	NPC31274
0.8058	Intermediate Similarity	NPC63698
0.8041	Intermediate Similarity	NPC257182
0.8041	Intermediate Similarity	NPC246679
0.8039	Intermediate Similarity	NPC271274
0.8039	Intermediate Similarity	NPC95178
0.8039	Intermediate Similarity	NPC70843
0.8039	Intermediate Similarity	NPC29989
0.8039	Intermediate Similarity	NPC188677

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 NPC270547 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1138
0.2-0.3	1372
0.3-0.4	3034
0.4-0.5	1920
0.5-0.6	1051
0.6-0.7	353
0.7-0.8	58
0.8-0.85	6
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9186	High Similarity	NPD111	Approved
0.9121	High Similarity	NPD2934	Approved
0.9121	High Similarity	NPD1432	Clinical (unspecified phase)
0.9121	High Similarity	NPD2933	Approved
0.9022	High Similarity	NPD2859	Approved
0.9022	High Similarity	NPD2860	Approved
0.8737	High Similarity	NPD3020	Approved
0.8617	High Similarity	NPD1809	Phase 2
0.8367	Intermediate Similarity	NPD940	Approved
0.8367	Intermediate Similarity	NPD846	Approved
0.8265	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD844	Approved
0.8211	Intermediate Similarity	NPD845	Approved
0.8081	Intermediate Similarity	NPD1242	Phase 1
0.7981	Intermediate Similarity	NPD3021	Approved
0.7981	Intermediate Similarity	NPD3022	Approved
0.7959	Intermediate Similarity	NPD288	Approved
0.7907	Intermediate Similarity	NPD9087	Approved
0.79	Intermediate Similarity	NPD3028	Approved
0.785	Intermediate Similarity	NPD2229	Approved
0.785	Intermediate Similarity	NPD2228	Approved
0.785	Intermediate Similarity	NPD2234	Approved
0.7843	Intermediate Similarity	NPD9608	Approved
0.7843	Intermediate Similarity	NPD9610	Approved
0.783	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD9088	Approved
0.7685	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4059	Approved
0.7658	Intermediate Similarity	NPD3091	Approved
0.7547	Intermediate Similarity	NPD2684	Approved
0.7525	Intermediate Similarity	NPD9273	Approved
0.7524	Intermediate Similarity	NPD1445	Approved
0.7524	Intermediate Similarity	NPD1444	Approved
0.7522	Intermediate Similarity	NPD3019	Approved
0.7522	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD228	Approved
0.7477	Intermediate Similarity	NPD4750	Phase 3
0.7477	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD9294	Approved
0.7419	Intermediate Similarity	NPD9089	Approved
0.7404	Intermediate Similarity	NPD9500	Approved
0.7391	Intermediate Similarity	NPD3092	Approved
0.7387	Intermediate Similarity	NPD6671	Approved
0.7387	Intermediate Similarity	NPD7157	Approved
0.7368	Intermediate Similarity	NPD4589	Approved
0.7358	Intermediate Similarity	NPD3134	Approved
0.7358	Intermediate Similarity	NPD968	Approved
0.7315	Intermediate Similarity	NPD1792	Phase 2
0.7312	Intermediate Similarity	NPD9093	Approved
0.7297	Intermediate Similarity	NPD1793	Approved
0.7297	Intermediate Similarity	NPD1791	Approved
0.729	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD1357	Approved
0.7281	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7843	Approved
0.7273	Intermediate Similarity	NPD9377	Approved
0.7273	Intermediate Similarity	NPD9379	Approved
0.7273	Intermediate Similarity	NPD821	Approved
0.7273	Intermediate Similarity	NPD7635	Approved
0.7257	Intermediate Similarity	NPD856	Approved
0.7257	Intermediate Similarity	NPD16	Approved
0.7245	Intermediate Similarity	NPD9295	Approved
0.7232	Intermediate Similarity	NPD255	Approved
0.7232	Intermediate Similarity	NPD256	Approved
0.7217	Intermediate Similarity	NPD1751	Approved
0.7217	Intermediate Similarity	NPD3095	Discontinued
0.7217	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5303	Approved
0.7193	Intermediate Similarity	NPD5304	Approved
0.7156	Intermediate Similarity	NPD5451	Approved
0.7155	Intermediate Similarity	NPD3421	Phase 3
0.7155	Intermediate Similarity	NPD3143	Discontinued
0.7143	Intermediate Similarity	NPD3094	Phase 2
0.713	Intermediate Similarity	NPD4093	Discontinued
0.713	Intermediate Similarity	NPD2342	Discontinued
0.713	Intermediate Similarity	NPD1358	Approved
0.713	Intermediate Similarity	NPD290	Approved
0.7105	Intermediate Similarity	NPD317	Approved
0.7105	Intermediate Similarity	NPD318	Approved
0.7094	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2668	Approved
0.7069	Intermediate Similarity	NPD2667	Approved
0.7043	Intermediate Similarity	NPD9545	Approved
0.7043	Intermediate Similarity	NPD7330	Discontinued
0.7034	Intermediate Similarity	NPD2561	Approved
0.7034	Intermediate Similarity	NPD3070	Discontinued
0.7034	Intermediate Similarity	NPD2562	Approved
0.7025	Intermediate Similarity	NPD5736	Approved
0.7018	Intermediate Similarity	NPD9568	Approved
0.701	Intermediate Similarity	NPD9073	Approved
0.7009	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4103	Phase 2
0.7	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD9618	Approved
0.6991	Remote Similarity	NPD475	Phase 2
0.6991	Remote Similarity	NPD9614	Approved
0.6975	Remote Similarity	NPD6582	Phase 2
0.6975	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6583	Phase 3
0.6975	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4659	Approved
0.697	Remote Similarity	NPD9094	Approved
0.6964	Remote Similarity	NPD5535	Approved
0.6942	Remote Similarity	NPD2194	Approved
0.6942	Remote Similarity	NPD2195	Approved
0.6942	Remote Similarity	NPD4624	Approved
0.6923	Remote Similarity	NPD4626	Approved
0.6923	Remote Similarity	NPD2286	Discontinued
0.6909	Remote Similarity	NPD74	Approved
0.6909	Remote Similarity	NPD9266	Approved
0.6903	Remote Similarity	NPD5283	Phase 1
0.6897	Remote Similarity	NPD1548	Phase 1
0.6897	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD9296	Approved
0.6885	Remote Similarity	NPD3637	Approved
0.6885	Remote Similarity	NPD3635	Approved
0.6885	Remote Similarity	NPD3636	Approved
0.687	Remote Similarity	NPD7636	Approved
0.687	Remote Similarity	NPD9493	Approved
0.6864	Remote Similarity	NPD3847	Discontinued
0.6864	Remote Similarity	NPD3023	Approved
0.6864	Remote Similarity	NPD3026	Approved
0.686	Remote Similarity	NPD3055	Approved
0.686	Remote Similarity	NPD3053	Approved
0.6842	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3024	Approved
0.6838	Remote Similarity	NPD3025	Approved
0.6833	Remote Similarity	NPD1755	Approved
0.6829	Remote Similarity	NPD2605	Approved
0.6829	Remote Similarity	NPD2606	Approved
0.6822	Remote Similarity	NPD4818	Approved
0.6822	Remote Similarity	NPD4817	Approved
0.6818	Remote Similarity	NPD9263	Approved
0.6818	Remote Similarity	NPD9264	Approved
0.6818	Remote Similarity	NPD9267	Approved
0.681	Remote Similarity	NPD9615	Approved
0.681	Remote Similarity	NPD9613	Approved
0.681	Remote Similarity	NPD9616	Approved
0.6807	Remote Similarity	NPD422	Phase 1
0.6803	Remote Similarity	NPD6584	Phase 3
0.6803	Remote Similarity	NPD7451	Discontinued
0.68	Remote Similarity	NPD6663	Approved
0.678	Remote Similarity	NPD9384	Approved
0.678	Remote Similarity	NPD9381	Approved
0.678	Remote Similarity	NPD1778	Approved
0.6777	Remote Similarity	NPD5310	Approved
0.6777	Remote Similarity	NPD6696	Suspended
0.6777	Remote Similarity	NPD5311	Approved
0.6774	Remote Similarity	NPD5155	Approved
0.6774	Remote Similarity	NPD7095	Approved
0.6774	Remote Similarity	NPD5156	Approved
0.6752	Remote Similarity	NPD1759	Phase 1
0.6752	Remote Similarity	NPD316	Approved
0.675	Remote Similarity	NPD2233	Approved
0.675	Remote Similarity	NPD2232	Approved
0.675	Remote Similarity	NPD2230	Approved
0.675	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4208	Discontinued
0.6748	Remote Similarity	NPD4212	Discontinued
0.6724	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3496	Discontinued
0.6721	Remote Similarity	NPD1129	Approved
0.6721	Remote Similarity	NPD1134	Approved
0.6721	Remote Similarity	NPD1133	Approved
0.6721	Remote Similarity	NPD1135	Approved
0.6721	Remote Similarity	NPD1131	Approved
0.6699	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD9244	Approved
0.6694	Remote Similarity	NPD3685	Discontinued
0.6694	Remote Similarity	NPD3594	Approved
0.6694	Remote Similarity	NPD4908	Phase 1
0.6694	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD3595	Approved
0.6694	Remote Similarity	NPD9622	Approved
0.6694	Remote Similarity	NPD4749	Approved
0.6694	Remote Similarity	NPD4207	Discontinued
0.6667	Remote Similarity	NPD5536	Phase 2
0.6667	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1610	Phase 2
0.6667	Remote Similarity	NPD1758	Phase 1
0.6667	Remote Similarity	NPD1535	Discovery
0.664	Remote Similarity	NPD3136	Phase 2
0.664	Remote Similarity	NPD3027	Phase 3
0.6639	Remote Similarity	NPD6516	Phase 2
0.6639	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5846	Approved
0.6614	Remote Similarity	NPD3620	Phase 2
0.6614	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2861	Phase 2
0.6612	Remote Similarity	NPD3972	Approved
0.6612	Remote Similarity	NPD1481	Phase 2
0.661	Remote Similarity	NPD1894	Discontinued
0.6609	Remote Similarity	NPD1241	Discontinued
0.6607	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3680	Approved
0.6606	Remote Similarity	NPD4231	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