NPASS Compound

Structure

NPC6369 OpenBabel07101718282D 27 29 0 0 1 0 0 0 0 0999 V2000 -2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4152 3.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 5.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 4.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 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 15 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 20 1 0 0 0 0 9 16 2 0 0 0 0 9 21 1 0 0 0 0 10 18 2 0 0 0 0 10 19 1 0 0 0 0 11 26 1 0 0 0 0 11 27 1 0 0 0 0 12 1 1 6 0 0 0 12 13 1 0 0 0 0 13 2 1 6 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 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:	4.225
LogD:	4.006
LogS:	-4.694
# 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:	3.322
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.049
MDCK Permeability:	2.144568134099245e-05
Pgp-inhibitor:	0.06
Pgp-substrate:	0.114
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	97.69843292236328%
Volume Distribution (VD):	1.57
Pgp-substrate:	2.2266170978546143%

ADMET: Metabolism

CYP1A2-inhibitor:	0.913
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.924
CYP2C19-substrate:	0.594
CYP2C9-inhibitor:	0.672
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.956
CYP2D6-substrate:	0.934
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.519

ADMET: Excretion

Clearance (CL):	16.756
Half-life (T1/2):	0.583

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.779
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.298
Skin Sensitization:	0.938
Carcinogencity:	0.839
Eye Corrosion:	0.005
Eye Irritation:	0.888
Respiratory Toxicity:	0.778

Download Data

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

Natural Product: NPC6369

Natural Product ID:	NPC6369
*Common Name:**	Rel-Saurulignan D
IUPAC Name:	6-[(2R,3S)-4-(5-hydroxy-2,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,3-benzodioxol-5-ol
Synonyms:
Standard InCHIKey:	IQTGLBVEPWUBII-OLZOCXBDSA-N
Standard InCHI:	InChI=1S/C21H26O6/c1-12(5-14-8-20-21(9-16(14)22)27-11-26-20)13(2)6-15-7-17(23)19(25-4)10-18(15)24-3/h7-10,12-13,22-23H,5-6,11H2,1-4H3/t12-,13+/m1/s1
SMILES:	C[C@H](Cc1cc2c(cc1O)OCO2)[C@@H](C)Cc1cc(c(cc1OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104947
PubChem CID:	76310170
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
IC50	2
Others	3

Activity Type	# Activity
NON-MOLECULAR	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	30000.0	nM	PMID[498550]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29400.0	nM	PMID[498550]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	96.8	%	PMID[498550]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	85.2	%	PMID[498550]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	26.7	%	PMID[498550]

☑ 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 NPC6369 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	411
0.1-0.2	1689
0.2-0.3	4618
0.3-0.4	12008
0.4-0.5	6389
0.5-0.6	4305
0.6-0.7	7512
0.7-0.8	4322
0.8-0.85	893
0.85-0.9	444
0.9-0.95	96
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC30951
0.9924	High Similarity	NPC284464
0.9847	High Similarity	NPC197166
0.9699	High Similarity	NPC9068
0.9562	High Similarity	NPC307466
0.9485	High Similarity	NPC184641
0.9485	High Similarity	NPC133934
0.9485	High Similarity	NPC184684
0.9478	High Similarity	NPC474039
0.947	High Similarity	NPC471390
0.947	High Similarity	NPC471391
0.9416	High Similarity	NPC474808
0.9394	High Similarity	NPC6451
0.9348	High Similarity	NPC121661
0.9348	High Similarity	NPC73467
0.9343	High Similarity	NPC191231
0.9338	High Similarity	NPC177868
0.9318	High Similarity	NPC232275
0.9318	High Similarity	NPC12275
0.9318	High Similarity	NPC474356
0.9318	High Similarity	NPC45715
0.9281	High Similarity	NPC197352
0.9281	High Similarity	NPC189239
0.9281	High Similarity	NPC166506
0.9281	High Similarity	NPC110763
0.9242	High Similarity	NPC299221
0.9242	High Similarity	NPC234488
0.9242	High Similarity	NPC63574
0.9242	High Similarity	NPC224157
0.9242	High Similarity	NPC192687
0.9242	High Similarity	NPC311680
0.9242	High Similarity	NPC184814
0.9242	High Similarity	NPC51840
0.922	High Similarity	NPC301961
0.922	High Similarity	NPC166584
0.9214	High Similarity	NPC226540
0.9214	High Similarity	NPC33832
0.9214	High Similarity	NPC154971
0.9214	High Similarity	NPC252286
0.9203	High Similarity	NPC41782
0.9197	High Similarity	NPC160283
0.9197	High Similarity	NPC254759
0.9179	High Similarity	NPC196937
0.9167	High Similarity	NPC58164
0.9167	High Similarity	NPC10225
0.9167	High Similarity	NPC470633
0.9167	High Similarity	NPC190144
0.9167	High Similarity	NPC228769
0.9149	High Similarity	NPC116019
0.9137	High Similarity	NPC298317
0.9137	High Similarity	NPC185071
0.9137	High Similarity	NPC12728
0.9137	High Similarity	NPC255566
0.913	High Similarity	NPC311530
0.913	High Similarity	NPC247291
0.9124	High Similarity	NPC290714
0.9124	High Similarity	NPC292882
0.9124	High Similarity	NPC201404
0.9124	High Similarity	NPC53722
0.9104	High Similarity	NPC204215
0.9104	High Similarity	NPC471505
0.9104	High Similarity	NPC175067
0.9091	High Similarity	NPC266691
0.9085	High Similarity	NPC71726
0.9084	High Similarity	NPC76451
0.9071	High Similarity	NPC472712
0.9071	High Similarity	NPC118385
0.9071	High Similarity	NPC473046
0.9071	High Similarity	NPC187774
0.9071	High Similarity	NPC472713
0.9065	High Similarity	NPC103637
0.9065	High Similarity	NPC230538
0.9065	High Similarity	NPC36531
0.9065	High Similarity	NPC107161
0.9065	High Similarity	NPC229172
0.9044	High Similarity	NPC150534
0.9037	High Similarity	NPC112237
0.9037	High Similarity	NPC158331
0.9037	High Similarity	NPC58585
0.9015	High Similarity	NPC324112
0.9015	High Similarity	NPC159968
0.9015	High Similarity	NPC236791
0.9015	High Similarity	NPC127587
0.9015	High Similarity	NPC74817
0.9015	High Similarity	NPC82679
0.9015	High Similarity	NPC124452
0.9015	High Similarity	NPC169474
0.9015	High Similarity	NPC293054
0.9015	High Similarity	NPC246620
0.9015	High Similarity	NPC282000
0.9007	High Similarity	NPC178014
0.9007	High Similarity	NPC11422
0.9007	High Similarity	NPC42716
0.9007	High Similarity	NPC477702
0.9007	High Similarity	NPC474749
0.9007	High Similarity	NPC180953
0.9	High Similarity	NPC324962
0.9	High Similarity	NPC477616
0.9	High Similarity	NPC85264
0.9	High Similarity	NPC102044
0.9	High Similarity	NPC47633
0.9	High Similarity	NPC81638
0.8986	High Similarity	NPC245207
0.8986	High Similarity	NPC127218
0.8986	High Similarity	NPC319647
0.8986	High Similarity	NPC25966
0.8973	High Similarity	NPC159922
0.8971	High Similarity	NPC145722
0.8971	High Similarity	NPC276026
0.8971	High Similarity	NPC7515
0.8971	High Similarity	NPC188378
0.8971	High Similarity	NPC289258
0.8971	High Similarity	NPC244983
0.8971	High Similarity	NPC256776
0.8971	High Similarity	NPC185680
0.8971	High Similarity	NPC326095
0.8971	High Similarity	NPC555
0.8971	High Similarity	NPC469659
0.8971	High Similarity	NPC56764
0.8971	High Similarity	NPC206737
0.8971	High Similarity	NPC287745
0.8963	High Similarity	NPC106739
0.8958	High Similarity	NPC472710
0.8958	High Similarity	NPC472709
0.8958	High Similarity	NPC24425
0.8955	High Similarity	NPC126836
0.8955	High Similarity	NPC214860
0.8951	High Similarity	NPC175976
0.8947	High Similarity	NPC28765
0.8947	High Similarity	NPC154866
0.8944	High Similarity	NPC162193
0.8944	High Similarity	NPC212890
0.8939	High Similarity	NPC18924
0.8939	High Similarity	NPC28730
0.8939	High Similarity	NPC44748
0.8939	High Similarity	NPC78974
0.8939	High Similarity	NPC223136
0.8939	High Similarity	NPC214406
0.8939	High Similarity	NPC274356
0.8939	High Similarity	NPC103823
0.8936	High Similarity	NPC280092
0.8936	High Similarity	NPC63879
0.8936	High Similarity	NPC172171
0.8936	High Similarity	NPC45257
0.8936	High Similarity	NPC239254
0.8936	High Similarity	NPC12641
0.8936	High Similarity	NPC93323
0.8929	High Similarity	NPC5262
0.8929	High Similarity	NPC472714
0.8921	High Similarity	NPC27495
0.8921	High Similarity	NPC309124
0.8921	High Similarity	NPC184797
0.8921	High Similarity	NPC259519
0.8913	High Similarity	NPC201145
0.8913	High Similarity	NPC6262
0.8913	High Similarity	NPC185908
0.8913	High Similarity	NPC283949
0.8913	High Similarity	NPC276490
0.8913	High Similarity	NPC25111
0.8913	High Similarity	NPC90615
0.8913	High Similarity	NPC73535
0.8913	High Similarity	NPC272157
0.8905	High Similarity	NPC101624
0.8905	High Similarity	NPC126409
0.8905	High Similarity	NPC180602
0.8905	High Similarity	NPC135777
0.8905	High Similarity	NPC240279
0.8905	High Similarity	NPC165155
0.8905	High Similarity	NPC55239
0.8905	High Similarity	NPC142547
0.8905	High Similarity	NPC99572
0.8905	High Similarity	NPC236522
0.8905	High Similarity	NPC34103
0.8905	High Similarity	NPC141765
0.8905	High Similarity	NPC184938
0.8905	High Similarity	NPC214853
0.8905	High Similarity	NPC134968
0.8905	High Similarity	NPC24490
0.8897	High Similarity	NPC475756
0.8889	High Similarity	NPC474017
0.8881	High Similarity	NPC45824
0.8881	High Similarity	NPC39657
0.8881	High Similarity	NPC227902
0.8873	High Similarity	NPC475868
0.8872	High Similarity	NPC266555
0.8872	High Similarity	NPC252131
0.8865	High Similarity	NPC265154
0.8864	High Similarity	NPC82483
0.8864	High Similarity	NPC475169
0.8864	High Similarity	NPC233410
0.8864	High Similarity	NPC105925
0.8864	High Similarity	NPC221077
0.8864	High Similarity	NPC116907
0.8864	High Similarity	NPC472093
0.8864	High Similarity	NPC298757
0.8864	High Similarity	NPC60885
0.8864	High Similarity	NPC117214
0.8864	High Similarity	NPC203133
0.8864	High Similarity	NPC299584
0.8864	High Similarity	NPC251855

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 NPC6369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	962
0.2-0.3	1910
0.3-0.4	2879
0.4-0.5	1548
0.5-0.6	905
0.6-0.7	519
0.7-0.8	83
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8741	High Similarity	NPD3027	Phase 3
0.8456	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD6234	Discontinued
0.8286	Intermediate Similarity	NPD1613	Approved
0.8286	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD37	Approved
0.8148	Intermediate Similarity	NPD3705	Approved
0.8117	Intermediate Similarity	NPD4965	Approved
0.8117	Intermediate Similarity	NPD4967	Phase 2
0.8117	Intermediate Similarity	NPD4966	Approved
0.8013	Intermediate Similarity	NPD1653	Approved
0.8	Intermediate Similarity	NPD7228	Approved
0.7929	Intermediate Similarity	NPD3018	Phase 2
0.7911	Intermediate Similarity	NPD7199	Phase 2
0.7879	Intermediate Similarity	NPD5283	Phase 1
0.7872	Intermediate Similarity	NPD4908	Phase 1
0.7812	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD2861	Phase 2
0.7778	Intermediate Similarity	NPD3818	Discontinued
0.777	Intermediate Similarity	NPD2982	Phase 2
0.777	Intermediate Similarity	NPD2983	Phase 2
0.7762	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2801	Approved
0.7754	Intermediate Similarity	NPD1610	Phase 2
0.7727	Intermediate Similarity	NPD228	Approved
0.7718	Intermediate Similarity	NPD6674	Discontinued
0.7698	Intermediate Similarity	NPD2981	Phase 2
0.7664	Intermediate Similarity	NPD1357	Approved
0.7643	Intermediate Similarity	NPD4749	Approved
0.7632	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1934	Approved
0.7576	Intermediate Similarity	NPD7074	Phase 3
0.7576	Intermediate Similarity	NPD3021	Approved
0.7576	Intermediate Similarity	NPD3022	Approved
0.7547	Intermediate Similarity	NPD3882	Suspended
0.7534	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3620	Phase 2
0.7518	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1091	Approved
0.7485	Intermediate Similarity	NPD7240	Approved
0.7483	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7472	Approved
0.7467	Intermediate Similarity	NPD7266	Discontinued
0.7464	Intermediate Similarity	NPD1548	Phase 1
0.7456	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4625	Phase 3
0.744	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2978	Approved
0.7421	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2977	Approved
0.7415	Intermediate Similarity	NPD4060	Phase 1
0.7397	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3540	Phase 1
0.7321	Intermediate Similarity	NPD6797	Phase 2
0.7317	Intermediate Similarity	NPD6232	Discontinued
0.7313	Intermediate Similarity	NPD4750	Phase 3
0.731	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5494	Approved
0.729	Intermediate Similarity	NPD1511	Approved
0.7289	Intermediate Similarity	NPD7473	Discontinued
0.7285	Intermediate Similarity	NPD3539	Phase 1
0.7278	Intermediate Similarity	NPD7251	Discontinued
0.7273	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6671	Approved
0.7235	Intermediate Similarity	NPD7808	Phase 3
0.7229	Intermediate Similarity	NPD6166	Phase 2
0.7229	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7124	Phase 2
0.7222	Intermediate Similarity	NPD6696	Suspended
0.7205	Intermediate Similarity	NPD1465	Phase 2
0.7202	Intermediate Similarity	NPD5844	Phase 1
0.7197	Intermediate Similarity	NPD1512	Approved
0.7181	Intermediate Similarity	NPD1558	Phase 1
0.7179	Intermediate Similarity	NPD4357	Discontinued
0.7178	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6559	Discontinued
0.7171	Intermediate Similarity	NPD2935	Discontinued
0.717	Intermediate Similarity	NPD4005	Discontinued
0.7162	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3817	Phase 2
0.7152	Intermediate Similarity	NPD6111	Discontinued
0.7151	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3384	Approved
0.7143	Intermediate Similarity	NPD3382	Approved
0.7143	Intermediate Similarity	NPD3383	Approved
0.7135	Intermediate Similarity	NPD7549	Discontinued
0.7133	Intermediate Similarity	NPD422	Phase 1
0.7124	Intermediate Similarity	NPD1375	Discontinued
0.7115	Intermediate Similarity	NPD5058	Phase 3
0.7078	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6100	Approved
0.7059	Intermediate Similarity	NPD6099	Approved
0.7055	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2219	Phase 1
0.7045	Intermediate Similarity	NPD846	Approved
0.7045	Intermediate Similarity	NPD940	Approved
0.7032	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5177	Phase 3
0.7021	Intermediate Similarity	NPD5536	Phase 2
0.702	Intermediate Similarity	NPD230	Phase 1
0.702	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD7028	Phase 2
0.7019	Intermediate Similarity	NPD4675	Approved
0.7019	Intermediate Similarity	NPD4678	Approved
0.7013	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7680	Approved
0.6987	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3892	Phase 2
0.6977	Remote Similarity	NPD7685	Pre-registration
0.697	Remote Similarity	NPD1242	Phase 1
0.697	Remote Similarity	NPD4055	Discovery
0.6954	Remote Similarity	NPD2238	Phase 2
0.6954	Remote Similarity	NPD1240	Approved
0.6933	Remote Similarity	NPD5109	Approved
0.6933	Remote Similarity	NPD5111	Phase 2
0.6933	Remote Similarity	NPD5110	Phase 2
0.6923	Remote Similarity	NPD4237	Approved
0.6923	Remote Similarity	NPD3060	Approved
0.6923	Remote Similarity	NPD4236	Phase 3
0.6919	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2532	Approved
0.6918	Remote Similarity	NPD2533	Approved
0.6918	Remote Similarity	NPD2534	Approved
0.6918	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4380	Phase 2
0.6905	Remote Similarity	NPD3787	Discontinued
0.6903	Remote Similarity	NPD5762	Approved
0.6903	Remote Similarity	NPD5763	Approved
0.6901	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3020	Approved
0.6893	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2674	Phase 3
0.6883	Remote Similarity	NPD1510	Phase 2
0.6883	Remote Similarity	NPD4108	Discontinued
0.6879	Remote Similarity	NPD7157	Approved
0.6879	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4110	Phase 3
0.6879	Remote Similarity	NPD709	Approved
0.6879	Remote Similarity	NPD3750	Approved
0.6875	Remote Similarity	NPD4626	Approved
0.6875	Remote Similarity	NPD5126	Approved
0.6875	Remote Similarity	NPD5125	Phase 3
0.6871	Remote Similarity	NPD5089	Approved
0.6871	Remote Similarity	NPD5090	Approved
0.6871	Remote Similarity	NPD8651	Approved
0.6867	Remote Similarity	NPD5604	Discontinued
0.6867	Remote Similarity	NPD7095	Approved
0.6863	Remote Similarity	NPD1607	Approved
0.6863	Remote Similarity	NPD4097	Suspended
0.6861	Remote Similarity	NPD2684	Approved
0.6857	Remote Similarity	NPD8054	Approved
0.6857	Remote Similarity	NPD8053	Approved
0.6849	Remote Similarity	NPD2233	Approved
0.6849	Remote Similarity	NPD2232	Approved
0.6849	Remote Similarity	NPD2230	Approved
0.6842	Remote Similarity	NPD943	Approved
0.6838	Remote Similarity	NPD968	Approved
0.6836	Remote Similarity	NPD6843	Phase 3
0.6836	Remote Similarity	NPD6842	Approved
0.6836	Remote Similarity	NPD6841	Approved
0.6835	Remote Similarity	NPD6190	Approved
0.6828	Remote Similarity	NPD3496	Discontinued
0.6821	Remote Similarity	NPD3144	Approved
0.6821	Remote Similarity	NPD3145	Approved
0.6815	Remote Similarity	NPD1652	Phase 2
0.6813	Remote Similarity	NPD7447	Phase 1
0.6805	Remote Similarity	NPD7229	Phase 3
0.6797	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3657	Discovery
0.6797	Remote Similarity	NPD5124	Phase 1
0.6788	Remote Similarity	NPD8455	Phase 2
0.6786	Remote Similarity	NPD1138	Approved
0.6786	Remote Similarity	NPD7843	Approved
0.6786	Remote Similarity	NPD7635	Approved
0.678	Remote Similarity	NPD4663	Approved
0.6776	Remote Similarity	NPD6233	Phase 2
0.6774	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5588	Approved
0.6772	Remote Similarity	NPD7466	Approved
0.6772	Remote Similarity	NPD6331	Phase 2
0.6772	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7075	Discontinued
0.6765	Remote Similarity	NPD3926	Phase 2
0.6761	Remote Similarity	NPD6387	Discontinued
0.6757	Remote Similarity	NPD2922	Phase 1
0.675	Remote Similarity	NPD6799	Approved
0.675	Remote Similarity	NPD7212	Phase 2
0.675	Remote Similarity	NPD7213	Phase 3

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