NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	151.1
Volume:	167.541
LogP:	0.653
LogD:	0.761
LogS:	-0.521
# 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:	0.664
Synthetic Accessibility Score:	2.459
Fsp3:	0.333
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:	-5.016
MDCK Permeability:	0.00041594391223043203
Pgp-inhibitor:	0.0
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.331
Plasma Protein Binding (PPB):	14.943376541137695%
Volume Distribution (VD):	2.193
Pgp-substrate:	78.76326751708984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.187
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.094
CYP2D6-inhibitor:	0.536
CYP2D6-substrate:	0.851
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	7.638
Half-life (T1/2):	0.467

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.675
Maximum Recommended Daily Dose:	0.11
Skin Sensitization:	0.079
Carcinogencity:	0.036
Eye Corrosion:	0.004
Eye Irritation:	0.03
Respiratory Toxicity:	0.704

Download Data

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

Natural Product: NPC164514

Natural Product ID:	NPC164514
*Common Name:**	Phenylpropanolamine
IUPAC Name:	2-amino-1-phenylpropan-1-ol
Synonyms:	Phenylpropanolamine
Standard InCHIKey:	DLNKOYKMWOXYQA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3
SMILES:	OC(c1ccccc1)C(N)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL61006
PubChem CID:	4786
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12088434]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21465337]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21707257]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19472	Thymus vulgaris	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
EC50	3
Ki	8
Others	24

Activity Type	# Activity
Individual Protein	22
NON-MOLECULAR	1
Organism	4
Others	5
SELECTIVITY GROUP	4
TISSUE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT219	Individual Protein	Alpha-1a adrenergic receptor	Rattus norvegicus	Ki	=	9772.37	nM	PMID[568785]
NPT4554	Individual Protein	Alpha-1b adrenergic receptor	Mesocricetus auratus	Ki	=	9549.93	nM	PMID[568785]
NPT3048	Individual Protein	Alpha-1d adrenergic receptor	Rattus norvegicus	Ki	=	8511.38	nM	PMID[568785]
NPT4893	Individual Protein	Alpha-1a adrenergic receptor	Oryctolagus cuniculus	pD2	=	3.63	n.a.	PMID[568785]
NPT4893	Individual Protein	Alpha-1a adrenergic receptor	Oryctolagus cuniculus	Efficacy	=	68.0	%	PMID[568785]
NPT220	Individual Protein	Alpha-1b adrenergic receptor	Rattus norvegicus	pD2	=	3.55	n.a.	PMID[568785]
NPT220	Individual Protein	Alpha-1b adrenergic receptor	Rattus norvegicus	Efficacy	=	34.0	%	PMID[568785]
NPT3048	Individual Protein	Alpha-1d adrenergic receptor	Rattus norvegicus	pD2	=	4.12	n.a.	PMID[568785]
NPT3048	Individual Protein	Alpha-1d adrenergic receptor	Rattus norvegicus	Efficacy	=	91.0	%	PMID[568785]
NPT222	Individual Protein	Alpha-2a adrenergic receptor	Homo sapiens	Ki	=	275.42	nM	PMID[568785]
NPT3059	Individual Protein	Alpha-2b adrenergic receptor	Rattus norvegicus	Ki	=	263.03	nM	PMID[568785]
NPT4894	Individual Protein	Alpha-2a adrenergic receptor	Rattus norvegicus	pD2	=	5.17	n.a.	PMID[568785]
NPT4894	Individual Protein	Alpha-2a adrenergic receptor	Rattus norvegicus	Efficacy	=	85.0	%	PMID[568785]
NPT3048	Individual Protein	Alpha-1d adrenergic receptor	Rattus norvegicus	Efficacy	=	91.0	%	PMID[568786]
NPT3048	Individual Protein	Alpha-1d adrenergic receptor	Rattus norvegicus	EC50	=	75857.76	nM	PMID[568786]
NPT220	Individual Protein	Alpha-1b adrenergic receptor	Rattus norvegicus	Efficacy	=	34.0	%	PMID[568786]
NPT220	Individual Protein	Alpha-1b adrenergic receptor	Rattus norvegicus	EC50	=	281838.29	nM	PMID[568786]
NPT4893	Individual Protein	Alpha-1a adrenergic receptor	Oryctolagus cuniculus	Efficacy	=	68.0	%	PMID[568786]
NPT4893	Individual Protein	Alpha-1a adrenergic receptor	Oryctolagus cuniculus	EC50	=	234422.88	nM	PMID[568786]
NPT3048	Individual Protein	Alpha-1d adrenergic receptor	Rattus norvegicus	Ki	=	8511.38	nM	PMID[568786]
NPT4554	Individual Protein	Alpha-1b adrenergic receptor	Mesocricetus auratus	Ki	=	9549.93	nM	PMID[568786]
NPT219	Individual Protein	Alpha-1a adrenergic receptor	Rattus norvegicus	Ki	=	9772.37	nM	PMID[568786]
NPT2	Others	Unspecified		Selectivity	=	1.0	n.a.	PMID[568785]
NPT2	Others	Unspecified		Selectivity	=	0.2	n.a.	PMID[568785]
NPT2	Others	Unspecified		Selectivity	=	0.03	n.a.	PMID[568785]
NPT1016	Organism	Canis familiaris	Canis lupus familiaris	ED delta5	=	1100.0	nM kg-1	PMID[568785]
NPT1016	Organism	Canis familiaris	Canis lupus familiaris	ED delta20	=	330.0	nM kg-1	PMID[568785]
NPT1016	Organism	Canis familiaris	Canis lupus familiaris	Ratio	=	0.4	n.a.	PMID[568785]
NPT1016	Organism	Canis familiaris	Canis lupus familiaris	Selectivity Index	=	0.4	n.a.	PMID[568786]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	66.0	%	PMID[568787]
NPT28178	SELECTIVITY GROUP	Alpha adrenergic receptor 1A and 1B	Rattus norvegicus	Selectivity	=	1.0	n.a.	PMID[568785]
NPT28179	SELECTIVITY GROUP	Alpha adrenergic receptor 1A and 1D	Rattus norvegicus	Selectivity	=	1.0	n.a.	PMID[568785]
NPT28180	TISSUE	Vas deferens	Rattus norvegicus	Activity	<	5.0	%	PMID[568787]

☑ 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 NPC164514 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	110
0.1-0.2	1257
0.2-0.3	7028
0.3-0.4	13880
0.4-0.5	14395
0.5-0.6	4924
0.6-0.7	938
0.7-0.8	134
0.8-0.85	15
0.85-0.9	3
0.9-0.95	5
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC108606
1.0	High Similarity	NPC303611
1.0	High Similarity	NPC226096
1.0	High Similarity	NPC290515
0.967	High Similarity	NPC20142
0.967	High Similarity	NPC215351
0.9479	High Similarity	NPC226778
0.9479	High Similarity	NPC147000
0.9479	High Similarity	NPC304761
0.9479	High Similarity	NPC150254
0.9271	High Similarity	NPC327226
0.8969	High Similarity	NPC214200
0.8969	High Similarity	NPC228400
0.8462	Intermediate Similarity	NPC290566
0.8462	Intermediate Similarity	NPC145638
0.8352	Intermediate Similarity	NPC87299
0.8352	Intermediate Similarity	NPC99394
0.8352	Intermediate Similarity	NPC103326
0.8352	Intermediate Similarity	NPC329319
0.8242	Intermediate Similarity	NPC117180
0.8172	Intermediate Similarity	NPC304538
0.8165	Intermediate Similarity	NPC213
0.8165	Intermediate Similarity	NPC10286
0.8119	Intermediate Similarity	NPC125732
0.8113	Intermediate Similarity	NPC24777
0.8105	Intermediate Similarity	NPC211237
0.8077	Intermediate Similarity	NPC211551
0.8058	Intermediate Similarity	NPC68055
0.8018	Intermediate Similarity	NPC137096
0.7944	Intermediate Similarity	NPC65855
0.7944	Intermediate Similarity	NPC292758
0.7879	Intermediate Similarity	NPC265521
0.7872	Intermediate Similarity	NPC172984
0.7802	Intermediate Similarity	NPC66655
0.7685	Intermediate Similarity	NPC97811
0.766	Intermediate Similarity	NPC133050
0.7652	Intermediate Similarity	NPC118522
0.7652	Intermediate Similarity	NPC169207
0.7652	Intermediate Similarity	NPC115627
0.7629	Intermediate Similarity	NPC93843
0.7611	Intermediate Similarity	NPC106551
0.7611	Intermediate Similarity	NPC281686
0.7611	Intermediate Similarity	NPC188867
0.7576	Intermediate Similarity	NPC1793
0.7573	Intermediate Similarity	NPC10781
0.7573	Intermediate Similarity	NPC122493
0.7573	Intermediate Similarity	NPC293628
0.7565	Intermediate Similarity	NPC283760
0.7551	Intermediate Similarity	NPC198747
0.7549	Intermediate Similarity	NPC58674
0.7524	Intermediate Similarity	NPC289381
0.7524	Intermediate Similarity	NPC29601
0.7524	Intermediate Similarity	NPC155847
0.7522	Intermediate Similarity	NPC101139
0.75	Intermediate Similarity	NPC474544
0.75	Intermediate Similarity	NPC1986
0.75	Intermediate Similarity	NPC146703
0.75	Intermediate Similarity	NPC26524
0.7477	Intermediate Similarity	NPC88267
0.7477	Intermediate Similarity	NPC21890
0.7477	Intermediate Similarity	NPC194390
0.7477	Intermediate Similarity	NPC224610
0.7477	Intermediate Similarity	NPC113326
0.7473	Intermediate Similarity	NPC112609
0.7473	Intermediate Similarity	NPC113000
0.7473	Intermediate Similarity	NPC108218
0.7473	Intermediate Similarity	NPC122327
0.7451	Intermediate Similarity	NPC325292
0.7451	Intermediate Similarity	NPC138117
0.7431	Intermediate Similarity	NPC186469
0.7423	Intermediate Similarity	NPC168855
0.7414	Intermediate Similarity	NPC239697
0.7411	Intermediate Similarity	NPC146422
0.7407	Intermediate Similarity	NPC42383
0.7404	Intermediate Similarity	NPC324569
0.7396	Intermediate Similarity	NPC475199
0.7396	Intermediate Similarity	NPC283012
0.7383	Intermediate Similarity	NPC178902
0.7368	Intermediate Similarity	NPC192623
0.7355	Intermediate Similarity	NPC236347
0.7355	Intermediate Similarity	NPC322366
0.7355	Intermediate Similarity	NPC323775
0.735	Intermediate Similarity	NPC326232
0.7347	Intermediate Similarity	NPC474354
0.734	Intermediate Similarity	NPC224544
0.7328	Intermediate Similarity	NPC317784
0.7328	Intermediate Similarity	NPC142638
0.7321	Intermediate Similarity	NPC269340
0.7308	Intermediate Similarity	NPC313650
0.7304	Intermediate Similarity	NPC2265
0.7281	Intermediate Similarity	NPC118202
0.7273	Intermediate Similarity	NPC474211
0.7255	Intermediate Similarity	NPC226438
0.7255	Intermediate Similarity	NPC79917
0.7255	Intermediate Similarity	NPC300017
0.7253	Intermediate Similarity	NPC208302
0.725	Intermediate Similarity	NPC307020
0.7248	Intermediate Similarity	NPC67043
0.7234	Intermediate Similarity	NPC98269
0.7234	Intermediate Similarity	NPC290638
0.7234	Intermediate Similarity	NPC325662
0.7228	Intermediate Similarity	NPC199567
0.7227	Intermediate Similarity	NPC474862
0.7217	Intermediate Similarity	NPC317254
0.7212	Intermediate Similarity	NPC303045
0.7212	Intermediate Similarity	NPC161972
0.7204	Intermediate Similarity	NPC189371
0.72	Intermediate Similarity	NPC208757
0.7196	Intermediate Similarity	NPC316797
0.7193	Intermediate Similarity	NPC59387
0.719	Intermediate Similarity	NPC474479
0.7188	Intermediate Similarity	NPC328178
0.7182	Intermediate Similarity	NPC231705
0.7182	Intermediate Similarity	NPC327481
0.7179	Intermediate Similarity	NPC85276
0.7179	Intermediate Similarity	NPC314992
0.7172	Intermediate Similarity	NPC99482
0.717	Intermediate Similarity	NPC107619
0.717	Intermediate Similarity	NPC474073
0.7157	Intermediate Similarity	NPC316108
0.7143	Intermediate Similarity	NPC21959
0.7143	Intermediate Similarity	NPC229235
0.7143	Intermediate Similarity	NPC3371
0.7143	Intermediate Similarity	NPC258056
0.7143	Intermediate Similarity	NPC326079
0.7143	Intermediate Similarity	NPC25565
0.713	Intermediate Similarity	NPC318154
0.7129	Intermediate Similarity	NPC407
0.7129	Intermediate Similarity	NPC307235
0.7129	Intermediate Similarity	NPC23167
0.712	Intermediate Similarity	NPC329595
0.712	Intermediate Similarity	NPC326599
0.7117	Intermediate Similarity	NPC142297
0.7083	Intermediate Similarity	NPC27581
0.7083	Intermediate Similarity	NPC469894
0.708	Intermediate Similarity	NPC474149
0.7075	Intermediate Similarity	NPC33168
0.7075	Intermediate Similarity	NPC475439
0.7075	Intermediate Similarity	NPC473501
0.7064	Intermediate Similarity	NPC164859
0.7059	Intermediate Similarity	NPC190663
0.7059	Intermediate Similarity	NPC25493
0.7059	Intermediate Similarity	NPC27974
0.7059	Intermediate Similarity	NPC113460
0.7059	Intermediate Similarity	NPC104216
0.7059	Intermediate Similarity	NPC470877
0.7054	Intermediate Similarity	NPC153690
0.7037	Intermediate Similarity	NPC469481
0.703	Intermediate Similarity	NPC197783
0.703	Intermediate Similarity	NPC155393
0.7021	Intermediate Similarity	NPC276699
0.7019	Intermediate Similarity	NPC128645
0.7016	Intermediate Similarity	NPC469666
0.701	Intermediate Similarity	NPC164449
0.701	Intermediate Similarity	NPC184030
0.701	Intermediate Similarity	NPC309279
0.7009	Intermediate Similarity	NPC160548
0.7009	Intermediate Similarity	NPC175852
0.7009	Intermediate Similarity	NPC82963
0.7009	Intermediate Similarity	NPC210529
0.6992	Remote Similarity	NPC141739
0.6992	Remote Similarity	NPC320242
0.6992	Remote Similarity	NPC136112
0.6991	Remote Similarity	NPC172046
0.699	Remote Similarity	NPC209764
0.699	Remote Similarity	NPC159178
0.699	Remote Similarity	NPC471307
0.699	Remote Similarity	NPC258219
0.699	Remote Similarity	NPC78041
0.699	Remote Similarity	NPC74936
0.699	Remote Similarity	NPC177420
0.699	Remote Similarity	NPC242240
0.699	Remote Similarity	NPC123273
0.699	Remote Similarity	NPC141139
0.699	Remote Similarity	NPC280347
0.699	Remote Similarity	NPC318325
0.699	Remote Similarity	NPC121872
0.6983	Remote Similarity	NPC115803
0.6975	Remote Similarity	NPC319950
0.6967	Remote Similarity	NPC285394
0.6967	Remote Similarity	NPC140359
0.6967	Remote Similarity	NPC13020
0.6964	Remote Similarity	NPC37584
0.6961	Remote Similarity	NPC304760
0.6949	Remote Similarity	NPC311737
0.6949	Remote Similarity	NPC38458
0.6947	Remote Similarity	NPC139658
0.6947	Remote Similarity	NPC168861
0.6944	Remote Similarity	NPC132078
0.6944	Remote Similarity	NPC78119
0.6944	Remote Similarity	NPC12730
0.6944	Remote Similarity	NPC128723
0.6944	Remote Similarity	NPC216468
0.6944	Remote Similarity	NPC51333
0.6942	Remote Similarity	NPC160493
0.6931	Remote Similarity	NPC248817
0.6931	Remote Similarity	NPC175313
0.6931	Remote Similarity	NPC286904
0.6929	Remote Similarity	NPC88667
0.6923	Remote Similarity	NPC78954

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 NPC164514 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	111
0.1-0.2	604
0.2-0.3	1093
0.3-0.4	2701
0.4-0.5	2619
0.5-0.6	1449
0.6-0.7	466
0.7-0.8	87
0.8-0.85	9
0.85-0.9	4
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD9611	Approved
1.0	High Similarity	NPD9609	Approved
1.0	High Similarity	NPD9612	Approved
0.9479	High Similarity	NPD310	Approved
0.9479	High Similarity	NPD311	Approved
0.9479	High Similarity	NPD314	Approved
0.9479	High Similarity	NPD10	Approved
0.9479	High Similarity	NPD309	Approved
0.9479	High Similarity	NPD315	Approved
0.8878	High Similarity	NPD854	Approved
0.8878	High Similarity	NPD855	Approved
0.8585	High Similarity	NPD9618	Approved
0.8585	High Similarity	NPD9614	Approved
0.8515	High Similarity	NPD9608	Approved
0.8515	High Similarity	NPD9610	Approved
0.8462	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.8349	Intermediate Similarity	NPD317	Approved
0.8349	Intermediate Similarity	NPD318	Approved
0.8273	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD1710	Approved
0.8182	Intermediate Similarity	NPD828	Approved
0.8113	Intermediate Similarity	NPD550	Approved
0.8113	Intermediate Similarity	NPD551	Approved
0.8018	Intermediate Similarity	NPD9613	Approved
0.8018	Intermediate Similarity	NPD9615	Approved
0.8018	Intermediate Similarity	NPD16	Approved
0.8018	Intermediate Similarity	NPD9616	Approved
0.8018	Intermediate Similarity	NPD856	Approved
0.7946	Intermediate Similarity	NPD316	Approved
0.7913	Intermediate Similarity	NPD2561	Approved
0.7913	Intermediate Similarity	NPD4273	Approved
0.7913	Intermediate Similarity	NPD2562	Approved
0.7879	Intermediate Similarity	NPD1812	Approved
0.7879	Intermediate Similarity	NPD1814	Approved
0.7845	Intermediate Similarity	NPD9622	Approved
0.7802	Intermediate Similarity	NPD9294	Approved
0.7768	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD770	Discontinued
0.7664	Intermediate Similarity	NPD810	Approved
0.7664	Intermediate Similarity	NPD812	Approved
0.7664	Intermediate Similarity	NPD811	Approved
0.7652	Intermediate Similarity	NPD9384	Approved
0.7652	Intermediate Similarity	NPD9381	Approved
0.7627	Intermediate Similarity	NPD9587	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD3719	Approved
0.7624	Intermediate Similarity	NPD3718	Approved
0.7619	Intermediate Similarity	NPD4719	Phase 2
0.7611	Intermediate Similarity	NPD9568	Approved
0.7573	Intermediate Similarity	NPD9566	Approved
0.7563	Intermediate Similarity	NPD1133	Approved
0.7563	Intermediate Similarity	NPD1134	Approved
0.7563	Intermediate Similarity	NPD1135	Approved
0.7563	Intermediate Similarity	NPD1129	Approved
0.7563	Intermediate Similarity	NPD1131	Approved
0.7545	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD596	Approved
0.7521	Intermediate Similarity	NPD600	Approved
0.75	Intermediate Similarity	NPD2559	Approved
0.75	Intermediate Similarity	NPD2551	Approved
0.75	Intermediate Similarity	NPD599	Approved
0.75	Intermediate Similarity	NPD602	Approved
0.7473	Intermediate Similarity	NPD9589	Approved
0.7473	Intermediate Similarity	NPD9590	Approved
0.7473	Intermediate Similarity	NPD9593	Approved
0.7473	Intermediate Similarity	NPD80	Approved
0.7473	Intermediate Similarity	NPD9591	Approved
0.7473	Intermediate Similarity	NPD9592	Approved
0.7473	Intermediate Similarity	NPD9588	Approved
0.7473	Intermediate Similarity	NPD9594	Approved
0.7453	Intermediate Similarity	NPD4817	Approved
0.7453	Intermediate Similarity	NPD4818	Approved
0.7411	Intermediate Similarity	NPD9379	Approved
0.7411	Intermediate Similarity	NPD9377	Approved
0.7398	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD598	Approved
0.7398	Intermediate Similarity	NPD601	Approved
0.7398	Intermediate Similarity	NPD864	Approved
0.7398	Intermediate Similarity	NPD865	Approved
0.7398	Intermediate Similarity	NPD597	Approved
0.7368	Intermediate Similarity	NPD7508	Discontinued
0.7355	Intermediate Similarity	NPD858	Approved
0.7355	Intermediate Similarity	NPD9620	Approved
0.7355	Intermediate Similarity	NPD9621	Approved
0.7355	Intermediate Similarity	NPD9619	Approved
0.7355	Intermediate Similarity	NPD859	Approved
0.7339	Intermediate Similarity	NPD1130	Approved
0.7339	Intermediate Similarity	NPD1136	Approved
0.7339	Intermediate Similarity	NPD1132	Approved
0.7317	Intermediate Similarity	NPD3136	Phase 2
0.7315	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD593	Approved
0.7281	Intermediate Similarity	NPD595	Approved
0.725	Intermediate Similarity	NPD4659	Approved
0.7232	Intermediate Similarity	NPD4254	Approved
0.7232	Intermediate Similarity	NPD4253	Approved
0.7222	Intermediate Similarity	NPD3681	Approved
0.7222	Intermediate Similarity	NPD3683	Approved
0.7222	Intermediate Similarity	NPD3682	Approved
0.7222	Intermediate Similarity	NPD4231	Approved
0.7222	Intermediate Similarity	NPD4229	Approved
0.7222	Intermediate Similarity	NPD4658	Approved
0.7222	Intermediate Similarity	NPD4656	Approved
0.7222	Intermediate Similarity	NPD3680	Approved
0.7217	Intermediate Similarity	NPD256	Approved
0.7217	Intermediate Similarity	NPD255	Approved
0.72	Intermediate Similarity	NPD829	Discontinued
0.7196	Intermediate Similarity	NPD2555	Approved
0.7196	Intermediate Similarity	NPD2553	Approved
0.7196	Intermediate Similarity	NPD2558	Approved
0.7196	Intermediate Similarity	NPD2550	Approved
0.7196	Intermediate Similarity	NPD2552	Approved
0.7196	Intermediate Similarity	NPD2549	Approved
0.7184	Intermediate Similarity	NPD6690	Approved
0.7182	Intermediate Similarity	NPD1445	Approved
0.7182	Intermediate Similarity	NPD1444	Approved
0.7179	Intermediate Similarity	NPD2217	Approved
0.7179	Intermediate Similarity	NPD2218	Phase 2
0.7167	Intermediate Similarity	NPD2231	Phase 2
0.7167	Intermediate Similarity	NPD2235	Phase 2
0.7165	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2568	Approved
0.7165	Intermediate Similarity	NPD3052	Approved
0.7165	Intermediate Similarity	NPD3054	Approved
0.7158	Intermediate Similarity	NPD293	Approved
0.7158	Intermediate Similarity	NPD295	Approved
0.7158	Intermediate Similarity	NPD296	Approved
0.7155	Intermediate Similarity	NPD3123	Discovery
0.7155	Intermediate Similarity	NPD5500	Discontinued
0.7131	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4103	Phase 2
0.713	Intermediate Similarity	NPD4188	Approved
0.713	Intermediate Similarity	NPD4189	Approved
0.7117	Intermediate Similarity	NPD9532	Phase 3
0.7109	Intermediate Similarity	NPD3555	Approved
0.7109	Intermediate Similarity	NPD3553	Approved
0.7109	Intermediate Similarity	NPD3552	Approved
0.7109	Intermediate Similarity	NPD3554	Approved
0.7073	Intermediate Similarity	NPD558	Phase 2
0.7073	Intermediate Similarity	NPD7451	Discontinued
0.7059	Intermediate Similarity	NPD5723	Approved
0.7049	Intermediate Similarity	NPD196	Phase 1
0.7043	Intermediate Similarity	NPD592	Approved
0.7043	Intermediate Similarity	NPD594	Approved
0.704	Intermediate Similarity	NPD4274	Approved
0.704	Intermediate Similarity	NPD3720	Discontinued
0.704	Intermediate Similarity	NPD4275	Approved
0.7031	Intermediate Similarity	NPD817	Approved
0.7031	Intermediate Similarity	NPD823	Approved
0.7027	Intermediate Similarity	NPD3524	Approved
0.7027	Intermediate Similarity	NPD3526	Approved
0.7018	Intermediate Similarity	NPD9508	Approved
0.7018	Intermediate Similarity	NPD4572	Approved
0.7018	Intermediate Similarity	NPD4573	Approved
0.7018	Intermediate Similarity	NPD4571	Approved
0.7016	Intermediate Similarity	NPD767	Phase 1
0.7009	Intermediate Similarity	NPD9495	Approved
0.7009	Intermediate Similarity	NPD253	Approved
0.7	Intermediate Similarity	NPD3048	Approved
0.7	Intermediate Similarity	NPD3047	Approved
0.7	Intermediate Similarity	NPD3046	Approved
0.6992	Remote Similarity	NPD3055	Approved
0.6992	Remote Similarity	NPD3053	Approved
0.6992	Remote Similarity	NPD1818	Approved
0.6992	Remote Similarity	NPD1817	Approved
0.6992	Remote Similarity	NPD1794	Approved
0.6992	Remote Similarity	NPD1820	Approved
0.6992	Remote Similarity	NPD1819	Approved
0.6991	Remote Similarity	NPD1792	Phase 2
0.6979	Remote Similarity	NPD9563	Approved
0.6979	Remote Similarity	NPD9564	Approved
0.6979	Remote Similarity	NPD79	Approved
0.6967	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5159	Phase 2
0.6967	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5157	Phase 1
0.6964	Remote Similarity	NPD6406	Approved
0.6953	Remote Similarity	NPD555	Phase 2
0.6947	Remote Similarity	NPD7978	Discontinued
0.6944	Remote Similarity	NPD9712	Approved
0.6942	Remote Similarity	NPD3974	Phase 2
0.6937	Remote Similarity	NPD5717	Approved
0.6935	Remote Similarity	NPD2195	Approved
0.6935	Remote Similarity	NPD2194	Approved
0.6929	Remote Similarity	NPD839	Approved
0.6929	Remote Similarity	NPD6405	Approved
0.6929	Remote Similarity	NPD840	Approved
0.6929	Remote Similarity	NPD259	Phase 1
0.6929	Remote Similarity	NPD6407	Approved
0.6917	Remote Similarity	NPD7725	Approved
0.6917	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7342	Discontinued
0.6909	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4718	Approved
0.6903	Remote Similarity	NPD4720	Approved
0.6903	Remote Similarity	NPD4717	Approved
0.6899	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2234	Approved
0.6897	Remote Similarity	NPD2229	Approved
0.6897	Remote Similarity	NPD2228	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