NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	133.05
Volume:	139.053
LogP:	1.587
LogD:	1.835
LogS:	-1.922
# Rotatable Bonds:	0
TPSA:	36.02
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	2.081
Fsp3:	0.0
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:	-4.403
MDCK Permeability:	1.3703011973120738e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.781
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.19
Plasma Protein Binding (PPB):	67.94717407226562%
Volume Distribution (VD):	1.417
Pgp-substrate:	25.52804946899414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.499
CYP2C19-inhibitor:	0.549
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.582
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.149

ADMET: Excretion

Clearance (CL):	14.345
Half-life (T1/2):	0.883

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.17
AMES Toxicity:	0.387
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.645
Skin Sensitization:	0.904
Carcinogencity:	0.578
Eye Corrosion:	0.784
Eye Irritation:	0.992
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC184964

Natural Product ID:	NPC184964
*Common Name:**	1H-Indol-5-Ol
IUPAC Name:	1H-indol-5-ol
Synonyms:	5-Hydroxyindole
Standard InCHIKey:	LMIQERWZRIFWNZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H
SMILES:	Oc1ccc2c(c1)cc[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404923
PubChem CID:	16054
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

☑ 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
EC50	1
IC50	7
Kd	1
Others	15
Potency	8

Activity Type	# Activity
Cell Line	2
Individual Protein	20
NON-MOLECULAR	3
Organism	1
Others	2
Protein Family	1
SINGLE PROTEIN	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT410	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Homo sapiens	EC50	=	1000000.0	nM	PMID[493750]
NPT2520	Individual Protein	Leukotriene A4 hydrolase	Homo sapiens	IC50	>	1000000.0	nM	PMID[493751]
NPT2520	Individual Protein	Leukotriene A4 hydrolase	Homo sapiens	IC50	>	2000000.0	nM	PMID[493751]
NPT319	Cell Line	B16	Mus musculus	Activity	=	100.0	%	PMID[493752]
NPT319	Cell Line	B16	Mus musculus	IC50	=	13000.0	nM	PMID[493752]
NPT2739	Individual Protein	Tyrosinase	Mus musculus	Activity	=	62.0	%	PMID[493752]
NPT2739	Individual Protein	Tyrosinase	Mus musculus	IC50	=	68000.0	nM	PMID[493752]
NPT45	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	7943.3	nM	PMID[493754]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	14125.4	nM	PMID[493754]
NPT1416	Individual Protein	Neuropeptide S receptor	Homo sapiens	Potency	=	5011.9	nM	PMID[493754]
NPT4	Individual Protein	Large T antigen	Simian virus 40	IC50	n.a.	80220.0	nM	PMID[493754]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	4466.8	nM	PMID[493754]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	7.33	%	PMID[493755]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	8199.5	nM	PMID[493754]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[493754]
NPT410	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Homo sapiens	%max	=	541.0	%	PMID[493759]
NPT5045	Individual Protein	DNA repair protein RAD51 homolog 1	Homo sapiens	Kd	=	2100000.0	nM	PMID[493760]
NPT2581	Individual Protein	Sulfotransferase 1A1	Homo sapiens	Vmax	=	12.84	nmol/min/mg	PMID[493761]
NPT2581	Individual Protein	Sulfotransferase 1A1	Homo sapiens	Km	=	6620.0	nM	PMID[493761]
NPT2581	Individual Protein	Sulfotransferase 1A1	Homo sapiens	Vmax/Km	=	1.94	n.a.	PMID[493761]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Activity	=	54.0	%	PMID[493752]
NPT2264	Protein Family	Heat shock protein HSP90	Homo sapiens	IC50	>	50000.0	nM	PMID[493753]
NPT2	Others	Unspecified		IC50	=	2230.0	nM	PMID[493754]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	10000.0	nM	PMID[493754]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[493754]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	79.8	%	PMID[493756]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	>	90.1	%	PMID[493757]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	79.8	%	PMID[493757]
NPT1	Others	Radical scavenging activity		Activity	=	2.6	10'3/M/s	PMID[493758]
NPT25158	SINGLE PROTEIN	Estrogen sulfotransferase	Homo sapiens	Km	=	575000.0	nM	PMID[493761]
NPT25158	SINGLE PROTEIN	Estrogen sulfotransferase	Homo sapiens	Vmax	=	3.66	nmol/min/mg	PMID[493761]
NPT25158	SINGLE PROTEIN	Estrogen sulfotransferase	Homo sapiens	Vmax/Km	=	0.006	n.a.	PMID[493761]

☑ 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 NPC184964 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	712
0.1-0.2	9290
0.2-0.3	8699
0.3-0.4	14410
0.4-0.5	5134
0.5-0.6	2358
0.6-0.7	1538
0.7-0.8	472
0.8-0.85	51
0.85-0.9	21
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9753	High Similarity	NPC220765
0.9693	High Similarity	NPC204717
0.9634	High Similarity	NPC314002
0.9576	High Similarity	NPC171171
0.9294	High Similarity	NPC99666
0.9186	High Similarity	NPC326634
0.9152	High Similarity	NPC96890
0.9133	High Similarity	NPC222018
0.908	High Similarity	NPC77555
0.908	High Similarity	NPC156704
0.9059	High Similarity	NPC46580
0.8927	High Similarity	NPC45459
0.8927	High Similarity	NPC213308
0.8927	High Similarity	NPC315491
0.8914	High Similarity	NPC251090
0.8908	High Similarity	NPC307963
0.8895	High Similarity	NPC296527
0.8844	High Similarity	NPC76748
0.8793	High Similarity	NPC92111
0.8786	High Similarity	NPC32771
0.8712	High Similarity	NPC131718
0.8647	High Similarity	NPC88363
0.8634	High Similarity	NPC88008
0.8626	High Similarity	NPC475070
0.8606	High Similarity	NPC102423
0.8596	High Similarity	NPC242209
0.8587	High Similarity	NPC171787
0.8538	High Similarity	NPC42979
0.8529	High Similarity	NPC224764
0.8427	Intermediate Similarity	NPC324149
0.8424	Intermediate Similarity	NPC230869
0.8404	Intermediate Similarity	NPC219087
0.8402	Intermediate Similarity	NPC314940
0.8402	Intermediate Similarity	NPC473764
0.8398	Intermediate Similarity	NPC192315
0.8396	Intermediate Similarity	NPC5145
0.836	Intermediate Similarity	NPC266931
0.836	Intermediate Similarity	NPC477610
0.8352	Intermediate Similarity	NPC476167
0.8324	Intermediate Similarity	NPC72980
0.8307	Intermediate Similarity	NPC316981
0.8306	Intermediate Similarity	NPC176538
0.8304	Intermediate Similarity	NPC313791
0.8304	Intermediate Similarity	NPC474409
0.8278	Intermediate Similarity	NPC106937
0.8258	Intermediate Similarity	NPC128751
0.8258	Intermediate Similarity	NPC246700
0.8254	Intermediate Similarity	NPC246518
0.8232	Intermediate Similarity	NPC276517
0.8212	Intermediate Similarity	NPC106833
0.8212	Intermediate Similarity	NPC469497
0.8187	Intermediate Similarity	NPC477609
0.8182	Intermediate Similarity	NPC176127
0.8155	Intermediate Similarity	NPC279918
0.8148	Intermediate Similarity	NPC159856
0.8144	Intermediate Similarity	NPC74360
0.814	Intermediate Similarity	NPC252590
0.8135	Intermediate Similarity	NPC304926
0.8135	Intermediate Similarity	NPC476041
0.8108	Intermediate Similarity	NPC249040
0.8107	Intermediate Similarity	NPC282231
0.8103	Intermediate Similarity	NPC276657
0.8095	Intermediate Similarity	NPC476465
0.8087	Intermediate Similarity	NPC13880
0.8075	Intermediate Similarity	NPC476098
0.8072	Intermediate Similarity	NPC469765
0.8072	Intermediate Similarity	NPC469760
0.8072	Intermediate Similarity	NPC469786
0.8072	Intermediate Similarity	NPC73952
0.8072	Intermediate Similarity	NPC25008
0.8072	Intermediate Similarity	NPC469763
0.8072	Intermediate Similarity	NPC259644
0.8042	Intermediate Similarity	NPC183777
0.8024	Intermediate Similarity	NPC80597
0.8024	Intermediate Similarity	NPC212376
0.8024	Intermediate Similarity	NPC70922
0.8024	Intermediate Similarity	NPC75540
0.8024	Intermediate Similarity	NPC211572
0.8021	Intermediate Similarity	NPC211813
0.799	Intermediate Similarity	NPC142901
0.7989	Intermediate Similarity	NPC477113
0.798	Intermediate Similarity	NPC130570
0.7978	Intermediate Similarity	NPC212535
0.7976	Intermediate Similarity	NPC469785
0.7965	Intermediate Similarity	NPC49954
0.7965	Intermediate Similarity	NPC54988
0.7965	Intermediate Similarity	NPC160105
0.7965	Intermediate Similarity	NPC474561
0.7958	Intermediate Similarity	NPC476116
0.7953	Intermediate Similarity	NPC311276
0.7952	Intermediate Similarity	NPC105818
0.7952	Intermediate Similarity	NPC24678
0.7947	Intermediate Similarity	NPC270918
0.7946	Intermediate Similarity	NPC153042
0.7937	Intermediate Similarity	NPC470500
0.7929	Intermediate Similarity	NPC469762
0.7927	Intermediate Similarity	NPC128084
0.7927	Intermediate Similarity	NPC314372
0.7919	Intermediate Similarity	NPC78020
0.7919	Intermediate Similarity	NPC63751
0.7914	Intermediate Similarity	NPC121772
0.7914	Intermediate Similarity	NPC190296
0.7889	Intermediate Similarity	NPC94943
0.7877	Intermediate Similarity	NPC48938
0.7876	Intermediate Similarity	NPC208284
0.787	Intermediate Similarity	NPC141353
0.7853	Intermediate Similarity	NPC111275
0.7853	Intermediate Similarity	NPC60553
0.785	Intermediate Similarity	NPC245348
0.7848	Intermediate Similarity	NPC82295
0.7833	Intermediate Similarity	NPC190007
0.7822	Intermediate Similarity	NPC477607
0.7822	Intermediate Similarity	NPC477608
0.7819	Intermediate Similarity	NPC315957
0.7817	Intermediate Similarity	NPC264285
0.7814	Intermediate Similarity	NPC83111
0.7812	Intermediate Similarity	NPC477111
0.7802	Intermediate Similarity	NPC278434
0.7801	Intermediate Similarity	NPC476121
0.7801	Intermediate Similarity	NPC476124
0.779	Intermediate Similarity	NPC163421
0.779	Intermediate Similarity	NPC188387
0.7784	Intermediate Similarity	NPC314603
0.7784	Intermediate Similarity	NPC329541
0.7778	Intermediate Similarity	NPC232727
0.7772	Intermediate Similarity	NPC80596
0.7772	Intermediate Similarity	NPC6215
0.7754	Intermediate Similarity	NPC90229
0.7747	Intermediate Similarity	NPC315555
0.7746	Intermediate Similarity	NPC40779
0.7746	Intermediate Similarity	NPC194640
0.774	Intermediate Similarity	NPC203468
0.774	Intermediate Similarity	NPC110500
0.774	Intermediate Similarity	NPC149155
0.7737	Intermediate Similarity	NPC135887
0.7737	Intermediate Similarity	NPC199277
0.7732	Intermediate Similarity	NPC11464
0.7723	Intermediate Similarity	NPC60006
0.7722	Intermediate Similarity	NPC71037
0.7716	Intermediate Similarity	NPC477110
0.7714	Intermediate Similarity	NPC201700
0.7709	Intermediate Similarity	NPC55772
0.7707	Intermediate Similarity	NPC207686
0.7697	Intermediate Similarity	NPC267885
0.7696	Intermediate Similarity	NPC245816
0.7696	Intermediate Similarity	NPC223427
0.7696	Intermediate Similarity	NPC476138
0.7688	Intermediate Similarity	NPC213530
0.7688	Intermediate Similarity	NPC193267
0.768	Intermediate Similarity	NPC469358
0.7674	Intermediate Similarity	NPC92796
0.7674	Intermediate Similarity	NPC135141
0.7656	Intermediate Similarity	NPC285558
0.7654	Intermediate Similarity	NPC261195
0.7654	Intermediate Similarity	NPC96102
0.7654	Intermediate Similarity	NPC29886
0.7654	Intermediate Similarity	NPC151939
0.7654	Intermediate Similarity	NPC248454
0.7654	Intermediate Similarity	NPC59269
0.7644	Intermediate Similarity	NPC470678
0.7641	Intermediate Similarity	NPC309845
0.7637	Intermediate Similarity	NPC84478
0.7632	Intermediate Similarity	NPC19872
0.7632	Intermediate Similarity	NPC329793
0.7629	Intermediate Similarity	NPC18348
0.7626	Intermediate Similarity	NPC470799
0.7626	Intermediate Similarity	NPC8022
0.7619	Intermediate Similarity	NPC471957
0.7619	Intermediate Similarity	NPC306376
0.7612	Intermediate Similarity	NPC473317
0.7611	Intermediate Similarity	NPC126709
0.7611	Intermediate Similarity	NPC248041
0.7611	Intermediate Similarity	NPC283219
0.7607	Intermediate Similarity	NPC84911
0.7607	Intermediate Similarity	NPC105127
0.76	Intermediate Similarity	NPC471178
0.7596	Intermediate Similarity	NPC15102
0.7577	Intermediate Similarity	NPC193777
0.7574	Intermediate Similarity	NPC16352
0.7569	Intermediate Similarity	NPC300688
0.756	Intermediate Similarity	NPC15801
0.7553	Intermediate Similarity	NPC131017
0.7538	Intermediate Similarity	NPC469928
0.7528	Intermediate Similarity	NPC470498
0.7527	Intermediate Similarity	NPC233936
0.7527	Intermediate Similarity	NPC154339
0.7527	Intermediate Similarity	NPC95783
0.7515	Intermediate Similarity	NPC110126
0.7515	Intermediate Similarity	NPC73767
0.7513	Intermediate Similarity	NPC200836
0.7513	Intermediate Similarity	NPC53144
0.7513	Intermediate Similarity	NPC475774
0.7512	Intermediate Similarity	NPC295228
0.7512	Intermediate Similarity	NPC477549
0.75	Intermediate Similarity	NPC125597
0.75	Intermediate Similarity	NPC469727
0.7487	Intermediate Similarity	NPC470549
0.7487	Intermediate Similarity	NPC128823
0.7487	Intermediate Similarity	NPC321428
0.7486	Intermediate Similarity	NPC163055

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 NPC184964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	824
0.2-0.3	643
0.3-0.4	1721
0.4-0.5	2600
0.5-0.6	2062
0.6-0.7	792
0.7-0.8	123
0.8-0.85	7
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.924	High Similarity	NPD5575	Clinical (unspecified phase)
0.8927	High Similarity	NPD484	Approved
0.8908	High Similarity	NPD1038	Approved
0.8693	High Similarity	NPD1304	Clinical (unspecified phase)
0.8547	High Similarity	NPD7948	Phase 1
0.8278	Intermediate Similarity	NPD802	Phase 2
0.8272	Intermediate Similarity	NPD5612	Discontinued
0.8272	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD9705	Discontinued
0.8155	Intermediate Similarity	NPD112	Approved
0.815	Intermediate Similarity	NPD5065	Approved
0.815	Intermediate Similarity	NPD9690	Approved
0.8095	Intermediate Similarity	NPD2187	Approved
0.8095	Intermediate Similarity	NPD2189	Approved
0.809	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD3825	Phase 3
0.7935	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD9695	Approved
0.7874	Intermediate Similarity	NPD1325	Approved
0.7874	Intermediate Similarity	NPD1326	Approved
0.7874	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1392	Approved
0.7819	Intermediate Similarity	NPD1739	Approved
0.7819	Intermediate Similarity	NPD1740	Approved
0.7778	Intermediate Similarity	NPD4511	Phase 1
0.7744	Intermediate Similarity	NPD1592	Phase 3
0.774	Intermediate Similarity	NPD482	Approved
0.7727	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD425	Approved
0.7657	Intermediate Similarity	NPD424	Approved
0.7656	Intermediate Similarity	NPD4795	Phase 2
0.7654	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD6242	Discontinued
0.7644	Intermediate Similarity	NPD3928	Approved
0.7644	Intermediate Similarity	NPD3931	Approved
0.7588	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2094	Phase 2
0.7582	Intermediate Similarity	NPD2095	Phase 2
0.7582	Intermediate Similarity	NPD2092	Phase 2
0.7579	Intermediate Similarity	NPD3814	Phase 1
0.7569	Intermediate Similarity	NPD6595	Phase 3
0.7541	Intermediate Similarity	NPD2096	Phase 2
0.7541	Intermediate Similarity	NPD2091	Phase 2
0.754	Intermediate Similarity	NPD9689	Approved
0.7538	Intermediate Similarity	NPD7112	Discontinued
0.7515	Intermediate Similarity	NPD786	Approved
0.7513	Intermediate Similarity	NPD949	Phase 1
0.7512	Intermediate Similarity	NPD4845	Discontinued
0.75	Intermediate Similarity	NPD926	Approved
0.75	Intermediate Similarity	NPD925	Approved
0.7487	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD1768	Approved
0.7475	Intermediate Similarity	NPD3330	Phase 1
0.7463	Intermediate Similarity	NPD7603	Discontinued
0.7447	Intermediate Similarity	NPD3404	Approved
0.7443	Intermediate Similarity	NPD5140	Approved
0.7443	Intermediate Similarity	NPD5138	Approved
0.7436	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1722	Approved
0.7424	Intermediate Similarity	NPD5067	Phase 2
0.7424	Intermediate Similarity	NPD5066	Phase 2
0.7416	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8395	Approved
0.7396	Intermediate Similarity	NPD2175	Phase 3
0.7396	Intermediate Similarity	NPD2176	Approved
0.7396	Intermediate Similarity	NPD2177	Approved
0.7396	Intermediate Similarity	NPD8396	Approved
0.7394	Intermediate Similarity	NPD459	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5559	Phase 2
0.7389	Intermediate Similarity	NPD750	Phase 2
0.7385	Intermediate Similarity	NPD32	Approved
0.7385	Intermediate Similarity	NPD31	Approved
0.7385	Intermediate Similarity	NPD4037	Approved
0.7385	Intermediate Similarity	NPD5901	Discontinued
0.7385	Intermediate Similarity	NPD4036	Approved
0.7385	Intermediate Similarity	NPD4039	Approved
0.7385	Intermediate Similarity	NPD4122	Approved
0.7385	Intermediate Similarity	NPD4034	Approved
0.7385	Intermediate Similarity	NPD4038	Approved
0.7385	Intermediate Similarity	NPD4035	Approved
0.7385	Intermediate Similarity	NPD4033	Approved
0.7363	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5658	Approved
0.7326	Intermediate Similarity	NPD8431	Approved
0.7318	Intermediate Similarity	NPD2781	Approved
0.731	Intermediate Similarity	NPD7452	Approved
0.731	Intermediate Similarity	NPD7222	Phase 2
0.731	Intermediate Similarity	NPD7453	Approved
0.7306	Intermediate Similarity	NPD9688	Approved
0.7306	Intermediate Similarity	NPD9687	Approved
0.7303	Intermediate Similarity	NPD2780	Approved
0.7303	Intermediate Similarity	NPD2782	Approved
0.7297	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2952	Discontinued
0.7291	Intermediate Similarity	NPD3354	Phase 2
0.7287	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6975	Discontinued
0.7277	Intermediate Similarity	NPD4418	Discontinued
0.7273	Intermediate Similarity	NPD706	Phase 1
0.7268	Intermediate Similarity	NPD2144	Approved
0.7264	Intermediate Similarity	NPD2616	Phase 3
0.7264	Intermediate Similarity	NPD2615	Phase 3
0.7259	Intermediate Similarity	NPD3003	Approved
0.7241	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2383	Phase 1
0.7232	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4463	Approved
0.7225	Intermediate Similarity	NPD4462	Approved
0.7222	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5255	Approved
0.7175	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6159	Phase 2
0.7173	Intermediate Similarity	NPD994	Phase 2
0.7173	Intermediate Similarity	NPD996	Phase 2
0.7172	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7558	Phase 2
0.7168	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3100	Discontinued
0.716	Intermediate Similarity	NPD9080	Approved
0.7151	Intermediate Similarity	NPD3038	Discontinued
0.715	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6290	Phase 2
0.7135	Intermediate Similarity	NPD4076	Approved
0.7135	Intermediate Similarity	NPD3813	Approved
0.7135	Intermediate Similarity	NPD4079	Approved
0.7127	Intermediate Similarity	NPD2844	Phase 3
0.7127	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2172	Phase 1
0.7122	Intermediate Similarity	NPD2021	Discontinued
0.712	Intermediate Similarity	NPD2380	Approved
0.712	Intermediate Similarity	NPD2381	Approved
0.712	Intermediate Similarity	NPD5100	Phase 3
0.712	Intermediate Similarity	NPD2382	Approved
0.7114	Intermediate Similarity	NPD3013	Phase 3
0.7114	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1219	Approved
0.7113	Intermediate Similarity	NPD1218	Approved
0.711	Intermediate Similarity	NPD4703	Approved
0.711	Intermediate Similarity	NPD4702	Approved
0.71	Intermediate Similarity	NPD2916	Discontinued
0.7095	Intermediate Similarity	NPD1684	Approved
0.7095	Intermediate Similarity	NPD1685	Approved
0.7087	Intermediate Similarity	NPD3402	Phase 1
0.7086	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6158	Phase 2
0.7083	Intermediate Similarity	NPD3923	Approved
0.7083	Intermediate Similarity	NPD3922	Approved
0.7083	Intermediate Similarity	NPD3921	Approved
0.7083	Intermediate Similarity	NPD3924	Approved
0.7081	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3506	Approved
0.7081	Intermediate Similarity	NPD3505	Approved
0.7079	Intermediate Similarity	NPD7470	Discontinued
0.7079	Intermediate Similarity	NPD5936	Approved
0.7079	Intermediate Similarity	NPD5939	Approved
0.7068	Intermediate Similarity	NPD5117	Phase 2
0.7059	Intermediate Similarity	NPD3178	Discontinued
0.7053	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2762	Phase 2
0.7035	Intermediate Similarity	NPD5426	Phase 3
0.7022	Intermediate Similarity	NPD9382	Approved
0.7022	Intermediate Similarity	NPD9383	Approved
0.7021	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5596	Phase 2
0.7016	Intermediate Similarity	NPD4021	Phase 2
0.7015	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4502	Phase 2
0.6989	Remote Similarity	NPD2882	Phase 1
0.6979	Remote Similarity	NPD1213	Phase 3
0.6976	Remote Similarity	NPD5902	Approved
0.6976	Remote Similarity	NPD5903	Approved
0.6968	Remote Similarity	NPD4204	Approved
0.6968	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4203	Approved
0.6966	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD862	Approved
0.6961	Remote Similarity	NPD863	Approved
0.6961	Remote Similarity	NPD861	Approved
0.6961	Remote Similarity	NPD8093	Discontinued
0.6959	Remote Similarity	NPD4551	Phase 2
0.6954	Remote Similarity	NPD5999	Phase 2
0.6952	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD9284	Approved
0.6949	Remote Similarity	NPD2837	Discontinued
0.6944	Remote Similarity	NPD4454	Phase 2
0.6944	Remote Similarity	NPD1403	Approved
0.6944	Remote Similarity	NPD1404	Approved
0.6943	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5913	Phase 3
0.6942	Remote Similarity	NPD6147	Clinical (unspecified phase)

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