NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.09
Volume:	223.61
LogP:	2.584
LogD:	2.708
LogS:	-2.787
# Rotatable Bonds:	4
TPSA:	36.92
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	2.546
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.504
MDCK Permeability:	2.7141259124618955e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.445
Plasma Protein Binding (PPB):	90.13349151611328%
Volume Distribution (VD):	1.081
Pgp-substrate:	6.142799377441406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.887
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.118
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.87
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.906
CYP3A4-substrate:	0.5

ADMET: Excretion

Clearance (CL):	11.466
Half-life (T1/2):	0.571

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.742
Carcinogencity:	0.945
Eye Corrosion:	0.008
Eye Irritation:	0.592
Respiratory Toxicity:	0.399

Download Data

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

Natural Product: NPC191768

Natural Product ID:	NPC191768
*Common Name:**	4,6-Dimethoxy-5-Prop-2-Enyl-1,3-Benzodioxole
IUPAC Name:	4,6-dimethoxy-5-prop-2-enyl-1,3-benzodioxole
Synonyms:
Standard InCHIKey:	DLXIQKGNIITZEK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H14O4/c1-4-5-8-9(13-2)6-10-12(11(8)14-3)16-7-15-10/h4,6H,1,5,7H2,2-3H3
SMILES:	C=CCc1c(OC)cc2c(c1OC)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506190
PubChem CID:	15699856
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	whole plants	Sendai, Miyagi Prefecture, Japan	2000-Sep	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17397219]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	twig	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	aerial parts	Kego Nature Reserve, Hatinh Province, Vietnam	2008-DEC	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	stem	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	inflorescence	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	Kego Nature Reserve, Hatinh Province, Vietnam	2008-DEC	PMID[21973101]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22940450]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1912	Acanthosyris paulo-alvinii	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6614	Rubus pileatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO61	Phoebe grandis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO992	Betula alnoides	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5657	Oocystis polymorpha	Species	Oocystaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	IC50	=	34200.0	nM	PMID[568514]

☑ 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 NPC191768 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	498
0.1-0.2	2088
0.2-0.3	7519
0.3-0.4	12182
0.4-0.5	3474
0.5-0.6	5765
0.6-0.7	8309
0.7-0.8	2384
0.8-0.85	392
0.85-0.9	75
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC283170
1.0	High Similarity	NPC92869
0.9829	High Similarity	NPC211231
0.9487	High Similarity	NPC119949
0.9322	High Similarity	NPC308217
0.9316	High Similarity	NPC33271
0.9153	High Similarity	NPC52464
0.9153	High Similarity	NPC304208
0.9032	High Similarity	NPC52593
0.9032	High Similarity	NPC473960
0.8992	High Similarity	NPC73071
0.8984	High Similarity	NPC58585
0.8934	High Similarity	NPC285289
0.8923	High Similarity	NPC197166
0.8917	High Similarity	NPC474612
0.8864	High Similarity	NPC284464
0.8862	High Similarity	NPC270326
0.8855	High Similarity	NPC20796
0.8846	High Similarity	NPC240915
0.8837	High Similarity	NPC471391
0.8837	High Similarity	NPC471390
0.8814	High Similarity	NPC204120
0.8797	High Similarity	NPC300798
0.8797	High Similarity	NPC58137
0.8788	High Similarity	NPC9068
0.8788	High Similarity	NPC6369
0.8788	High Similarity	NPC30951
0.8769	High Similarity	NPC145722
0.8769	High Similarity	NPC7163
0.8769	High Similarity	NPC185680
0.8769	High Similarity	NPC256776
0.875	High Similarity	NPC184814
0.875	High Similarity	NPC63574
0.8731	High Similarity	NPC472562
0.8731	High Similarity	NPC80326
0.8731	High Similarity	NPC174522
0.872	High Similarity	NPC183446
0.8718	High Similarity	NPC31279
0.8712	High Similarity	NPC196420
0.871	High Similarity	NPC264885
0.871	High Similarity	NPC194626
0.8692	High Similarity	NPC196937
0.8692	High Similarity	NPC266848
0.8692	High Similarity	NPC136750
0.8682	High Similarity	NPC192255
0.8667	High Similarity	NPC474808
0.8644	High Similarity	NPC203924
0.8636	High Similarity	NPC32189
0.8632	High Similarity	NPC165386
0.8632	High Similarity	NPC127326
0.8615	High Similarity	NPC65183
0.8615	High Similarity	NPC72046
0.8615	High Similarity	NPC7744
0.8615	High Similarity	NPC261812
0.8605	High Similarity	NPC470624
0.8605	High Similarity	NPC237169
0.8571	High Similarity	NPC261714
0.8561	High Similarity	NPC189474
0.855	High Similarity	NPC112237
0.8537	High Similarity	NPC475961
0.8537	High Similarity	NPC254625
0.8527	High Similarity	NPC58164
0.8527	High Similarity	NPC228769
0.8527	High Similarity	NPC153547
0.8527	High Similarity	NPC470633
0.8527	High Similarity	NPC10225
0.8519	High Similarity	NPC312199
0.8516	High Similarity	NPC474670
0.8516	High Similarity	NPC202904
0.8516	High Similarity	NPC189248
0.8507	High Similarity	NPC53722
0.8507	High Similarity	NPC201404
0.8507	High Similarity	NPC290714
0.8507	High Similarity	NPC292487
0.8504	High Similarity	NPC64391
0.8496	Intermediate Similarity	NPC172818
0.8496	Intermediate Similarity	NPC25695
0.8496	Intermediate Similarity	NPC143895
0.8485	Intermediate Similarity	NPC474478
0.8485	Intermediate Similarity	NPC31530
0.8478	Intermediate Similarity	NPC162193
0.8478	Intermediate Similarity	NPC33832
0.8462	Intermediate Similarity	NPC51840
0.8462	Intermediate Similarity	NPC224157
0.8462	Intermediate Similarity	NPC234488
0.8462	Intermediate Similarity	NPC258483
0.8462	Intermediate Similarity	NPC240722
0.8462	Intermediate Similarity	NPC192687
0.8462	Intermediate Similarity	NPC311680
0.8462	Intermediate Similarity	NPC244799
0.8462	Intermediate Similarity	NPC299221
0.8455	Intermediate Similarity	NPC63083
0.845	Intermediate Similarity	NPC19694
0.8444	Intermediate Similarity	NPC216434
0.8444	Intermediate Similarity	NPC103448
0.8443	Intermediate Similarity	NPC123948
0.8438	Intermediate Similarity	NPC112596
0.8438	Intermediate Similarity	NPC285725
0.8438	Intermediate Similarity	NPC50683
0.8438	Intermediate Similarity	NPC112571
0.8433	Intermediate Similarity	NPC185908
0.8421	Intermediate Similarity	NPC150534
0.8421	Intermediate Similarity	NPC25333
0.8421	Intermediate Similarity	NPC148893
0.8421	Intermediate Similarity	NPC49235
0.8409	Intermediate Similarity	NPC1474
0.8406	Intermediate Similarity	NPC307466
0.8406	Intermediate Similarity	NPC474749
0.8406	Intermediate Similarity	NPC205316
0.8406	Intermediate Similarity	NPC11422
0.8406	Intermediate Similarity	NPC178014
0.8406	Intermediate Similarity	NPC42716
0.84	Intermediate Similarity	NPC472596
0.8387	Intermediate Similarity	NPC15805
0.8387	Intermediate Similarity	NPC20674
0.8385	Intermediate Similarity	NPC27239
0.8385	Intermediate Similarity	NPC190144
0.8385	Intermediate Similarity	NPC150809
0.8385	Intermediate Similarity	NPC123127
0.8372	Intermediate Similarity	NPC474821
0.8372	Intermediate Similarity	NPC242032
0.8359	Intermediate Similarity	NPC105925
0.8358	Intermediate Similarity	NPC104167
0.8358	Intermediate Similarity	NPC11453
0.8358	Intermediate Similarity	NPC121651
0.8357	Intermediate Similarity	NPC301961
0.8357	Intermediate Similarity	NPC166584
0.8346	Intermediate Similarity	NPC474600
0.8333	Intermediate Similarity	NPC6451
0.8333	Intermediate Similarity	NPC319969
0.8333	Intermediate Similarity	NPC137669
0.8333	Intermediate Similarity	NPC477886
0.8321	Intermediate Similarity	NPC474295
0.8321	Intermediate Similarity	NPC229172
0.8321	Intermediate Similarity	NPC184684
0.8321	Intermediate Similarity	NPC103637
0.8321	Intermediate Similarity	NPC311057
0.8321	Intermediate Similarity	NPC476399
0.8321	Intermediate Similarity	NPC133934
0.8321	Intermediate Similarity	NPC184641
0.8321	Intermediate Similarity	NPC36531
0.8321	Intermediate Similarity	NPC41782
0.8321	Intermediate Similarity	NPC230538
0.832	Intermediate Similarity	NPC344161
0.832	Intermediate Similarity	NPC222175
0.8308	Intermediate Similarity	NPC31707
0.8308	Intermediate Similarity	NPC165128
0.8308	Intermediate Similarity	NPC158471
0.8308	Intermediate Similarity	NPC57119
0.8308	Intermediate Similarity	NPC222127
0.8308	Intermediate Similarity	NPC266691
0.8308	Intermediate Similarity	NPC226862
0.8308	Intermediate Similarity	NPC82862
0.8296	Intermediate Similarity	NPC474039
0.8296	Intermediate Similarity	NPC283949
0.8295	Intermediate Similarity	NPC103823
0.8295	Intermediate Similarity	NPC28730
0.8295	Intermediate Similarity	NPC88297
0.8295	Intermediate Similarity	NPC214406
0.8295	Intermediate Similarity	NPC186845
0.8295	Intermediate Similarity	NPC44748
0.8295	Intermediate Similarity	NPC474632
0.8295	Intermediate Similarity	NPC223953
0.8295	Intermediate Similarity	NPC78974
0.8295	Intermediate Similarity	NPC18924
0.8295	Intermediate Similarity	NPC223136
0.8295	Intermediate Similarity	NPC9891
0.8286	Intermediate Similarity	NPC116019
0.8284	Intermediate Similarity	NPC236522
0.8284	Intermediate Similarity	NPC474139
0.8284	Intermediate Similarity	NPC234865
0.8273	Intermediate Similarity	NPC476450
0.8273	Intermediate Similarity	NPC180953
0.8271	Intermediate Similarity	NPC215833
0.8271	Intermediate Similarity	NPC36437
0.8271	Intermediate Similarity	NPC233018
0.8271	Intermediate Similarity	NPC69513
0.8271	Intermediate Similarity	NPC241341
0.8268	Intermediate Similarity	NPC246967
0.8268	Intermediate Similarity	NPC135414
0.8268	Intermediate Similarity	NPC261661
0.8268	Intermediate Similarity	NPC474864
0.8261	Intermediate Similarity	NPC81638
0.8261	Intermediate Similarity	NPC324962
0.8261	Intermediate Similarity	NPC76415
0.8261	Intermediate Similarity	NPC218510
0.8258	Intermediate Similarity	NPC82111
0.8258	Intermediate Similarity	NPC232275
0.8258	Intermediate Similarity	NPC45715
0.8258	Intermediate Similarity	NPC12275
0.8258	Intermediate Similarity	NPC474356
0.8258	Intermediate Similarity	NPC469698
0.8258	Intermediate Similarity	NPC227160
0.8258	Intermediate Similarity	NPC473412
0.8244	Intermediate Similarity	NPC45824
0.8239	Intermediate Similarity	NPC474560
0.8235	Intermediate Similarity	NPC113550
0.8231	Intermediate Similarity	NPC246620
0.8231	Intermediate Similarity	NPC8050
0.8231	Intermediate Similarity	NPC82679

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 NPC191768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	1022
0.2-0.3	2341
0.3-0.4	2639
0.4-0.5	1404
0.5-0.6	905
0.6-0.7	388
0.7-0.8	42
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8629	High Similarity	NPD3705	Approved
0.8092	Intermediate Similarity	NPD3018	Phase 2
0.7984	Intermediate Similarity	NPD2981	Phase 2
0.797	Intermediate Similarity	NPD3027	Phase 3
0.7953	Intermediate Similarity	NPD1357	Approved
0.7923	Intermediate Similarity	NPD2982	Phase 2
0.7923	Intermediate Similarity	NPD2983	Phase 2
0.7895	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1613	Approved
0.7793	Intermediate Similarity	NPD1653	Approved
0.776	Intermediate Similarity	NPD5283	Phase 1
0.7742	Intermediate Similarity	NPD228	Approved
0.7724	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD37	Approved
0.7534	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD3539	Phase 1
0.75	Intermediate Similarity	NPD1091	Approved
0.7465	Intermediate Similarity	NPD3540	Phase 1
0.7464	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4965	Approved
0.7434	Intermediate Similarity	NPD4966	Approved
0.7434	Intermediate Similarity	NPD4967	Phase 2
0.7355	Intermediate Similarity	NPD7199	Phase 2
0.7343	Intermediate Similarity	NPD1375	Discontinued
0.7338	Intermediate Similarity	NPD6234	Discontinued
0.7328	Intermediate Similarity	NPD1548	Phase 1
0.7279	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6111	Discontinued
0.7252	Intermediate Similarity	NPD5536	Phase 2
0.7239	Intermediate Similarity	NPD1610	Phase 2
0.7239	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD2801	Approved
0.7179	Intermediate Similarity	NPD5494	Approved
0.7161	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1247	Approved
0.7125	Intermediate Similarity	NPD3818	Discontinued
0.7123	Intermediate Similarity	NPD6674	Discontinued
0.7122	Intermediate Similarity	NPD4908	Phase 1
0.7095	Intermediate Similarity	NPD7124	Phase 2
0.7063	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1137	Approved
0.7054	Intermediate Similarity	NPD1139	Approved
0.705	Intermediate Similarity	NPD2861	Phase 2
0.7047	Intermediate Similarity	NPD5297	Approved
0.7039	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3496	Discontinued
0.7032	Intermediate Similarity	NPD3817	Phase 2
0.7027	Intermediate Similarity	NPD2219	Phase 1
0.7027	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7228	Approved
0.7016	Intermediate Similarity	NPD940	Approved
0.7016	Intermediate Similarity	NPD846	Approved
0.7013	Intermediate Similarity	NPD3384	Approved
0.7013	Intermediate Similarity	NPD1934	Approved
0.7013	Intermediate Similarity	NPD3382	Approved
0.7013	Intermediate Similarity	NPD3383	Approved
0.7008	Intermediate Similarity	NPD1358	Approved
0.7008	Intermediate Similarity	NPD290	Approved
0.7007	Intermediate Similarity	NPD4749	Approved
0.7006	Intermediate Similarity	NPD919	Approved
0.7	Intermediate Similarity	NPD1138	Approved
0.7	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1424	Approved
0.6987	Remote Similarity	NPD3882	Suspended
0.6978	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7054	Approved
0.6972	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.697	Remote Similarity	NPD709	Approved
0.697	Remote Similarity	NPD6671	Approved
0.6957	Remote Similarity	NPD2922	Phase 1
0.6953	Remote Similarity	NPD2684	Approved
0.6944	Remote Similarity	NPD2492	Phase 1
0.6933	Remote Similarity	NPD1511	Approved
0.6933	Remote Similarity	NPD4357	Discontinued
0.6933	Remote Similarity	NPD7472	Approved
0.6933	Remote Similarity	NPD7074	Phase 3
0.6909	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4237	Approved
0.6892	Remote Similarity	NPD1652	Phase 2
0.6892	Remote Similarity	NPD4236	Phase 3
0.6889	Remote Similarity	NPD5691	Approved
0.6884	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD230	Phase 1
0.6875	Remote Similarity	NPD1933	Approved
0.6875	Remote Similarity	NPD447	Suspended
0.6871	Remote Similarity	NPD7266	Discontinued
0.687	Remote Similarity	NPD7843	Approved
0.6861	Remote Similarity	NPD1611	Approved
0.6859	Remote Similarity	NPD2977	Approved
0.6859	Remote Similarity	NPD2978	Approved
0.6848	Remote Similarity	NPD7240	Approved
0.6842	Remote Similarity	NPD1512	Approved
0.6842	Remote Similarity	NPD7157	Approved
0.6839	Remote Similarity	NPD5090	Approved
0.6839	Remote Similarity	NPD5089	Approved
0.6838	Remote Similarity	NPD4626	Approved
0.6835	Remote Similarity	NPD6696	Suspended
0.6831	Remote Similarity	NPD4625	Phase 3
0.6824	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7808	Phase 3
0.6806	Remote Similarity	NPD1558	Phase 1
0.6803	Remote Similarity	NPD3454	Phase 3
0.68	Remote Similarity	NPD1242	Phase 1
0.6788	Remote Similarity	NPD6797	Phase 2
0.6783	Remote Similarity	NPD1296	Phase 2
0.6783	Remote Similarity	NPD5110	Phase 2
0.6783	Remote Similarity	NPD5111	Phase 2
0.6783	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5109	Approved
0.6774	Remote Similarity	NPD4675	Approved
0.6774	Remote Similarity	NPD4678	Approved
0.677	Remote Similarity	NPD6232	Discontinued
0.6768	Remote Similarity	NPD5844	Phase 1
0.6761	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5058	Phase 3
0.6755	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4585	Approved
0.6747	Remote Similarity	NPD7251	Discontinued
0.6733	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1349	Approved
0.6732	Remote Similarity	NPD1350	Approved
0.6732	Remote Similarity	NPD1351	Approved
0.673	Remote Similarity	NPD4055	Discovery
0.6728	Remote Similarity	NPD3926	Phase 2
0.6715	Remote Similarity	NPD1778	Approved
0.6714	Remote Similarity	NPD8651	Approved
0.6713	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4005	Discontinued
0.6691	Remote Similarity	NPD1182	Approved
0.669	Remote Similarity	NPD1240	Approved
0.6689	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6788	Approved
0.6667	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3134	Approved
0.6667	Remote Similarity	NPD5718	Phase 2
0.6667	Remote Similarity	NPD968	Approved
0.6667	Remote Similarity	NPD7028	Phase 2
0.6647	Remote Similarity	NPD6559	Discontinued
0.6646	Remote Similarity	NPD5677	Discontinued
0.6646	Remote Similarity	NPD7473	Discontinued
0.6645	Remote Similarity	NPD4210	Discontinued
0.6644	Remote Similarity	NPD3657	Discovery
0.6643	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD596	Approved
0.6643	Remote Similarity	NPD600	Approved
0.6641	Remote Similarity	NPD556	Approved
0.6641	Remote Similarity	NPD5451	Approved
0.6641	Remote Similarity	NPD4750	Phase 3
0.6625	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7466	Approved
0.6623	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3748	Approved
0.6622	Remote Similarity	NPD1510	Phase 2
0.6622	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD2674	Phase 3
0.6621	Remote Similarity	NPD839	Approved
0.6621	Remote Similarity	NPD840	Approved
0.6618	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5535	Approved
0.6614	Remote Similarity	NPD291	Approved
0.6607	Remote Similarity	NPD7549	Discontinued
0.6604	Remote Similarity	NPD5353	Approved
0.6603	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6799	Approved
0.6601	Remote Similarity	NPD1774	Approved
0.6599	Remote Similarity	NPD1607	Approved
0.6599	Remote Similarity	NPD2653	Approved
0.6594	Remote Similarity	NPD17	Approved
0.6593	Remote Similarity	NPD6387	Discontinued
0.6585	Remote Similarity	NPD6166	Phase 2
0.6585	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD920	Approved
0.6577	Remote Similarity	NPD2796	Approved
0.6575	Remote Similarity	NPD4060	Phase 1
0.6575	Remote Similarity	NPD3620	Phase 2
0.6575	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD9494	Approved
0.6571	Remote Similarity	NPD1840	Phase 2
0.6569	Remote Similarity	NPD7534	Approved
0.6569	Remote Similarity	NPD7533	Approved
0.6564	Remote Similarity	NPD3787	Discontinued
0.6558	Remote Similarity	NPD2532	Approved
0.6558	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD2533	Approved
0.6558	Remote Similarity	NPD4739	Approved
0.6558	Remote Similarity	NPD3146	Approved
0.6558	Remote Similarity	NPD2534	Approved
0.6556	Remote Similarity	NPD5698	Clinical (unspecified phase)

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