NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	165.12
Volume:	184.837
LogP:	1.4
LogD:	1.206
LogS:	-0.498
# Rotatable Bonds:	3
TPSA:	23.47
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.733
Synthetic Accessibility Score:	1.646
Fsp3:	0.4
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:	-4.498
MDCK Permeability:	1.0061078683065716e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.993
Plasma Protein Binding (PPB):	33.07265853881836%
Volume Distribution (VD):	2.928
Pgp-substrate:	72.69076538085938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.901
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.596
CYP2D6-inhibitor:	0.486
CYP2D6-substrate:	0.927
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	12.408
Half-life (T1/2):	0.817

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.443
Skin Sensitization:	0.922
Carcinogencity:	0.169
Eye Corrosion:	0.839
Eye Irritation:	0.288
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC155847

Natural Product ID:	NPC155847
*Common Name:**	Hordenine
IUPAC Name:	4-[2-(dimethylamino)ethyl]phenol
Synonyms:	Hordenine
Standard InCHIKey:	KUBCEEMXQZUPDQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3
SMILES:	CN(CCc1ccc(cc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505789
PubChem CID:	68313
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO22132	NPC155847	Other	Sprout Seedling	6.3	6.3	6.3	mg/100g	Database [DUKE]

☑ 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
AC50	3
ED50	1
IC50	2
Others	10
Potency	6

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	3
Organism	6
Others	10
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	39.0	%	PMID[475954]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[475955]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	47.3	nM	PMID[475956]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	13324.4	nM	PMID[475956]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	0.6	nM	PMID[475956]
NPT32	Organism	Mus musculus	Mus musculus	ED50	>	400.0	umol.kg-1	PMID[475957]
NPT2	Others	Unspecified		AC50	n.a.	44668.4	nM	PMID[475958]
NPT2	Others	Unspecified		Ac50	n.a.	5.012	uM	PMID[475958]
NPT2	Others	Unspecified		Ac50	n.a.	44.67	uM	PMID[475958]
NPT2	Others	Unspecified		Ac50	n.a.	8.913	uM	PMID[475958]
NPT2	Others	Unspecified		AC50	n.a.	5011.9	nM	PMID[475958]
NPT2	Others	Unspecified		AC50	n.a.	8912.5	nM	PMID[475958]
NPT2	Others	Unspecified		Inhibition	=	30.0	%	PMID[475959]
NPT2	Others	Unspecified		Inhibition	=	70.0	%	PMID[475959]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-2.76	%	PMID[475960]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	15.28	%	PMID[475961]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.13	%	PMID[475962]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[475963]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[475963]
NPT2	Others	Unspecified		Potency	n.a.	6.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	6007	nM	PubChem BioAssay data set

☑ 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 NPC155847 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	142
0.1-0.2	2415
0.2-0.3	10001
0.3-0.4	8770
0.4-0.5	10356
0.5-0.6	8182
0.6-0.7	2256
0.7-0.8	508
0.8-0.85	54
0.85-0.9	10
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC289381
0.9184	High Similarity	NPC178902
0.9072	High Similarity	NPC125732
0.8911	High Similarity	NPC231705
0.8824	High Similarity	NPC142297
0.871	High Similarity	NPC197783
0.8654	High Similarity	NPC258056
0.8617	High Similarity	NPC23167
0.8602	High Similarity	NPC175313
0.8602	High Similarity	NPC248817
0.86	High Similarity	NPC29601
0.8571	High Similarity	NPC474149
0.8558	High Similarity	NPC96224
0.8558	High Similarity	NPC24101
0.8558	High Similarity	NPC153690
0.8526	High Similarity	NPC25493
0.8526	High Similarity	NPC113460
0.8519	High Similarity	NPC213
0.8519	High Similarity	NPC10286
0.8495	Intermediate Similarity	NPC124436
0.8495	Intermediate Similarity	NPC265146
0.8438	Intermediate Similarity	NPC280347
0.8438	Intermediate Similarity	NPC318325
0.8438	Intermediate Similarity	NPC258219
0.8438	Intermediate Similarity	NPC177420
0.8438	Intermediate Similarity	NPC123273
0.8438	Intermediate Similarity	NPC242240
0.8431	Intermediate Similarity	NPC68055
0.8421	Intermediate Similarity	NPC184169
0.8351	Intermediate Similarity	NPC55561
0.8302	Intermediate Similarity	NPC145638
0.8302	Intermediate Similarity	NPC290566
0.8288	Intermediate Similarity	NPC85276
0.8265	Intermediate Similarity	NPC304541
0.8265	Intermediate Similarity	NPC155908
0.8257	Intermediate Similarity	NPC142599
0.8257	Intermediate Similarity	NPC118202
0.8247	Intermediate Similarity	NPC98772
0.8229	Intermediate Similarity	NPC307235
0.8229	Intermediate Similarity	NPC407
0.8218	Intermediate Similarity	NPC107619
0.8182	Intermediate Similarity	NPC138117
0.8182	Intermediate Similarity	NPC325292
0.8182	Intermediate Similarity	NPC317254
0.8163	Intermediate Similarity	NPC300017
0.8163	Intermediate Similarity	NPC151764
0.8144	Intermediate Similarity	NPC104216
0.8144	Intermediate Similarity	NPC27974
0.8125	Intermediate Similarity	NPC155393
0.81	Intermediate Similarity	NPC316301
0.81	Intermediate Similarity	NPC27323
0.8081	Intermediate Similarity	NPC270547
0.8081	Intermediate Similarity	NPC45040
0.8081	Intermediate Similarity	NPC204210
0.8073	Intermediate Similarity	NPC146422
0.8058	Intermediate Similarity	NPC228400
0.8058	Intermediate Similarity	NPC214200
0.8036	Intermediate Similarity	NPC137096
0.8021	Intermediate Similarity	NPC286904
0.8021	Intermediate Similarity	NPC150837
0.802	Intermediate Similarity	NPC8392
0.802	Intermediate Similarity	NPC26244
0.802	Intermediate Similarity	NPC313650
0.8017	Intermediate Similarity	NPC307020
0.8	Intermediate Similarity	NPC181709
0.8	Intermediate Similarity	NPC59387
0.7982	Intermediate Similarity	NPC321133
0.7946	Intermediate Similarity	NPC82963
0.7941	Intermediate Similarity	NPC473388
0.7925	Intermediate Similarity	NPC42383
0.7921	Intermediate Similarity	NPC151715
0.7921	Intermediate Similarity	NPC128062
0.7913	Intermediate Similarity	NPC56634
0.79	Intermediate Similarity	NPC306074
0.7895	Intermediate Similarity	NPC283760
0.7895	Intermediate Similarity	NPC319950
0.7879	Intermediate Similarity	NPC70436
0.7876	Intermediate Similarity	NPC311737
0.7876	Intermediate Similarity	NPC38458
0.7876	Intermediate Similarity	NPC283468
0.7864	Intermediate Similarity	NPC225464
0.7864	Intermediate Similarity	NPC260000
0.7864	Intermediate Similarity	NPC77492
0.7843	Intermediate Similarity	NPC274678
0.7822	Intermediate Similarity	NPC210497
0.7822	Intermediate Similarity	NPC162314
0.7822	Intermediate Similarity	NPC94139
0.7822	Intermediate Similarity	NPC3358
0.7822	Intermediate Similarity	NPC306884
0.7822	Intermediate Similarity	NPC55903
0.7822	Intermediate Similarity	NPC147284
0.7815	Intermediate Similarity	NPC218323
0.781	Intermediate Similarity	NPC327226
0.7807	Intermediate Similarity	NPC122009
0.78	Intermediate Similarity	NPC300478
0.78	Intermediate Similarity	NPC192
0.7797	Intermediate Similarity	NPC171372
0.7788	Intermediate Similarity	NPC106551
0.7788	Intermediate Similarity	NPC122005
0.7788	Intermediate Similarity	NPC80027
0.7788	Intermediate Similarity	NPC281686
0.7788	Intermediate Similarity	NPC252821
0.7788	Intermediate Similarity	NPC280869
0.7788	Intermediate Similarity	NPC92730
0.7788	Intermediate Similarity	NPC128723
0.7788	Intermediate Similarity	NPC188867
0.7778	Intermediate Similarity	NPC19680
0.7767	Intermediate Similarity	NPC82664
0.7767	Intermediate Similarity	NPC292730
0.7767	Intermediate Similarity	NPC202986
0.7767	Intermediate Similarity	NPC132271
0.7767	Intermediate Similarity	NPC216520
0.775	Intermediate Similarity	NPC268763
0.775	Intermediate Similarity	NPC8305
0.775	Intermediate Similarity	NPC66177
0.7745	Intermediate Similarity	NPC152415
0.7745	Intermediate Similarity	NPC245187
0.7745	Intermediate Similarity	NPC81010
0.7745	Intermediate Similarity	NPC32977
0.7739	Intermediate Similarity	NPC268572
0.7739	Intermediate Similarity	NPC43275
0.7723	Intermediate Similarity	NPC231150
0.7714	Intermediate Similarity	NPC225506
0.7706	Intermediate Similarity	NPC97811
0.7692	Intermediate Similarity	NPC32674
0.7692	Intermediate Similarity	NPC142577
0.7692	Intermediate Similarity	NPC474862
0.7692	Intermediate Similarity	NPC109955
0.767	Intermediate Similarity	NPC107522
0.767	Intermediate Similarity	NPC286006
0.767	Intermediate Similarity	NPC144682
0.7667	Intermediate Similarity	NPC305717
0.7667	Intermediate Similarity	NPC236347
0.7667	Intermediate Similarity	NPC323775
0.7664	Intermediate Similarity	NPC147000
0.7664	Intermediate Similarity	NPC304761
0.7664	Intermediate Similarity	NPC150254
0.7664	Intermediate Similarity	NPC226778
0.7658	Intermediate Similarity	NPC166837
0.7647	Intermediate Similarity	NPC271440
0.7636	Intermediate Similarity	NPC172046
0.7623	Intermediate Similarity	NPC259665
0.7623	Intermediate Similarity	NPC126859
0.7623	Intermediate Similarity	NPC89769
0.7619	Intermediate Similarity	NPC132078
0.7619	Intermediate Similarity	NPC245561
0.7619	Intermediate Similarity	NPC78119
0.7619	Intermediate Similarity	NPC171843
0.7619	Intermediate Similarity	NPC216468
0.7619	Intermediate Similarity	NPC51333
0.7611	Intermediate Similarity	NPC115803
0.7607	Intermediate Similarity	NPC284078
0.7596	Intermediate Similarity	NPC259512
0.7596	Intermediate Similarity	NPC312132
0.7586	Intermediate Similarity	NPC239697
0.7583	Intermediate Similarity	NPC318965
0.7573	Intermediate Similarity	NPC289769
0.7573	Intermediate Similarity	NPC76938
0.7573	Intermediate Similarity	NPC20142
0.7573	Intermediate Similarity	NPC215351
0.757	Intermediate Similarity	NPC196479
0.7561	Intermediate Similarity	NPC257390
0.7547	Intermediate Similarity	NPC52472
0.7547	Intermediate Similarity	NPC253746
0.7547	Intermediate Similarity	NPC213730
0.7547	Intermediate Similarity	NPC211885
0.7545	Intermediate Similarity	NPC146530
0.7544	Intermediate Similarity	NPC37302
0.7542	Intermediate Similarity	NPC268348
0.7542	Intermediate Similarity	NPC27581
0.7541	Intermediate Similarity	NPC124802
0.7524	Intermediate Similarity	NPC108606
0.7524	Intermediate Similarity	NPC290515
0.7524	Intermediate Similarity	NPC201967
0.7524	Intermediate Similarity	NPC164514
0.7524	Intermediate Similarity	NPC474073
0.7524	Intermediate Similarity	NPC79241
0.7524	Intermediate Similarity	NPC303611
0.7524	Intermediate Similarity	NPC226096
0.7524	Intermediate Similarity	NPC152097
0.7524	Intermediate Similarity	NPC6597
0.7521	Intermediate Similarity	NPC118522
0.7521	Intermediate Similarity	NPC169207
0.7521	Intermediate Similarity	NPC115627
0.7521	Intermediate Similarity	NPC263835
0.75	Intermediate Similarity	NPC222146
0.75	Intermediate Similarity	NPC32714
0.75	Intermediate Similarity	NPC120719
0.748	Intermediate Similarity	NPC120251
0.7477	Intermediate Similarity	NPC7686
0.7477	Intermediate Similarity	NPC472585
0.7477	Intermediate Similarity	NPC40258
0.7477	Intermediate Similarity	NPC101025
0.7477	Intermediate Similarity	NPC471578
0.7477	Intermediate Similarity	NPC110764
0.7477	Intermediate Similarity	NPC316052
0.7477	Intermediate Similarity	NPC91461
0.7476	Intermediate Similarity	NPC29373
0.7458	Intermediate Similarity	NPC318357
0.7455	Intermediate Similarity	NPC186469

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 NPC155847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	124
0.1-0.2	779
0.2-0.3	1096
0.3-0.4	2256
0.4-0.5	2473
0.5-0.6	1644
0.6-0.7	615
0.7-0.8	138
0.8-0.85	20
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8911	High Similarity	NPD1444	Approved
0.8911	High Similarity	NPD1445	Approved
0.89	High Similarity	NPD9610	Approved
0.89	High Similarity	NPD9608	Approved
0.8857	High Similarity	NPD2229	Approved
0.8857	High Similarity	NPD2234	Approved
0.8857	High Similarity	NPD2228	Approved
0.8654	High Similarity	NPD1792	Phase 2
0.8495	Intermediate Similarity	NPD111	Approved
0.8426	Intermediate Similarity	NPD1791	Approved
0.8426	Intermediate Similarity	NPD1793	Approved
0.8378	Intermediate Similarity	NPD4093	Discontinued
0.8364	Intermediate Similarity	NPD16	Approved
0.8364	Intermediate Similarity	NPD856	Approved
0.8364	Intermediate Similarity	NPD317	Approved
0.8364	Intermediate Similarity	NPD318	Approved
0.8302	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD5304	Approved
0.8288	Intermediate Similarity	NPD5303	Approved
0.8142	Intermediate Similarity	NPD1751	Approved
0.8142	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.81	Intermediate Similarity	NPD2933	Approved
0.81	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.81	Intermediate Similarity	NPD2934	Approved
0.8073	Intermediate Similarity	NPD9377	Approved
0.8073	Intermediate Similarity	NPD9379	Approved
0.8036	Intermediate Similarity	NPD9616	Approved
0.8036	Intermediate Similarity	NPD9613	Approved
0.8036	Intermediate Similarity	NPD9615	Approved
0.802	Intermediate Similarity	NPD2859	Approved
0.802	Intermediate Similarity	NPD2860	Approved
0.8017	Intermediate Similarity	NPD4659	Approved
0.7982	Intermediate Similarity	NPD2667	Approved
0.7982	Intermediate Similarity	NPD2668	Approved
0.7981	Intermediate Similarity	NPD854	Approved
0.7981	Intermediate Similarity	NPD855	Approved
0.7965	Intermediate Similarity	NPD316	Approved
0.7931	Intermediate Similarity	NPD2561	Approved
0.7931	Intermediate Similarity	NPD2562	Approved
0.7881	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD4103	Phase 2
0.781	Intermediate Similarity	NPD4817	Approved
0.781	Intermediate Similarity	NPD4818	Approved
0.7797	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD3020	Approved
0.7788	Intermediate Similarity	NPD9568	Approved
0.7768	Intermediate Similarity	NPD9618	Approved
0.7768	Intermediate Similarity	NPD9614	Approved
0.7759	Intermediate Similarity	NPD1671	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3637	Approved
0.775	Intermediate Similarity	NPD3636	Approved
0.775	Intermediate Similarity	NPD3635	Approved
0.7731	Intermediate Similarity	NPD1133	Approved
0.7731	Intermediate Similarity	NPD1135	Approved
0.7731	Intermediate Similarity	NPD1134	Approved
0.7731	Intermediate Similarity	NPD1131	Approved
0.7731	Intermediate Similarity	NPD3055	Approved
0.7731	Intermediate Similarity	NPD3053	Approved
0.7731	Intermediate Similarity	NPD1129	Approved
0.7699	Intermediate Similarity	NPD255	Approved
0.7699	Intermediate Similarity	NPD256	Approved
0.7692	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD2606	Approved
0.7686	Intermediate Similarity	NPD2605	Approved
0.767	Intermediate Similarity	NPD844	Approved
0.767	Intermediate Similarity	NPD1809	Phase 2
0.7667	Intermediate Similarity	NPD9621	Approved
0.7667	Intermediate Similarity	NPD9619	Approved
0.7667	Intermediate Similarity	NPD9620	Approved
0.7664	Intermediate Similarity	NPD10	Approved
0.7664	Intermediate Similarity	NPD309	Approved
0.7664	Intermediate Similarity	NPD314	Approved
0.7664	Intermediate Similarity	NPD315	Approved
0.7664	Intermediate Similarity	NPD310	Approved
0.7664	Intermediate Similarity	NPD311	Approved
0.7647	Intermediate Similarity	NPD5311	Approved
0.7647	Intermediate Similarity	NPD5310	Approved
0.7647	Intermediate Similarity	NPD845	Approved
0.7642	Intermediate Similarity	NPD940	Approved
0.7642	Intermediate Similarity	NPD846	Approved
0.7623	Intermediate Similarity	NPD5156	Approved
0.7623	Intermediate Similarity	NPD5155	Approved
0.7607	Intermediate Similarity	NPD3421	Phase 3
0.7596	Intermediate Similarity	NPD288	Approved
0.757	Intermediate Similarity	NPD3683	Approved
0.757	Intermediate Similarity	NPD4658	Approved
0.757	Intermediate Similarity	NPD4231	Approved
0.757	Intermediate Similarity	NPD4656	Approved
0.757	Intermediate Similarity	NPD3681	Approved
0.757	Intermediate Similarity	NPD3682	Approved
0.757	Intermediate Similarity	NPD3680	Approved
0.757	Intermediate Similarity	NPD4229	Approved
0.7563	Intermediate Similarity	NPD1755	Approved
0.7541	Intermediate Similarity	NPD3595	Approved
0.7541	Intermediate Similarity	NPD3594	Approved
0.7524	Intermediate Similarity	NPD9609	Approved
0.7524	Intermediate Similarity	NPD9611	Approved
0.7524	Intermediate Similarity	NPD9612	Approved
0.7521	Intermediate Similarity	NPD9381	Approved
0.7521	Intermediate Similarity	NPD9384	Approved
0.7479	Intermediate Similarity	NPD2232	Approved
0.7479	Intermediate Similarity	NPD2233	Approved
0.7479	Intermediate Similarity	NPD2230	Approved
0.7456	Intermediate Similarity	NPD595	Approved
0.7456	Intermediate Similarity	NPD593	Approved
0.7455	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD598	Approved
0.7419	Intermediate Similarity	NPD601	Approved
0.7419	Intermediate Similarity	NPD597	Approved
0.7417	Intermediate Similarity	NPD6583	Phase 3
0.7417	Intermediate Similarity	NPD9622	Approved
0.7417	Intermediate Similarity	NPD6582	Phase 2
0.7411	Intermediate Similarity	NPD4254	Approved
0.7411	Intermediate Similarity	NPD4253	Approved
0.7383	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1242	Phase 1
0.7377	Intermediate Similarity	NPD7451	Discontinued
0.736	Intermediate Similarity	NPD1130	Approved
0.736	Intermediate Similarity	NPD1132	Approved
0.736	Intermediate Similarity	NPD829	Discontinued
0.736	Intermediate Similarity	NPD1136	Approved
0.7358	Intermediate Similarity	NPD9273	Approved
0.735	Intermediate Similarity	NPD1759	Phase 1
0.735	Intermediate Similarity	NPD2486	Discontinued
0.7333	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD9087	Approved
0.728	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD1758	Phase 1
0.7257	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD9376	Approved
0.7236	Intermediate Similarity	NPD599	Approved
0.7236	Intermediate Similarity	NPD602	Approved
0.7236	Intermediate Similarity	NPD858	Approved
0.7236	Intermediate Similarity	NPD6584	Phase 3
0.7236	Intermediate Similarity	NPD2195	Approved
0.7236	Intermediate Similarity	NPD859	Approved
0.7236	Intermediate Similarity	NPD2194	Approved
0.7232	Intermediate Similarity	NPD4720	Approved
0.7232	Intermediate Similarity	NPD4717	Approved
0.7232	Intermediate Similarity	NPD4718	Approved
0.7222	Intermediate Similarity	NPD6405	Approved
0.7222	Intermediate Similarity	NPD6407	Approved
0.7209	Intermediate Similarity	NPD1753	Discontinued
0.72	Intermediate Similarity	NPD3136	Phase 2
0.7193	Intermediate Similarity	NPD2500	Approved
0.7193	Intermediate Similarity	NPD2499	Approved
0.7188	Intermediate Similarity	NPD3052	Approved
0.7188	Intermediate Similarity	NPD2568	Approved
0.7188	Intermediate Similarity	NPD3054	Approved
0.7182	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3596	Phase 2
0.7168	Intermediate Similarity	NPD3021	Approved
0.7168	Intermediate Similarity	NPD3022	Approved
0.7167	Intermediate Similarity	NPD3294	Phase 2
0.7165	Intermediate Similarity	NPD3062	Approved
0.7165	Intermediate Similarity	NPD3059	Approved
0.7165	Intermediate Similarity	NPD3061	Approved
0.7143	Intermediate Similarity	NPD2595	Approved
0.7143	Intermediate Similarity	NPD2594	Approved
0.7132	Intermediate Similarity	NPD3552	Approved
0.7132	Intermediate Similarity	NPD3554	Approved
0.7132	Intermediate Similarity	NPD3555	Approved
0.7132	Intermediate Similarity	NPD3553	Approved
0.7131	Intermediate Similarity	NPD1669	Approved
0.713	Intermediate Similarity	NPD821	Approved
0.713	Intermediate Similarity	NPD1105	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD2674	Phase 3
0.7087	Intermediate Similarity	NPD5745	Approved
0.7087	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD3028	Approved
0.7059	Intermediate Similarity	NPD6581	Approved
0.7059	Intermediate Similarity	NPD6580	Approved
0.7054	Intermediate Similarity	NPD817	Approved
0.7054	Intermediate Similarity	NPD5314	Approved
0.7054	Intermediate Similarity	NPD810	Approved
0.7054	Intermediate Similarity	NPD811	Approved
0.7054	Intermediate Similarity	NPD812	Approved
0.7054	Intermediate Similarity	NPD823	Approved
0.7043	Intermediate Similarity	NPD228	Approved
0.704	Intermediate Similarity	NPD9569	Approved
0.7034	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2238	Phase 2
0.7031	Intermediate Similarity	NPD6346	Approved
0.701	Intermediate Similarity	NPD9088	Approved
0.7009	Intermediate Similarity	NPD475	Phase 2
0.7008	Intermediate Similarity	NPD3144	Approved
0.7008	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3145	Approved
0.7	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4719	Phase 2
0.6992	Remote Similarity	NPD1421	Approved
0.6992	Remote Similarity	NPD1420	Approved
0.6992	Remote Similarity	NPD2428	Approved
0.6992	Remote Similarity	NPD2429	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