NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	124.05
Volume:	130.743
LogP:	0.632
LogD:	0.863
LogS:	-0.346
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	1.672
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.246
MDCK Permeability:	2.16193529922748e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.769
30% Bioavailability (F30%):	0.311

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	26.59345245361328%
Volume Distribution (VD):	1.232
Pgp-substrate:	70.97503662109375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.638
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.204
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.336
CYP2D6-inhibitor:	0.211
CYP2D6-substrate:	0.616
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	12.09
Half-life (T1/2):	0.911

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.499
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.862
Carcinogencity:	0.085
Eye Corrosion:	0.127
Eye Irritation:	0.992
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC312304

Natural Product ID:	NPC312304
*Common Name:**	3-(Hydroxymethyl)Phenol
IUPAC Name:	3-(hydroxymethyl)phenol
Synonyms:
Standard InCHIKey:	OKVJCVWFVRATSG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H8O2/c8-5-6-2-1-3-7(9)4-6/h1-4,8-9H,5H2
SMILES:	OCc1cccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3337531
PubChem CID:	102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000033] Benzyl alcohols

*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
NPO33084	Geosmithia langdonii	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25084548]
NPO33084	Geosmithia langdonii	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30298736]

☑ 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
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	34000.0	nM	PMID[494443]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	52300.0	nM	PMID[494443]

☑ 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 NPC312304 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	353
0.1-0.2	2083
0.2-0.3	7403
0.3-0.4	12293
0.4-0.5	6858
0.5-0.6	9182
0.6-0.7	3473
0.7-0.8	804
0.8-0.85	190
0.85-0.9	45
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9341	High Similarity	NPC474073
0.9341	High Similarity	NPC88420
0.9186	High Similarity	NPC150837
0.914	High Similarity	NPC130103
0.914	High Similarity	NPC174911
0.9111	High Similarity	NPC29373
0.9101	High Similarity	NPC300017
0.9101	High Similarity	NPC300478
0.9101	High Similarity	NPC47950
0.9091	High Similarity	NPC27974
0.9091	High Similarity	NPC104216
0.8947	High Similarity	NPC471228
0.8947	High Similarity	NPC235762
0.8936	High Similarity	NPC294741
0.8901	High Similarity	NPC138117
0.8901	High Similarity	NPC325292
0.8889	High Similarity	NPC192
0.8854	High Similarity	NPC475225
0.8854	High Similarity	NPC323810
0.8842	High Similarity	NPC110764
0.883	High Similarity	NPC131587
0.8791	High Similarity	NPC231150
0.875	High Similarity	NPC286904
0.8723	High Similarity	NPC475078
0.8723	High Similarity	NPC152097
0.871	High Similarity	NPC274678
0.871	High Similarity	NPC313650
0.8696	High Similarity	NPC162314
0.8696	High Similarity	NPC210497
0.8696	High Similarity	NPC147284
0.8696	High Similarity	NPC3358
0.8696	High Similarity	NPC94139
0.8696	High Similarity	NPC306884
0.8696	High Similarity	NPC55903
0.8667	High Similarity	NPC19680
0.866	High Similarity	NPC130817
0.866	High Similarity	NPC12278
0.8652	High Similarity	NPC155393
0.8636	High Similarity	NPC265146
0.8636	High Similarity	NPC124436
0.8632	High Similarity	NPC260775
0.8602	High Similarity	NPC76938
0.8602	High Similarity	NPC245187
0.8586	High Similarity	NPC474352
0.8586	High Similarity	NPC66834
0.8571	High Similarity	NPC471350
0.8556	High Similarity	NPC407
0.8556	High Similarity	NPC23167
0.8556	High Similarity	NPC307235
0.8542	High Similarity	NPC48730
0.8542	High Similarity	NPC70677
0.8542	High Similarity	NPC130756
0.8542	High Similarity	NPC12931
0.8542	High Similarity	NPC248396
0.8542	High Similarity	NPC129373
0.8539	High Similarity	NPC248817
0.8539	High Similarity	NPC175313
0.8526	High Similarity	NPC109955
0.8511	High Similarity	NPC257182
0.8511	High Similarity	NPC32714
0.8511	High Similarity	NPC107522
0.8495	Intermediate Similarity	NPC295295
0.8462	Intermediate Similarity	NPC25493
0.8462	Intermediate Similarity	NPC113460
0.8454	Intermediate Similarity	NPC80800
0.8454	Intermediate Similarity	NPC12221
0.8444	Intermediate Similarity	NPC197783
0.8438	Intermediate Similarity	NPC51333
0.8438	Intermediate Similarity	NPC216468
0.8438	Intermediate Similarity	NPC78119
0.8438	Intermediate Similarity	NPC128723
0.8438	Intermediate Similarity	NPC132078
0.8421	Intermediate Similarity	NPC283711
0.8421	Intermediate Similarity	NPC312132
0.8421	Intermediate Similarity	NPC259512
0.8421	Intermediate Similarity	NPC202986
0.8416	Intermediate Similarity	NPC473524
0.84	Intermediate Similarity	NPC61033
0.84	Intermediate Similarity	NPC305603
0.8387	Intermediate Similarity	NPC45040
0.8387	Intermediate Similarity	NPC304541
0.837	Intermediate Similarity	NPC123273
0.837	Intermediate Similarity	NPC242240
0.837	Intermediate Similarity	NPC318325
0.837	Intermediate Similarity	NPC258219
0.837	Intermediate Similarity	NPC280347
0.837	Intermediate Similarity	NPC177420
0.8367	Intermediate Similarity	NPC108497
0.8367	Intermediate Similarity	NPC233827
0.8353	Intermediate Similarity	NPC66655
0.8352	Intermediate Similarity	NPC184169
0.8351	Intermediate Similarity	NPC166761
0.8351	Intermediate Similarity	NPC72729
0.8351	Intermediate Similarity	NPC213730
0.8351	Intermediate Similarity	NPC10588
0.8333	Intermediate Similarity	NPC32674
0.8333	Intermediate Similarity	NPC79241
0.8333	Intermediate Similarity	NPC156313
0.8333	Intermediate Similarity	NPC6597
0.8333	Intermediate Similarity	NPC291789
0.8317	Intermediate Similarity	NPC169450
0.8317	Intermediate Similarity	NPC241549
0.8316	Intermediate Similarity	NPC222146
0.8316	Intermediate Similarity	NPC286006
0.8283	Intermediate Similarity	NPC475580
0.8283	Intermediate Similarity	NPC93831
0.828	Intermediate Similarity	NPC55561
0.8265	Intermediate Similarity	NPC94343
0.8265	Intermediate Similarity	NPC284011
0.8265	Intermediate Similarity	NPC471578
0.8265	Intermediate Similarity	NPC477685
0.8265	Intermediate Similarity	NPC143659
0.8265	Intermediate Similarity	NPC91461
0.8265	Intermediate Similarity	NPC101025
0.8265	Intermediate Similarity	NPC72947
0.8265	Intermediate Similarity	NPC40258
0.8265	Intermediate Similarity	NPC7686
0.8265	Intermediate Similarity	NPC100340
0.8247	Intermediate Similarity	NPC299762
0.8247	Intermediate Similarity	NPC33675
0.8235	Intermediate Similarity	NPC62258
0.8235	Intermediate Similarity	NPC98392
0.8235	Intermediate Similarity	NPC316052
0.8235	Intermediate Similarity	NPC55617
0.8218	Intermediate Similarity	NPC233320
0.8211	Intermediate Similarity	NPC128062
0.8211	Intermediate Similarity	NPC152415
0.8211	Intermediate Similarity	NPC27323
0.8211	Intermediate Similarity	NPC151715
0.8211	Intermediate Similarity	NPC316301
0.82	Intermediate Similarity	NPC47284
0.8191	Intermediate Similarity	NPC155908
0.8191	Intermediate Similarity	NPC204210
0.8191	Intermediate Similarity	NPC306074
0.8191	Intermediate Similarity	NPC270547
0.8182	Intermediate Similarity	NPC222522
0.8182	Intermediate Similarity	NPC168303
0.8182	Intermediate Similarity	NPC477802
0.8182	Intermediate Similarity	NPC249828
0.8182	Intermediate Similarity	NPC168393
0.8182	Intermediate Similarity	NPC269212
0.8182	Intermediate Similarity	NPC71002
0.8182	Intermediate Similarity	NPC477801
0.8182	Intermediate Similarity	NPC53051
0.8182	Intermediate Similarity	NPC242342
0.8182	Intermediate Similarity	NPC146798
0.8182	Intermediate Similarity	NPC196479
0.8182	Intermediate Similarity	NPC85479
0.8182	Intermediate Similarity	NPC94351
0.8182	Intermediate Similarity	NPC106396
0.8182	Intermediate Similarity	NPC117180
0.8182	Intermediate Similarity	NPC24404
0.8182	Intermediate Similarity	NPC302219
0.8182	Intermediate Similarity	NPC313030
0.8173	Intermediate Similarity	NPC228452
0.8173	Intermediate Similarity	NPC302371
0.8172	Intermediate Similarity	NPC98772
0.8163	Intermediate Similarity	NPC275053
0.8163	Intermediate Similarity	NPC248573
0.8163	Intermediate Similarity	NPC223393
0.8163	Intermediate Similarity	NPC161571
0.8155	Intermediate Similarity	NPC120982
0.8155	Intermediate Similarity	NPC132720
0.8155	Intermediate Similarity	NPC174096
0.8155	Intermediate Similarity	NPC226401
0.8155	Intermediate Similarity	NPC147634
0.8155	Intermediate Similarity	NPC471535
0.8155	Intermediate Similarity	NPC79793
0.8137	Intermediate Similarity	NPC262365
0.8125	Intermediate Similarity	NPC246679
0.8125	Intermediate Similarity	NPC26244
0.8119	Intermediate Similarity	NPC19149
0.8119	Intermediate Similarity	NPC54765
0.8119	Intermediate Similarity	NPC67250
0.8119	Intermediate Similarity	NPC53740
0.8119	Intermediate Similarity	NPC155072
0.8105	Intermediate Similarity	NPC271440
0.8105	Intermediate Similarity	NPC181709
0.81	Intermediate Similarity	NPC241891
0.81	Intermediate Similarity	NPC120719
0.81	Intermediate Similarity	NPC102216
0.81	Intermediate Similarity	NPC471511
0.81	Intermediate Similarity	NPC474603
0.81	Intermediate Similarity	NPC272029
0.81	Intermediate Similarity	NPC12987
0.81	Intermediate Similarity	NPC30506
0.8095	Intermediate Similarity	NPC261343
0.8095	Intermediate Similarity	NPC471485
0.809	Intermediate Similarity	NPC87299
0.809	Intermediate Similarity	NPC103326
0.809	Intermediate Similarity	NPC329319
0.809	Intermediate Similarity	NPC99394
0.8081	Intermediate Similarity	NPC252105
0.8081	Intermediate Similarity	NPC137415
0.8081	Intermediate Similarity	NPC11280
0.8081	Intermediate Similarity	NPC294186
0.8081	Intermediate Similarity	NPC147310
0.8081	Intermediate Similarity	NPC166313
0.8081	Intermediate Similarity	NPC192032
0.8081	Intermediate Similarity	NPC24407

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 NPC312304 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	1028
0.2-0.3	1718
0.3-0.4	2917
0.4-0.5	1773
0.5-0.6	968
0.6-0.7	335
0.7-0.8	52
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD111	Approved
0.8542	High Similarity	NPD289	Clinical (unspecified phase)
0.8511	High Similarity	NPD844	Approved
0.8421	Intermediate Similarity	NPD288	Approved
0.8353	Intermediate Similarity	NPD9294	Approved
0.8211	Intermediate Similarity	NPD2934	Approved
0.8211	Intermediate Similarity	NPD2933	Approved
0.8211	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1242	Phase 1
0.8125	Intermediate Similarity	NPD2859	Approved
0.8125	Intermediate Similarity	NPD2860	Approved
0.8061	Intermediate Similarity	NPD3020	Approved
0.8046	Intermediate Similarity	NPD9088	Approved
0.8019	Intermediate Similarity	NPD9618	Approved
0.8019	Intermediate Similarity	NPD9614	Approved
0.8	Intermediate Similarity	NPD9087	Approved
0.7941	Intermediate Similarity	NPD968	Approved
0.7917	Intermediate Similarity	NPD845	Approved
0.7798	Intermediate Similarity	NPD9616	Approved
0.7798	Intermediate Similarity	NPD9615	Approved
0.7798	Intermediate Similarity	NPD9613	Approved
0.7778	Intermediate Similarity	NPD9273	Approved
0.7767	Intermediate Similarity	NPD1444	Approved
0.7767	Intermediate Similarity	NPD1445	Approved
0.7736	Intermediate Similarity	NPD228	Approved
0.7727	Intermediate Similarity	NPD316	Approved
0.7723	Intermediate Similarity	NPD940	Approved
0.7723	Intermediate Similarity	NPD846	Approved
0.7714	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD3021	Approved
0.7714	Intermediate Similarity	NPD3022	Approved
0.7647	Intermediate Similarity	NPD9500	Approved
0.7642	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD9381	Approved
0.7589	Intermediate Similarity	NPD9384	Approved
0.7576	Intermediate Similarity	NPD1809	Phase 2
0.7568	Intermediate Similarity	NPD3091	Approved
0.7547	Intermediate Similarity	NPD1792	Phase 2
0.7547	Intermediate Similarity	NPD4750	Phase 3
0.7524	Intermediate Similarity	NPD2342	Discontinued
0.7524	Intermediate Similarity	NPD290	Approved
0.75	Intermediate Similarity	NPD7635	Approved
0.75	Intermediate Similarity	NPD9377	Approved
0.75	Intermediate Similarity	NPD9295	Approved
0.75	Intermediate Similarity	NPD9089	Approved
0.75	Intermediate Similarity	NPD9379	Approved
0.7455	Intermediate Similarity	NPD6671	Approved
0.7404	Intermediate Similarity	NPD9610	Approved
0.7404	Intermediate Similarity	NPD9608	Approved
0.7391	Intermediate Similarity	NPD9093	Approved
0.7328	Intermediate Similarity	NPD9622	Approved
0.7304	Intermediate Similarity	NPD3092	Approved
0.7304	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2684	Approved
0.7241	Intermediate Similarity	NPD2235	Phase 2
0.7241	Intermediate Similarity	NPD2231	Phase 2
0.7207	Intermediate Similarity	NPD1791	Approved
0.7207	Intermediate Similarity	NPD1793	Approved
0.7204	Intermediate Similarity	NPD9250	Approved
0.7203	Intermediate Similarity	NPD3094	Phase 2
0.7196	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1357	Approved
0.7168	Intermediate Similarity	NPD16	Approved
0.7168	Intermediate Similarity	NPD856	Approved
0.7168	Intermediate Similarity	NPD318	Approved
0.7168	Intermediate Similarity	NPD317	Approved
0.7143	Intermediate Similarity	NPD9621	Approved
0.7143	Intermediate Similarity	NPD9620	Approved
0.7143	Intermediate Similarity	NPD9619	Approved
0.713	Intermediate Similarity	NPD74	Approved
0.713	Intermediate Similarity	NPD3095	Discontinued
0.713	Intermediate Similarity	NPD9266	Approved
0.7117	Intermediate Similarity	NPD2234	Approved
0.7117	Intermediate Similarity	NPD2229	Approved
0.7117	Intermediate Similarity	NPD2228	Approved
0.7115	Intermediate Similarity	NPD3028	Approved
0.7091	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD9495	Approved
0.7083	Intermediate Similarity	NPD9073	Approved
0.708	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD9244	Approved
0.7069	Intermediate Similarity	NPD3496	Discontinued
0.7041	Intermediate Similarity	NPD9094	Approved
0.7037	Intermediate Similarity	NPD9263	Approved
0.7037	Intermediate Similarity	NPD9264	Approved
0.7037	Intermediate Similarity	NPD9267	Approved
0.7027	Intermediate Similarity	NPD7843	Approved
0.7027	Intermediate Similarity	NPD821	Approved
0.7	Intermediate Similarity	NPD599	Approved
0.7	Intermediate Similarity	NPD858	Approved
0.7	Intermediate Similarity	NPD9365	Approved
0.7	Intermediate Similarity	NPD602	Approved
0.7	Intermediate Similarity	NPD859	Approved
0.6991	Remote Similarity	NPD7157	Approved
0.6983	Remote Similarity	NPD2932	Approved
0.6983	Remote Similarity	NPD4059	Approved
0.6983	Remote Similarity	NPD1778	Approved
0.6983	Remote Similarity	NPD2286	Discontinued
0.6983	Remote Similarity	NPD3019	Approved
0.6983	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3027	Phase 3
0.6964	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD9296	Approved
0.6957	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1182	Approved
0.6957	Remote Similarity	NPD9545	Approved
0.6957	Remote Similarity	NPD1548	Phase 1
0.6949	Remote Similarity	NPD2233	Approved
0.6949	Remote Similarity	NPD2230	Approved
0.6949	Remote Similarity	NPD2232	Approved
0.6942	Remote Similarity	NPD2861	Phase 2
0.6931	Remote Similarity	NPD9251	Approved
0.693	Remote Similarity	NPD9493	Approved
0.6923	Remote Similarity	NPD9611	Approved
0.6923	Remote Similarity	NPD9612	Approved
0.6923	Remote Similarity	NPD9609	Approved
0.6911	Remote Similarity	NPD597	Approved
0.6911	Remote Similarity	NPD601	Approved
0.6911	Remote Similarity	NPD598	Approved
0.6903	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD497	Approved
0.6897	Remote Similarity	NPD4093	Discontinued
0.6891	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD600	Approved
0.6885	Remote Similarity	NPD596	Approved
0.6864	Remote Similarity	NPD1201	Approved
0.6864	Remote Similarity	NPD1610	Phase 2
0.6864	Remote Similarity	NPD1091	Approved
0.686	Remote Similarity	NPD558	Phase 2
0.686	Remote Similarity	NPD6584	Phase 3
0.6855	Remote Similarity	NPD1130	Approved
0.6855	Remote Similarity	NPD1136	Approved
0.6855	Remote Similarity	NPD1132	Approved
0.6842	Remote Similarity	NPD255	Approved
0.6842	Remote Similarity	NPD256	Approved
0.6842	Remote Similarity	NPD709	Approved
0.6838	Remote Similarity	NPD4626	Approved
0.6838	Remote Similarity	NPD1751	Approved
0.6822	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD495	Approved
0.6814	Remote Similarity	NPD498	Approved
0.6814	Remote Similarity	NPD5283	Phase 1
0.6814	Remote Similarity	NPD496	Approved
0.6807	Remote Similarity	NPD2562	Approved
0.6807	Remote Similarity	NPD2561	Approved
0.6803	Remote Similarity	NPD5736	Approved
0.68	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3059	Approved
0.68	Remote Similarity	NPD3062	Approved
0.68	Remote Similarity	NPD3061	Approved
0.68	Remote Similarity	NPD1613	Approved
0.6789	Remote Similarity	NPD3134	Approved
0.6783	Remote Similarity	NPD9568	Approved
0.678	Remote Similarity	NPD1981	Approved
0.678	Remote Similarity	NPD1983	Approved
0.678	Remote Similarity	NPD1980	Approved
0.6765	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1237	Approved
0.6754	Remote Similarity	NPD475	Phase 2
0.6752	Remote Similarity	NPD5585	Approved
0.675	Remote Similarity	NPD4659	Approved
0.675	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1755	Approved
0.6733	Remote Similarity	NPD9256	Approved
0.6733	Remote Similarity	NPD9258	Approved
0.6729	Remote Similarity	NPD855	Approved
0.6729	Remote Similarity	NPD854	Approved
0.6727	Remote Similarity	NPD1358	Approved
0.6721	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.672	Remote Similarity	NPD839	Approved
0.672	Remote Similarity	NPD840	Approved
0.6694	Remote Similarity	NPD5310	Approved
0.6694	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5311	Approved
0.6693	Remote Similarity	NPD5314	Approved
0.6693	Remote Similarity	NPD823	Approved
0.6693	Remote Similarity	NPD817	Approved
0.6693	Remote Similarity	NPD2568	Approved
0.6667	Remote Similarity	NPD1759	Phase 1
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD2238	Phase 2
0.6667	Remote Similarity	NPD9269	Phase 2
0.6667	Remote Similarity	NPD1840	Phase 2
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1134	Approved
0.6639	Remote Similarity	NPD1135	Approved
0.6639	Remote Similarity	NPD3055	Approved
0.6639	Remote Similarity	NPD4103	Phase 2
0.6639	Remote Similarity	NPD3053	Approved
0.6639	Remote Similarity	NPD1131	Approved
0.6639	Remote Similarity	NPD1129	Approved
0.6639	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1133	Approved
0.6639	Remote Similarity	NPD1470	Approved
0.6639	Remote Similarity	NPD3421	Phase 3
0.6634	Remote Similarity	NPD9249	Phase 1

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