NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	137.08
Volume:	150.245
LogP:	0.311
LogD:	0.424
LogS:	-0.616
# Rotatable Bonds:	2
TPSA:	46.25
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.636
Synthetic Accessibility Score:	1.625
Fsp3:	0.25
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:	-4.863
MDCK Permeability:	7.20978932804428e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.624
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.629

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	16.950313568115234%
Volume Distribution (VD):	2.958
Pgp-substrate:	75.18946838378906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.401
CYP1A2-substrate:	0.755
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.158
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.832
CYP2D6-inhibitor:	0.436
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	13.101
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.926
Maximum Recommended Daily Dose:	0.402
Skin Sensitization:	0.873
Carcinogencity:	0.091
Eye Corrosion:	0.962
Eye Irritation:	0.45
Respiratory Toxicity:	0.813

Download Data

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

Natural Product: NPC125732

Natural Product ID:	NPC125732
*Common Name:**	Tyramine
IUPAC Name:	4-(2-aminoethyl)phenol
Synonyms:	Tyramine
Standard InCHIKey:	DZGWFCGJZKJUFP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
SMILES:	c1cc(ccc1CCN)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL11608
PubChem CID:	5610
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
NPO21556	NPC125732	n.a.	Sclerotia	0.070 ± 0.015	n.a.	n.a.	%	PMID[20527951]

☑ 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	1
EC50	7
IC50	7
Kd	4
Ki	5
Others	29
Potency	22

Activity Type	# Activity
Cell Line	1
Individual Protein	46
Organism	10
Others	13
Protein Family	4
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2805	Individual Protein	Dopamine beta-hydroxylase	Bos taurus	Km	=	2000000.0	nM	PMID[515557]
NPT2805	Individual Protein	Dopamine beta-hydroxylase	Bos taurus	k cat	=	85.0	s-1	PMID[515557]
NPT243	Individual Protein	Dopamine D2 receptor	Homo sapiens	Ki	>	17000.0	nM	PMID[515559]
NPT245	Individual Protein	Dopamine D4 receptor	Homo sapiens	Ki	>	35000.0	nM	PMID[515559]
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	Ki	=	390000.0	nM	PMID[515560]
NPT243	Individual Protein	Dopamine D2 receptor	Homo sapiens	Ki	=	160000.0	nM	PMID[515560]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Ki	=	294000.0	nM	PMID[515561]
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	KL	=	390000.0	nM	PMID[515562]
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	Log 1/KL	=	-5.59	n.a.	PMID[515562]
NPT2805	Individual Protein	Dopamine beta-hydroxylase	Bos taurus	Km	=	2000000.0	nM	PMID[515564]
NPT2805	Individual Protein	Dopamine beta-hydroxylase	Bos taurus	k cat	=	121.0	s-1	PMID[515564]
NPT2805	Individual Protein	Dopamine beta-hydroxylase	Bos taurus	Ratio	=	60000.0	n.a.	PMID[515564]
NPT1779	Individual Protein	Serotonin 2b (5-HT2b) receptor	Rattus norvegicus	Kd	=	7943.28	nM	PMID[515565]
NPT425	Individual Protein	Serotonin 3a (5-HT3a) receptor	Homo sapiens	EC50	=	26000.0	nM	PMID[515568]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Activity	=	25.9	/s	PMID[515571]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[515572]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	39810.7	nM	PMID[515573]
NPT583	Individual Protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	31622.8	nM	PMID[515572]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	751.9	nM	PMID[515574]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	29.1	nM	PMID[515574]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	Km	=	514000.0	nM	PMID[515576]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Km	=	104700.0	nM	PMID[515576]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	Vmax	=	301.4	nmol/min/mg	PMID[515576]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Vmax	=	28.9	nmol/min/mg	PMID[515576]
NPT1153	Individual Protein	Monocarboxylate transporter 10	Rattus norvegicus	Activity	=	20.0	%	PMID[515578]
NPT613	Individual Protein	Solute carrier family 22 member 1	Homo sapiens	Activity	=	107.0	uM	PMID[515580]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[515572]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[515572]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[515575]
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	Potency	n.a.	8199.5	nM	PMID[515574]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	32642.7	nM	PMID[515572]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Km	=	540000.0	nM	PMID[515583]
NPT244	Individual Protein	Dopamine D3 receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[515572]
NPT4320	Individual Protein	Trace amine-associated receptor 1	Rattus norvegicus	EC50	=	69.0	nM	PMID[515588]
NPT2	Others	Unspecified		Potency	n.a.	6007	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	16930.1	nM	PubChem BioAssay data set
NPT4410	Others	Opioid receptor (mu and kappa)	Cavia porcellus	Ratio	<	0.00007	n.a.	PMID[515556]
NPT4410	Others	Opioid receptor (mu and kappa)	Cavia porcellus	EC50	>	0.001	n.a.	PMID[515556]
NPT3590	Protein Family	Opioid receptor	Rattus norvegicus	EC50	>	0.001	n.a.	PMID[515556]
NPT3590	Protein Family	Opioid receptor	Rattus norvegicus	Ratio	<	0.000087	n.a.	PMID[515556]
NPT2	Others	Unspecified		Ratio	=	42000.0	M-1 s-1	PMID[515557]
NPT1530	Protein Family	Serotonin (5-HT) receptor	Rattus norvegicus	Kd	=	8511.38	nM	PMID[515558]
NPT2	Others	Unspecified		-Log KD	=	-2.3	n.a.	PMID[515563]
NPT1530	Protein Family	Serotonin (5-HT) receptor	Rattus norvegicus	Kd	=	8511.38	nM	PMID[515565]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	23.0	%	PMID[515566]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Kd	=	2000000.0	nM	PMID[515567]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	160000.0	nM	PMID[515569]
NPT976	Individual Protein	Trace amine-associated receptor 1	Homo sapiens	EC50	=	731.0	nM	PMID[515570]
NPT976	Individual Protein	Trace amine-associated receptor 1	Homo sapiens	Emax	=	91.0	%	PMID[515570]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[515572]
NPT2	Others	Unspecified		Potency	=	18356.4	nM	PMID[515572]
NPT864	Individual Protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	12589.3	nM	PMID[515572]
NPT95	Individual Protein	Muscarinic acetylcholine receptor M1	Rattus norvegicus	Potency	=	50.1	nM	PMID[515573]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	3.3	nM	PMID[515572]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	4256.2	nM	PMID[515575]
NPT698	Individual Protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	266.5	nM	PMID[515574]
NPT698	Individual Protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	6.7	nM	PMID[515575]
NPT35	Others	n.a.		EC50	>	29902.0	nM	PMID[515572]
NPT976	Individual Protein	Trace amine-associated receptor 1	Homo sapiens	IC50	=	881.84	nM	PMID[515572]
NPT35	Others	n.a.		IC50	>	29902.0	nM	PMID[515572]
NPT976	Individual Protein	Trace amine-associated receptor 1	Homo sapiens	EC50	=	177.71	nM	PMID[515572]
NPT2645	Organism	Giardia intestinalis	Giardia intestinalis	IC50	=	68.9	ug.mL-1	PMID[515581]
NPT3535	Organism	Entamoeba histolytica HM-1:IMSS	Entamoeba histolytica HM-1:IMSS	IC50	=	54.2	ug.mL-1	PMID[515581]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	59.9	%	PMID[515582]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	85.38	%	PMID[515582]
NPT2	Others	Unspecified		Potency	n.a.	31622.8	nM	PMID[515585]
NPT2	Others	Unspecified		pKb	<	3.7	n.a.	PMID[515586]
NPT2	Others	Unspecified		Ac50	n.a.	0.631	uM	PMID[515587]
NPT2	Others	Unspecified		AC50	n.a.	631.0	nM	PMID[515587]
NPT605	Organism	Homo sapiens	Homo sapiens	DILI_severity_class	=	0.0	n.a.	PMID[515589]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	7.67	%	PMID[515590]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.15	%	PMID[515591]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[515592]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[515592]

☑ 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 NPC125732 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	219
0.1-0.2	3061
0.2-0.3	11483
0.3-0.4	7711
0.4-0.5	10860
0.5-0.6	7263
0.6-0.7	1631
0.7-0.8	394
0.8-0.85	57
0.85-0.9	12
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9278	High Similarity	NPC68055
0.9271	High Similarity	NPC29601
0.9109	High Similarity	NPC145638
0.9109	High Similarity	NPC290566
0.9072	High Similarity	NPC289381
0.9072	High Similarity	NPC155847
0.8889	High Similarity	NPC178902
0.8846	High Similarity	NPC146422
0.8762	High Similarity	NPC59387
0.8696	High Similarity	NPC175313
0.8673	High Similarity	NPC107619
0.8627	High Similarity	NPC231705
0.8602	High Similarity	NPC197783
0.8598	High Similarity	NPC10286
0.8598	High Similarity	NPC213
0.8587	High Similarity	NPC265146
0.8544	High Similarity	NPC142297
0.8529	High Similarity	NPC42383
0.8519	High Similarity	NPC188867
0.8519	High Similarity	NPC281686
0.8519	High Similarity	NPC106551
0.8511	High Similarity	NPC23167
0.8495	Intermediate Similarity	NPC248817
0.8462	Intermediate Similarity	NPC153690
0.8462	Intermediate Similarity	NPC96224
0.8462	Intermediate Similarity	NPC24101
0.8421	Intermediate Similarity	NPC25493
0.8421	Intermediate Similarity	NPC113460
0.8387	Intermediate Similarity	NPC124436
0.8381	Intermediate Similarity	NPC258056
0.8367	Intermediate Similarity	NPC20142
0.8367	Intermediate Similarity	NPC215351
0.8364	Intermediate Similarity	NPC85276
0.8333	Intermediate Similarity	NPC280347
0.8333	Intermediate Similarity	NPC242240
0.8333	Intermediate Similarity	NPC115803
0.8333	Intermediate Similarity	NPC258219
0.8333	Intermediate Similarity	NPC318325
0.8333	Intermediate Similarity	NPC177420
0.8333	Intermediate Similarity	NPC123273
0.8316	Intermediate Similarity	NPC184169
0.8302	Intermediate Similarity	NPC474149
0.8288	Intermediate Similarity	NPC283760
0.8288	Intermediate Similarity	NPC239697
0.8286	Intermediate Similarity	NPC97811
0.8247	Intermediate Similarity	NPC55561
0.8247	Intermediate Similarity	NPC151764
0.8247	Intermediate Similarity	NPC300017
0.8229	Intermediate Similarity	NPC104216
0.8214	Intermediate Similarity	NPC115627
0.8214	Intermediate Similarity	NPC118522
0.8214	Intermediate Similarity	NPC169207
0.8211	Intermediate Similarity	NPC155393
0.8208	Intermediate Similarity	NPC172046
0.8163	Intermediate Similarity	NPC155908
0.8163	Intermediate Similarity	NPC304541
0.8163	Intermediate Similarity	NPC45040
0.8144	Intermediate Similarity	NPC98772
0.8142	Intermediate Similarity	NPC318357
0.8125	Intermediate Similarity	NPC407
0.8125	Intermediate Similarity	NPC307235
0.8119	Intermediate Similarity	NPC290515
0.8119	Intermediate Similarity	NPC164514
0.8119	Intermediate Similarity	NPC108606
0.8119	Intermediate Similarity	NPC226096
0.8119	Intermediate Similarity	NPC303611
0.8108	Intermediate Similarity	NPC137096
0.8081	Intermediate Similarity	NPC325292
0.8081	Intermediate Similarity	NPC138117
0.8041	Intermediate Similarity	NPC27974
0.8036	Intermediate Similarity	NPC317784
0.8036	Intermediate Similarity	NPC142638
0.8019	Intermediate Similarity	NPC186469
0.8	Intermediate Similarity	NPC316301
0.8	Intermediate Similarity	NPC142599
0.8	Intermediate Similarity	NPC128062
0.8	Intermediate Similarity	NPC27323
0.8	Intermediate Similarity	NPC118202
0.8	Intermediate Similarity	NPC151715
0.798	Intermediate Similarity	NPC204210
0.798	Intermediate Similarity	NPC270547
0.7931	Intermediate Similarity	NPC140359
0.7931	Intermediate Similarity	NPC13020
0.7928	Intermediate Similarity	NPC317254
0.7921	Intermediate Similarity	NPC274678
0.7921	Intermediate Similarity	NPC26244
0.7921	Intermediate Similarity	NPC8392
0.7921	Intermediate Similarity	NPC313650
0.7917	Intermediate Similarity	NPC286904
0.7917	Intermediate Similarity	NPC150837
0.7913	Intermediate Similarity	NPC27581
0.7909	Intermediate Similarity	NPC26524
0.79	Intermediate Similarity	NPC181709
0.7885	Intermediate Similarity	NPC327226
0.7879	Intermediate Similarity	NPC192
0.7879	Intermediate Similarity	NPC300478
0.7857	Intermediate Similarity	NPC82963
0.7843	Intermediate Similarity	NPC473388
0.7843	Intermediate Similarity	NPC216520
0.7843	Intermediate Similarity	NPC292730
0.7843	Intermediate Similarity	NPC202986
0.7843	Intermediate Similarity	NPC82664
0.7843	Intermediate Similarity	NPC132271
0.7826	Intermediate Similarity	NPC326079
0.7822	Intermediate Similarity	NPC32977
0.7822	Intermediate Similarity	NPC81010
0.78	Intermediate Similarity	NPC306074
0.7797	Intermediate Similarity	NPC318965
0.7788	Intermediate Similarity	NPC311737
0.7788	Intermediate Similarity	NPC283468
0.7788	Intermediate Similarity	NPC38458
0.7778	Intermediate Similarity	NPC318777
0.7778	Intermediate Similarity	NPC70436
0.7767	Intermediate Similarity	NPC109955
0.7767	Intermediate Similarity	NPC77492
0.7767	Intermediate Similarity	NPC260000
0.7767	Intermediate Similarity	NPC225464
0.7767	Intermediate Similarity	NPC32674
0.7767	Intermediate Similarity	NPC315921
0.7745	Intermediate Similarity	NPC286006
0.7736	Intermediate Similarity	NPC304761
0.7736	Intermediate Similarity	NPC150254
0.7736	Intermediate Similarity	NPC226778
0.7736	Intermediate Similarity	NPC147000
0.7731	Intermediate Similarity	NPC236347
0.7731	Intermediate Similarity	NPC323775
0.7727	Intermediate Similarity	NPC21890
0.7723	Intermediate Similarity	NPC271440
0.7723	Intermediate Similarity	NPC147284
0.7723	Intermediate Similarity	NPC210497
0.7723	Intermediate Similarity	NPC3358
0.7723	Intermediate Similarity	NPC306884
0.7723	Intermediate Similarity	NPC162314
0.7723	Intermediate Similarity	NPC55903
0.7723	Intermediate Similarity	NPC94139
0.7719	Intermediate Similarity	NPC122009
0.7692	Intermediate Similarity	NPC80027
0.7692	Intermediate Similarity	NPC122005
0.7692	Intermediate Similarity	NPC245561
0.7692	Intermediate Similarity	NPC280869
0.7692	Intermediate Similarity	NPC132078
0.7692	Intermediate Similarity	NPC128723
0.7692	Intermediate Similarity	NPC92730
0.7692	Intermediate Similarity	NPC78119
0.7692	Intermediate Similarity	NPC216468
0.7692	Intermediate Similarity	NPC51333
0.7692	Intermediate Similarity	NPC252821
0.7677	Intermediate Similarity	NPC19680
0.7667	Intermediate Similarity	NPC145888
0.7667	Intermediate Similarity	NPC161593
0.7667	Intermediate Similarity	NPC16031
0.7652	Intermediate Similarity	NPC319950
0.7652	Intermediate Similarity	NPC268572
0.7647	Intermediate Similarity	NPC152415
0.7647	Intermediate Similarity	NPC76938
0.7647	Intermediate Similarity	NPC245187
0.7632	Intermediate Similarity	NPC120075
0.7624	Intermediate Similarity	NPC231150
0.7619	Intermediate Similarity	NPC225506
0.7619	Intermediate Similarity	NPC52472
0.7619	Intermediate Similarity	NPC213730
0.7603	Intermediate Similarity	NPC325651
0.7596	Intermediate Similarity	NPC201967
0.7573	Intermediate Similarity	NPC32714
0.7573	Intermediate Similarity	NPC144682
0.7573	Intermediate Similarity	NPC107522
0.7547	Intermediate Similarity	NPC91461
0.7547	Intermediate Similarity	NPC7686
0.7547	Intermediate Similarity	NPC110764
0.7547	Intermediate Similarity	NPC40258
0.7541	Intermediate Similarity	NPC474087
0.7525	Intermediate Similarity	NPC312304
0.7525	Intermediate Similarity	NPC47950
0.7524	Intermediate Similarity	NPC171843
0.7524	Intermediate Similarity	NPC131587
0.7524	Intermediate Similarity	NPC275104
0.7524	Intermediate Similarity	NPC130193
0.7521	Intermediate Similarity	NPC284078
0.75	Intermediate Similarity	NPC312132
0.75	Intermediate Similarity	NPC259512
0.75	Intermediate Similarity	NPC43275
0.748	Intermediate Similarity	NPC48909
0.748	Intermediate Similarity	NPC326966
0.748	Intermediate Similarity	NPC326599
0.748	Intermediate Similarity	NPC329595
0.7477	Intermediate Similarity	NPC470202
0.7477	Intermediate Similarity	NPC135784
0.7477	Intermediate Similarity	NPC196479
0.7477	Intermediate Similarity	NPC168829
0.7476	Intermediate Similarity	NPC289769
0.7458	Intermediate Similarity	NPC142577
0.7458	Intermediate Similarity	NPC474862
0.7456	Intermediate Similarity	NPC222982
0.7456	Intermediate Similarity	NPC160179
0.7453	Intermediate Similarity	NPC253746
0.7453	Intermediate Similarity	NPC211885
0.7453	Intermediate Similarity	NPC248573
0.7453	Intermediate Similarity	NPC275053
0.7453	Intermediate Similarity	NPC223393
0.7453	Intermediate Similarity	NPC161571

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 NPC125732 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	943
0.2-0.3	1104
0.3-0.4	2711
0.4-0.5	2329
0.5-0.6	1354
0.6-0.7	414
0.7-0.8	118
0.8-0.85	12
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9583	High Similarity	NPD9608	Approved
0.9583	High Similarity	NPD9610	Approved
0.9109	High Similarity	NPD9380	Clinical (unspecified phase)
0.8846	High Similarity	NPD9379	Approved
0.8846	High Similarity	NPD9377	Approved
0.8519	High Similarity	NPD9568	Approved
0.844	Intermediate Similarity	NPD317	Approved
0.844	Intermediate Similarity	NPD16	Approved
0.844	Intermediate Similarity	NPD318	Approved
0.844	Intermediate Similarity	NPD856	Approved
0.8387	Intermediate Similarity	NPD111	Approved
0.8333	Intermediate Similarity	NPD9618	Approved
0.8333	Intermediate Similarity	NPD9614	Approved
0.8214	Intermediate Similarity	NPD9384	Approved
0.8214	Intermediate Similarity	NPD9381	Approved
0.8119	Intermediate Similarity	NPD9612	Approved
0.8119	Intermediate Similarity	NPD9611	Approved
0.8119	Intermediate Similarity	NPD9609	Approved
0.8108	Intermediate Similarity	NPD9613	Approved
0.8108	Intermediate Similarity	NPD9616	Approved
0.8108	Intermediate Similarity	NPD9615	Approved
0.8095	Intermediate Similarity	NPD1444	Approved
0.8095	Intermediate Similarity	NPD1445	Approved
0.8091	Intermediate Similarity	NPD256	Approved
0.8091	Intermediate Similarity	NPD255	Approved
0.8073	Intermediate Similarity	NPD2228	Approved
0.8073	Intermediate Similarity	NPD2229	Approved
0.8073	Intermediate Similarity	NPD2234	Approved
0.8036	Intermediate Similarity	NPD316	Approved
0.8	Intermediate Similarity	NPD2934	Approved
0.8	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2561	Approved
0.8	Intermediate Similarity	NPD2933	Approved
0.8	Intermediate Similarity	NPD2562	Approved
0.7931	Intermediate Similarity	NPD9622	Approved
0.7921	Intermediate Similarity	NPD2859	Approved
0.7921	Intermediate Similarity	NPD2860	Approved
0.787	Intermediate Similarity	NPD1792	Phase 2
0.7863	Intermediate Similarity	NPD5310	Approved
0.7863	Intermediate Similarity	NPD5311	Approved
0.7863	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD1131	Approved
0.7797	Intermediate Similarity	NPD1133	Approved
0.7797	Intermediate Similarity	NPD3053	Approved
0.7797	Intermediate Similarity	NPD3055	Approved
0.7797	Intermediate Similarity	NPD1135	Approved
0.7797	Intermediate Similarity	NPD1129	Approved
0.7797	Intermediate Similarity	NPD1134	Approved
0.7767	Intermediate Similarity	NPD9273	Approved
0.7736	Intermediate Similarity	NPD314	Approved
0.7736	Intermediate Similarity	NPD310	Approved
0.7736	Intermediate Similarity	NPD309	Approved
0.7736	Intermediate Similarity	NPD315	Approved
0.7736	Intermediate Similarity	NPD10	Approved
0.7736	Intermediate Similarity	NPD311	Approved
0.7731	Intermediate Similarity	NPD2194	Approved
0.7731	Intermediate Similarity	NPD9619	Approved
0.7731	Intermediate Similarity	NPD9621	Approved
0.7731	Intermediate Similarity	NPD9620	Approved
0.7731	Intermediate Similarity	NPD7451	Discontinued
0.7731	Intermediate Similarity	NPD2195	Approved
0.7692	Intermediate Similarity	NPD3020	Approved
0.7679	Intermediate Similarity	NPD1793	Approved
0.7679	Intermediate Similarity	NPD1791	Approved
0.7667	Intermediate Similarity	NPD9569	Approved
0.7652	Intermediate Similarity	NPD4093	Discontinued
0.7573	Intermediate Similarity	NPD1809	Phase 2
0.7573	Intermediate Similarity	NPD844	Approved
0.7565	Intermediate Similarity	NPD5303	Approved
0.7565	Intermediate Similarity	NPD5304	Approved
0.7563	Intermediate Similarity	NPD196	Phase 1
0.7549	Intermediate Similarity	NPD845	Approved
0.7547	Intermediate Similarity	NPD846	Approved
0.7547	Intermediate Similarity	NPD940	Approved
0.7541	Intermediate Similarity	NPD3136	Phase 2
0.7522	Intermediate Similarity	NPD595	Approved
0.7522	Intermediate Similarity	NPD593	Approved
0.75	Intermediate Similarity	NPD288	Approved
0.748	Intermediate Similarity	NPD601	Approved
0.748	Intermediate Similarity	NPD597	Approved
0.748	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD598	Approved
0.7453	Intermediate Similarity	NPD1242	Phase 1
0.7436	Intermediate Similarity	NPD1751	Approved
0.7436	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6407	Approved
0.7419	Intermediate Similarity	NPD259	Phase 1
0.7419	Intermediate Similarity	NPD1130	Approved
0.7419	Intermediate Similarity	NPD1132	Approved
0.7419	Intermediate Similarity	NPD6405	Approved
0.7419	Intermediate Similarity	NPD829	Discontinued
0.7419	Intermediate Similarity	NPD1136	Approved
0.7414	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD9536	Phase 1
0.7398	Intermediate Similarity	NPD9537	Phase 1
0.7395	Intermediate Similarity	NPD2235	Phase 2
0.7395	Intermediate Similarity	NPD2231	Phase 2
0.7391	Intermediate Similarity	NPD9087	Approved
0.736	Intermediate Similarity	NPD3062	Approved
0.736	Intermediate Similarity	NPD3061	Approved
0.736	Intermediate Similarity	NPD3059	Approved
0.7333	Intermediate Similarity	NPD4659	Approved
0.7302	Intermediate Similarity	NPD555	Phase 2
0.7295	Intermediate Similarity	NPD599	Approved
0.7295	Intermediate Similarity	NPD859	Approved
0.7295	Intermediate Similarity	NPD257	Approved
0.7295	Intermediate Similarity	NPD858	Approved
0.7295	Intermediate Similarity	NPD602	Approved
0.7295	Intermediate Similarity	NPD258	Approved
0.729	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2667	Approved
0.7288	Intermediate Similarity	NPD2668	Approved
0.7265	Intermediate Similarity	NPD1759	Phase 1
0.7258	Intermediate Similarity	NPD9718	Approved
0.725	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3052	Approved
0.7244	Intermediate Similarity	NPD823	Approved
0.7244	Intermediate Similarity	NPD817	Approved
0.7244	Intermediate Similarity	NPD2568	Approved
0.7244	Intermediate Similarity	NPD3054	Approved
0.7244	Intermediate Similarity	NPD5314	Approved
0.7222	Intermediate Similarity	NPD854	Approved
0.7222	Intermediate Similarity	NPD855	Approved
0.7213	Intermediate Similarity	NPD4103	Phase 2
0.7213	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3553	Approved
0.7188	Intermediate Similarity	NPD3552	Approved
0.7188	Intermediate Similarity	NPD3554	Approved
0.7188	Intermediate Similarity	NPD3555	Approved
0.7179	Intermediate Similarity	NPD1758	Phase 1
0.7177	Intermediate Similarity	NPD2614	Approved
0.7177	Intermediate Similarity	NPD596	Approved
0.7177	Intermediate Similarity	NPD600	Approved
0.7154	Intermediate Similarity	NPD558	Phase 2
0.7132	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1814	Approved
0.7115	Intermediate Similarity	NPD1812	Approved
0.7097	Intermediate Similarity	NPD3635	Approved
0.7097	Intermediate Similarity	NPD3636	Approved
0.7097	Intermediate Similarity	NPD3637	Approved
0.7083	Intermediate Similarity	NPD9088	Approved
0.7083	Intermediate Similarity	NPD3421	Phase 3
0.7083	Intermediate Similarity	NPD1671	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1980	Approved
0.7083	Intermediate Similarity	NPD1983	Approved
0.7083	Intermediate Similarity	NPD1981	Approved
0.708	Intermediate Similarity	NPD3021	Approved
0.708	Intermediate Similarity	NPD3022	Approved
0.7077	Intermediate Similarity	NPD7450	Phase 2
0.7077	Intermediate Similarity	NPD1538	Phase 1
0.7077	Intermediate Similarity	NPD9570	Approved
0.7077	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1519	Approved
0.7077	Intermediate Similarity	NPD1537	Approved
0.7064	Intermediate Similarity	NPD4818	Approved
0.7064	Intermediate Similarity	NPD4817	Approved
0.7063	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2428	Approved
0.7049	Intermediate Similarity	NPD2429	Approved
0.7049	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD821	Approved
0.704	Intermediate Similarity	NPD3594	Approved
0.704	Intermediate Similarity	NPD2606	Approved
0.704	Intermediate Similarity	NPD2605	Approved
0.704	Intermediate Similarity	NPD3595	Approved
0.7025	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7978	Discontinued
0.7023	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2554	Approved
0.7	Intermediate Similarity	NPD4658	Approved
0.7	Intermediate Similarity	NPD3680	Approved
0.7	Intermediate Similarity	NPD3683	Approved
0.7	Intermediate Similarity	NPD3682	Approved
0.7	Intermediate Similarity	NPD4656	Approved
0.7	Intermediate Similarity	NPD4229	Approved
0.7	Intermediate Similarity	NPD2556	Approved
0.7	Intermediate Similarity	NPD4231	Approved
0.7	Intermediate Similarity	NPD3681	Approved
0.6984	Remote Similarity	NPD5155	Approved
0.6984	Remote Similarity	NPD5156	Approved
0.6979	Remote Similarity	NPD9294	Approved
0.6972	Remote Similarity	NPD3028	Approved
0.6957	Remote Similarity	NPD228	Approved
0.6953	Remote Similarity	NPD826	Approved
0.6953	Remote Similarity	NPD825	Approved
0.6947	Remote Similarity	NPD1523	Approved
0.6947	Remote Similarity	NPD1522	Approved
0.6937	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1820	Approved
0.6935	Remote Similarity	NPD1819	Approved
0.6935	Remote Similarity	NPD1818	Approved
0.6935	Remote Similarity	NPD1817	Approved
0.6923	Remote Similarity	NPD475	Phase 2
0.6923	Remote Similarity	NPD1536	Approved
0.6917	Remote Similarity	NPD3049	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