NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.09
Volume:	206.081
LogP:	1.954
LogD:	2.049
LogS:	-2.08
# Rotatable Bonds:	3
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.803
Synthetic Accessibility Score:	2.221
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.595
MDCK Permeability:	1.4518507668981329e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.259
Plasma Protein Binding (PPB):	92.28430938720703%
Volume Distribution (VD):	1.238
Pgp-substrate:	7.494772911071777%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.18
CYP2C19-substrate:	0.799
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.161
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.237
CYP3A4-substrate:	0.42

ADMET: Excretion

Clearance (CL):	10.238
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.188
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.072
Skin Sensitization:	0.875
Carcinogencity:	0.204
Eye Corrosion:	0.793
Eye Irritation:	0.974
Respiratory Toxicity:	0.462

Download Data

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

Natural Product: NPC259638

Natural Product ID:	NPC259638
*Common Name:**	2,3-Dimethoxy-5-(1-Propenyl)Phenol
IUPAC Name:	2,3-dimethoxy-5-[(E)-prop-1-enyl]phenol
Synonyms:
Standard InCHIKey:	JBHSIYWHUIBYPL-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C11H14O3/c1-4-5-8-6-9(12)11(14-3)10(7-8)13-2/h4-7,12H,1-3H3/b5-4+
SMILES:	C/C=C/c1cc(c(c(c1)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489518
PubChem CID:	10997885
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO6580	Smirnowia iranica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502308]
NPO6580	Smirnowia iranica	Species	Fabaceae	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
IC50	7

Activity Type	# Activity
Cell Line	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	281000.0	nM	PMID[450133]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	=	267000.0	nM	PMID[450133]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	372000.0	nM	PMID[450133]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	395000.0	nM	PMID[450133]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	200000.0	nM	PMID[450133]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	800000.0	nM	PMID[450133]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	>	800000.0	nM	PMID[450133]

☑ 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 NPC259638 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	355
0.1-0.2	2138
0.2-0.3	7784
0.3-0.4	12061
0.4-0.5	3590
0.5-0.6	5115
0.6-0.7	7743
0.7-0.8	2981
0.8-0.85	562
0.85-0.9	252
0.9-0.95	109
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC193067
0.982	High Similarity	NPC20674
0.9732	High Similarity	NPC229401
0.9558	High Similarity	NPC232084
0.9558	High Similarity	NPC61516
0.9558	High Similarity	NPC247364
0.9558	High Similarity	NPC10932
0.9478	High Similarity	NPC262253
0.9478	High Similarity	NPC71579
0.9478	High Similarity	NPC473411
0.9469	High Similarity	NPC226629
0.9397	High Similarity	NPC238810
0.9391	High Similarity	NPC49341
0.9316	High Similarity	NPC5796
0.9316	High Similarity	NPC206487
0.9316	High Similarity	NPC183446
0.931	High Similarity	NPC41562
0.9304	High Similarity	NPC166759
0.9273	High Similarity	NPC203924
0.9266	High Similarity	NPC7097
0.9266	High Similarity	NPC246358
0.9266	High Similarity	NPC233731
0.9266	High Similarity	NPC36108
0.9266	High Similarity	NPC165386
0.9237	High Similarity	NPC299584
0.9237	High Similarity	NPC472093
0.9237	High Similarity	NPC58279
0.9237	High Similarity	NPC298757
0.9237	High Similarity	NPC265483
0.9237	High Similarity	NPC271985
0.9237	High Similarity	NPC251855
0.9237	High Similarity	NPC116907
0.9237	High Similarity	NPC300326
0.9237	High Similarity	NPC221077
0.9237	High Similarity	NPC57490
0.9237	High Similarity	NPC117214
0.9237	High Similarity	NPC60885
0.9237	High Similarity	NPC475169
0.9237	High Similarity	NPC82483
0.9237	High Similarity	NPC208950
0.9237	High Similarity	NPC233410
0.9237	High Similarity	NPC234400
0.9237	High Similarity	NPC193544
0.9237	High Similarity	NPC203133
0.9237	High Similarity	NPC17943
0.9231	High Similarity	NPC197757
0.9231	High Similarity	NPC165375
0.9231	High Similarity	NPC220598
0.9231	High Similarity	NPC228922
0.9224	High Similarity	NPC285289
0.9224	High Similarity	NPC145780
0.9217	High Similarity	NPC474565
0.9204	High Similarity	NPC221049
0.916	High Similarity	NPC28730
0.916	High Similarity	NPC18924
0.916	High Similarity	NPC78974
0.916	High Similarity	NPC214406
0.916	High Similarity	NPC44748
0.916	High Similarity	NPC103823
0.916	High Similarity	NPC223136
0.9107	High Similarity	NPC204120
0.9099	High Similarity	NPC173746
0.9099	High Similarity	NPC78918
0.9099	High Similarity	NPC257124
0.9099	High Similarity	NPC156840
0.9099	High Similarity	NPC8547
0.9099	High Similarity	NPC139617
0.9083	High Similarity	NPC266555
0.9083	High Similarity	NPC82679
0.9083	High Similarity	NPC293054
0.9083	High Similarity	NPC282000
0.9083	High Similarity	NPC169474
0.9083	High Similarity	NPC246620
0.9083	High Similarity	NPC324112
0.9083	High Similarity	NPC236791
0.9083	High Similarity	NPC124452
0.9083	High Similarity	NPC210355
0.9083	High Similarity	NPC159968
0.9083	High Similarity	NPC74817
0.9083	High Similarity	NPC127587
0.9068	High Similarity	NPC84086
0.9068	High Similarity	NPC233526
0.9068	High Similarity	NPC95168
0.9068	High Similarity	NPC282496
0.9068	High Similarity	NPC136319
0.9052	High Similarity	NPC177475
0.9052	High Similarity	NPC35071
0.9052	High Similarity	NPC148615
0.9043	High Similarity	NPC63083
0.9043	High Similarity	NPC255675
0.9018	High Similarity	NPC280606
0.9008	High Similarity	NPC206615
0.9008	High Similarity	NPC98631
0.9008	High Similarity	NPC470213
0.9008	High Similarity	NPC109275
0.9008	High Similarity	NPC154866
0.9008	High Similarity	NPC186843
0.9	High Similarity	NPC76451
0.8992	High Similarity	NPC228972
0.8992	High Similarity	NPC122792
0.8991	High Similarity	NPC164576
0.8974	High Similarity	NPC199023
0.8966	High Similarity	NPC320987
0.8966	High Similarity	NPC181969
0.8934	High Similarity	NPC10225
0.8934	High Similarity	NPC228769
0.8934	High Similarity	NPC48315
0.8934	High Similarity	NPC170844
0.8934	High Similarity	NPC476968
0.8934	High Similarity	NPC470633
0.8934	High Similarity	NPC58164
0.8929	High Similarity	NPC90520
0.8929	High Similarity	NPC296920
0.8917	High Similarity	NPC105925
0.8908	High Similarity	NPC121115
0.8899	High Similarity	NPC307875
0.8898	High Similarity	NPC75713
0.8898	High Similarity	NPC310373
0.8898	High Similarity	NPC470804
0.887	High Similarity	NPC123948
0.8862	High Similarity	NPC472338
0.8862	High Similarity	NPC126836
0.8862	High Similarity	NPC311680
0.8862	High Similarity	NPC234488
0.8862	High Similarity	NPC51840
0.8862	High Similarity	NPC299221
0.886	High Similarity	NPC228287
0.886	High Similarity	NPC180508
0.8852	High Similarity	NPC28765
0.8843	High Similarity	NPC112596
0.8843	High Similarity	NPC223953
0.8839	High Similarity	NPC94045
0.8824	High Similarity	NPC209567
0.8824	High Similarity	NPC135414
0.8824	High Similarity	NPC246967
0.8824	High Similarity	NPC270326
0.8824	High Similarity	NPC474864
0.8803	High Similarity	NPC135961
0.8793	High Similarity	NPC52464
0.8793	High Similarity	NPC33271
0.8793	High Similarity	NPC304208
0.879	High Similarity	NPC472597
0.879	High Similarity	NPC470096
0.879	High Similarity	NPC474017
0.879	High Similarity	NPC474356
0.879	High Similarity	NPC470095
0.879	High Similarity	NPC12275
0.879	High Similarity	NPC45715
0.878	High Similarity	NPC212015
0.878	High Similarity	NPC45824
0.877	High Similarity	NPC252131
0.877	High Similarity	NPC236760
0.877	High Similarity	NPC470699
0.8761	High Similarity	NPC195873
0.8739	High Similarity	NPC476343
0.8739	High Similarity	NPC227894
0.872	High Similarity	NPC35932
0.872	High Similarity	NPC86655
0.872	High Similarity	NPC201587
0.872	High Similarity	NPC253105
0.872	High Similarity	NPC184447
0.872	High Similarity	NPC16208
0.872	High Similarity	NPC160991
0.872	High Similarity	NPC6451
0.872	High Similarity	NPC7903
0.872	High Similarity	NPC202762
0.871	High Similarity	NPC214860
0.871	High Similarity	NPC91291
0.8707	High Similarity	NPC203113
0.8707	High Similarity	NPC141090
0.8699	High Similarity	NPC266691
0.8699	High Similarity	NPC19694
0.8689	High Similarity	NPC245060
0.8689	High Similarity	NPC181361
0.8673	High Similarity	NPC168657
0.8651	High Similarity	NPC132895
0.8651	High Similarity	NPC36661
0.8651	High Similarity	NPC158331
0.8651	High Similarity	NPC32778
0.8651	High Similarity	NPC471391
0.8651	High Similarity	NPC168059
0.8651	High Similarity	NPC229442
0.8651	High Similarity	NPC475840
0.8651	High Similarity	NPC471390
0.8644	High Similarity	NPC311595
0.8644	High Similarity	NPC24474
0.8644	High Similarity	NPC308217
0.8644	High Similarity	NPC15805
0.8644	High Similarity	NPC119949
0.8644	High Similarity	NPC475961
0.8644	High Similarity	NPC254625
0.864	High Similarity	NPC232275
0.8632	High Similarity	NPC474933
0.8632	High Similarity	NPC39793
0.8632	High Similarity	NPC164386
0.8632	High Similarity	NPC293619
0.8632	High Similarity	NPC195466
0.8629	High Similarity	NPC470258
0.8629	High Similarity	NPC210623
0.8629	High Similarity	NPC285339

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 NPC259638 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	1045
0.2-0.3	2195
0.3-0.4	2690
0.4-0.5	1457
0.5-0.6	865
0.6-0.7	481
0.7-0.8	68
0.8-0.85	5
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9099	High Similarity	NPD228	Approved
0.8934	High Similarity	NPD3027	Phase 3
0.8548	High Similarity	NPD1529	Clinical (unspecified phase)
0.8468	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD2982	Phase 2
0.8443	Intermediate Similarity	NPD2983	Phase 2
0.8425	Intermediate Similarity	NPD1613	Approved
0.8425	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8361	Intermediate Similarity	NPD2981	Phase 2
0.8175	Intermediate Similarity	NPD3018	Phase 2
0.8145	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD9296	Approved
0.8036	Intermediate Similarity	NPD1242	Phase 1
0.8033	Intermediate Similarity	NPD1357	Approved
0.7951	Intermediate Similarity	NPD1548	Phase 1
0.7891	Intermediate Similarity	NPD9494	Approved
0.7863	Intermediate Similarity	NPD1558	Phase 1
0.784	Intermediate Similarity	NPD1610	Phase 2
0.7833	Intermediate Similarity	NPD5283	Phase 1
0.771	Intermediate Similarity	NPD3145	Approved
0.771	Intermediate Similarity	NPD3144	Approved
0.7698	Intermediate Similarity	NPD422	Phase 1
0.7669	Intermediate Similarity	NPD230	Phase 1
0.7652	Intermediate Similarity	NPD940	Approved
0.7652	Intermediate Similarity	NPD846	Approved
0.7652	Intermediate Similarity	NPD2674	Phase 3
0.7627	Intermediate Similarity	NPD290	Approved
0.7606	Intermediate Similarity	NPD1653	Approved
0.7581	Intermediate Similarity	NPD5536	Phase 2
0.7578	Intermediate Similarity	NPD4749	Approved
0.7571	Intermediate Similarity	NPD4357	Discontinued
0.7563	Intermediate Similarity	NPD2684	Approved
0.7559	Intermediate Similarity	NPD3705	Approved
0.7557	Intermediate Similarity	NPD4908	Phase 1
0.7554	Intermediate Similarity	NPD2219	Phase 1
0.7523	Intermediate Similarity	NPD9094	Approved
0.7518	Intermediate Similarity	NPD3540	Phase 1
0.7517	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD291	Approved
0.75	Intermediate Similarity	NPD3022	Approved
0.7466	Intermediate Similarity	NPD2801	Approved
0.7463	Intermediate Similarity	NPD3620	Phase 2
0.7463	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1511	Approved
0.7445	Intermediate Similarity	NPD3539	Phase 1
0.7444	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6111	Discontinued
0.7405	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4625	Phase 3
0.7365	Intermediate Similarity	NPD3882	Suspended
0.7343	Intermediate Similarity	NPD1512	Approved
0.7317	Intermediate Similarity	NPD7843	Approved
0.7313	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD1091	Approved
0.728	Intermediate Similarity	NPD7157	Approved
0.726	Intermediate Similarity	NPD4675	Approved
0.726	Intermediate Similarity	NPD4678	Approved
0.725	Intermediate Similarity	NPD968	Approved
0.7248	Intermediate Similarity	NPD111	Approved
0.723	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4750	Phase 3
0.7206	Intermediate Similarity	NPD1240	Approved
0.719	Intermediate Similarity	NPD1358	Approved
0.7183	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD9377	Approved
0.7177	Intermediate Similarity	NPD9379	Approved
0.7163	Intermediate Similarity	NPD3060	Approved
0.7152	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD6671	Approved
0.7143	Intermediate Similarity	NPD9295	Approved
0.7133	Intermediate Similarity	NPD7124	Phase 2
0.7132	Intermediate Similarity	NPD9384	Approved
0.7132	Intermediate Similarity	NPD9381	Approved
0.7101	Intermediate Similarity	NPD1607	Approved
0.7099	Intermediate Similarity	NPD9269	Phase 2
0.7092	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD2861	Phase 2
0.7083	Intermediate Similarity	NPD5297	Approved
0.7075	Intermediate Similarity	NPD4005	Discontinued
0.7059	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD37	Approved
0.7045	Intermediate Similarity	NPD9622	Approved
0.7045	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4237	Approved
0.7042	Intermediate Similarity	NPD4236	Phase 3
0.704	Intermediate Similarity	NPD821	Approved
0.7034	Intermediate Similarity	NPD1424	Approved
0.7032	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6166	Phase 2
0.7031	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD447	Suspended
0.7021	Intermediate Similarity	NPD1375	Discontinued
0.7021	Intermediate Similarity	NPD7266	Discontinued
0.702	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD9365	Approved
0.7007	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD1778	Approved
0.7	Intermediate Similarity	NPD1510	Phase 2
0.6983	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD2934	Approved
0.6983	Remote Similarity	NPD2933	Approved
0.6977	Remote Similarity	NPD7534	Approved
0.6977	Remote Similarity	NPD7533	Approved
0.6972	Remote Similarity	NPD9089	Approved
0.6967	Remote Similarity	NPD3134	Approved
0.6966	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD943	Approved
0.6957	Remote Similarity	NPD4060	Phase 1
0.6954	Remote Similarity	NPD3817	Phase 2
0.6939	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD556	Approved
0.6929	Remote Similarity	NPD9299	Approved
0.6923	Remote Similarity	NPD2860	Approved
0.6923	Remote Similarity	NPD844	Approved
0.6923	Remote Similarity	NPD2859	Approved
0.6923	Remote Similarity	NPD1652	Phase 2
0.6918	Remote Similarity	NPD4123	Phase 3
0.6912	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4965	Approved
0.6908	Remote Similarity	NPD4967	Phase 2
0.6908	Remote Similarity	NPD4966	Approved
0.6903	Remote Similarity	NPD6232	Discontinued
0.6899	Remote Similarity	NPD7054	Approved
0.6891	Remote Similarity	NPD3020	Approved
0.6889	Remote Similarity	NPD9619	Approved
0.6889	Remote Similarity	NPD6584	Phase 3
0.6889	Remote Similarity	NPD9620	Approved
0.6889	Remote Similarity	NPD9621	Approved
0.6887	Remote Similarity	NPD1465	Phase 2
0.6881	Remote Similarity	NPD9093	Approved
0.6871	Remote Similarity	NPD1350	Approved
0.6871	Remote Similarity	NPD1351	Approved
0.6871	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1349	Approved
0.6867	Remote Similarity	NPD5090	Approved
0.6867	Remote Similarity	NPD5089	Approved
0.6866	Remote Similarity	NPD8651	Approved
0.6866	Remote Similarity	NPD2922	Phase 1
0.6864	Remote Similarity	NPD288	Approved
0.6863	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7472	Approved
0.6855	Remote Similarity	NPD7074	Phase 3
0.6846	Remote Similarity	NPD9545	Approved
0.6846	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1608	Approved
0.6839	Remote Similarity	NPD7199	Phase 2
0.6835	Remote Similarity	NPD7228	Approved
0.6835	Remote Similarity	NPD3818	Discontinued
0.6835	Remote Similarity	NPD2238	Phase 2
0.6833	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6099	Approved
0.6831	Remote Similarity	NPD2161	Phase 2
0.6831	Remote Similarity	NPD6100	Approved
0.6828	Remote Similarity	NPD6190	Approved
0.6812	Remote Similarity	NPD5718	Phase 2
0.6812	Remote Similarity	NPD5110	Phase 2
0.6812	Remote Similarity	NPD5109	Approved
0.6812	Remote Similarity	NPD5111	Phase 2
0.6806	Remote Similarity	NPD5177	Phase 3
0.68	Remote Similarity	NPD5451	Approved
0.6794	Remote Similarity	NPD9268	Approved
0.6783	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3686	Approved
0.6779	Remote Similarity	NPD3687	Approved
0.6776	Remote Similarity	NPD2978	Approved
0.6776	Remote Similarity	NPD2977	Approved
0.6772	Remote Similarity	NPD7473	Discontinued
0.6763	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4055	Discovery
0.6752	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD709	Approved
0.6742	Remote Similarity	NPD5846	Approved
0.6742	Remote Similarity	NPD2667	Approved
0.6742	Remote Similarity	NPD6516	Phase 2
0.6742	Remote Similarity	NPD2668	Approved
0.6741	Remote Similarity	NPD6696	Suspended
0.6741	Remote Similarity	NPD1283	Approved
0.6739	Remote Similarity	NPD7095	Approved
0.6739	Remote Similarity	NPD3180	Approved
0.6739	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3179	Approved
0.6738	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7153	Discontinued
0.6736	Remote Similarity	NPD1549	Phase 2
0.6733	Remote Similarity	NPD824	Approved
0.6733	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD1182	Approved
0.6716	Remote Similarity	NPD2232	Approved
0.6716	Remote Similarity	NPD2230	Approved
0.6716	Remote Similarity	NPD2233	Approved
0.6713	Remote Similarity	NPD1551	Phase 2

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