NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	165.12
Volume:	184.837
LogP:	1.83
LogD:	1.584
LogS:	-2.568
# Rotatable Bonds:	3
TPSA:	35.25
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	2.045
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:	-4.729
MDCK Permeability:	6.356553785735741e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.321
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.816
Plasma Protein Binding (PPB):	29.727203369140625%
Volume Distribution (VD):	4.789
Pgp-substrate:	70.91429901123047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.702
CYP1A2-substrate:	0.625
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.282
CYP2D6-inhibitor:	0.95
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.103
CYP3A4-substrate:	0.403

ADMET: Excretion

Clearance (CL):	10.731
Half-life (T1/2):	0.464

ADMET: Toxicity

hERG Blockers:	0.189
Human Hepatotoxicity (H-HT):	0.401
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.933
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.232
Carcinogencity:	0.064
Eye Corrosion:	0.01
Eye Irritation:	0.028
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC21890

Natural Product ID:	NPC21890
*Common Name:**	1-(3-Methoxyphenyl)Propan-2-Amine
IUPAC Name:	1-(3-methoxyphenyl)propan-2-amine
Synonyms:
Standard InCHIKey:	VEJWNIYARKAHFI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H15NO/c1-8(11)6-9-4-3-5-10(7-9)12-2/h3-5,7-8H,6,11H2,1-2H3
SMILES:	COc1cccc(c1)CC(N)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL16247
PubChem CID:	152234
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines [CHEMONTID:0000188] Amphetamines and derivatives

*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]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21707257]
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]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12935	Thymus quinquecostatus	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
Kd	4
Ki	7
Others	6

Activity Type	# Activity
Individual Protein	4
Organism	5
Others	1
Protein Family	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1778	Individual Protein	Serotonin 2a (5-HT2a) receptor	Rattus norvegicus	Ki	>	10000.0	nM	PMID[509804]
NPT438	Individual Protein	Serotonin 2c (5-HT2c) receptor	Rattus norvegicus	Ki	>	10000.0	nM	PMID[509804]
NPT1779	Individual Protein	Serotonin 2b (5-HT2b) receptor	Rattus norvegicus	Kd	=	1202.26	nM	PMID[509807]
NPT1778	Individual Protein	Serotonin 2a (5-HT2a) receptor	Rattus norvegicus	Ki	>	10000.0	nM	PMID[509808]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	DOM	=	8.0	%	PMID[509801]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	DOM	=	10.0	%	PMID[509801]
NPT1530	Protein Family	Serotonin (5-HT) receptor	Rattus norvegicus	Kd	=	1174.9	nM	PMID[509801]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	No. of animals	=	5.0	n.a.	PMID[509801]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	No. of animals	=	3.0	n.a.	PMID[509801]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	No. of animals	=	1.0	n.a.	PMID[509801]
NPT1776	Protein Family	Serotonin 1 (5-HT1) receptor	Rattus norvegicus	Ki	=	2660.0	nM	PMID[509802]
NPT1777	Protein Family	Serotonin 2 (5-HT2) receptor	Rattus norvegicus	Ki	=	7850.0	nM	PMID[509802]
NPT1530	Protein Family	Serotonin (5-HT) receptor	Rattus norvegicus	Kd	=	1174.9	nM	PMID[509803]
NPT1776	Protein Family	Serotonin 1 (5-HT1) receptor	Rattus norvegicus	Ki	=	2660.0	nM	PMID[509805]
NPT1777	Protein Family	Serotonin 2 (5-HT2) receptor	Rattus norvegicus	Ki	=	7850.0	nM	PMID[509805]
NPT1530	Protein Family	Serotonin (5-HT) receptor	Rattus norvegicus	Kd	=	1174.9	nM	PMID[509806]
NPT2	Others	Unspecified		KDNB	=	0.96	n.a.	PMID[509807]

☑ 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 NPC21890 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	200
0.1-0.2	2857
0.2-0.3	11013
0.3-0.4	6962
0.4-0.5	9176
0.5-0.6	9438
0.6-0.7	2726
0.7-0.8	309
0.8-0.85	8
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC97811
0.9057	High Similarity	NPC186469
0.9048	High Similarity	NPC42383
0.9035	High Similarity	NPC211992
0.8929	High Similarity	NPC120075
0.8909	High Similarity	NPC26524
0.8475	Intermediate Similarity	NPC298486
0.843	Intermediate Similarity	NPC291847
0.8403	Intermediate Similarity	NPC140359
0.8403	Intermediate Similarity	NPC13020
0.8333	Intermediate Similarity	NPC68055
0.8182	Intermediate Similarity	NPC105513
0.8131	Intermediate Similarity	NPC470161
0.8099	Intermediate Similarity	NPC217277
0.8	Intermediate Similarity	NPC321956
0.7937	Intermediate Similarity	NPC329595
0.7937	Intermediate Similarity	NPC326599
0.7917	Intermediate Similarity	NPC17388
0.7917	Intermediate Similarity	NPC289330
0.7917	Intermediate Similarity	NPC53596
0.7917	Intermediate Similarity	NPC471308
0.7917	Intermediate Similarity	NPC160120
0.7905	Intermediate Similarity	NPC71853
0.7857	Intermediate Similarity	NPC262641
0.7846	Intermediate Similarity	NPC253429
0.7838	Intermediate Similarity	NPC12870
0.7838	Intermediate Similarity	NPC24327
0.781	Intermediate Similarity	NPC99886
0.781	Intermediate Similarity	NPC177844
0.781	Intermediate Similarity	NPC259134
0.781	Intermediate Similarity	NPC8002
0.7803	Intermediate Similarity	NPC66518
0.7768	Intermediate Similarity	NPC241224
0.7768	Intermediate Similarity	NPC292792
0.7727	Intermediate Similarity	NPC125732
0.7724	Intermediate Similarity	NPC471314
0.7724	Intermediate Similarity	NPC471315
0.7692	Intermediate Similarity	NPC146422
0.7674	Intermediate Similarity	NPC160692
0.7667	Intermediate Similarity	NPC137096
0.7661	Intermediate Similarity	NPC328267
0.7638	Intermediate Similarity	NPC471306
0.7638	Intermediate Similarity	NPC471321
0.7623	Intermediate Similarity	NPC321133
0.7619	Intermediate Similarity	NPC301713
0.7589	Intermediate Similarity	NPC300166
0.7589	Intermediate Similarity	NPC12714
0.7589	Intermediate Similarity	NPC310905
0.7578	Intermediate Similarity	NPC135173
0.7568	Intermediate Similarity	NPC100870
0.7565	Intermediate Similarity	NPC233320
0.7561	Intermediate Similarity	NPC318357
0.7559	Intermediate Similarity	NPC153990
0.7541	Intermediate Similarity	NPC43275
0.754	Intermediate Similarity	NPC320242
0.754	Intermediate Similarity	NPC136112
0.754	Intermediate Similarity	NPC141739
0.7523	Intermediate Similarity	NPC471581
0.75	Intermediate Similarity	NPC146530
0.75	Intermediate Similarity	NPC75440
0.75	Intermediate Similarity	NPC309982
0.75	Intermediate Similarity	NPC294249
0.7478	Intermediate Similarity	NPC30416
0.7477	Intermediate Similarity	NPC226096
0.7477	Intermediate Similarity	NPC95755
0.7477	Intermediate Similarity	NPC303611
0.7477	Intermediate Similarity	NPC108606
0.7477	Intermediate Similarity	NPC164514
0.7477	Intermediate Similarity	NPC290515
0.7462	Intermediate Similarity	NPC118419
0.7459	Intermediate Similarity	NPC85276
0.7458	Intermediate Similarity	NPC166837
0.7456	Intermediate Similarity	NPC12987
0.7456	Intermediate Similarity	NPC474603
0.7436	Intermediate Similarity	NPC290566
0.7436	Intermediate Similarity	NPC145638
0.7436	Intermediate Similarity	NPC24777
0.7424	Intermediate Similarity	NPC11147
0.7422	Intermediate Similarity	NPC172403
0.7407	Intermediate Similarity	NPC323204
0.7405	Intermediate Similarity	NPC325568
0.7391	Intermediate Similarity	NPC288760
0.7373	Intermediate Similarity	NPC475852
0.7373	Intermediate Similarity	NPC2682
0.7373	Intermediate Similarity	NPC303521
0.7373	Intermediate Similarity	NPC137685
0.7368	Intermediate Similarity	NPC298224
0.7357	Intermediate Similarity	NPC60538
0.7357	Intermediate Similarity	NPC207824
0.735	Intermediate Similarity	NPC241549
0.7345	Intermediate Similarity	NPC29601
0.7339	Intermediate Similarity	NPC118522
0.7339	Intermediate Similarity	NPC169207
0.7339	Intermediate Similarity	NPC263835
0.7339	Intermediate Similarity	NPC115627
0.7333	Intermediate Similarity	NPC314682
0.7333	Intermediate Similarity	NPC59661
0.7328	Intermediate Similarity	NPC130595
0.7328	Intermediate Similarity	NPC88667
0.7328	Intermediate Similarity	NPC93882
0.7328	Intermediate Similarity	NPC214869
0.7321	Intermediate Similarity	NPC175298
0.7313	Intermediate Similarity	NPC318591
0.7313	Intermediate Similarity	NPC231163
0.7311	Intermediate Similarity	NPC156840
0.7311	Intermediate Similarity	NPC257124
0.7311	Intermediate Similarity	NPC195873
0.7311	Intermediate Similarity	NPC173746
0.7311	Intermediate Similarity	NPC8547
0.7311	Intermediate Similarity	NPC275627
0.7308	Intermediate Similarity	NPC160193
0.7304	Intermediate Similarity	NPC38209
0.7304	Intermediate Similarity	NPC38079
0.7304	Intermediate Similarity	NPC108875
0.7293	Intermediate Similarity	NPC235633
0.7287	Intermediate Similarity	NPC251571
0.7281	Intermediate Similarity	NPC84325
0.728	Intermediate Similarity	NPC183262
0.7279	Intermediate Similarity	NPC188163
0.7279	Intermediate Similarity	NPC213206
0.7279	Intermediate Similarity	NPC474915
0.7279	Intermediate Similarity	NPC470925
0.7279	Intermediate Similarity	NPC204546
0.7279	Intermediate Similarity	NPC328750
0.7273	Intermediate Similarity	NPC313737
0.7273	Intermediate Similarity	NPC285078
0.7273	Intermediate Similarity	NPC6854
0.7265	Intermediate Similarity	NPC35543
0.7265	Intermediate Similarity	NPC258171
0.7265	Intermediate Similarity	NPC227894
0.7257	Intermediate Similarity	NPC471576
0.7254	Intermediate Similarity	NPC76213
0.7254	Intermediate Similarity	NPC277669
0.7252	Intermediate Similarity	NPC476570
0.7252	Intermediate Similarity	NPC114102
0.7244	Intermediate Similarity	NPC211218
0.7241	Intermediate Similarity	NPC473855
0.7241	Intermediate Similarity	NPC470393
0.7231	Intermediate Similarity	NPC155838
0.7227	Intermediate Similarity	NPC168657
0.7227	Intermediate Similarity	NPC226914
0.7227	Intermediate Similarity	NPC31279
0.7222	Intermediate Similarity	NPC27974
0.7218	Intermediate Similarity	NPC218530
0.7217	Intermediate Similarity	NPC305205
0.7213	Intermediate Similarity	NPC10286
0.7213	Intermediate Similarity	NPC213
0.7207	Intermediate Similarity	NPC215351
0.7207	Intermediate Similarity	NPC20142
0.7203	Intermediate Similarity	NPC245115
0.7197	Intermediate Similarity	NPC97870
0.7197	Intermediate Similarity	NPC307123
0.7197	Intermediate Similarity	NPC247018
0.7193	Intermediate Similarity	NPC289381
0.7193	Intermediate Similarity	NPC13755
0.7193	Intermediate Similarity	NPC155847
0.719	Intermediate Similarity	NPC204120
0.719	Intermediate Similarity	NPC303522
0.719	Intermediate Similarity	NPC165106
0.7188	Intermediate Similarity	NPC95733
0.7188	Intermediate Similarity	NPC272463
0.7188	Intermediate Similarity	NPC62101
0.7185	Intermediate Similarity	NPC193528
0.7184	Intermediate Similarity	NPC124576
0.7179	Intermediate Similarity	NPC1065
0.7179	Intermediate Similarity	NPC113457
0.7179	Intermediate Similarity	NPC164576
0.7176	Intermediate Similarity	NPC52029
0.7176	Intermediate Similarity	NPC35961
0.7176	Intermediate Similarity	NPC195749
0.7167	Intermediate Similarity	NPC470723
0.7155	Intermediate Similarity	NPC147000
0.7155	Intermediate Similarity	NPC226778
0.7155	Intermediate Similarity	NPC150254
0.7155	Intermediate Similarity	NPC304761
0.7154	Intermediate Similarity	NPC16031
0.7154	Intermediate Similarity	NPC145888
0.7154	Intermediate Similarity	NPC188867
0.7154	Intermediate Similarity	NPC106551
0.7154	Intermediate Similarity	NPC281686
0.7154	Intermediate Similarity	NPC161593
0.7143	Intermediate Similarity	NPC36108
0.7143	Intermediate Similarity	NPC82016
0.7143	Intermediate Similarity	NPC172046
0.7143	Intermediate Similarity	NPC7097
0.7143	Intermediate Similarity	NPC246358
0.7143	Intermediate Similarity	NPC233731
0.7143	Intermediate Similarity	NPC127326
0.7132	Intermediate Similarity	NPC124776
0.7132	Intermediate Similarity	NPC29477
0.7131	Intermediate Similarity	NPC276737
0.7131	Intermediate Similarity	NPC470837
0.7131	Intermediate Similarity	NPC22610
0.7131	Intermediate Similarity	NPC142599
0.713	Intermediate Similarity	NPC51633
0.713	Intermediate Similarity	NPC307425
0.7121	Intermediate Similarity	NPC308885
0.7121	Intermediate Similarity	NPC255550
0.712	Intermediate Similarity	NPC283760
0.7119	Intermediate Similarity	NPC251306

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 NPC21890 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	905
0.2-0.3	1162
0.3-0.4	2264
0.4-0.5	2339
0.5-0.6	1523
0.6-0.7	613
0.7-0.8	163
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8829	High Similarity	NPD595	Approved
0.8829	High Similarity	NPD593	Approved
0.8512	High Similarity	NPD596	Approved
0.8512	High Similarity	NPD600	Approved
0.8333	Intermediate Similarity	NPD9618	Approved
0.8333	Intermediate Similarity	NPD9614	Approved
0.8306	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD9610	Approved
0.8091	Intermediate Similarity	NPD9608	Approved
0.8087	Intermediate Similarity	NPD592	Approved
0.8087	Intermediate Similarity	NPD594	Approved
0.8049	Intermediate Similarity	NPD558	Phase 2
0.8017	Intermediate Similarity	NPD2231	Phase 2
0.8017	Intermediate Similarity	NPD2235	Phase 2
0.7917	Intermediate Similarity	NPD2554	Approved
0.7917	Intermediate Similarity	NPD2556	Approved
0.7886	Intermediate Similarity	NPD196	Phase 1
0.7874	Intermediate Similarity	NPD2245	Discovery
0.7833	Intermediate Similarity	NPD3049	Approved
0.7829	Intermediate Similarity	NPD2989	Phase 2
0.7829	Intermediate Similarity	NPD2986	Phase 2
0.7805	Intermediate Similarity	NPD1420	Approved
0.7805	Intermediate Similarity	NPD1421	Approved
0.7734	Intermediate Similarity	NPD840	Approved
0.7734	Intermediate Similarity	NPD839	Approved
0.7717	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9379	Approved
0.7692	Intermediate Similarity	NPD9377	Approved
0.7667	Intermediate Similarity	NPD9613	Approved
0.7667	Intermediate Similarity	NPD9615	Approved
0.7667	Intermediate Similarity	NPD9616	Approved
0.7661	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD2429	Approved
0.7661	Intermediate Similarity	NPD1669	Approved
0.7661	Intermediate Similarity	NPD2428	Approved
0.7661	Intermediate Similarity	NPD9622	Approved
0.7656	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD2668	Approved
0.7623	Intermediate Similarity	NPD2667	Approved
0.7619	Intermediate Similarity	NPD7905	Discontinued
0.7603	Intermediate Similarity	NPD316	Approved
0.7581	Intermediate Similarity	NPD2232	Approved
0.7581	Intermediate Similarity	NPD2230	Approved
0.7581	Intermediate Similarity	NPD2233	Approved
0.7578	Intermediate Similarity	NPD1024	Discontinued
0.7557	Intermediate Similarity	NPD2653	Approved
0.754	Intermediate Similarity	NPD1820	Approved
0.754	Intermediate Similarity	NPD1817	Approved
0.754	Intermediate Similarity	NPD1794	Approved
0.754	Intermediate Similarity	NPD1818	Approved
0.754	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD1819	Approved
0.75	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD9612	Approved
0.7477	Intermediate Similarity	NPD9611	Approved
0.7477	Intermediate Similarity	NPD9609	Approved
0.7464	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD4474	Approved
0.7462	Intermediate Similarity	NPD4475	Approved
0.7459	Intermediate Similarity	NPD2486	Discontinued
0.7436	Intermediate Similarity	NPD550	Approved
0.7436	Intermediate Similarity	NPD551	Approved
0.7436	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD3052	Approved
0.7424	Intermediate Similarity	NPD3054	Approved
0.7414	Intermediate Similarity	NPD9624	Approved
0.7407	Intermediate Similarity	NPD7153	Discontinued
0.7405	Intermediate Similarity	NPD3109	Approved
0.7405	Intermediate Similarity	NPD3110	Approved
0.7385	Intermediate Similarity	NPD5718	Phase 2
0.7385	Intermediate Similarity	NPD1039	Discontinued
0.7377	Intermediate Similarity	NPD317	Approved
0.7377	Intermediate Similarity	NPD318	Approved
0.7355	Intermediate Similarity	NPD2557	Approved
0.7355	Intermediate Similarity	NPD709	Approved
0.7353	Intermediate Similarity	NPD3060	Approved
0.7353	Intermediate Similarity	NPD4162	Approved
0.7344	Intermediate Similarity	NPD3690	Phase 2
0.7344	Intermediate Similarity	NPD2195	Approved
0.7344	Intermediate Similarity	NPD3691	Phase 2
0.7344	Intermediate Similarity	NPD2194	Approved
0.7339	Intermediate Similarity	NPD9381	Approved
0.7339	Intermediate Similarity	NPD9384	Approved
0.7328	Intermediate Similarity	NPD259	Phase 1
0.7328	Intermediate Similarity	NPD2674	Phase 3
0.7328	Intermediate Similarity	NPD1444	Approved
0.7328	Intermediate Similarity	NPD1445	Approved
0.7313	Intermediate Similarity	NPD2154	Approved
0.7313	Intermediate Similarity	NPD2156	Approved
0.7313	Intermediate Similarity	NPD2155	Approved
0.7311	Intermediate Similarity	NPD228	Approved
0.7308	Intermediate Similarity	NPD3167	Approved
0.7308	Intermediate Similarity	NPD3166	Approved
0.7308	Intermediate Similarity	NPD3165	Approved
0.7308	Intermediate Similarity	NPD3164	Approved
0.7295	Intermediate Similarity	NPD3596	Phase 2
0.7287	Intermediate Similarity	NPD1712	Approved
0.7286	Intermediate Similarity	NPD7526	Approved
0.7286	Intermediate Similarity	NPD52	Approved
0.7286	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD3294	Phase 2
0.7279	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3053	Approved
0.7266	Intermediate Similarity	NPD3055	Approved
0.7258	Intermediate Similarity	NPD3445	Approved
0.7258	Intermediate Similarity	NPD2595	Approved
0.7258	Intermediate Similarity	NPD2594	Approved
0.7258	Intermediate Similarity	NPD3443	Approved
0.7258	Intermediate Similarity	NPD3444	Approved
0.7252	Intermediate Similarity	NPD1336	Approved
0.725	Intermediate Similarity	NPD821	Approved
0.7231	Intermediate Similarity	NPD2614	Approved
0.7218	Intermediate Similarity	NPD555	Phase 2
0.7209	Intermediate Similarity	NPD599	Approved
0.7209	Intermediate Similarity	NPD602	Approved
0.7197	Intermediate Similarity	NPD1130	Approved
0.7197	Intermediate Similarity	NPD3532	Approved
0.7197	Intermediate Similarity	NPD3531	Approved
0.7197	Intermediate Similarity	NPD1423	Approved
0.7197	Intermediate Similarity	NPD3530	Approved
0.7197	Intermediate Similarity	NPD1132	Approved
0.7197	Intermediate Similarity	NPD1136	Approved
0.7194	Intermediate Similarity	NPD2120	Phase 2
0.719	Intermediate Similarity	NPD5283	Phase 1
0.7177	Intermediate Similarity	NPD6581	Approved
0.7177	Intermediate Similarity	NPD6580	Approved
0.7176	Intermediate Similarity	NPD3180	Approved
0.7176	Intermediate Similarity	NPD5746	Approved
0.7176	Intermediate Similarity	NPD3179	Approved
0.7155	Intermediate Similarity	NPD310	Approved
0.7155	Intermediate Similarity	NPD314	Approved
0.7155	Intermediate Similarity	NPD10	Approved
0.7155	Intermediate Similarity	NPD311	Approved
0.7155	Intermediate Similarity	NPD309	Approved
0.7155	Intermediate Similarity	NPD315	Approved
0.7154	Intermediate Similarity	NPD9568	Approved
0.7154	Intermediate Similarity	NPD9569	Approved
0.7154	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2407	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD1792	Phase 2
0.7132	Intermediate Similarity	NPD3156	Discontinued
0.7132	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4098	Discontinued
0.7131	Intermediate Similarity	NPD1793	Approved
0.7131	Intermediate Similarity	NPD1791	Approved
0.7122	Intermediate Similarity	NPD5241	Discontinued
0.7122	Intermediate Similarity	NPD3692	Discontinued
0.7121	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD601	Approved
0.7121	Intermediate Similarity	NPD597	Approved
0.7121	Intermediate Similarity	NPD598	Approved
0.7121	Intermediate Similarity	NPD3145	Approved
0.7121	Intermediate Similarity	NPD3144	Approved
0.712	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6382	Discontinued
0.7119	Intermediate Similarity	NPD5374	Approved
0.7119	Intermediate Similarity	NPD5373	Approved
0.7113	Intermediate Similarity	NPD4727	Phase 1
0.7113	Intermediate Similarity	NPD6031	Approved
0.7113	Intermediate Similarity	NPD6030	Approved
0.7111	Intermediate Similarity	NPD6896	Approved
0.7111	Intermediate Similarity	NPD1536	Approved
0.7111	Intermediate Similarity	NPD6895	Approved
0.7101	Intermediate Similarity	NPD2460	Phase 3
0.7101	Intermediate Similarity	NPD2458	Approved
0.7101	Intermediate Similarity	NPD2459	Approved
0.7097	Intermediate Similarity	NPD856	Approved
0.7097	Intermediate Similarity	NPD16	Approved
0.7092	Intermediate Similarity	NPD3158	Phase 1
0.7092	Intermediate Similarity	NPD3157	Approved
0.7077	Intermediate Similarity	NPD859	Approved
0.7077	Intermediate Similarity	NPD858	Approved
0.7077	Intermediate Similarity	NPD9621	Approved
0.7077	Intermediate Similarity	NPD6584	Phase 3
0.7077	Intermediate Similarity	NPD2987	Approved
0.7077	Intermediate Similarity	NPD2990	Approved
0.7077	Intermediate Similarity	NPD9620	Approved
0.7077	Intermediate Similarity	NPD9619	Approved
0.7068	Intermediate Similarity	NPD3163	Approved
0.7068	Intermediate Similarity	NPD5745	Approved
0.7068	Intermediate Similarity	NPD3162	Approved
0.7068	Intermediate Similarity	NPD7477	Discontinued
0.7063	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2684	Approved
0.7055	Intermediate Similarity	NPD2977	Approved
0.7055	Intermediate Similarity	NPD2978	Approved
0.7054	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2922	Phase 1
0.705	Intermediate Similarity	NPD5754	Discontinued
0.7045	Intermediate Similarity	NPD5163	Phase 2
0.704	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD1182	Approved
0.7034	Intermediate Similarity	NPD811	Approved
0.7034	Intermediate Similarity	NPD812	Approved
0.7034	Intermediate Similarity	NPD810	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