NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	195.13
Volume:	210.924
LogP:	1.547
LogD:	1.145
LogS:	-2.093
# Rotatable Bonds:	4
TPSA:	44.48
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.793
Synthetic Accessibility Score:	2.271
Fsp3:	0.455
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:	-4.698
MDCK Permeability:	2.699474134715274e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.453
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.629
Plasma Protein Binding (PPB):	19.72275733947754%
Volume Distribution (VD):	3.518
Pgp-substrate:	67.29528045654297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.834
CYP1A2-substrate:	0.59
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.414
CYP2D6-inhibitor:	0.864
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.09
CYP3A4-substrate:	0.568

ADMET: Excretion

Clearance (CL):	7.865
Half-life (T1/2):	0.665

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.914
Maximum Recommended Daily Dose:	0.089
Skin Sensitization:	0.468
Carcinogencity:	0.147
Eye Corrosion:	0.005
Eye Irritation:	0.015
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC211992

Natural Product ID:	NPC211992
*Common Name:**	1-(2,3-Dimethoxyphenyl)Propan-2-Amine
IUPAC Name:	1-(2,3-dimethoxyphenyl)propan-2-amine
Synonyms:
Standard InCHIKey:	DHLWJXGSZDJWKK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H17NO2/c1-8(12)7-9-5-4-6-10(13-2)11(9)14-3/h4-6,8H,7,12H2,1-3H3
SMILES:	COc1c(cccc1OC)CC(N)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL280855
PubChem CID:	91255
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	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	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	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]
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
Kd	2
Ki	2
Others	1

Activity Type	# Activity
Individual Protein	3
Organism	1
Protein Family	1

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	=	4280.0	nM	PMID[508793]
NPT438	Individual Protein	Serotonin 2c (5-HT2c) receptor	Rattus norvegicus	Ki	>	10000.0	nM	PMID[508793]
NPT1779	Individual Protein	Serotonin 2b (5-HT2b) receptor	Rattus norvegicus	Kd	=	2884.03	nM	PMID[508794]
NPT1530	Protein Family	Serotonin (5-HT) receptor	Rattus norvegicus	Kd	=	2884.03	nM	PMID[508792]
NPT605	Organism	Homo sapiens	Homo sapiens	Relative activity	=	1.0	n.a.	PMID[508794]

☑ 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 NPC211992 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	218
0.1-0.2	2655
0.2-0.3	11572
0.3-0.4	6656
0.4-0.5	7524
0.5-0.6	10175
0.6-0.7	3310
0.7-0.8	555
0.8-0.85	23
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9224	High Similarity	NPC120075
0.9035	High Similarity	NPC21890
0.8926	High Similarity	NPC298486
0.8871	High Similarity	NPC291847
0.8699	High Similarity	NPC140359
0.8699	High Similarity	NPC13020
0.8684	High Similarity	NPC186469
0.8629	High Similarity	NPC105513
0.8448	Intermediate Similarity	NPC97811
0.8409	Intermediate Similarity	NPC253429
0.8295	Intermediate Similarity	NPC262641
0.825	Intermediate Similarity	NPC26524
0.8231	Intermediate Similarity	NPC326599
0.8231	Intermediate Similarity	NPC329595
0.819	Intermediate Similarity	NPC42383
0.8106	Intermediate Similarity	NPC160692
0.8103	Intermediate Similarity	NPC292792
0.8088	Intermediate Similarity	NPC66518
0.8062	Intermediate Similarity	NPC301713
0.8	Intermediate Similarity	NPC153990
0.8	Intermediate Similarity	NPC172403
0.7934	Intermediate Similarity	NPC195873
0.7931	Intermediate Similarity	NPC12714
0.7931	Intermediate Similarity	NPC310905
0.7914	Intermediate Similarity	NPC294249
0.7895	Intermediate Similarity	NPC93882
0.7895	Intermediate Similarity	NPC118419
0.7895	Intermediate Similarity	NPC130595
0.7887	Intermediate Similarity	NPC207824
0.7887	Intermediate Similarity	NPC60538
0.7883	Intermediate Similarity	NPC314682
0.7879	Intermediate Similarity	NPC160193
0.7852	Intermediate Similarity	NPC11147
0.7851	Intermediate Similarity	NPC137685
0.7836	Intermediate Similarity	NPC313737
0.7836	Intermediate Similarity	NPC6854
0.7836	Intermediate Similarity	NPC285078
0.7826	Intermediate Similarity	NPC188163
0.7826	Intermediate Similarity	NPC213206
0.7826	Intermediate Similarity	NPC328750
0.7826	Intermediate Similarity	NPC323204
0.7826	Intermediate Similarity	NPC474915
0.7808	Intermediate Similarity	NPC203784
0.7808	Intermediate Similarity	NPC170503
0.7808	Intermediate Similarity	NPC126519
0.7793	Intermediate Similarity	NPC2295
0.7793	Intermediate Similarity	NPC477564
0.7778	Intermediate Similarity	NPC218530
0.7778	Intermediate Similarity	NPC277669
0.7778	Intermediate Similarity	NPC76213
0.7761	Intermediate Similarity	NPC214869
0.775	Intermediate Similarity	NPC258171
0.7746	Intermediate Similarity	NPC106295
0.7746	Intermediate Similarity	NPC476144
0.7746	Intermediate Similarity	NPC210437
0.7746	Intermediate Similarity	NPC16107
0.7746	Intermediate Similarity	NPC51957
0.7724	Intermediate Similarity	NPC146422
0.771	Intermediate Similarity	NPC141739
0.771	Intermediate Similarity	NPC136112
0.7692	Intermediate Similarity	NPC7467
0.7687	Intermediate Similarity	NPC308885
0.7687	Intermediate Similarity	NPC114102
0.7687	Intermediate Similarity	NPC255550
0.7669	Intermediate Similarity	NPC155838
0.7661	Intermediate Similarity	NPC204120
0.7661	Intermediate Similarity	NPC165106
0.7656	Intermediate Similarity	NPC53596
0.7656	Intermediate Similarity	NPC17388
0.7656	Intermediate Similarity	NPC471308
0.7656	Intermediate Similarity	NPC160120
0.7656	Intermediate Similarity	NPC289330
0.7642	Intermediate Similarity	NPC8547
0.7642	Intermediate Similarity	NPC257124
0.7642	Intermediate Similarity	NPC156840
0.7642	Intermediate Similarity	NPC173746
0.7638	Intermediate Similarity	NPC474612
0.7626	Intermediate Similarity	NPC59661
0.7622	Intermediate Similarity	NPC476151
0.7612	Intermediate Similarity	NPC35961
0.7612	Intermediate Similarity	NPC52029
0.7612	Intermediate Similarity	NPC195749
0.7609	Intermediate Similarity	NPC193528
0.7606	Intermediate Similarity	NPC185838
0.7603	Intermediate Similarity	NPC114124
0.7603	Intermediate Similarity	NPC227894
0.7597	Intermediate Similarity	NPC183262
0.7589	Intermediate Similarity	NPC476567
0.7589	Intermediate Similarity	NPC136860
0.7589	Intermediate Similarity	NPC128019
0.7578	Intermediate Similarity	NPC308217
0.7568	Intermediate Similarity	NPC37205
0.7568	Intermediate Similarity	NPC160931
0.7563	Intermediate Similarity	NPC12870
0.7563	Intermediate Similarity	NPC68055
0.7563	Intermediate Similarity	NPC24327
0.7561	Intermediate Similarity	NPC31279
0.7559	Intermediate Similarity	NPC52464
0.7559	Intermediate Similarity	NPC304208
0.7557	Intermediate Similarity	NPC217277
0.7556	Intermediate Similarity	NPC476570
0.754	Intermediate Similarity	NPC47194
0.754	Intermediate Similarity	NPC475815
0.754	Intermediate Similarity	NPC473264
0.7537	Intermediate Similarity	NPC469977
0.7536	Intermediate Similarity	NPC42793
0.7536	Intermediate Similarity	NPC231884
0.7536	Intermediate Similarity	NPC167944
0.7534	Intermediate Similarity	NPC326316
0.7534	Intermediate Similarity	NPC81733
0.7521	Intermediate Similarity	NPC470161
0.752	Intermediate Similarity	NPC303522
0.7517	Intermediate Similarity	NPC103379
0.7517	Intermediate Similarity	NPC477565
0.75	Intermediate Similarity	NPC39103
0.75	Intermediate Similarity	NPC187022
0.75	Intermediate Similarity	NPC179825
0.75	Intermediate Similarity	NPC85276
0.75	Intermediate Similarity	NPC191376
0.75	Intermediate Similarity	NPC477838
0.75	Intermediate Similarity	NPC321505
0.75	Intermediate Similarity	NPC2770
0.75	Intermediate Similarity	NPC55300
0.75	Intermediate Similarity	NPC477837
0.75	Intermediate Similarity	NPC203924
0.75	Intermediate Similarity	NPC80129
0.7483	Intermediate Similarity	NPC130926
0.7482	Intermediate Similarity	NPC318591
0.7482	Intermediate Similarity	NPC231163
0.7481	Intermediate Similarity	NPC471314
0.7481	Intermediate Similarity	NPC471315
0.7481	Intermediate Similarity	NPC470706
0.748	Intermediate Similarity	NPC127326
0.748	Intermediate Similarity	NPC81067
0.748	Intermediate Similarity	NPC9341
0.748	Intermediate Similarity	NPC7097
0.748	Intermediate Similarity	NPC246358
0.748	Intermediate Similarity	NPC233731
0.748	Intermediate Similarity	NPC36108
0.7464	Intermediate Similarity	NPC475828
0.7463	Intermediate Similarity	NPC157740
0.7463	Intermediate Similarity	NPC99798
0.7463	Intermediate Similarity	NPC191302
0.7463	Intermediate Similarity	NPC251571
0.7459	Intermediate Similarity	NPC233320
0.7451	Intermediate Similarity	NPC35627
0.7451	Intermediate Similarity	NPC86144
0.7451	Intermediate Similarity	NPC81247
0.7451	Intermediate Similarity	NPC304659
0.7451	Intermediate Similarity	NPC476573
0.745	Intermediate Similarity	NPC190931
0.7448	Intermediate Similarity	NPC475959
0.7448	Intermediate Similarity	NPC24233
0.7448	Intermediate Similarity	NPC147390
0.7448	Intermediate Similarity	NPC428
0.7448	Intermediate Similarity	NPC476571
0.7448	Intermediate Similarity	NPC246587
0.7448	Intermediate Similarity	NPC135538
0.7444	Intermediate Similarity	NPC320242
0.744	Intermediate Similarity	NPC165646
0.7429	Intermediate Similarity	NPC210086
0.7422	Intermediate Similarity	NPC293619
0.7422	Intermediate Similarity	NPC164386
0.7419	Intermediate Similarity	NPC179309
0.741	Intermediate Similarity	NPC7018
0.741	Intermediate Similarity	NPC131204
0.741	Intermediate Similarity	NPC301050
0.7407	Intermediate Similarity	NPC471321
0.7407	Intermediate Similarity	NPC246974
0.7407	Intermediate Similarity	NPC147247
0.7407	Intermediate Similarity	NPC471306
0.7388	Intermediate Similarity	NPC156944
0.7388	Intermediate Similarity	NPC251466
0.7385	Intermediate Similarity	NPC169207
0.7385	Intermediate Similarity	NPC115627
0.7385	Intermediate Similarity	NPC118522
0.7383	Intermediate Similarity	NPC172765
0.7383	Intermediate Similarity	NPC110416
0.7383	Intermediate Similarity	NPC249797
0.7383	Intermediate Similarity	NPC207757
0.7383	Intermediate Similarity	NPC216459
0.7383	Intermediate Similarity	NPC2413
0.7383	Intermediate Similarity	NPC127674
0.7383	Intermediate Similarity	NPC276588
0.7383	Intermediate Similarity	NPC54379
0.7383	Intermediate Similarity	NPC5238
0.7383	Intermediate Similarity	NPC41178
0.7383	Intermediate Similarity	NPC204828
0.7383	Intermediate Similarity	NPC138487
0.7383	Intermediate Similarity	NPC193949
0.7383	Intermediate Similarity	NPC39701
0.7383	Intermediate Similarity	NPC469817
0.7383	Intermediate Similarity	NPC295691
0.7383	Intermediate Similarity	NPC189266
0.7383	Intermediate Similarity	NPC184026
0.7383	Intermediate Similarity	NPC278799
0.7377	Intermediate Similarity	NPC30416
0.7372	Intermediate Similarity	NPC88667
0.7368	Intermediate Similarity	NPC300955
0.7364	Intermediate Similarity	NPC212743

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 NPC211992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	904
0.2-0.3	1338
0.3-0.4	2327
0.4-0.5	2328
0.5-0.6	1334
0.6-0.7	591
0.7-0.8	156
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8644	High Similarity	NPD593	Approved
0.8644	High Similarity	NPD595	Approved
0.8594	High Similarity	NPD554	Clinical (unspecified phase)
0.8504	High Similarity	NPD600	Approved
0.8504	High Similarity	NPD596	Approved
0.8154	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD2653	Approved
0.7956	Intermediate Similarity	NPD7153	Discontinued
0.7943	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2674	Phase 3
0.7872	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD5718	Phase 2
0.7805	Intermediate Similarity	NPD594	Approved
0.7805	Intermediate Similarity	NPD592	Approved
0.777	Intermediate Similarity	NPD4162	Approved
0.777	Intermediate Similarity	NPD3060	Approved
0.7769	Intermediate Similarity	NPD2922	Phase 1
0.7761	Intermediate Similarity	NPD840	Approved
0.7761	Intermediate Similarity	NPD839	Approved
0.7746	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1424	Approved
0.7746	Intermediate Similarity	NPD4584	Approved
0.7742	Intermediate Similarity	NPD9618	Approved
0.7742	Intermediate Similarity	NPD9614	Approved
0.7724	Intermediate Similarity	NPD9379	Approved
0.7724	Intermediate Similarity	NPD9377	Approved
0.7717	Intermediate Similarity	NPD3049	Approved
0.771	Intermediate Similarity	NPD1794	Approved
0.7698	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9622	Approved
0.7692	Intermediate Similarity	NPD52	Approved
0.7692	Intermediate Similarity	NPD7526	Approved
0.7687	Intermediate Similarity	NPD3145	Approved
0.7687	Intermediate Similarity	NPD3144	Approved
0.7661	Intermediate Similarity	NPD5283	Phase 1
0.7656	Intermediate Similarity	NPD2554	Approved
0.7656	Intermediate Similarity	NPD2556	Approved
0.7652	Intermediate Similarity	NPD558	Phase 2
0.7642	Intermediate Similarity	NPD228	Approved
0.7639	Intermediate Similarity	NPD6031	Approved
0.7639	Intermediate Similarity	NPD6030	Approved
0.763	Intermediate Similarity	NPD3530	Approved
0.763	Intermediate Similarity	NPD3531	Approved
0.763	Intermediate Similarity	NPD3532	Approved
0.7615	Intermediate Similarity	NPD2231	Phase 2
0.7615	Intermediate Similarity	NPD2235	Phase 2
0.7612	Intermediate Similarity	NPD1024	Discontinued
0.7609	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD1421	Approved
0.7557	Intermediate Similarity	NPD1420	Approved
0.7554	Intermediate Similarity	NPD2161	Phase 2
0.7552	Intermediate Similarity	NPD1774	Approved
0.7536	Intermediate Similarity	NPD6896	Approved
0.7536	Intermediate Similarity	NPD6895	Approved
0.7535	Intermediate Similarity	NPD5241	Discontinued
0.7518	Intermediate Similarity	NPD5177	Phase 3
0.7517	Intermediate Similarity	NPD5976	Discontinued
0.75	Intermediate Similarity	NPD2245	Discovery
0.75	Intermediate Similarity	NPD7298	Approved
0.7482	Intermediate Similarity	NPD2155	Approved
0.7482	Intermediate Similarity	NPD2154	Approved
0.7482	Intermediate Similarity	NPD2156	Approved
0.7465	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD2986	Phase 2
0.7464	Intermediate Similarity	NPD2989	Phase 2
0.745	Intermediate Similarity	NPD4585	Approved
0.745	Intermediate Similarity	NPD2977	Approved
0.745	Intermediate Similarity	NPD2978	Approved
0.7447	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3053	Approved
0.7444	Intermediate Similarity	NPD1818	Approved
0.7444	Intermediate Similarity	NPD1819	Approved
0.7444	Intermediate Similarity	NPD3055	Approved
0.7444	Intermediate Similarity	NPD1820	Approved
0.7444	Intermediate Similarity	NPD1817	Approved
0.7426	Intermediate Similarity	NPD1336	Approved
0.7385	Intermediate Similarity	NPD9381	Approved
0.7385	Intermediate Similarity	NPD9384	Approved
0.7376	Intermediate Similarity	NPD1375	Discontinued
0.7372	Intermediate Similarity	NPD1130	Approved
0.7372	Intermediate Similarity	NPD1132	Approved
0.7372	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD259	Phase 1
0.7372	Intermediate Similarity	NPD1136	Approved
0.7368	Intermediate Similarity	NPD196	Phase 1
0.7364	Intermediate Similarity	NPD2486	Discontinued
0.7355	Intermediate Similarity	NPD9610	Approved
0.7355	Intermediate Similarity	NPD9608	Approved
0.7348	Intermediate Similarity	NPD2233	Approved
0.7348	Intermediate Similarity	NPD2230	Approved
0.7348	Intermediate Similarity	NPD2232	Approved
0.7347	Intermediate Similarity	NPD3687	Approved
0.7347	Intermediate Similarity	NPD3686	Approved
0.7343	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD601	Approved
0.7299	Intermediate Similarity	NPD598	Approved
0.7299	Intermediate Similarity	NPD597	Approved
0.7299	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4017	Approved
0.7293	Intermediate Similarity	NPD1669	Approved
0.7293	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3641	Approved
0.7279	Intermediate Similarity	NPD3639	Approved
0.7279	Intermediate Similarity	NPD3640	Phase 3
0.7273	Intermediate Similarity	NPD4236	Phase 3
0.7273	Intermediate Similarity	NPD4237	Approved
0.7266	Intermediate Similarity	NPD555	Phase 2
0.726	Intermediate Similarity	NPD4739	Approved
0.7259	Intermediate Similarity	NPD7905	Discontinued
0.7259	Intermediate Similarity	NPD3691	Phase 2
0.7259	Intermediate Similarity	NPD3690	Phase 2
0.7254	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD2668	Approved
0.7252	Intermediate Similarity	NPD2667	Approved
0.7246	Intermediate Similarity	NPD3162	Approved
0.7246	Intermediate Similarity	NPD4474	Approved
0.7246	Intermediate Similarity	NPD3163	Approved
0.7246	Intermediate Similarity	NPD4475	Approved
0.7226	Intermediate Similarity	NPD3166	Approved
0.7226	Intermediate Similarity	NPD3165	Approved
0.7226	Intermediate Similarity	NPD3164	Approved
0.7226	Intermediate Similarity	NPD3167	Approved
0.7222	Intermediate Similarity	NPD6331	Phase 2
0.7211	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD9569	Approved
0.7206	Intermediate Similarity	NPD1712	Approved
0.7197	Intermediate Similarity	NPD3294	Phase 2
0.7194	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4055	Discovery
0.7176	Intermediate Similarity	NPD1797	Approved
0.7176	Intermediate Similarity	NPD1798	Approved
0.7174	Intermediate Similarity	NPD5111	Phase 2
0.7174	Intermediate Similarity	NPD5110	Phase 2
0.7174	Intermediate Similarity	NPD5109	Approved
0.7172	Intermediate Similarity	NPD2677	Approved
0.7172	Intermediate Similarity	NPD3692	Discontinued
0.7164	Intermediate Similarity	NPD2428	Approved
0.7164	Intermediate Similarity	NPD2429	Approved
0.7163	Intermediate Similarity	NPD6111	Discontinued
0.7161	Intermediate Similarity	NPD6107	Approved
0.7154	Intermediate Similarity	NPD9615	Approved
0.7154	Intermediate Similarity	NPD9616	Approved
0.7154	Intermediate Similarity	NPD9613	Approved
0.7154	Intermediate Similarity	NPD5536	Phase 2
0.7143	Intermediate Similarity	NPD1341	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9620	Approved
0.7132	Intermediate Similarity	NPD9621	Approved
0.7132	Intermediate Similarity	NPD709	Approved
0.7132	Intermediate Similarity	NPD9619	Approved
0.7132	Intermediate Similarity	NPD2557	Approved
0.7124	Intermediate Similarity	NPD6788	Approved
0.7123	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7124	Phase 2
0.7122	Intermediate Similarity	NPD1423	Approved
0.7115	Intermediate Similarity	NPD4166	Phase 2
0.7111	Intermediate Similarity	NPD5311	Approved
0.7111	Intermediate Similarity	NPD5310	Approved
0.7111	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3180	Approved
0.7101	Intermediate Similarity	NPD3179	Approved
0.7099	Intermediate Similarity	NPD316	Approved
0.7092	Intermediate Similarity	NPD3052	Approved
0.7092	Intermediate Similarity	NPD817	Approved
0.7092	Intermediate Similarity	NPD823	Approved
0.7092	Intermediate Similarity	NPD3054	Approved
0.7086	Intermediate Similarity	NPD5089	Approved
0.7086	Intermediate Similarity	NPD5090	Approved
0.7086	Intermediate Similarity	NPD4772	Phase 2
0.7086	Intermediate Similarity	NPD4773	Phase 2
0.7078	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4005	Discontinued
0.7067	Intermediate Similarity	NPD3455	Phase 2
0.7063	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5160	Discontinued
0.7055	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1039	Discontinued
0.7045	Intermediate Similarity	NPD1357	Approved
0.7045	Intermediate Similarity	NPD3444	Approved
0.7045	Intermediate Similarity	NPD3443	Approved
0.7045	Intermediate Similarity	NPD3445	Approved
0.7044	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD290	Approved
0.7039	Intermediate Similarity	NPD5720	Discontinued
0.7023	Intermediate Similarity	NPD1103	Approved
0.7023	Intermediate Similarity	NPD1102	Approved
0.702	Intermediate Similarity	NPD4180	Approved
0.702	Intermediate Similarity	NPD4179	Approved
0.7015	Intermediate Similarity	NPD3705	Approved
0.7007	Intermediate Similarity	NPD2120	Phase 2
0.7006	Intermediate Similarity	NPD3051	Approved
0.7	Intermediate Similarity	NPD7477	Discontinued
0.7	Intermediate Similarity	NPD2883	Discontinued
0.6993	Remote Similarity	NPD5772	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