NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	158.07
Volume:	177.307
LogP:	3.317
LogD:	3.277
LogS:	-4.0
# Rotatable Bonds:	1
TPSA:	9.23
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.62
Synthetic Accessibility Score:	1.238
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.372
MDCK Permeability:	2.0278570445952937e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.84
30% Bioavailability (F30%):	0.832

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.591
Plasma Protein Binding (PPB):	96.27035522460938%
Volume Distribution (VD):	1.211
Pgp-substrate:	4.014597415924072%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.872
CYP2C19-substrate:	0.451
CYP2C9-inhibitor:	0.395
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.643
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.251
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	10.749
Half-life (T1/2):	0.317

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.117
Drug-inuced Liver Injury (DILI):	0.82
AMES Toxicity:	0.752
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.225
Skin Sensitization:	0.899
Carcinogencity:	0.865
Eye Corrosion:	0.829
Eye Irritation:	0.994
Respiratory Toxicity:	0.069

Download Data

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

Natural Product: NPC241224

Natural Product ID:	NPC241224
*Common Name:**	2-Methoxynaphthalene
IUPAC Name:	2-methoxynaphthalene
Synonyms:	2-Methoxy-Naphthalene; 2-Methoxynaphthalene
Standard InCHIKey:	LUZDYPLAQQGJEA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H10O/c1-12-11-7-6-9-4-2-3-5-10(9)8-11/h2-8H,1H3
SMILES:	COc1ccc2ccccc2c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL195857
PubChem CID:	7119
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO5949	Pericarpium arecae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO5949	Pericarpium arecae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
IC50	5
Others	1
Potency	3

Activity Type	# Activity
Individual Protein	6
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	13000.0	nM	PMID[456253]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	62000.0	nM	PMID[456254]
NPT1420	Individual Protein	Cytochrome P450 2A5	Mus musculus	IC50	=	4600.0	nM	PMID[456254]
NPT1420	Individual Protein	Cytochrome P450 2A5	Mus musculus	IC50	=	4602.57	nM	PMID[456255]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	61944.11	nM	PMID[456255]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT27	Others	Unspecified		Ratio	=	13.4	n.a.	PMID[456254]
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set

☑ 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 NPC241224 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	728
0.1-0.2	2434
0.2-0.3	8736
0.3-0.4	10368
0.4-0.5	4129
0.5-0.6	9587
0.6-0.7	5332
0.7-0.8	1303
0.8-0.85	64
0.85-0.9	14
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC300166
0.8958	High Similarity	NPC321956
0.8854	High Similarity	NPC71853
0.8846	High Similarity	NPC75440
0.8824	High Similarity	NPC474603
0.8824	High Similarity	NPC12987
0.8807	High Similarity	NPC25648
0.875	High Similarity	NPC99886
0.875	High Similarity	NPC177844
0.875	High Similarity	NPC8002
0.875	High Similarity	NPC259134
0.87	High Similarity	NPC470161
0.8679	High Similarity	NPC475852
0.8679	High Similarity	NPC303521
0.8641	High Similarity	NPC292792
0.8624	High Similarity	NPC283169
0.8611	High Similarity	NPC165106
0.8598	High Similarity	NPC470723
0.8571	High Similarity	NPC103916
0.8545	High Similarity	NPC33900
0.8545	High Similarity	NPC312105
0.8544	High Similarity	NPC12870
0.8544	High Similarity	NPC24327
0.8515	High Similarity	NPC32674
0.8491	Intermediate Similarity	NPC201959
0.8476	Intermediate Similarity	NPC113457
0.8468	Intermediate Similarity	NPC195466
0.8455	Intermediate Similarity	NPC475815
0.8455	Intermediate Similarity	NPC473264
0.8455	Intermediate Similarity	NPC47194
0.8447	Intermediate Similarity	NPC310905
0.8447	Intermediate Similarity	NPC12714
0.844	Intermediate Similarity	NPC35344
0.844	Intermediate Similarity	NPC141003
0.8431	Intermediate Similarity	NPC100870
0.8411	Intermediate Similarity	NPC82016
0.84	Intermediate Similarity	NPC471581
0.8393	Intermediate Similarity	NPC63010
0.8378	Intermediate Similarity	NPC81067
0.8378	Intermediate Similarity	NPC9341
0.8364	Intermediate Similarity	NPC470837
0.8333	Intermediate Similarity	NPC129176
0.8333	Intermediate Similarity	NPC2682
0.8333	Intermediate Similarity	NPC102639
0.8319	Intermediate Similarity	NPC15805
0.8288	Intermediate Similarity	NPC167934
0.8257	Intermediate Similarity	NPC90520
0.8257	Intermediate Similarity	NPC296920
0.8241	Intermediate Similarity	NPC474272
0.823	Intermediate Similarity	NPC474040
0.8224	Intermediate Similarity	NPC35543
0.8214	Intermediate Similarity	NPC141090
0.8205	Intermediate Similarity	NPC138248
0.8205	Intermediate Similarity	NPC228503
0.8205	Intermediate Similarity	NPC111088
0.819	Intermediate Similarity	NPC298224
0.819	Intermediate Similarity	NPC30462
0.8182	Intermediate Similarity	NPC280606
0.8174	Intermediate Similarity	NPC100108
0.8174	Intermediate Similarity	NPC212559
0.8174	Intermediate Similarity	NPC277798
0.8165	Intermediate Similarity	NPC137685
0.8158	Intermediate Similarity	NPC281298
0.8158	Intermediate Similarity	NPC310338
0.8155	Intermediate Similarity	NPC175298
0.8155	Intermediate Similarity	NPC156313
0.8148	Intermediate Similarity	NPC245115
0.8142	Intermediate Similarity	NPC244816
0.8142	Intermediate Similarity	NPC50521
0.8142	Intermediate Similarity	NPC221549
0.8142	Intermediate Similarity	NPC474933
0.8142	Intermediate Similarity	NPC293619
0.8136	Intermediate Similarity	NPC105718
0.8136	Intermediate Similarity	NPC278955
0.8131	Intermediate Similarity	NPC30416
0.8113	Intermediate Similarity	NPC327811
0.8113	Intermediate Similarity	NPC38079
0.8113	Intermediate Similarity	NPC254965
0.8113	Intermediate Similarity	NPC38209
0.8113	Intermediate Similarity	NPC108875
0.8091	Intermediate Similarity	NPC156840
0.8091	Intermediate Similarity	NPC257124
0.8091	Intermediate Similarity	NPC8547
0.8091	Intermediate Similarity	NPC173746
0.8087	Intermediate Similarity	NPC95614
0.8087	Intermediate Similarity	NPC165133
0.8087	Intermediate Similarity	NPC227217
0.8087	Intermediate Similarity	NPC232316
0.8087	Intermediate Similarity	NPC117780
0.8087	Intermediate Similarity	NPC344161
0.8087	Intermediate Similarity	NPC242885
0.8087	Intermediate Similarity	NPC56214
0.8077	Intermediate Similarity	NPC471576
0.807	Intermediate Similarity	NPC474214
0.807	Intermediate Similarity	NPC470626
0.8067	Intermediate Similarity	NPC170485
0.8056	Intermediate Similarity	NPC227894
0.8056	Intermediate Similarity	NPC258171
0.8056	Intermediate Similarity	NPC233320
0.8053	Intermediate Similarity	NPC203113
0.8037	Intermediate Similarity	NPC473855
0.8037	Intermediate Similarity	NPC470393
0.8036	Intermediate Similarity	NPC22610
0.8036	Intermediate Similarity	NPC180508
0.8036	Intermediate Similarity	NPC228287
0.8036	Intermediate Similarity	NPC276737
0.8034	Intermediate Similarity	NPC152946
0.8019	Intermediate Similarity	NPC305205
0.8	Intermediate Similarity	NPC475961
0.8	Intermediate Similarity	NPC473221
0.8	Intermediate Similarity	NPC474320
0.8	Intermediate Similarity	NPC100129
0.8	Intermediate Similarity	NPC53781
0.8	Intermediate Similarity	NPC31279
0.8	Intermediate Similarity	NPC106511
0.8	Intermediate Similarity	NPC13755
0.8	Intermediate Similarity	NPC94045
0.8	Intermediate Similarity	NPC254625
0.7983	Intermediate Similarity	NPC17348
0.7983	Intermediate Similarity	NPC113495
0.7983	Intermediate Similarity	NPC228771
0.7983	Intermediate Similarity	NPC232387
0.7983	Intermediate Similarity	NPC29008
0.7983	Intermediate Similarity	NPC9067
0.7983	Intermediate Similarity	NPC105031
0.7983	Intermediate Similarity	NPC266705
0.7981	Intermediate Similarity	NPC95755
0.7966	Intermediate Similarity	NPC84086
0.7965	Intermediate Similarity	NPC808
0.7965	Intermediate Similarity	NPC53906
0.7963	Intermediate Similarity	NPC1065
0.7963	Intermediate Similarity	NPC326801
0.7961	Intermediate Similarity	NPC274678
0.7949	Intermediate Similarity	NPC126935
0.7949	Intermediate Similarity	NPC477886
0.7949	Intermediate Similarity	NPC80241
0.7949	Intermediate Similarity	NPC312713
0.7949	Intermediate Similarity	NPC216929
0.7949	Intermediate Similarity	NPC172676
0.7949	Intermediate Similarity	NPC38996
0.7949	Intermediate Similarity	NPC57268
0.7949	Intermediate Similarity	NPC65933
0.7949	Intermediate Similarity	NPC160380
0.7949	Intermediate Similarity	NPC301641
0.7946	Intermediate Similarity	NPC204120
0.7946	Intermediate Similarity	NPC303522
0.7944	Intermediate Similarity	NPC109637
0.7934	Intermediate Similarity	NPC215300
0.7934	Intermediate Similarity	NPC38017
0.7934	Intermediate Similarity	NPC23012
0.7928	Intermediate Similarity	NPC275627
0.7925	Intermediate Similarity	NPC307425
0.7925	Intermediate Similarity	NPC51633
0.7917	Intermediate Similarity	NPC177925
0.7917	Intermediate Similarity	NPC82299
0.7909	Intermediate Similarity	NPC7097
0.7909	Intermediate Similarity	NPC58865
0.7909	Intermediate Similarity	NPC36108
0.7909	Intermediate Similarity	NPC127326
0.7909	Intermediate Similarity	NPC233731
0.7909	Intermediate Similarity	NPC246358
0.7899	Intermediate Similarity	NPC5796
0.7899	Intermediate Similarity	NPC206487
0.7899	Intermediate Similarity	NPC75432
0.7895	Intermediate Similarity	NPC150624
0.7895	Intermediate Similarity	NPC123948
0.789	Intermediate Similarity	NPC251306
0.7885	Intermediate Similarity	NPC202986
0.7881	Intermediate Similarity	NPC85488
0.787	Intermediate Similarity	NPC42383
0.787	Intermediate Similarity	NPC475269
0.787	Intermediate Similarity	NPC238115
0.787	Intermediate Similarity	NPC288760
0.7864	Intermediate Similarity	NPC245187
0.7863	Intermediate Similarity	NPC131868
0.7863	Intermediate Similarity	NPC207613
0.7863	Intermediate Similarity	NPC472596
0.7851	Intermediate Similarity	NPC471986
0.7851	Intermediate Similarity	NPC177167
0.785	Intermediate Similarity	NPC233827
0.785	Intermediate Similarity	NPC179686
0.785	Intermediate Similarity	NPC168393
0.785	Intermediate Similarity	NPC192596
0.7838	Intermediate Similarity	NPC179309
0.7833	Intermediate Similarity	NPC4286
0.7833	Intermediate Similarity	NPC76119
0.783	Intermediate Similarity	NPC107101
0.7826	Intermediate Similarity	NPC69261
0.7826	Intermediate Similarity	NPC280001
0.7826	Intermediate Similarity	NPC470759
0.7826	Intermediate Similarity	NPC33270
0.7826	Intermediate Similarity	NPC185738
0.7826	Intermediate Similarity	NPC15860
0.7826	Intermediate Similarity	NPC127894
0.7826	Intermediate Similarity	NPC86947
0.7826	Intermediate Similarity	NPC219070
0.7818	Intermediate Similarity	NPC97811
0.7818	Intermediate Similarity	NPC233835
0.7818	Intermediate Similarity	NPC11554
0.7818	Intermediate Similarity	NPC241549

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 NPC241224 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	646
0.1-0.2	929
0.2-0.3	1507
0.3-0.4	2685
0.4-0.5	1751
0.5-0.6	1039
0.6-0.7	461
0.7-0.8	125
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8649	High Similarity	NPD1651	Approved
0.8611	High Similarity	NPD5283	Phase 1
0.8455	Intermediate Similarity	NPD709	Approved
0.8421	Intermediate Similarity	NPD1281	Approved
0.8276	Intermediate Similarity	NPD1669	Approved
0.8241	Intermediate Similarity	NPD5451	Approved
0.8205	Intermediate Similarity	NPD1283	Approved
0.812	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD228	Approved
0.8034	Intermediate Similarity	NPD1840	Phase 2
0.8	Intermediate Similarity	NPD5691	Approved
0.7966	Intermediate Similarity	NPD5327	Phase 3
0.7949	Intermediate Similarity	NPD1611	Approved
0.7931	Intermediate Similarity	NPD4626	Approved
0.7857	Intermediate Similarity	NPD5535	Approved
0.7845	Intermediate Similarity	NPD3445	Approved
0.7845	Intermediate Similarity	NPD3443	Approved
0.7845	Intermediate Similarity	NPD3444	Approved
0.7826	Intermediate Similarity	NPD5536	Phase 2
0.7818	Intermediate Similarity	NPD2684	Approved
0.7805	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD968	Approved
0.7769	Intermediate Similarity	NPD4624	Approved
0.7759	Intermediate Similarity	NPD1182	Approved
0.775	Intermediate Similarity	NPD1876	Approved
0.7739	Intermediate Similarity	NPD3596	Phase 2
0.7736	Intermediate Similarity	NPD3020	Approved
0.7692	Intermediate Similarity	NPD5585	Approved
0.7692	Intermediate Similarity	NPD2933	Approved
0.7692	Intermediate Similarity	NPD2934	Approved
0.768	Intermediate Similarity	NPD2979	Phase 3
0.7661	Intermediate Similarity	NPD5109	Approved
0.7661	Intermediate Similarity	NPD5110	Phase 2
0.7661	Intermediate Similarity	NPD5111	Phase 2
0.7652	Intermediate Similarity	NPD7157	Approved
0.7647	Intermediate Similarity	NPD3705	Approved
0.7636	Intermediate Similarity	NPD3134	Approved
0.7632	Intermediate Similarity	NPD1241	Discontinued
0.7627	Intermediate Similarity	NPD2667	Approved
0.7627	Intermediate Similarity	NPD2668	Approved
0.7627	Intermediate Similarity	NPD17	Approved
0.7619	Intermediate Similarity	NPD2859	Approved
0.7619	Intermediate Similarity	NPD2860	Approved
0.7607	Intermediate Similarity	NPD6581	Approved
0.7607	Intermediate Similarity	NPD6580	Approved
0.7583	Intermediate Similarity	NPD2230	Approved
0.7583	Intermediate Similarity	NPD2232	Approved
0.7583	Intermediate Similarity	NPD2233	Approved
0.7568	Intermediate Similarity	NPD1358	Approved
0.7544	Intermediate Similarity	NPD821	Approved
0.7544	Intermediate Similarity	NPD7843	Approved
0.7542	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD4060	Phase 1
0.7524	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2557	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD6671	Approved
0.748	Intermediate Similarity	NPD6584	Phase 3
0.746	Intermediate Similarity	NPD4475	Approved
0.746	Intermediate Similarity	NPD4474	Approved
0.7458	Intermediate Similarity	NPD1548	Phase 1
0.7442	Intermediate Similarity	NPD4108	Discontinued
0.744	Intermediate Similarity	NPD4625	Phase 3
0.7438	Intermediate Similarity	NPD1608	Approved
0.7438	Intermediate Similarity	NPD2981	Phase 2
0.7438	Intermediate Similarity	NPD3972	Approved
0.7434	Intermediate Similarity	NPD3021	Approved
0.7434	Intermediate Similarity	NPD3022	Approved
0.7422	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2861	Phase 2
0.7417	Intermediate Similarity	NPD3847	Discontinued
0.7411	Intermediate Similarity	NPD2342	Discontinued
0.7411	Intermediate Similarity	NPD290	Approved
0.7402	Intermediate Similarity	NPD4140	Approved
0.7402	Intermediate Similarity	NPD3109	Approved
0.7402	Intermediate Similarity	NPD3110	Approved
0.7385	Intermediate Similarity	NPD2438	Suspended
0.7385	Intermediate Similarity	NPD2531	Phase 2
0.7383	Intermediate Similarity	NPD288	Approved
0.7381	Intermediate Similarity	NPD1039	Discontinued
0.7377	Intermediate Similarity	NPD4359	Approved
0.7377	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD2982	Phase 2
0.7377	Intermediate Similarity	NPD2983	Phase 2
0.736	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6387	Discontinued
0.7344	Intermediate Similarity	NPD5735	Approved
0.7339	Intermediate Similarity	NPD3028	Approved
0.7339	Intermediate Similarity	NPD1242	Phase 1
0.7339	Intermediate Similarity	NPD7905	Discontinued
0.7333	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6516	Phase 2
0.7333	Intermediate Similarity	NPD5846	Approved
0.7328	Intermediate Similarity	NPD498	Approved
0.7328	Intermediate Similarity	NPD495	Approved
0.7328	Intermediate Similarity	NPD496	Approved
0.7327	Intermediate Similarity	NPD111	Approved
0.7323	Intermediate Similarity	NPD8032	Phase 2
0.7311	Intermediate Similarity	NPD1894	Discontinued
0.7304	Intermediate Similarity	NPD1139	Approved
0.7304	Intermediate Similarity	NPD1137	Approved
0.7302	Intermediate Similarity	NPD3027	Phase 3
0.7302	Intermediate Similarity	NPD7095	Approved
0.7302	Intermediate Similarity	NPD1024	Discontinued
0.7295	Intermediate Similarity	NPD1244	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD844	Approved
0.7287	Intermediate Similarity	NPD4097	Suspended
0.7287	Intermediate Similarity	NPD6353	Approved
0.728	Intermediate Similarity	NPD3018	Phase 2
0.7266	Intermediate Similarity	NPD3620	Phase 2
0.7266	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD497	Approved
0.725	Intermediate Similarity	NPD3049	Approved
0.725	Intermediate Similarity	NPD1357	Approved
0.7244	Intermediate Similarity	NPD5718	Phase 2
0.7241	Intermediate Similarity	NPD7635	Approved
0.7241	Intermediate Similarity	NPD1138	Approved
0.7236	Intermediate Similarity	NPD6543	Approved
0.7236	Intermediate Similarity	NPD6542	Approved
0.7236	Intermediate Similarity	NPD6582	Phase 2
0.7236	Intermediate Similarity	NPD6539	Approved
0.7236	Intermediate Similarity	NPD6583	Phase 3
0.7236	Intermediate Similarity	NPD2428	Approved
0.7236	Intermediate Similarity	NPD2429	Approved
0.7236	Intermediate Similarity	NPD6540	Phase 3
0.7232	Intermediate Similarity	NPD9697	Approved
0.7222	Intermediate Similarity	NPD4908	Phase 1
0.7209	Intermediate Similarity	NPD3657	Discovery
0.719	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2556	Approved
0.719	Intermediate Similarity	NPD2554	Approved
0.7182	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6541	Approved
0.7177	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2922	Phase 1
0.7177	Intermediate Similarity	NPD6538	Approved
0.7176	Intermediate Similarity	NPD2156	Approved
0.7176	Intermediate Similarity	NPD2154	Approved
0.7176	Intermediate Similarity	NPD2155	Approved
0.7167	Intermediate Similarity	NPD2486	Discontinued
0.7167	Intermediate Similarity	NPD3091	Approved
0.7165	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2231	Phase 2
0.7154	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD2808	Discontinued
0.7143	Intermediate Similarity	NPD1712	Approved
0.7143	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2238	Phase 2
0.7131	Intermediate Similarity	NPD3496	Discontinued
0.713	Intermediate Similarity	NPD1792	Phase 2
0.7119	Intermediate Similarity	NPD595	Approved
0.7119	Intermediate Similarity	NPD593	Approved
0.7109	Intermediate Similarity	NPD7294	Phase 1
0.7109	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4093	Discontinued
0.7099	Intermediate Similarity	NPD6896	Approved
0.7099	Intermediate Similarity	NPD6895	Approved
0.709	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1535	Discovery
0.7063	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7018	Phase 2
0.7054	Intermediate Similarity	NPD4870	Approved
0.7049	Intermediate Similarity	NPD1778	Approved
0.7049	Intermediate Similarity	NPD2286	Discontinued
0.7049	Intermediate Similarity	NPD3095	Discontinued
0.7048	Intermediate Similarity	NPD9295	Approved
0.7045	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1398	Phase 1
0.7023	Intermediate Similarity	NPD2157	Approved
0.7016	Intermediate Similarity	NPD1481	Phase 2
0.7015	Intermediate Similarity	NPD7037	Approved
0.7008	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1558	Phase 1
0.7	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1613	Approved
0.6992	Remote Similarity	NPD4476	Approved
0.6992	Remote Similarity	NPD4477	Approved
0.6992	Remote Similarity	NPD3294	Phase 2
0.6991	Remote Similarity	NPD3046	Approved
0.6991	Remote Similarity	NPD3047	Approved
0.6991	Remote Similarity	NPD3048	Approved
0.6985	Remote Similarity	NPD5241	Discontinued
0.6985	Remote Similarity	NPD3301	Approved
0.6984	Remote Similarity	NPD4098	Discontinued
0.6977	Remote Similarity	NPD1336	Approved
0.6972	Remote Similarity	NPD1809	Phase 2
0.6967	Remote Similarity	NPD6382	Discontinued
0.6967	Remote Similarity	NPD2594	Approved
0.6967	Remote Similarity	NPD2595	Approved
0.6967	Remote Similarity	NPD3024	Approved
0.6967	Remote Similarity	NPD3025	Approved
0.696	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.696	Remote Similarity	NPD4749	Approved
0.6947	Remote Similarity	NPD6355	Discontinued
0.6944	Remote Similarity	NPD845	Approved
0.6935	Remote Similarity	NPD422	Phase 1

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