NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.15
Volume:	240.388
LogP:	4.413
LogD:	4.172
LogS:	-3.915
# Rotatable Bonds:	6
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	2.022
Fsp3:	0.429
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:	-4.573
MDCK Permeability:	1.4973390534578357e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.883

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.155
Plasma Protein Binding (PPB):	98.63434600830078%
Volume Distribution (VD):	1.31
Pgp-substrate:	0.9696120619773865%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.532
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.229
CYP2C9-inhibitor:	0.734
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.281
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	4.452
Half-life (T1/2):	0.884

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.171
Skin Sensitization:	0.938
Carcinogencity:	0.063
Eye Corrosion:	0.969
Eye Irritation:	0.989
Respiratory Toxicity:	0.175

Download Data

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

Natural Product: NPC25493

Natural Product ID:	NPC25493
*Common Name:**	Gibbilimbol C
IUPAC Name:	4-[(E)-oct-4-enyl]phenol
Synonyms:	4-[(4'E)-Octenyl]Phenol
Standard InCHIKey:	WHTYMTFJEIRTRO-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C14H20O/c1-2-3-4-5-6-7-8-13-9-11-14(15)12-10-13/h4-5,9-12,15H,2-3,6-8H2,1H3/b5-4+
SMILES:	CCC/C=C/CCCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447769
PubChem CID:	11820250
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
NPO27498	Piper gibbilimbum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677279]
NPO27498	Piper gibbilimbum	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
ED50	1
LD50	1
MIC	2
Others	2

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	7.8	ug ml-1	PMID[479441]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	5.5	ug ml-1	PMID[479441]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	2.0	ug.mL-1	PMID[479441]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	2.0	ug.mL-1	PMID[479441]
NPT314	Organism	Bacillus cereus	Bacillus cereus	IZ	<	2.0	mm	PMID[479441]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	<	2.0	mm	PMID[479441]

☑ 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 NPC25493 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
1.0	High Similarity	NPC113460
0.9881	High Similarity	NPC242240
0.9881	High Similarity	NPC318325
0.9881	High Similarity	NPC280347
0.9881	High Similarity	NPC177420
0.9881	High Similarity	NPC123273
0.988	High Similarity	NPC23167
0.9765	High Similarity	NPC55561
0.9759	High Similarity	NPC197783
0.9647	High Similarity	NPC258219
0.9643	High Similarity	NPC184169
0.9639	High Similarity	NPC175313
0.9639	High Similarity	NPC248817
0.9518	High Similarity	NPC124436
0.9518	High Similarity	NPC265146
0.9432	High Similarity	NPC316301
0.9432	High Similarity	NPC27323
0.9425	High Similarity	NPC304541
0.9419	High Similarity	NPC98772
0.9412	High Similarity	NPC407
0.9412	High Similarity	NPC307235
0.9326	High Similarity	NPC26244
0.9318	High Similarity	NPC138117
0.9318	High Similarity	NPC325292
0.931	High Similarity	NPC300017
0.9302	High Similarity	NPC27974
0.9294	High Similarity	NPC155393
0.9222	High Similarity	NPC473388
0.9213	High Similarity	NPC151715
0.9205	High Similarity	NPC204210
0.9205	High Similarity	NPC270547
0.9205	High Similarity	NPC155908
0.9205	High Similarity	NPC45040
0.9176	High Similarity	NPC286904
0.9121	High Similarity	NPC225464
0.9121	High Similarity	NPC77492
0.9111	High Similarity	NPC313650
0.9111	High Similarity	NPC8392
0.9101	High Similarity	NPC3358
0.9101	High Similarity	NPC306884
0.9101	High Similarity	NPC162314
0.9101	High Similarity	NPC94139
0.9101	High Similarity	NPC210497
0.9101	High Similarity	NPC147284
0.9091	High Similarity	NPC192
0.908	High Similarity	NPC104216
0.9022	High Similarity	NPC122005
0.9022	High Similarity	NPC92730
0.9022	High Similarity	NPC128723
0.9022	High Similarity	NPC252821
0.9	High Similarity	NPC152415
0.9	High Similarity	NPC128062
0.8989	High Similarity	NPC306074
0.8977	High Similarity	NPC70436
0.8953	High Similarity	NPC150837
0.8925	High Similarity	NPC225506
0.8913	High Similarity	NPC260000
0.8901	High Similarity	NPC274678
0.8901	High Similarity	NPC144682
0.8889	High Similarity	NPC55903
0.8889	High Similarity	NPC181709
0.8876	High Similarity	NPC300478
0.8817	High Similarity	NPC78119
0.8817	High Similarity	NPC132078
0.8817	High Similarity	NPC51333
0.8817	High Similarity	NPC80027
0.8817	High Similarity	NPC280869
0.8817	High Similarity	NPC216468
0.8804	High Similarity	NPC202986
0.8804	High Similarity	NPC216520
0.8804	High Similarity	NPC132271
0.8804	High Similarity	NPC292730
0.8804	High Similarity	NPC82664
0.8791	High Similarity	NPC245187
0.8791	High Similarity	NPC76938
0.8791	High Similarity	NPC289769
0.8778	High Similarity	NPC231150
0.8737	High Similarity	NPC196479
0.8723	High Similarity	NPC211885
0.8723	High Similarity	NPC213730
0.871	High Similarity	NPC152097
0.871	High Similarity	NPC32674
0.871	High Similarity	NPC474073
0.871	High Similarity	NPC6597
0.871	High Similarity	NPC109955
0.871	High Similarity	NPC79241
0.871	High Similarity	NPC107619
0.8696	High Similarity	NPC222146
0.8696	High Similarity	NPC32714
0.8681	High Similarity	NPC271440
0.8652	High Similarity	NPC19680
0.8632	High Similarity	NPC7686
0.8632	High Similarity	NPC91461
0.8632	High Similarity	NPC40258
0.8617	High Similarity	NPC260775
0.8617	High Similarity	NPC245561
0.8617	High Similarity	NPC299762
0.8617	High Similarity	NPC33675
0.8602	High Similarity	NPC312132
0.8602	High Similarity	NPC259512
0.8587	High Similarity	NPC81010
0.8587	High Similarity	NPC32977
0.8557	High Similarity	NPC233396
0.8557	High Similarity	NPC303141
0.8557	High Similarity	NPC154899
0.8557	High Similarity	NPC138942
0.8542	High Similarity	NPC168829
0.8526	High Similarity	NPC155847
0.8526	High Similarity	NPC72729
0.8526	High Similarity	NPC130756
0.8526	High Similarity	NPC70677
0.8526	High Similarity	NPC12931
0.8526	High Similarity	NPC289381
0.8526	High Similarity	NPC52472
0.8526	High Similarity	NPC166761
0.8526	High Similarity	NPC248396
0.8526	High Similarity	NPC129373
0.8526	High Similarity	NPC48730
0.8511	High Similarity	NPC475078
0.8511	High Similarity	NPC201967
0.8495	Intermediate Similarity	NPC286006
0.8495	Intermediate Similarity	NPC107522
0.8478	Intermediate Similarity	NPC29373
0.8469	Intermediate Similarity	NPC92623
0.8469	Intermediate Similarity	NPC271274
0.8469	Intermediate Similarity	NPC113457
0.8469	Intermediate Similarity	NPC135464
0.8469	Intermediate Similarity	NPC477814
0.8462	Intermediate Similarity	NPC151764
0.8462	Intermediate Similarity	NPC312304
0.8462	Intermediate Similarity	NPC47950
0.8454	Intermediate Similarity	NPC288411
0.8454	Intermediate Similarity	NPC119860
0.8454	Intermediate Similarity	NPC120719
0.8454	Intermediate Similarity	NPC8931
0.8454	Intermediate Similarity	NPC120693
0.8454	Intermediate Similarity	NPC261573
0.8438	Intermediate Similarity	NPC252105
0.8438	Intermediate Similarity	NPC110764
0.8438	Intermediate Similarity	NPC472585
0.8438	Intermediate Similarity	NPC471578
0.8438	Intermediate Similarity	NPC101025
0.8421	Intermediate Similarity	NPC171843
0.8421	Intermediate Similarity	NPC100870
0.8421	Intermediate Similarity	NPC125732
0.8421	Intermediate Similarity	NPC130193
0.8384	Intermediate Similarity	NPC228737
0.8372	Intermediate Similarity	NPC133050
0.837	Intermediate Similarity	NPC321956
0.8367	Intermediate Similarity	NPC474839
0.8367	Intermediate Similarity	NPC243677
0.8351	Intermediate Similarity	NPC62351
0.8351	Intermediate Similarity	NPC313030
0.8351	Intermediate Similarity	NPC471228
0.8351	Intermediate Similarity	NPC146798
0.8351	Intermediate Similarity	NPC24404
0.8351	Intermediate Similarity	NPC178902
0.8351	Intermediate Similarity	NPC108497
0.8351	Intermediate Similarity	NPC106396
0.8351	Intermediate Similarity	NPC71002
0.8351	Intermediate Similarity	NPC222522
0.8351	Intermediate Similarity	NPC135784
0.8351	Intermediate Similarity	NPC168303
0.8351	Intermediate Similarity	NPC85479
0.8351	Intermediate Similarity	NPC94351
0.8351	Intermediate Similarity	NPC470202
0.8351	Intermediate Similarity	NPC302219
0.8351	Intermediate Similarity	NPC235762
0.8351	Intermediate Similarity	NPC242342
0.8351	Intermediate Similarity	NPC53051
0.8351	Intermediate Similarity	NPC249828
0.8333	Intermediate Similarity	NPC253746
0.8333	Intermediate Similarity	NPC174911
0.8333	Intermediate Similarity	NPC10588
0.8333	Intermediate Similarity	NPC294741
0.8316	Intermediate Similarity	NPC156313
0.83	Intermediate Similarity	NPC31274
0.83	Intermediate Similarity	NPC61885
0.83	Intermediate Similarity	NPC75440
0.83	Intermediate Similarity	NPC317305
0.83	Intermediate Similarity	NPC63698
0.83	Intermediate Similarity	NPC11554
0.8298	Intermediate Similarity	NPC246679
0.8295	Intermediate Similarity	NPC304538
0.8283	Intermediate Similarity	NPC231705
0.8283	Intermediate Similarity	NPC69332
0.8283	Intermediate Similarity	NPC188677
0.8283	Intermediate Similarity	NPC29989
0.8283	Intermediate Similarity	NPC21594
0.8283	Intermediate Similarity	NPC70843
0.8283	Intermediate Similarity	NPC95178
0.8276	Intermediate Similarity	NPC87299
0.8276	Intermediate Similarity	NPC99394
0.8276	Intermediate Similarity	NPC103326
0.8276	Intermediate Similarity	NPC329319
0.8265	Intermediate Similarity	NPC254965
0.8265	Intermediate Similarity	NPC471511
0.8265	Intermediate Similarity	NPC12278
0.8265	Intermediate Similarity	NPC327811
0.8265	Intermediate Similarity	NPC475225

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 NPC25493 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
0.9518	High Similarity	NPD111	Approved
0.9432	High Similarity	NPD2933	Approved
0.9432	High Similarity	NPD1432	Clinical (unspecified phase)
0.9432	High Similarity	NPD2934	Approved
0.9326	High Similarity	NPD2859	Approved
0.9326	High Similarity	NPD2860	Approved
0.9022	High Similarity	NPD3020	Approved
0.8901	High Similarity	NPD844	Approved
0.8901	High Similarity	NPD1809	Phase 2
0.8889	High Similarity	NPD845	Approved
0.883	High Similarity	NPD940	Approved
0.883	High Similarity	NPD846	Approved
0.8602	High Similarity	NPD288	Approved
0.8454	Intermediate Similarity	NPD9608	Approved
0.8454	Intermediate Similarity	NPD9610	Approved
0.8333	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD3022	Approved
0.8218	Intermediate Similarity	NPD3021	Approved
0.8193	Intermediate Similarity	NPD9087	Approved
0.8144	Intermediate Similarity	NPD1242	Phase 1
0.8144	Intermediate Similarity	NPD3028	Approved
0.81	Intermediate Similarity	NPD1445	Approved
0.81	Intermediate Similarity	NPD1444	Approved
0.7907	Intermediate Similarity	NPD9294	Approved
0.7905	Intermediate Similarity	NPD2228	Approved
0.7905	Intermediate Similarity	NPD2234	Approved
0.7905	Intermediate Similarity	NPD2229	Approved
0.7885	Intermediate Similarity	NPD228	Approved
0.7864	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD1792	Phase 2
0.7816	Intermediate Similarity	NPD9088	Approved
0.7767	Intermediate Similarity	NPD2684	Approved
0.7755	Intermediate Similarity	NPD9273	Approved
0.7714	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4750	Phase 3
0.7642	Intermediate Similarity	NPD9379	Approved
0.7642	Intermediate Similarity	NPD9377	Approved
0.7642	Intermediate Similarity	NPD821	Approved
0.7624	Intermediate Similarity	NPD9500	Approved
0.7615	Intermediate Similarity	NPD856	Approved
0.7615	Intermediate Similarity	NPD16	Approved
0.7593	Intermediate Similarity	NPD255	Approved
0.7593	Intermediate Similarity	NPD256	Approved
0.7573	Intermediate Similarity	NPD968	Approved
0.757	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5304	Approved
0.7545	Intermediate Similarity	NPD3091	Approved
0.7545	Intermediate Similarity	NPD5303	Approved
0.75	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2342	Discontinued
0.75	Intermediate Similarity	NPD1793	Approved
0.75	Intermediate Similarity	NPD1791	Approved
0.7477	Intermediate Similarity	NPD7843	Approved
0.7477	Intermediate Similarity	NPD4093	Discontinued
0.7477	Intermediate Similarity	NPD7635	Approved
0.7473	Intermediate Similarity	NPD9089	Approved
0.7455	Intermediate Similarity	NPD317	Approved
0.7455	Intermediate Similarity	NPD318	Approved
0.7431	Intermediate Similarity	NPD6671	Approved
0.7411	Intermediate Similarity	NPD2932	Approved
0.7411	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD4059	Approved
0.7411	Intermediate Similarity	NPD1751	Approved
0.7411	Intermediate Similarity	NPD4589	Approved
0.7411	Intermediate Similarity	NPD3019	Approved
0.7364	Intermediate Similarity	NPD9568	Approved
0.7363	Intermediate Similarity	NPD9093	Approved
0.7358	Intermediate Similarity	NPD5451	Approved
0.7339	Intermediate Similarity	NPD9614	Approved
0.7339	Intermediate Similarity	NPD475	Phase 2
0.7339	Intermediate Similarity	NPD9618	Approved
0.7333	Intermediate Similarity	NPD290	Approved
0.7292	Intermediate Similarity	NPD9295	Approved
0.729	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD3092	Approved
0.7273	Intermediate Similarity	NPD7157	Approved
0.7238	Intermediate Similarity	NPD3134	Approved
0.7234	Intermediate Similarity	NPD9073	Approved
0.7232	Intermediate Similarity	NPD9545	Approved
0.7232	Intermediate Similarity	NPD1548	Phase 1
0.7232	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD2561	Approved
0.7217	Intermediate Similarity	NPD2562	Approved
0.7193	Intermediate Similarity	NPD3421	Phase 3
0.7182	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1358	Approved
0.7168	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5535	Approved
0.7155	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6582	Phase 2
0.7155	Intermediate Similarity	NPD4659	Approved
0.7155	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD9615	Approved
0.7143	Intermediate Similarity	NPD9613	Approved
0.7143	Intermediate Similarity	NPD9616	Approved
0.713	Intermediate Similarity	NPD422	Phase 1
0.7105	Intermediate Similarity	NPD9381	Approved
0.7105	Intermediate Similarity	NPD9384	Approved
0.7105	Intermediate Similarity	NPD2667	Approved
0.7105	Intermediate Similarity	NPD3095	Discontinued
0.7105	Intermediate Similarity	NPD2668	Approved
0.7105	Intermediate Similarity	NPD2286	Discontinued
0.7105	Intermediate Similarity	NPD4626	Approved
0.7103	Intermediate Similarity	NPD9266	Approved
0.7103	Intermediate Similarity	NPD74	Approved
0.7091	Intermediate Similarity	NPD5283	Phase 1
0.708	Intermediate Similarity	NPD1759	Phase 1
0.708	Intermediate Similarity	NPD316	Approved
0.7059	Intermediate Similarity	NPD9612	Approved
0.7059	Intermediate Similarity	NPD9611	Approved
0.7059	Intermediate Similarity	NPD9609	Approved
0.7054	Intermediate Similarity	NPD9493	Approved
0.7043	Intermediate Similarity	NPD3143	Discontinued
0.7043	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD3847	Discontinued
0.7034	Intermediate Similarity	NPD3094	Phase 2
0.7034	Intermediate Similarity	NPD1135	Approved
0.7034	Intermediate Similarity	NPD3055	Approved
0.7034	Intermediate Similarity	NPD1129	Approved
0.7034	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3053	Approved
0.7034	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1133	Approved
0.7034	Intermediate Similarity	NPD1134	Approved
0.7034	Intermediate Similarity	NPD4103	Phase 2
0.7034	Intermediate Similarity	NPD1131	Approved
0.7019	Intermediate Similarity	NPD854	Approved
0.7019	Intermediate Similarity	NPD4818	Approved
0.7019	Intermediate Similarity	NPD4817	Approved
0.7019	Intermediate Similarity	NPD855	Approved
0.7018	Intermediate Similarity	NPD1357	Approved
0.701	Intermediate Similarity	NPD9094	Approved
0.7009	Intermediate Similarity	NPD9267	Approved
0.7009	Intermediate Similarity	NPD9264	Approved
0.7009	Intermediate Similarity	NPD9622	Approved
0.7009	Intermediate Similarity	NPD9263	Approved
0.6991	Remote Similarity	NPD1758	Phase 1
0.6983	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD1535	Discovery
0.6983	Remote Similarity	NPD1610	Phase 2
0.6975	Remote Similarity	NPD6584	Phase 3
0.6975	Remote Similarity	NPD2195	Approved
0.6975	Remote Similarity	NPD7451	Discontinued
0.6975	Remote Similarity	NPD2194	Approved
0.6952	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5311	Approved
0.6949	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5310	Approved
0.6937	Remote Similarity	NPD1241	Discontinued
0.6931	Remote Similarity	NPD9296	Approved
0.693	Remote Similarity	NPD7330	Discontinued
0.6923	Remote Similarity	NPD1616	Discontinued
0.6923	Remote Similarity	NPD3070	Discontinued
0.6923	Remote Similarity	NPD1481	Phase 2
0.6917	Remote Similarity	NPD3636	Approved
0.6917	Remote Similarity	NPD5736	Approved
0.6917	Remote Similarity	NPD3637	Approved
0.6917	Remote Similarity	NPD3635	Approved
0.6903	Remote Similarity	NPD3596	Phase 2
0.6903	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.69	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD9495	Approved
0.6887	Remote Similarity	NPD9244	Approved
0.6864	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1755	Approved
0.6864	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3685	Discontinued
0.686	Remote Similarity	NPD2605	Approved
0.686	Remote Similarity	NPD2606	Approved
0.686	Remote Similarity	NPD4908	Phase 1
0.6847	Remote Similarity	NPD1138	Approved
0.6842	Remote Similarity	NPD9491	Approved
0.6837	Remote Similarity	NPD1101	Approved
0.6833	Remote Similarity	NPD257	Approved
0.6833	Remote Similarity	NPD9619	Approved
0.6833	Remote Similarity	NPD258	Approved
0.6833	Remote Similarity	NPD9621	Approved
0.6833	Remote Similarity	NPD9620	Approved
0.6814	Remote Similarity	NPD709	Approved
0.681	Remote Similarity	NPD5846	Approved
0.681	Remote Similarity	NPD6516	Phase 2
0.6809	Remote Similarity	NPD9250	Approved
0.6803	Remote Similarity	NPD3136	Phase 2
0.6803	Remote Similarity	NPD3027	Phase 3
0.6803	Remote Similarity	NPD5155	Approved
0.6803	Remote Similarity	NPD5156	Approved
0.6792	Remote Similarity	NPD4658	Approved
0.6792	Remote Similarity	NPD4231	Approved
0.6792	Remote Similarity	NPD4229	Approved
0.6792	Remote Similarity	NPD3681	Approved
0.6792	Remote Similarity	NPD3680	Approved
0.6792	Remote Similarity	NPD3683	Approved
0.6792	Remote Similarity	NPD3682	Approved
0.6792	Remote Similarity	NPD4656	Approved
0.6783	Remote Similarity	NPD1894	Discontinued
0.6783	Remote Similarity	NPD6580	Approved
0.6783	Remote Similarity	NPD6581	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