NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	190.07
Volume:	190.795
LogP:	0.219
LogD:	-0.011
LogS:	-1.457
# Rotatable Bonds:	2
TPSA:	79.11
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	2.181
Fsp3:	0.1
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:	-4.808
MDCK Permeability:	5.2654736464319285e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.895
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.876
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.893
Plasma Protein Binding (PPB):	59.37310791015625%
Volume Distribution (VD):	0.916
Pgp-substrate:	46.64173889160156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.736
CYP1A2-substrate:	0.308
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.238
CYP2D6-substrate:	0.68
CYP3A4-inhibitor:	0.097
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	12.699
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.728
AMES Toxicity:	0.264
Rat Oral Acute Toxicity:	0.319
Maximum Recommended Daily Dose:	0.281
Skin Sensitization:	0.662
Carcinogencity:	0.144
Eye Corrosion:	0.004
Eye Irritation:	0.182
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC46580

Natural Product ID:	NPC46580
*Common Name:**	6-Hydroxy-1H-Indole-3-Acetamide
IUPAC Name:	2-(6-hydroxy-1H-indol-3-yl)acetamide
Synonyms:
Standard InCHIKey:	PGXXGODNTPWQHZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H10N2O2/c11-10(14)3-6-5-12-9-4-7(13)1-2-8(6)9/h1-2,4-5,12-13H,3H2,(H2,11,14)
SMILES:	OC(=N)Cc1c[nH]c2c1ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449280
PubChem CID:	286538
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004162] Hydroxyindoles

*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
NPO10633	Agrocybe cylindracea	Species	Bolbitiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9249978]
NPO10633	Agrocybe cylindracea	Species	Bolbitiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	3.9	ug.mL-1	PMID[572198]

☑ 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 NPC46580 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	589
0.1-0.2	6056
0.2-0.3	11418
0.3-0.4	14067
0.4-0.5	5519
0.5-0.6	2645
0.6-0.7	1609
0.7-0.8	686
0.8-0.85	73
0.85-0.9	22
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9518	High Similarity	NPC96890
0.9298	High Similarity	NPC314002
0.9294	High Similarity	NPC220765
0.924	High Similarity	NPC204717
0.9205	High Similarity	NPC326634
0.92	High Similarity	NPC99666
0.9153	High Similarity	NPC242209
0.9133	High Similarity	NPC171171
0.9118	High Similarity	NPC72980
0.9059	High Similarity	NPC184964
0.8933	High Similarity	NPC106937
0.8855	High Similarity	NPC131718
0.8785	High Similarity	NPC77555
0.8785	High Similarity	NPC156704
0.8772	High Similarity	NPC474409
0.873	High Similarity	NPC316981
0.8667	High Similarity	NPC324149
0.8663	High Similarity	NPC183777
0.8641	High Similarity	NPC315491
0.8641	High Similarity	NPC213308
0.8641	High Similarity	NPC45459
0.8639	High Similarity	NPC102423
0.8636	High Similarity	NPC212535
0.8626	High Similarity	NPC251090
0.8626	High Similarity	NPC13880
0.8619	High Similarity	NPC307963
0.8601	High Similarity	NPC264285
0.8539	High Similarity	NPC94943
0.8526	High Similarity	NPC11464
0.85	High Similarity	NPC296527
0.85	High Similarity	NPC32771
0.8495	Intermediate Similarity	NPC232727
0.8483	Intermediate Similarity	NPC190007
0.8466	Intermediate Similarity	NPC42979
0.8462	Intermediate Similarity	NPC230869
0.8462	Intermediate Similarity	NPC193267
0.8462	Intermediate Similarity	NPC213530
0.8457	Intermediate Similarity	NPC224764
0.8453	Intermediate Similarity	NPC76748
0.8438	Intermediate Similarity	NPC128084
0.8432	Intermediate Similarity	NPC306376
0.8407	Intermediate Similarity	NPC92111
0.838	Intermediate Similarity	NPC84478
0.8368	Intermediate Similarity	NPC88008
0.836	Intermediate Similarity	NPC475070
0.836	Intermediate Similarity	NPC470500
0.836	Intermediate Similarity	NPC285558
0.8343	Intermediate Similarity	NPC313791
0.8333	Intermediate Similarity	NPC16352
0.8333	Intermediate Similarity	NPC5145
0.8333	Intermediate Similarity	NPC192315
0.8324	Intermediate Similarity	NPC222018
0.8307	Intermediate Similarity	NPC53144
0.8304	Intermediate Similarity	NPC279918
0.8299	Intermediate Similarity	NPC266931
0.8289	Intermediate Similarity	NPC476167
0.8281	Intermediate Similarity	NPC80596
0.828	Intermediate Similarity	NPC153042
0.8258	Intermediate Similarity	NPC88363
0.8256	Intermediate Similarity	NPC282231
0.8245	Intermediate Similarity	NPC121772
0.8214	Intermediate Similarity	NPC170114
0.8193	Intermediate Similarity	NPC159856
0.8191	Intermediate Similarity	NPC60621
0.8182	Intermediate Similarity	NPC70956
0.8182	Intermediate Similarity	NPC243834
0.8172	Intermediate Similarity	NPC276517
0.8163	Intermediate Similarity	NPC470549
0.8154	Intermediate Similarity	NPC219087
0.8144	Intermediate Similarity	NPC123976
0.8144	Intermediate Similarity	NPC167860
0.8135	Intermediate Similarity	NPC171787
0.8135	Intermediate Similarity	NPC18348
0.8118	Intermediate Similarity	NPC469760
0.8118	Intermediate Similarity	NPC73952
0.8118	Intermediate Similarity	NPC469765
0.8118	Intermediate Similarity	NPC469763
0.8118	Intermediate Similarity	NPC25008
0.8118	Intermediate Similarity	NPC469786
0.8118	Intermediate Similarity	NPC259644
0.8115	Intermediate Similarity	NPC200836
0.8114	Intermediate Similarity	NPC160105
0.8114	Intermediate Similarity	NPC474561
0.8114	Intermediate Similarity	NPC49954
0.8114	Intermediate Similarity	NPC54988
0.8112	Intermediate Similarity	NPC477610
0.8103	Intermediate Similarity	NPC311276
0.8103	Intermediate Similarity	NPC246518
0.8081	Intermediate Similarity	NPC469762
0.807	Intermediate Similarity	NPC70922
0.807	Intermediate Similarity	NPC212376
0.807	Intermediate Similarity	NPC80597
0.807	Intermediate Similarity	NPC211572
0.807	Intermediate Similarity	NPC75540
0.8068	Intermediate Similarity	NPC63751
0.8063	Intermediate Similarity	NPC135887
0.8063	Intermediate Similarity	NPC199277
0.8053	Intermediate Similarity	NPC176538
0.8053	Intermediate Similarity	NPC249040
0.8051	Intermediate Similarity	NPC85273
0.8034	Intermediate Similarity	NPC314603
0.8033	Intermediate Similarity	NPC188387
0.8033	Intermediate Similarity	NPC163421
0.803	Intermediate Similarity	NPC142901
0.8023	Intermediate Similarity	NPC469785
0.8023	Intermediate Similarity	NPC141353
0.8022	Intermediate Similarity	NPC48938
0.801	Intermediate Similarity	NPC310118
0.8	Intermediate Similarity	NPC24678
0.8	Intermediate Similarity	NPC111275
0.8	Intermediate Similarity	NPC105818
0.7976	Intermediate Similarity	NPC314372
0.797	Intermediate Similarity	NPC294620
0.7969	Intermediate Similarity	NPC475085
0.7969	Intermediate Similarity	NPC475112
0.7969	Intermediate Similarity	NPC291535
0.7966	Intermediate Similarity	NPC78020
0.7964	Intermediate Similarity	NPC190296
0.7949	Intermediate Similarity	NPC475910
0.7941	Intermediate Similarity	NPC319232
0.7941	Intermediate Similarity	NPC24370
0.7929	Intermediate Similarity	NPC469592
0.7929	Intermediate Similarity	NPC471080
0.7927	Intermediate Similarity	NPC476098
0.7927	Intermediate Similarity	NPC134848
0.7926	Intermediate Similarity	NPC329541
0.7923	Intermediate Similarity	NPC176127
0.7921	Intermediate Similarity	NPC473317
0.791	Intermediate Similarity	NPC74360
0.7903	Intermediate Similarity	NPC246700
0.7903	Intermediate Similarity	NPC128751
0.79	Intermediate Similarity	NPC304926
0.79	Intermediate Similarity	NPC476041
0.7898	Intermediate Similarity	NPC194640
0.7897	Intermediate Similarity	NPC193777
0.7892	Intermediate Similarity	NPC315555
0.7889	Intermediate Similarity	NPC110500
0.7889	Intermediate Similarity	NPC149155
0.7889	Intermediate Similarity	NPC203468
0.7884	Intermediate Similarity	NPC131017
0.7876	Intermediate Similarity	NPC211813
0.7871	Intermediate Similarity	NPC276657
0.7869	Intermediate Similarity	NPC71037
0.7865	Intermediate Similarity	NPC329747
0.7865	Intermediate Similarity	NPC19872
0.7861	Intermediate Similarity	NPC477609
0.7861	Intermediate Similarity	NPC106833
0.7861	Intermediate Similarity	NPC469497
0.785	Intermediate Similarity	NPC330009
0.785	Intermediate Similarity	NPC470799
0.785	Intermediate Similarity	NPC183407
0.785	Intermediate Similarity	NPC8022
0.7849	Intermediate Similarity	NPC278434
0.7845	Intermediate Similarity	NPC267885
0.7826	Intermediate Similarity	NPC469358
0.7826	Intermediate Similarity	NPC326363
0.7821	Intermediate Similarity	NPC473764
0.7821	Intermediate Similarity	NPC314940
0.7816	Intermediate Similarity	NPC110151
0.7806	Intermediate Similarity	NPC270918
0.7805	Intermediate Similarity	NPC125597
0.7802	Intermediate Similarity	NPC248454
0.7802	Intermediate Similarity	NPC59269
0.7797	Intermediate Similarity	NPC40779
0.7783	Intermediate Similarity	NPC477861
0.7772	Intermediate Similarity	NPC315957
0.7772	Intermediate Similarity	NPC469594
0.7766	Intermediate Similarity	NPC39679
0.7766	Intermediate Similarity	NPC210828
0.7766	Intermediate Similarity	NPC95783
0.7766	Intermediate Similarity	NPC86834
0.7766	Intermediate Similarity	NPC83111
0.7766	Intermediate Similarity	NPC476465
0.776	Intermediate Similarity	NPC283219
0.776	Intermediate Similarity	NPC55772
0.776	Intermediate Similarity	NPC126709
0.776	Intermediate Similarity	NPC248041
0.7756	Intermediate Similarity	NPC130570
0.7756	Intermediate Similarity	NPC122436
0.7753	Intermediate Similarity	NPC471178
0.7744	Intermediate Similarity	NPC223427
0.7742	Intermediate Similarity	NPC15102
0.7727	Intermediate Similarity	NPC476116
0.7727	Intermediate Similarity	NPC135141
0.7727	Intermediate Similarity	NPC92796
0.7723	Intermediate Similarity	NPC27041
0.7721	Intermediate Similarity	NPC78609
0.7714	Intermediate Similarity	NPC323752
0.7711	Intermediate Similarity	NPC96102
0.7708	Intermediate Similarity	NPC74153
0.7707	Intermediate Similarity	NPC470501
0.7705	Intermediate Similarity	NPC151939
0.77	Intermediate Similarity	NPC12344
0.77	Intermediate Similarity	NPC48353
0.7697	Intermediate Similarity	NPC97367
0.7685	Intermediate Similarity	NPC178858
0.768	Intermediate Similarity	NPC470498
0.768	Intermediate Similarity	NPC252590
0.7678	Intermediate Similarity	NPC325976
0.7676	Intermediate Similarity	NPC233936

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 NPC46580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	705
0.2-0.3	792
0.3-0.4	1476
0.4-0.5	2622
0.5-0.6	2149
0.6-0.7	931
0.7-0.8	158
0.8-0.85	8
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8933	High Similarity	NPD802	Phase 2
0.8889	High Similarity	NPD7948	Phase 1
0.8827	High Similarity	NPD5575	Clinical (unspecified phase)
0.8641	High Similarity	NPD484	Approved
0.8619	High Similarity	NPD1038	Approved
0.8315	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD1392	Approved
0.8214	Intermediate Similarity	NPD5612	Discontinued
0.8192	Intermediate Similarity	NPD5065	Approved
0.8132	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.804	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD1326	Approved
0.8023	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD1325	Approved
0.7906	Intermediate Similarity	NPD1768	Approved
0.7889	Intermediate Similarity	NPD482	Approved
0.7885	Intermediate Similarity	NPD7558	Phase 2
0.7846	Intermediate Similarity	NPD3003	Approved
0.7845	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD4511	Phase 1
0.7812	Intermediate Similarity	NPD3825	Phase 3
0.7812	Intermediate Similarity	NPD3814	Phase 1
0.7806	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD4795	Phase 2
0.7789	Intermediate Similarity	NPD3330	Phase 1
0.7772	Intermediate Similarity	NPD1739	Approved
0.7772	Intermediate Similarity	NPD1740	Approved
0.7766	Intermediate Similarity	NPD2189	Approved
0.7766	Intermediate Similarity	NPD5658	Approved
0.7766	Intermediate Similarity	NPD2187	Approved
0.7755	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2094	Phase 2
0.773	Intermediate Similarity	NPD2095	Phase 2
0.773	Intermediate Similarity	NPD2092	Phase 2
0.7717	Intermediate Similarity	NPD6595	Phase 3
0.7711	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2091	Phase 2
0.7688	Intermediate Similarity	NPD2096	Phase 2
0.7677	Intermediate Similarity	NPD2916	Discontinued
0.7654	Intermediate Similarity	NPD925	Approved
0.7654	Intermediate Similarity	NPD926	Approved
0.765	Intermediate Similarity	NPD5067	Phase 2
0.765	Intermediate Similarity	NPD5066	Phase 2
0.7629	Intermediate Similarity	NPD2176	Approved
0.7629	Intermediate Similarity	NPD2175	Phase 3
0.7629	Intermediate Similarity	NPD2177	Approved
0.7614	Intermediate Similarity	NPD5901	Discontinued
0.7611	Intermediate Similarity	NPD424	Approved
0.7611	Intermediate Similarity	NPD425	Approved
0.7602	Intermediate Similarity	NPD6975	Discontinued
0.7598	Intermediate Similarity	NPD5138	Approved
0.7598	Intermediate Similarity	NPD5140	Approved
0.7596	Intermediate Similarity	NPD7603	Discontinued
0.7596	Intermediate Similarity	NPD9690	Approved
0.7592	Intermediate Similarity	NPD3404	Approved
0.7588	Intermediate Similarity	NPD1592	Phase 3
0.7584	Intermediate Similarity	NPD112	Approved
0.7584	Intermediate Similarity	NPD9705	Discontinued
0.7574	Intermediate Similarity	NPD786	Approved
0.7569	Intermediate Similarity	NPD2781	Approved
0.7569	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD2782	Approved
0.7556	Intermediate Similarity	NPD2780	Approved
0.7541	Intermediate Similarity	NPD750	Phase 2
0.7537	Intermediate Similarity	NPD5902	Approved
0.7537	Intermediate Similarity	NPD5903	Approved
0.7528	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1722	Approved
0.7474	Intermediate Similarity	NPD2383	Phase 1
0.7474	Intermediate Similarity	NPD8431	Approved
0.7463	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5100	Phase 3
0.7449	Intermediate Similarity	NPD8395	Approved
0.7449	Intermediate Similarity	NPD8396	Approved
0.7449	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD459	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6242	Discontinued
0.7424	Intermediate Similarity	NPD3928	Approved
0.7424	Intermediate Similarity	NPD3931	Approved
0.7419	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2144	Approved
0.7419	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4463	Approved
0.7386	Intermediate Similarity	NPD4462	Approved
0.738	Intermediate Similarity	NPD4076	Approved
0.738	Intermediate Similarity	NPD4079	Approved
0.7377	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD9695	Approved
0.7363	Intermediate Similarity	NPD7453	Approved
0.7363	Intermediate Similarity	NPD7222	Phase 2
0.7363	Intermediate Similarity	NPD7452	Approved
0.7345	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7112	Discontinued
0.733	Intermediate Similarity	NPD706	Phase 1
0.7326	Intermediate Similarity	NPD3505	Approved
0.7326	Intermediate Similarity	NPD6159	Phase 2
0.7326	Intermediate Similarity	NPD3506	Approved
0.732	Intermediate Similarity	NPD6569	Phase 2
0.7313	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD4845	Discontinued
0.7304	Intermediate Similarity	NPD5939	Approved
0.7304	Intermediate Similarity	NPD5936	Approved
0.7302	Intermediate Similarity	NPD3038	Discontinued
0.7302	Intermediate Similarity	NPD6494	Phase 2
0.7302	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2844	Phase 3
0.7277	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6290	Phase 2
0.7273	Intermediate Similarity	NPD4702	Approved
0.7273	Intermediate Similarity	NPD4703	Approved
0.7273	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5426	Phase 3
0.726	Intermediate Similarity	NPD6985	Discontinued
0.7254	Intermediate Similarity	NPD4021	Phase 2
0.7253	Intermediate Similarity	NPD1684	Approved
0.7253	Intermediate Similarity	NPD1685	Approved
0.7245	Intermediate Similarity	NPD4418	Discontinued
0.7245	Intermediate Similarity	NPD3017	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8512	Phase 3
0.7241	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5255	Approved
0.7232	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD3100	Discontinued
0.7231	Intermediate Similarity	NPD3921	Approved
0.7231	Intermediate Similarity	NPD994	Phase 2
0.7231	Intermediate Similarity	NPD3923	Approved
0.7231	Intermediate Similarity	NPD3922	Approved
0.7231	Intermediate Similarity	NPD996	Phase 2
0.7231	Intermediate Similarity	NPD3924	Approved
0.7225	Intermediate Similarity	NPD7194	Discontinued
0.722	Intermediate Similarity	NPD7470	Discontinued
0.7216	Intermediate Similarity	NPD5117	Phase 2
0.7215	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4204	Approved
0.7211	Intermediate Similarity	NPD4203	Approved
0.7206	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3813	Approved
0.7196	Intermediate Similarity	NPD5559	Phase 2
0.7196	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2172	Phase 1
0.7184	Intermediate Similarity	NPD8093	Discontinued
0.7182	Intermediate Similarity	NPD9382	Approved
0.7182	Intermediate Similarity	NPD9383	Approved
0.7181	Intermediate Similarity	NPD2380	Approved
0.7181	Intermediate Similarity	NPD2381	Approved
0.7181	Intermediate Similarity	NPD2382	Approved
0.7181	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4038	Approved
0.7178	Intermediate Similarity	NPD4039	Approved
0.7178	Intermediate Similarity	NPD31	Approved
0.7178	Intermediate Similarity	NPD4037	Approved
0.7178	Intermediate Similarity	NPD4034	Approved
0.7178	Intermediate Similarity	NPD4035	Approved
0.7178	Intermediate Similarity	NPD4033	Approved
0.7178	Intermediate Similarity	NPD3397	Phase 2
0.7178	Intermediate Similarity	NPD4122	Approved
0.7178	Intermediate Similarity	NPD32	Approved
0.7178	Intermediate Similarity	NPD4036	Approved
0.7173	Intermediate Similarity	NPD5596	Phase 2
0.7173	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1229	Phase 2
0.7172	Intermediate Similarity	NPD2952	Discontinued
0.7164	Intermediate Similarity	NPD8073	Approved
0.7158	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6158	Phase 2
0.715	Intermediate Similarity	NPD8094	Discontinued
0.715	Intermediate Similarity	NPD2616	Phase 3
0.715	Intermediate Similarity	NPD2615	Phase 3
0.7136	Intermediate Similarity	NPD949	Phase 1
0.7136	Intermediate Similarity	NPD4502	Phase 2
0.7129	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD1213	Phase 3
0.7123	Intermediate Similarity	NPD1954	Phase 1
0.7121	Intermediate Similarity	NPD3127	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4551	Phase 2
0.7104	Intermediate Similarity	NPD1403	Approved
0.7104	Intermediate Similarity	NPD1404	Approved
0.7101	Intermediate Similarity	NPD3815	Phase 1
0.7101	Intermediate Similarity	NPD3816	Phase 1
0.7095	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5632	Approved
0.7092	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5913	Phase 3
0.7087	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3013	Phase 3
0.7085	Intermediate Similarity	NPD1622	Discontinued
0.7073	Intermediate Similarity	NPD2509	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