NPASS Compound

Structure

NPC197166 OpenBabel07101718242D 27 29 0 0 1 0 0 0 0 0999 V2000 -2.3902 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3902 0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9882 0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3902 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1222 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 -3.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6581 -4.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3902 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2562 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2562 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1222 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2562 -3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2562 0.0219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9882 -0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 12 1 0 0 0 0 5 14 1 0 0 0 0 6 13 1 0 0 0 0 6 15 1 0 0 0 0 7 14 2 0 0 0 0 7 18 1 0 0 0 0 8 15 2 0 0 0 0 8 20 1 0 0 0 0 9 16 2 0 0 0 0 9 19 1 0 0 0 0 10 17 2 0 0 0 0 10 21 1 0 0 0 0 11 26 1 0 0 0 0 11 27 1 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 13 2 1 1 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 21 2 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.17
Volume:	383.025
LogP:	4.063
LogD:	3.949
LogS:	-4.368
# Rotatable Bonds:	7
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.765
Synthetic Accessibility Score:	3.299
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.026
MDCK Permeability:	2.170657171518542e-05
Pgp-inhibitor:	0.046
Pgp-substrate:	0.112
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	97.95002746582031%
Volume Distribution (VD):	1.396
Pgp-substrate:	2.1565346717834473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.887
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.909
CYP2C19-substrate:	0.591
CYP2C9-inhibitor:	0.652
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.943
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.952
CYP3A4-substrate:	0.488

ADMET: Excretion

Clearance (CL):	16.95
Half-life (T1/2):	0.62

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.749
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.277
Skin Sensitization:	0.937
Carcinogencity:	0.806
Eye Corrosion:	0.006
Eye Irritation:	0.846
Respiratory Toxicity:	0.773

Download Data

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

Natural Product: NPC197166

Natural Product ID:	NPC197166
*Common Name:**	Rel-Saurulignan C
IUPAC Name:	6-[(2R,3S)-4-(2-hydroxy-4,5-dimethoxyphenyl)-2,3-dimethylbutyl]-1,3-benzodioxol-5-ol
Synonyms:
Standard InCHIKey:	HWEDUYYNFQNDIU-QWHCGFSZSA-N
Standard InCHI:	InChI=1S/C21H26O6/c1-12(5-14-7-18(24-3)19(25-4)9-16(14)22)13(2)6-15-8-20-21(10-17(15)23)27-11-26-20/h7-10,12-13,22-23H,5-6,11H2,1-4H3/t12-,13+/m0/s1
SMILES:	C[C@@H](Cc1cc(c(cc1O)OC)OC)[C@H](C)Cc1cc2c(cc1O)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104946
PubChem CID:	76331995
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	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
Others	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	73.0	%	PMID[575766]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	71.5	%	PMID[575766]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	7.0	%	PMID[575766]

☑ 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 NPC197166 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	398
0.1-0.2	1685
0.2-0.3	4512
0.3-0.4	12081
0.4-0.5	6326
0.5-0.6	4315
0.6-0.7	7805
0.7-0.8	4177
0.8-0.85	937
0.85-0.9	385
0.9-0.95	69
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC9068
0.9847	High Similarity	NPC30951
0.9847	High Similarity	NPC6369
0.9773	High Similarity	NPC284464
0.9556	High Similarity	NPC474808
0.9416	High Similarity	NPC307466
0.9385	High Similarity	NPC63574
0.9385	High Similarity	NPC184814
0.9385	High Similarity	NPC224157
0.9385	High Similarity	NPC192687
0.9348	High Similarity	NPC33832
0.9338	High Similarity	NPC184641
0.9338	High Similarity	NPC133934
0.9338	High Similarity	NPC184684
0.9328	High Similarity	NPC474039
0.9318	High Similarity	NPC196937
0.9318	High Similarity	NPC471390
0.9318	High Similarity	NPC471391
0.9308	High Similarity	NPC190144
0.9281	High Similarity	NPC116019
0.9259	High Similarity	NPC290714
0.9259	High Similarity	NPC201404
0.9259	High Similarity	NPC53722
0.9242	High Similarity	NPC6451
0.9214	High Similarity	NPC71726
0.9203	High Similarity	NPC73467
0.9203	High Similarity	NPC121661
0.9197	High Similarity	NPC229172
0.9197	High Similarity	NPC36531
0.9197	High Similarity	NPC230538
0.9197	High Similarity	NPC103637
0.9197	High Similarity	NPC191231
0.9191	High Similarity	NPC177868
0.9179	High Similarity	NPC150534
0.9173	High Similarity	NPC112237
0.9173	High Similarity	NPC58585
0.9167	High Similarity	NPC45715
0.9167	High Similarity	NPC232275
0.9167	High Similarity	NPC474356
0.9167	High Similarity	NPC12275
0.9137	High Similarity	NPC474749
0.9137	High Similarity	NPC42716
0.9137	High Similarity	NPC11422
0.9137	High Similarity	NPC197352
0.9137	High Similarity	NPC178014
0.9137	High Similarity	NPC189239
0.9137	High Similarity	NPC166506
0.9137	High Similarity	NPC180953
0.9137	High Similarity	NPC110763
0.913	High Similarity	NPC324962
0.9104	High Similarity	NPC145722
0.9104	High Similarity	NPC185680
0.9104	High Similarity	NPC256776
0.9091	High Similarity	NPC299221
0.9091	High Similarity	NPC311680
0.9091	High Similarity	NPC234488
0.9091	High Similarity	NPC51840
0.9078	High Similarity	NPC166584
0.9078	High Similarity	NPC301961
0.9071	High Similarity	NPC154971
0.9071	High Similarity	NPC252286
0.9071	High Similarity	NPC226540
0.9065	High Similarity	NPC172171
0.9065	High Similarity	NPC239254
0.9058	High Similarity	NPC41782
0.9051	High Similarity	NPC254759
0.9051	High Similarity	NPC27495
0.9051	High Similarity	NPC160283
0.9044	High Similarity	NPC185908
0.9044	High Similarity	NPC283949
0.9037	High Similarity	NPC236522
0.9015	High Similarity	NPC10225
0.9015	High Similarity	NPC470633
0.9015	High Similarity	NPC58164
0.9015	High Similarity	NPC228769
0.9	High Similarity	NPC475868
0.9	High Similarity	NPC105925
0.8993	High Similarity	NPC298317
0.8993	High Similarity	NPC185071
0.8993	High Similarity	NPC12728
0.8993	High Similarity	NPC255566
0.8986	High Similarity	NPC311530
0.8986	High Similarity	NPC247291
0.8978	High Similarity	NPC292487
0.8978	High Similarity	NPC292882
0.8971	High Similarity	NPC32189
0.8971	High Similarity	NPC173660
0.8955	High Similarity	NPC175067
0.8955	High Similarity	NPC261812
0.8955	High Similarity	NPC471505
0.8955	High Similarity	NPC72046
0.8955	High Similarity	NPC65183
0.8955	High Similarity	NPC204215
0.8947	High Similarity	NPC237169
0.8947	High Similarity	NPC470624
0.8939	High Similarity	NPC266691
0.8936	High Similarity	NPC162193
0.8931	High Similarity	NPC76451
0.8931	High Similarity	NPC223953
0.8929	High Similarity	NPC472712
0.8929	High Similarity	NPC118385
0.8929	High Similarity	NPC473046
0.8929	High Similarity	NPC472713
0.8929	High Similarity	NPC187774
0.8923	High Similarity	NPC92869
0.8923	High Similarity	NPC191768
0.8923	High Similarity	NPC283170
0.8921	High Similarity	NPC472562
0.8921	High Similarity	NPC107161
0.8921	High Similarity	NPC80326
0.8915	High Similarity	NPC211231
0.8913	High Similarity	NPC56091
0.8913	High Similarity	NPC46591
0.8913	High Similarity	NPC226547
0.8905	High Similarity	NPC196420
0.8897	High Similarity	NPC111655
0.8897	High Similarity	NPC195022
0.8889	High Similarity	NPC136750
0.8889	High Similarity	NPC266848
0.8889	High Similarity	NPC158331
0.8881	High Similarity	NPC240521
0.8881	High Similarity	NPC192255
0.8865	High Similarity	NPC477702
0.8864	High Similarity	NPC74817
0.8864	High Similarity	NPC246620
0.8864	High Similarity	NPC124452
0.8864	High Similarity	NPC202904
0.8864	High Similarity	NPC282000
0.8864	High Similarity	NPC293054
0.8864	High Similarity	NPC169474
0.8864	High Similarity	NPC236791
0.8864	High Similarity	NPC127587
0.8864	High Similarity	NPC159968
0.8864	High Similarity	NPC82679
0.8864	High Similarity	NPC189248
0.8864	High Similarity	NPC324112
0.8857	High Similarity	NPC81638
0.8857	High Similarity	NPC47633
0.8857	High Similarity	NPC477616
0.8857	High Similarity	NPC102044
0.8857	High Similarity	NPC85264
0.8849	High Similarity	NPC58137
0.8849	High Similarity	NPC300798
0.8846	High Similarity	NPC249788
0.8846	High Similarity	NPC282496
0.8846	High Similarity	NPC233526
0.8841	High Similarity	NPC245207
0.8841	High Similarity	NPC127218
0.8841	High Similarity	NPC25966
0.8841	High Similarity	NPC319647
0.8841	High Similarity	NPC471388
0.8836	High Similarity	NPC159922
0.8832	High Similarity	NPC172818
0.8832	High Similarity	NPC25695
0.8832	High Similarity	NPC205442
0.8824	High Similarity	NPC244983
0.8824	High Similarity	NPC56764
0.8824	High Similarity	NPC276026
0.8824	High Similarity	NPC188378
0.8824	High Similarity	NPC7515
0.8824	High Similarity	NPC287745
0.8824	High Similarity	NPC31530
0.8824	High Similarity	NPC555
0.8824	High Similarity	NPC206737
0.8824	High Similarity	NPC326095
0.8824	High Similarity	NPC289258
0.8824	High Similarity	NPC469659
0.8819	High Similarity	NPC472709
0.8819	High Similarity	NPC472710
0.8819	High Similarity	NPC177830
0.8819	High Similarity	NPC24425
0.8815	High Similarity	NPC106739
0.8815	High Similarity	NPC259742
0.8815	High Similarity	NPC104077
0.8815	High Similarity	NPC219671
0.8815	High Similarity	NPC147616
0.8815	High Similarity	NPC7744
0.8811	High Similarity	NPC175976
0.8811	High Similarity	NPC316676
0.8811	High Similarity	NPC325720
0.8811	High Similarity	NPC304821
0.8806	High Similarity	NPC126836
0.8806	High Similarity	NPC214860
0.8803	High Similarity	NPC212890
0.8797	High Similarity	NPC28765
0.8797	High Similarity	NPC154866
0.8794	High Similarity	NPC93323
0.8794	High Similarity	NPC280092
0.8794	High Similarity	NPC12641
0.8794	High Similarity	NPC63879
0.8794	High Similarity	NPC45257
0.8788	High Similarity	NPC473960
0.8788	High Similarity	NPC28730
0.8788	High Similarity	NPC274356
0.8788	High Similarity	NPC103823
0.8788	High Similarity	NPC214406
0.8788	High Similarity	NPC18924
0.8788	High Similarity	NPC44748
0.8788	High Similarity	NPC78974
0.8788	High Similarity	NPC223136

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 NPC197166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	953
0.2-0.3	1874
0.3-0.4	2850
0.4-0.5	1591
0.5-0.6	919
0.6-0.7	535
0.7-0.8	84
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8593	High Similarity	NPD3027	Phase 3
0.8389	Intermediate Similarity	NPD37	Approved
0.8309	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD3705	Approved
0.8248	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6234	Discontinued
0.8224	Intermediate Similarity	NPD4966	Approved
0.8224	Intermediate Similarity	NPD4965	Approved
0.8224	Intermediate Similarity	NPD4967	Phase 2
0.8143	Intermediate Similarity	NPD1613	Approved
0.8143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD3018	Phase 2
0.8	Intermediate Similarity	NPD5283	Phase 1
0.7986	Intermediate Similarity	NPD4908	Phase 1
0.7914	Intermediate Similarity	NPD2861	Phase 2
0.7898	Intermediate Similarity	NPD7199	Phase 2
0.7883	Intermediate Similarity	NPD2983	Phase 2
0.7883	Intermediate Similarity	NPD2982	Phase 2
0.7881	Intermediate Similarity	NPD1653	Approved
0.7875	Intermediate Similarity	NPD7228	Approved
0.7872	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1610	Phase 2
0.781	Intermediate Similarity	NPD2981	Phase 2
0.7799	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1357	Approved
0.7754	Intermediate Similarity	NPD4749	Approved
0.7733	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6674	Discontinued
0.7697	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3818	Discontinued
0.7628	Intermediate Similarity	NPD2801	Approved
0.7595	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD228	Approved
0.7574	Intermediate Similarity	NPD1548	Phase 1
0.7552	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1091	Approved
0.747	Intermediate Similarity	NPD7240	Approved
0.7455	Intermediate Similarity	NPD7074	Phase 3
0.7452	Intermediate Similarity	NPD1934	Approved
0.745	Intermediate Similarity	NPD3540	Phase 1
0.7424	Intermediate Similarity	NPD3022	Approved
0.7424	Intermediate Similarity	NPD3021	Approved
0.7424	Intermediate Similarity	NPD4750	Phase 3
0.7421	Intermediate Similarity	NPD3882	Suspended
0.7407	Intermediate Similarity	NPD6232	Discontinued
0.7403	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4060	Phase 1
0.7397	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3620	Phase 2
0.7394	Intermediate Similarity	NPD7054	Approved
0.7391	Intermediate Similarity	NPD5494	Approved
0.7383	Intermediate Similarity	NPD3539	Phase 1
0.7378	Intermediate Similarity	NPD7473	Discontinued
0.7376	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6671	Approved
0.7349	Intermediate Similarity	NPD7472	Approved
0.7337	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7266	Discontinued
0.7324	Intermediate Similarity	NPD6696	Suspended
0.7321	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7124	Phase 2
0.7312	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2977	Approved
0.7296	Intermediate Similarity	NPD2978	Approved
0.7296	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5844	Phase 1
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7261	Intermediate Similarity	NPD4005	Discontinued
0.726	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6111	Discontinued
0.7234	Intermediate Similarity	NPD422	Phase 1
0.7233	Intermediate Similarity	NPD3382	Approved
0.7233	Intermediate Similarity	NPD3384	Approved
0.7233	Intermediate Similarity	NPD3383	Approved
0.7219	Intermediate Similarity	NPD7549	Discontinued
0.7219	Intermediate Similarity	NPD7808	Phase 3
0.7219	Intermediate Similarity	NPD1375	Discontinued
0.7202	Intermediate Similarity	NPD6797	Phase 2
0.7193	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1511	Approved
0.716	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD7251	Discontinued
0.7154	Intermediate Similarity	NPD940	Approved
0.7154	Intermediate Similarity	NPD846	Approved
0.7152	Intermediate Similarity	NPD6100	Approved
0.7152	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD2219	Phase 1
0.7143	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5177	Phase 3
0.7122	Intermediate Similarity	NPD5536	Phase 2
0.7108	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6166	Phase 2
0.7107	Intermediate Similarity	NPD4675	Approved
0.7107	Intermediate Similarity	NPD7028	Phase 2
0.7107	Intermediate Similarity	NPD4678	Approved
0.7097	Intermediate Similarity	NPD5058	Phase 3
0.7081	Intermediate Similarity	NPD1465	Phase 2
0.7078	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3892	Phase 2
0.7077	Intermediate Similarity	NPD1242	Phase 1
0.707	Intermediate Similarity	NPD1512	Approved
0.7055	Intermediate Similarity	NPD4055	Discovery
0.7047	Intermediate Similarity	NPD1558	Phase 1
0.7047	Intermediate Similarity	NPD1240	Approved
0.7047	Intermediate Similarity	NPD2238	Phase 2
0.7039	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5111	Phase 2
0.7027	Intermediate Similarity	NPD5109	Approved
0.7027	Intermediate Similarity	NPD5110	Phase 2
0.7013	Intermediate Similarity	NPD3060	Approved
0.7013	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4237	Approved
0.7013	Intermediate Similarity	NPD4236	Phase 3
0.7006	Intermediate Similarity	NPD2532	Approved
0.7006	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD2534	Approved
0.7006	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3020	Approved
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6978	Remote Similarity	NPD709	Approved
0.6975	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1510	Phase 2
0.6974	Remote Similarity	NPD4108	Discontinued
0.6972	Remote Similarity	NPD4626	Approved
0.6968	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3750	Approved
0.6968	Remote Similarity	NPD4110	Phase 3
0.6957	Remote Similarity	NPD5089	Approved
0.6957	Remote Similarity	NPD5090	Approved
0.6954	Remote Similarity	NPD4097	Suspended
0.6954	Remote Similarity	NPD1607	Approved
0.6951	Remote Similarity	NPD5604	Discontinued
0.6944	Remote Similarity	NPD2232	Approved
0.6944	Remote Similarity	NPD2233	Approved
0.6944	Remote Similarity	NPD2230	Approved
0.694	Remote Similarity	NPD968	Approved
0.6923	Remote Similarity	NPD3496	Discontinued
0.6899	Remote Similarity	NPD7447	Phase 1
0.6894	Remote Similarity	NPD4380	Phase 2
0.6887	Remote Similarity	NPD5124	Phase 1
0.6887	Remote Similarity	NPD230	Phase 1
0.6887	Remote Similarity	NPD3657	Discovery
0.6887	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7229	Phase 3
0.6886	Remote Similarity	NPD3787	Discontinued
0.6885	Remote Similarity	NPD7680	Approved
0.6884	Remote Similarity	NPD1138	Approved
0.6884	Remote Similarity	NPD7635	Approved
0.6883	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5762	Approved
0.6883	Remote Similarity	NPD5763	Approved
0.6882	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7685	Pre-registration
0.6859	Remote Similarity	NPD7466	Approved
0.6859	Remote Similarity	NPD6331	Phase 2
0.6859	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6387	Discontinued
0.6857	Remote Similarity	NPD7157	Approved
0.6853	Remote Similarity	NPD5125	Phase 3
0.6853	Remote Similarity	NPD5126	Approved
0.6849	Remote Similarity	NPD2922	Phase 1
0.6849	Remote Similarity	NPD8651	Approved
0.6846	Remote Similarity	NPD7095	Approved
0.6845	Remote Similarity	NPD3926	Phase 2
0.6838	Remote Similarity	NPD2684	Approved
0.6835	Remote Similarity	NPD7213	Phase 3
0.6835	Remote Similarity	NPD7212	Phase 2
0.6832	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2563	Approved
0.6829	Remote Similarity	NPD2560	Approved
0.6828	Remote Similarity	NPD1608	Approved
0.6826	Remote Similarity	NPD1247	Approved
0.6818	Remote Similarity	NPD6841	Approved
0.6818	Remote Similarity	NPD6843	Phase 3
0.6818	Remote Similarity	NPD6842	Approved
0.6818	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1137	Approved
0.6812	Remote Similarity	NPD1139	Approved
0.6809	Remote Similarity	NPD7340	Approved
0.6803	Remote Similarity	NPD2797	Approved
0.6802	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6895	Approved
0.6797	Remote Similarity	NPD6896	Approved
0.6797	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1652	Phase 2
0.6792	Remote Similarity	NPD4123	Phase 3
0.6792	Remote Similarity	NPD7004	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