NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	137.08
Volume:	150.245
LogP:	0.443
LogD:	0.752
LogS:	0.14
# 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:	0.629
Synthetic Accessibility Score:	2.116
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:	-4.982
MDCK Permeability:	0.00019431560940574855
Pgp-inhibitor:	0.0
Pgp-substrate:	0.209
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	13.49345874786377%
Volume Distribution (VD):	1.658
Pgp-substrate:	76.30177307128906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.425
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.269
CYP2D6-inhibitor:	0.086
CYP2D6-substrate:	0.708
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	9.671
Half-life (T1/2):	0.769

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.769
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.291
Carcinogencity:	0.054
Eye Corrosion:	0.962
Eye Irritation:	0.236
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC20142

Natural Product ID:	NPC20142
*Common Name:**	2-Amino-1-Phenyl-Ethanol
IUPAC Name:	(1S)-2-amino-1-phenylethanol
Synonyms:
Standard InCHIKey:	ULSIYEODSMZIPX-MRVPVSSYSA-N
Standard InCHI:	InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2/t8-/m1/s1
SMILES:	NC[C@H](c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL19853
PubChem CID:	643217
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004707] Organic nitrogen compounds [CHEMONTID:0000278] Organonitrogen compounds [CHEMONTID:0002449] Amines [CHEMONTID:0003899] Aralkylamines

*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
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15577255]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30188125]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29463	Pogostemon cablin	Species	Lamiaceae	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
Others	28

Activity Type	# Activity
Individual Protein	13
Organism	1
Others	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Km	=	96000.0	nM	PMID[524461]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Km	=	108000.0	nM	PMID[524463]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Km	=	136000.0	nM	PMID[524464]
NPT1529	Individual Protein	Phenylethanolamine N-methyltransferase	Homo sapiens	Km	=	57000.0	nM	PMID[524465]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Km	=	34000.0	nM	PMID[524465]
NPT1529	Individual Protein	Phenylethanolamine N-methyltransferase	Homo sapiens	Km	=	120000.0	nM	PMID[524466]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Km	=	66000.0	nM	PMID[524466]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Km	=	96000.0	nM	PMID[524467]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Km	=	108000.0	nM	PMID[524468]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Km	=	70000.0	nM	PMID[524469]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Vmax	=	2.2	nM min-1 mg-1	PMID[524469]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Km	=	70000.0	nM	PMID[524471]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Vmax	=	2.2	nM min-1 (mg of protein)-1	PMID[524471]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibitory response	=	21.0	%	PMID[524460]
NPT27	Others	Unspecified		Vmax	=	0.92	nM/mg*min	PMID[524461]
NPT27	Others	Unspecified		Ratio	=	0.96	n.a.	PMID[524461]
NPT27	Others	Unspecified		Km	=	70000.0	nM	PMID[524462]
NPT27	Others	Unspecified		Vmax	=	2.2	n.a.	PMID[524462]
NPT27	Others	Unspecified		Ratio	=	310.0	n.a.	PMID[524462]
NPT27	Others	Unspecified		Vmax	=	1.75	nM/mg*min	PMID[524463]
NPT27	Others	Unspecified		Vmax / Kmax100	=	1.62	n.a.	PMID[524463]
NPT2	Others	Unspecified		Ratio	=	1.7	n.a.	PMID[524465]
NPT2	Others	Unspecified		Ratio	=	1.8	n.a.	PMID[524466]
NPT2	Others	Unspecified		Vmax	=	0.92	nM/mg*min	PMID[524467]
NPT2	Others	Unspecified		Vmax / Kmax100	=	0.93	n.a.	PMID[524467]
NPT2	Others	Unspecified		Vmax	=	1.75	nM/mg*min	PMID[524468]
NPT2	Others	Unspecified		Vmax / Kmax100	=	1.62	n.a.	PMID[524468]
NPT2	Others	Unspecified		Ratio	=	3.1	n.a.	PMID[524471]

☑ 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 NPC20142 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	135
0.1-0.2	1491
0.2-0.3	7285
0.3-0.4	13872
0.4-0.5	14098
0.5-0.6	4710
0.6-0.7	929
0.7-0.8	145
0.8-0.85	14
0.85-0.9	6
0.9-0.95	4
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC215351
0.967	High Similarity	NPC290515
0.967	High Similarity	NPC164514
0.967	High Similarity	NPC303611
0.967	High Similarity	NPC226096
0.967	High Similarity	NPC108606
0.9362	High Similarity	NPC327226
0.9167	High Similarity	NPC150254
0.9167	High Similarity	NPC304761
0.9167	High Similarity	NPC226778
0.9167	High Similarity	NPC147000
0.8713	High Similarity	NPC290566
0.8713	High Similarity	NPC145638
0.866	High Similarity	NPC228400
0.866	High Similarity	NPC214200
0.8523	High Similarity	NPC117180
0.8427	Intermediate Similarity	NPC99394
0.8427	Intermediate Similarity	NPC329319
0.8427	Intermediate Similarity	NPC87299
0.8427	Intermediate Similarity	NPC103326
0.837	Intermediate Similarity	NPC211237
0.8367	Intermediate Similarity	NPC125732
0.83	Intermediate Similarity	NPC68055
0.8242	Intermediate Similarity	NPC304538
0.8224	Intermediate Similarity	NPC10286
0.8224	Intermediate Similarity	NPC213
0.8125	Intermediate Similarity	NPC265521
0.8073	Intermediate Similarity	NPC137096
0.8068	Intermediate Similarity	NPC66655
0.7961	Intermediate Similarity	NPC211551
0.7935	Intermediate Similarity	NPC172984
0.7857	Intermediate Similarity	NPC115627
0.7857	Intermediate Similarity	NPC118522
0.7857	Intermediate Similarity	NPC169207
0.783	Intermediate Similarity	NPC24777
0.7745	Intermediate Similarity	NPC29601
0.7742	Intermediate Similarity	NPC146703
0.7727	Intermediate Similarity	NPC108218
0.7717	Intermediate Similarity	NPC133050
0.7684	Intermediate Similarity	NPC93843
0.7664	Intermediate Similarity	NPC292758
0.7664	Intermediate Similarity	NPC65855
0.7634	Intermediate Similarity	NPC283012
0.7634	Intermediate Similarity	NPC475199
0.7629	Intermediate Similarity	NPC1793
0.7615	Intermediate Similarity	NPC146422
0.7609	Intermediate Similarity	NPC192623
0.7604	Intermediate Similarity	NPC198747
0.76	Intermediate Similarity	NPC58674
0.7573	Intermediate Similarity	NPC155847
0.7573	Intermediate Similarity	NPC289381
0.7544	Intermediate Similarity	NPC326232
0.75	Intermediate Similarity	NPC208302
0.75	Intermediate Similarity	NPC138117
0.75	Intermediate Similarity	NPC106551
0.75	Intermediate Similarity	NPC188867
0.75	Intermediate Similarity	NPC281686
0.75	Intermediate Similarity	NPC325292
0.7477	Intermediate Similarity	NPC186469
0.7475	Intermediate Similarity	NPC300017
0.7474	Intermediate Similarity	NPC168855
0.7453	Intermediate Similarity	NPC42383
0.7451	Intermediate Similarity	NPC10781
0.7451	Intermediate Similarity	NPC122493
0.7451	Intermediate Similarity	NPC293628
0.7449	Intermediate Similarity	NPC199567
0.7429	Intermediate Similarity	NPC178902
0.7411	Intermediate Similarity	NPC101139
0.7407	Intermediate Similarity	NPC97811
0.7396	Intermediate Similarity	NPC99482
0.7396	Intermediate Similarity	NPC474354
0.7395	Intermediate Similarity	NPC236347
0.7395	Intermediate Similarity	NPC323775
0.7391	Intermediate Similarity	NPC224544
0.7387	Intermediate Similarity	NPC474544
0.7387	Intermediate Similarity	NPC59387
0.7387	Intermediate Similarity	NPC1986
0.7386	Intermediate Similarity	NPC229235
0.7379	Intermediate Similarity	NPC107619
0.7353	Intermediate Similarity	NPC21959
0.7353	Intermediate Similarity	NPC313650
0.7353	Intermediate Similarity	NPC3371
0.732	Intermediate Similarity	NPC474211
0.7304	Intermediate Similarity	NPC283760
0.7304	Intermediate Similarity	NPC239697
0.73	Intermediate Similarity	NPC79917
0.7282	Intermediate Similarity	NPC33168
0.7282	Intermediate Similarity	NPC324569
0.7273	Intermediate Similarity	NPC104216
0.7253	Intermediate Similarity	NPC189371
0.725	Intermediate Similarity	NPC322366
0.7248	Intermediate Similarity	NPC153690
0.7245	Intermediate Similarity	NPC155393
0.7238	Intermediate Similarity	NPC316797
0.7234	Intermediate Similarity	NPC328178
0.7234	Intermediate Similarity	NPC164449
0.7234	Intermediate Similarity	NPC309279
0.7234	Intermediate Similarity	NPC184030
0.7232	Intermediate Similarity	NPC26524
0.7228	Intermediate Similarity	NPC128645
0.7222	Intermediate Similarity	NPC231705
0.7217	Intermediate Similarity	NPC142638
0.7217	Intermediate Similarity	NPC85276
0.7217	Intermediate Similarity	NPC317784
0.7212	Intermediate Similarity	NPC160548
0.7212	Intermediate Similarity	NPC210529
0.7212	Intermediate Similarity	NPC474073
0.7212	Intermediate Similarity	NPC175852
0.7207	Intermediate Similarity	NPC21890
0.7196	Intermediate Similarity	NPC224610
0.7196	Intermediate Similarity	NPC88267
0.7196	Intermediate Similarity	NPC113326
0.7196	Intermediate Similarity	NPC194390
0.7182	Intermediate Similarity	NPC258056
0.7182	Intermediate Similarity	NPC172046
0.7172	Intermediate Similarity	NPC407
0.7172	Intermediate Similarity	NPC307235
0.7172	Intermediate Similarity	NPC23167
0.717	Intermediate Similarity	NPC318154
0.7168	Intermediate Similarity	NPC115803
0.7159	Intermediate Similarity	NPC78954
0.7159	Intermediate Similarity	NPC82770
0.7159	Intermediate Similarity	NPC239931
0.7156	Intermediate Similarity	NPC142297
0.7154	Intermediate Similarity	NPC326599
0.7154	Intermediate Similarity	NPC329595
0.7143	Intermediate Similarity	NPC216468
0.7143	Intermediate Similarity	NPC113000
0.7143	Intermediate Similarity	NPC51333
0.7143	Intermediate Similarity	NPC122327
0.7143	Intermediate Similarity	NPC78119
0.7143	Intermediate Similarity	NPC175313
0.7143	Intermediate Similarity	NPC112609
0.7143	Intermediate Similarity	NPC132078
0.7129	Intermediate Similarity	NPC300478
0.7129	Intermediate Similarity	NPC312304
0.7129	Intermediate Similarity	NPC47950
0.7129	Intermediate Similarity	NPC226438
0.7128	Intermediate Similarity	NPC469894
0.7117	Intermediate Similarity	NPC474149
0.71	Intermediate Similarity	NPC25493
0.71	Intermediate Similarity	NPC470877
0.71	Intermediate Similarity	NPC27974
0.71	Intermediate Similarity	NPC113460
0.7097	Intermediate Similarity	NPC208757
0.7091	Intermediate Similarity	NPC24101
0.7091	Intermediate Similarity	NPC96224
0.7083	Intermediate Similarity	NPC474479
0.7083	Intermediate Similarity	NPC121478
0.7083	Intermediate Similarity	NPC73637
0.7075	Intermediate Similarity	NPC469481
0.7075	Intermediate Similarity	NPC294741
0.7075	Intermediate Similarity	NPC469457
0.7075	Intermediate Similarity	NPC213730
0.7071	Intermediate Similarity	NPC197783
0.7065	Intermediate Similarity	NPC276699
0.7054	Intermediate Similarity	NPC269340
0.7043	Intermediate Similarity	NPC2265
0.7041	Intermediate Similarity	NPC265146
0.7034	Intermediate Similarity	NPC326079
0.703	Intermediate Similarity	NPC141139
0.703	Intermediate Similarity	NPC121872
0.703	Intermediate Similarity	NPC78041
0.703	Intermediate Similarity	NPC123273
0.703	Intermediate Similarity	NPC172128
0.703	Intermediate Similarity	NPC316108
0.703	Intermediate Similarity	NPC280347
0.703	Intermediate Similarity	NPC159178
0.703	Intermediate Similarity	NPC258219
0.703	Intermediate Similarity	NPC318325
0.703	Intermediate Similarity	NPC242240
0.703	Intermediate Similarity	NPC74936
0.703	Intermediate Similarity	NPC471307
0.703	Intermediate Similarity	NPC177420
0.703	Intermediate Similarity	NPC209764
0.703	Intermediate Similarity	NPC258627
0.7018	Intermediate Similarity	NPC118202
0.7009	Intermediate Similarity	NPC91461
0.7009	Intermediate Similarity	NPC40258
0.7009	Intermediate Similarity	NPC7686
0.7	Intermediate Similarity	NPC13020
0.7	Intermediate Similarity	NPC37584
0.7	Intermediate Similarity	NPC140359
0.7	Intermediate Similarity	NPC307020
0.7	Intermediate Similarity	NPC304760
0.6989	Remote Similarity	NPC139658
0.6981	Remote Similarity	NPC128723
0.6979	Remote Similarity	NPC165212
0.6975	Remote Similarity	NPC27581
0.6975	Remote Similarity	NPC474862
0.6972	Remote Similarity	NPC67043
0.697	Remote Similarity	NPC248817
0.697	Remote Similarity	NPC286904
0.697	Remote Similarity	NPC203076
0.6961	Remote Similarity	NPC55561
0.6961	Remote Similarity	NPC192
0.6957	Remote Similarity	NPC317254
0.6952	Remote Similarity	NPC289201
0.6944	Remote Similarity	NPC82426
0.6944	Remote Similarity	NPC91820

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 NPC20142 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	126
0.1-0.2	659
0.2-0.3	1159
0.3-0.4	2803
0.4-0.5	2516
0.5-0.6	1382
0.6-0.7	410
0.7-0.8	76
0.8-0.85	10
0.85-0.9	4
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.967	High Similarity	NPD9609	Approved
0.967	High Similarity	NPD9612	Approved
0.967	High Similarity	NPD9611	Approved
0.9167	High Similarity	NPD311	Approved
0.9167	High Similarity	NPD314	Approved
0.9167	High Similarity	NPD10	Approved
0.9167	High Similarity	NPD309	Approved
0.9167	High Similarity	NPD310	Approved
0.9167	High Similarity	NPD315	Approved
0.8713	High Similarity	NPD9380	Clinical (unspecified phase)
0.8571	High Similarity	NPD854	Approved
0.8571	High Similarity	NPD855	Approved
0.8302	Intermediate Similarity	NPD9618	Approved
0.8302	Intermediate Similarity	NPD9614	Approved
0.8218	Intermediate Similarity	NPD9608	Approved
0.8218	Intermediate Similarity	NPD9610	Approved
0.8073	Intermediate Similarity	NPD9613	Approved
0.8073	Intermediate Similarity	NPD9615	Approved
0.8073	Intermediate Similarity	NPD317	Approved
0.8073	Intermediate Similarity	NPD9616	Approved
0.8073	Intermediate Similarity	NPD16	Approved
0.8073	Intermediate Similarity	NPD856	Approved
0.8073	Intermediate Similarity	NPD828	Approved
0.8073	Intermediate Similarity	NPD318	Approved
0.8068	Intermediate Similarity	NPD9294	Approved
0.8	Intermediate Similarity	NPD316	Approved
0.8	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD1710	Approved
0.7857	Intermediate Similarity	NPD9384	Approved
0.7857	Intermediate Similarity	NPD9381	Approved
0.783	Intermediate Similarity	NPD550	Approved
0.783	Intermediate Similarity	NPD551	Approved
0.7757	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD2561	Approved
0.7652	Intermediate Similarity	NPD4273	Approved
0.7652	Intermediate Similarity	NPD2562	Approved
0.7615	Intermediate Similarity	NPD9379	Approved
0.7615	Intermediate Similarity	NPD9377	Approved
0.7586	Intermediate Similarity	NPD9622	Approved
0.7576	Intermediate Similarity	NPD1812	Approved
0.7576	Intermediate Similarity	NPD1814	Approved
0.7547	Intermediate Similarity	NPD2551	Approved
0.7547	Intermediate Similarity	NPD2559	Approved
0.7521	Intermediate Similarity	NPD9587	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4818	Approved
0.75	Intermediate Similarity	NPD9568	Approved
0.75	Intermediate Similarity	NPD4817	Approved
0.75	Intermediate Similarity	NPD3719	Approved
0.75	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3718	Approved
0.7458	Intermediate Similarity	NPD1129	Approved
0.7458	Intermediate Similarity	NPD1131	Approved
0.7458	Intermediate Similarity	NPD1134	Approved
0.7458	Intermediate Similarity	NPD1135	Approved
0.7458	Intermediate Similarity	NPD1133	Approved
0.7456	Intermediate Similarity	NPD770	Discontinued
0.7451	Intermediate Similarity	NPD9566	Approved
0.7429	Intermediate Similarity	NPD4231	Approved
0.7429	Intermediate Similarity	NPD4656	Approved
0.7429	Intermediate Similarity	NPD4658	Approved
0.7429	Intermediate Similarity	NPD3681	Approved
0.7429	Intermediate Similarity	NPD3683	Approved
0.7429	Intermediate Similarity	NPD4229	Approved
0.7429	Intermediate Similarity	NPD3682	Approved
0.7429	Intermediate Similarity	NPD3680	Approved
0.7395	Intermediate Similarity	NPD9621	Approved
0.7395	Intermediate Similarity	NPD9620	Approved
0.7395	Intermediate Similarity	NPD9619	Approved
0.7383	Intermediate Similarity	NPD811	Approved
0.7383	Intermediate Similarity	NPD812	Approved
0.7383	Intermediate Similarity	NPD810	Approved
0.7358	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD2235	Phase 2
0.735	Intermediate Similarity	NPD2231	Phase 2
0.7345	Intermediate Similarity	NPD5500	Discontinued
0.7333	Intermediate Similarity	NPD4719	Phase 2
0.7315	Intermediate Similarity	NPD9532	Phase 3
0.7273	Intermediate Similarity	NPD4253	Approved
0.7273	Intermediate Similarity	NPD600	Approved
0.7273	Intermediate Similarity	NPD4254	Approved
0.7273	Intermediate Similarity	NPD596	Approved
0.725	Intermediate Similarity	NPD858	Approved
0.725	Intermediate Similarity	NPD599	Approved
0.725	Intermediate Similarity	NPD558	Phase 2
0.725	Intermediate Similarity	NPD859	Approved
0.725	Intermediate Similarity	NPD602	Approved
0.7238	Intermediate Similarity	NPD2558	Approved
0.7238	Intermediate Similarity	NPD2550	Approved
0.7238	Intermediate Similarity	NPD2552	Approved
0.7238	Intermediate Similarity	NPD2555	Approved
0.7238	Intermediate Similarity	NPD2549	Approved
0.7238	Intermediate Similarity	NPD2553	Approved
0.7222	Intermediate Similarity	NPD1445	Approved
0.7222	Intermediate Similarity	NPD1444	Approved
0.7212	Intermediate Similarity	NPD253	Approved
0.7212	Intermediate Similarity	NPD9495	Approved
0.7207	Intermediate Similarity	NPD9508	Approved
0.717	Intermediate Similarity	NPD4188	Approved
0.717	Intermediate Similarity	NPD4189	Approved
0.7154	Intermediate Similarity	NPD601	Approved
0.7154	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD597	Approved
0.7154	Intermediate Similarity	NPD865	Approved
0.7154	Intermediate Similarity	NPD864	Approved
0.7154	Intermediate Similarity	NPD598	Approved
0.7143	Intermediate Similarity	NPD9593	Approved
0.7143	Intermediate Similarity	NPD9588	Approved
0.7143	Intermediate Similarity	NPD9592	Approved
0.7143	Intermediate Similarity	NPD9590	Approved
0.7143	Intermediate Similarity	NPD9594	Approved
0.7143	Intermediate Similarity	NPD80	Approved
0.7143	Intermediate Similarity	NPD9589	Approved
0.7143	Intermediate Similarity	NPD9712	Approved
0.7143	Intermediate Similarity	NPD9591	Approved
0.7119	Intermediate Similarity	NPD3974	Phase 2
0.7105	Intermediate Similarity	NPD255	Approved
0.7105	Intermediate Similarity	NPD256	Approved
0.7105	Intermediate Similarity	NPD7508	Discontinued
0.7097	Intermediate Similarity	NPD1132	Approved
0.7097	Intermediate Similarity	NPD1130	Approved
0.7097	Intermediate Similarity	NPD1136	Approved
0.7097	Intermediate Similarity	NPD829	Discontinued
0.7097	Intermediate Similarity	NPD6407	Approved
0.7097	Intermediate Similarity	NPD6405	Approved
0.7094	Intermediate Similarity	NPD5723	Approved
0.7091	Intermediate Similarity	NPD4717	Approved
0.7091	Intermediate Similarity	NPD4718	Approved
0.7091	Intermediate Similarity	NPD4720	Approved
0.7073	Intermediate Similarity	NPD3136	Phase 2
0.7071	Intermediate Similarity	NPD9538	Approved
0.7064	Intermediate Similarity	NPD3526	Approved
0.7064	Intermediate Similarity	NPD3524	Approved
0.7059	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD9710	Approved
0.7048	Intermediate Similarity	NPD9711	Approved
0.704	Intermediate Similarity	NPD3062	Approved
0.704	Intermediate Similarity	NPD3059	Approved
0.704	Intermediate Similarity	NPD3061	Approved
0.7037	Intermediate Similarity	NPD3046	Approved
0.7037	Intermediate Similarity	NPD3048	Approved
0.7037	Intermediate Similarity	NPD3047	Approved
0.7027	Intermediate Similarity	NPD9713	Approved
0.7027	Intermediate Similarity	NPD1792	Phase 2
0.7018	Intermediate Similarity	NPD593	Approved
0.7018	Intermediate Similarity	NPD595	Approved
0.7	Intermediate Similarity	NPD6406	Approved
0.7	Intermediate Similarity	NPD531	Approved
0.7	Intermediate Similarity	NPD4659	Approved
0.696	Remote Similarity	NPD839	Approved
0.696	Remote Similarity	NPD840	Approved
0.6949	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7725	Approved
0.6944	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD196	Phase 1
0.6935	Remote Similarity	NPD3720	Discontinued
0.6935	Remote Similarity	NPD4274	Approved
0.6935	Remote Similarity	NPD4275	Approved
0.693	Remote Similarity	NPD2229	Approved
0.693	Remote Similarity	NPD2234	Approved
0.693	Remote Similarity	NPD2228	Approved
0.6929	Remote Similarity	NPD817	Approved
0.6929	Remote Similarity	NPD3052	Approved
0.6929	Remote Similarity	NPD5314	Approved
0.6929	Remote Similarity	NPD2568	Approved
0.6929	Remote Similarity	NPD3054	Approved
0.6929	Remote Similarity	NPD823	Approved
0.6929	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2217	Approved
0.6923	Remote Similarity	NPD2218	Phase 2
0.6923	Remote Similarity	NPD4814	Discontinued
0.6923	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2500	Approved
0.6903	Remote Similarity	NPD2499	Approved
0.6897	Remote Similarity	NPD3123	Discovery
0.6893	Remote Similarity	NPD6690	Approved
0.6891	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD9273	Approved
0.6885	Remote Similarity	NPD4103	Phase 2
0.6885	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD1237	Approved
0.6875	Remote Similarity	NPD3554	Approved
0.6875	Remote Similarity	NPD3553	Approved
0.6875	Remote Similarity	NPD3552	Approved
0.6875	Remote Similarity	NPD3555	Approved
0.687	Remote Similarity	NPD1793	Approved
0.687	Remote Similarity	NPD1791	Approved
0.6869	Remote Similarity	NPD111	Approved
0.6852	Remote Similarity	NPD4119	Approved
0.6842	Remote Similarity	NPD9564	Approved
0.6842	Remote Similarity	NPD9563	Approved
0.6842	Remote Similarity	NPD296	Approved
0.6842	Remote Similarity	NPD9397	Approved
0.6842	Remote Similarity	NPD293	Approved
0.6842	Remote Similarity	NPD9393	Approved
0.6842	Remote Similarity	NPD79	Approved
0.6842	Remote Similarity	NPD295	Approved
0.6833	Remote Similarity	NPD3381	Discontinued
0.6833	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5350	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