NPASS Compound

Structure

CID116019 OpenBabel06191715472D 26 29 0 0 1 0 0 0 0 0999 V2000 4.4152 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -3.3090 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 3.5491 -1.8090 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 7.8793 -3.3090 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 7.2211 -5.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6224 -4.9781 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 4.4152 -3.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 1 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 -1.3090 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 7.8793 -4.3090 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 2.6831 -0.3090 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 7.0132 -1.8090 0.0000 O 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 8.2157 -5.8917 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 12 1 0 0 0 0 3 14 1 0 0 0 0 4 13 1 0 0 0 0 4 15 1 0 0 0 0 5 14 1 0 0 0 0 5 16 2 0 0 0 0 6 17 2 0 0 0 0 6 18 1 0 0 0 0 7 15 2 0 0 0 0 7 20 1 0 0 0 0 8 19 2 0 0 0 0 8 21 1 0 0 0 0 9 16 1 0 0 0 0 9 24 1 0 0 0 0 10 17 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 11 26 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 18 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	365.679
LogP:	4.468
LogD:	3.868
LogS:	-4.282
# Rotatable Bonds:	5
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.85
Synthetic Accessibility Score:	3.633
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.935
MDCK Permeability:	2.2690772311761975e-05
Pgp-inhibitor:	0.084
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.879

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	98.22201538085938%
Volume Distribution (VD):	1.102
Pgp-substrate:	3.089632272720337%

ADMET: Metabolism

CYP1A2-inhibitor:	0.831
CYP1A2-substrate:	0.44
CYP2C19-inhibitor:	0.885
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.448
CYP2C9-substrate:	0.29
CYP2D6-inhibitor:	0.964
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.897
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	16.173
Half-life (T1/2):	0.51

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.437
AMES Toxicity:	0.503
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.95
Carcinogencity:	0.889
Eye Corrosion:	0.003
Eye Irritation:	0.9
Respiratory Toxicity:	0.181

Download Data

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

Natural Product: NPC116019

Natural Product ID:	NPC116019
*Common Name:**	Saururin A
IUPAC Name:	6-[(2S,3R)-4-(6-hydroxy-1,3-dihydro-2-benzofuran-5-yl)-2,3-dimethylbutyl]-1,3-benzodioxol-5-ol
Synonyms:
Standard InCHIKey:	NFRPGCQSGHWKCJ-OLZOCXBDSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-12(3-14-5-16-9-24-10-17(16)6-18(14)22)13(2)4-15-7-20-21(8-19(15)23)26-11-25-20/h5-8,12-13,22-23H,3-4,9-11H2,1-2H3/t12-,13+/m1/s1
SMILES:	C[C@H](Cc1cc2COCc2cc1O)[C@@H](C)Cc1cc2c(cc1O)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491385
PubChem CID:	44576260
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	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT621	Tissue	Plasma	Homo sapiens	IC50	=	8500.0	nM	PMID[540404]

☑ 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 NPC116019 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	449
0.1-0.2	1725
0.2-0.3	4415
0.3-0.4	11503
0.4-0.5	7033
0.5-0.6	4229
0.6-0.7	8600
0.7-0.8	3701
0.8-0.85	803
0.85-0.9	215
0.9-0.95	22
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9507	High Similarity	NPC33832
0.9424	High Similarity	NPC9068
0.9375	High Similarity	NPC71726
0.9301	High Similarity	NPC180953
0.9296	High Similarity	NPC474808
0.9281	High Similarity	NPC197166
0.9149	High Similarity	NPC30951
0.9149	High Similarity	NPC6369
0.9103	High Similarity	NPC252286
0.9103	High Similarity	NPC154971
0.9097	High Similarity	NPC172171
0.9097	High Similarity	NPC239254
0.9091	High Similarity	NPC472562
0.9091	High Similarity	NPC191231
0.9085	High Similarity	NPC284464
0.9085	High Similarity	NPC177868
0.9048	High Similarity	NPC240521
0.9034	High Similarity	NPC42716
0.9034	High Similarity	NPC474749
0.9034	High Similarity	NPC11422
0.9034	High Similarity	NPC178014
0.9034	High Similarity	NPC475868
0.9034	High Similarity	NPC307466
0.9	High Similarity	NPC159922
0.8986	High Similarity	NPC24425
0.898	High Similarity	NPC166584
0.898	High Similarity	NPC301961
0.8973	High Similarity	NPC226540
0.8966	High Similarity	NPC73467
0.8966	High Similarity	NPC121661
0.8958	High Similarity	NPC41782
0.8958	High Similarity	NPC36531
0.8958	High Similarity	NPC184684
0.8958	High Similarity	NPC230538
0.8958	High Similarity	NPC229172
0.8958	High Similarity	NPC184641
0.8958	High Similarity	NPC133934
0.8958	High Similarity	NPC103637
0.8951	High Similarity	NPC103448
0.8951	High Similarity	NPC216434
0.8944	High Similarity	NPC196420
0.8944	High Similarity	NPC185908
0.8944	High Similarity	NPC283949
0.8936	High Similarity	NPC150534
0.8904	High Similarity	NPC189239
0.8904	High Similarity	NPC166506
0.8904	High Similarity	NPC205316
0.8904	High Similarity	NPC110763
0.8904	High Similarity	NPC197352
0.8897	High Similarity	NPC185071
0.8897	High Similarity	NPC298317
0.8897	High Similarity	NPC265154
0.8897	High Similarity	NPC255566
0.8897	High Similarity	NPC12728
0.8897	High Similarity	NPC324962
0.8881	High Similarity	NPC290714
0.8881	High Similarity	NPC53722
0.8881	High Similarity	NPC201404
0.8873	High Similarity	NPC32189
0.8859	High Similarity	NPC473989
0.8857	High Similarity	NPC72046
0.8857	High Similarity	NPC261812
0.8857	High Similarity	NPC65183
0.8844	High Similarity	NPC162193
0.8828	High Similarity	NPC80326
0.8828	High Similarity	NPC474295
0.8819	High Similarity	NPC226547
0.8819	High Similarity	NPC56091
0.8819	High Similarity	NPC46591
0.8811	High Similarity	NPC474039
0.8794	High Similarity	NPC266848
0.8794	High Similarity	NPC196937
0.8794	High Similarity	NPC136750
0.8786	High Similarity	NPC192255
0.8776	High Similarity	NPC477702
0.8776	High Similarity	NPC221318
0.8767	High Similarity	NPC102044
0.8767	High Similarity	NPC85264
0.8767	High Similarity	NPC47633
0.8767	High Similarity	NPC477616
0.8767	High Similarity	NPC258083
0.8759	High Similarity	NPC300798
0.8759	High Similarity	NPC58137
0.8742	High Similarity	NPC160196
0.8741	High Similarity	NPC205442
0.8733	High Similarity	NPC472710
0.8733	High Similarity	NPC225815
0.8733	High Similarity	NPC9933
0.8733	High Similarity	NPC260781
0.8733	High Similarity	NPC472709
0.8733	High Similarity	NPC145979
0.8733	High Similarity	NPC185955
0.8733	High Similarity	NPC214326
0.8733	High Similarity	NPC469706
0.8733	High Similarity	NPC182368
0.8733	High Similarity	NPC218041
0.8733	High Similarity	NPC469707
0.8732	High Similarity	NPC256776
0.8732	High Similarity	NPC145722
0.8732	High Similarity	NPC31530
0.8732	High Similarity	NPC185680
0.8725	High Similarity	NPC325720
0.8725	High Similarity	NPC316676
0.8723	High Similarity	NPC7744
0.8716	High Similarity	NPC212890
0.8714	High Similarity	NPC224157
0.8714	High Similarity	NPC63574
0.8714	High Similarity	NPC184814
0.8714	High Similarity	NPC192687
0.8707	High Similarity	NPC63879
0.8707	High Similarity	NPC93323
0.8707	High Similarity	NPC45257
0.8707	High Similarity	NPC280092
0.8707	High Similarity	NPC12641
0.8701	High Similarity	NPC115281
0.8701	High Similarity	NPC163527
0.8701	High Similarity	NPC181168
0.8701	High Similarity	NPC19947
0.8701	High Similarity	NPC207584
0.8699	High Similarity	NPC470917
0.8699	High Similarity	NPC287124
0.8699	High Similarity	NPC175838
0.8699	High Similarity	NPC174522
0.869	High Similarity	NPC259519
0.869	High Similarity	NPC160283
0.869	High Similarity	NPC254759
0.869	High Similarity	NPC27495
0.8681	High Similarity	NPC477938
0.8681	High Similarity	NPC266006
0.8675	High Similarity	NPC475756
0.8671	High Similarity	NPC165155
0.8671	High Similarity	NPC189474
0.8671	High Similarity	NPC236522
0.8671	High Similarity	NPC34103
0.8671	High Similarity	NPC126409
0.8671	High Similarity	NPC25333
0.8671	High Similarity	NPC49235
0.8671	High Similarity	NPC141765
0.8671	High Similarity	NPC148893
0.8671	High Similarity	NPC99572
0.8671	High Similarity	NPC135777
0.8671	High Similarity	NPC24490
0.8671	High Similarity	NPC142547
0.8671	High Similarity	NPC474139
0.8662	High Similarity	NPC471391
0.8662	High Similarity	NPC112237
0.8662	High Similarity	NPC58585
0.8662	High Similarity	NPC471390
0.8649	High Similarity	NPC469557
0.8643	High Similarity	NPC190144
0.8636	High Similarity	NPC237946
0.8636	High Similarity	NPC32373
0.863	High Similarity	NPC263261
0.863	High Similarity	NPC311530
0.863	High Similarity	NPC312199
0.863	High Similarity	NPC247291
0.863	High Similarity	NPC87725
0.8627	High Similarity	NPC188578
0.8627	High Similarity	NPC103197
0.8627	High Similarity	NPC30009
0.8627	High Similarity	NPC80918
0.8627	High Similarity	NPC312763
0.8621	High Similarity	NPC193666
0.8621	High Similarity	NPC212942
0.8621	High Similarity	NPC292487
0.8621	High Similarity	NPC114171
0.8621	High Similarity	NPC79622
0.8621	High Similarity	NPC230124
0.8621	High Similarity	NPC29868
0.8621	High Similarity	NPC6300
0.8621	High Similarity	NPC184613
0.8621	High Similarity	NPC292882
0.8621	High Similarity	NPC88640
0.8621	High Similarity	NPC123526
0.8618	High Similarity	NPC471154
0.8611	High Similarity	NPC121651
0.8611	High Similarity	NPC173660
0.8611	High Similarity	NPC11453
0.8609	High Similarity	NPC238140
0.8601	High Similarity	NPC90083
0.8601	High Similarity	NPC170779
0.8601	High Similarity	NPC209199
0.86	High Similarity	NPC304821
0.86	High Similarity	NPC130449
0.86	High Similarity	NPC248132
0.86	High Similarity	NPC270751
0.8592	High Similarity	NPC147616
0.8592	High Similarity	NPC6451
0.8592	High Similarity	NPC259742
0.8592	High Similarity	NPC104077
0.8592	High Similarity	NPC175067
0.8592	High Similarity	NPC204215
0.8592	High Similarity	NPC219671
0.8591	High Similarity	NPC112251
0.859	High Similarity	NPC91634
0.859	High Similarity	NPC268718
0.859	High Similarity	NPC150943
0.8582	High Similarity	NPC470624
0.8582	High Similarity	NPC258483
0.8582	High Similarity	NPC237169

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 NPC116019 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	967
0.2-0.3	1903
0.3-0.4	2880
0.4-0.5	1563
0.5-0.6	883
0.6-0.7	503
0.7-0.8	73
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8645	High Similarity	NPD6234	Discontinued
0.8636	High Similarity	NPD4966	Approved
0.8636	High Similarity	NPD4965	Approved
0.8636	High Similarity	NPD4967	Phase 2
0.8442	Intermediate Similarity	NPD37	Approved
0.8272	Intermediate Similarity	NPD7228	Approved
0.8201	Intermediate Similarity	NPD3705	Approved
0.8133	Intermediate Similarity	NPD6674	Discontinued
0.8125	Intermediate Similarity	NPD3027	Phase 3
0.7963	Intermediate Similarity	NPD7199	Phase 2
0.7877	Intermediate Similarity	NPD4625	Phase 3
0.7866	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7240	Approved
0.7838	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1613	Approved
0.7823	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4908	Phase 1
0.7679	Intermediate Similarity	NPD5844	Phase 1
0.7671	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6696	Suspended
0.7619	Intermediate Similarity	NPD2861	Phase 2
0.761	Intermediate Similarity	NPD1653	Approved
0.76	Intermediate Similarity	NPD4060	Phase 1
0.759	Intermediate Similarity	NPD6232	Discontinued
0.7586	Intermediate Similarity	NPD4749	Approved
0.7584	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1610	Phase 2
0.756	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD3018	Phase 2
0.7483	Intermediate Similarity	NPD3620	Phase 2
0.7483	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5283	Phase 1
0.7421	Intermediate Similarity	NPD2532	Approved
0.7421	Intermediate Similarity	NPD2534	Approved
0.7421	Intermediate Similarity	NPD2533	Approved
0.7412	Intermediate Similarity	NPD3818	Discontinued
0.7403	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5494	Approved
0.7361	Intermediate Similarity	NPD1357	Approved
0.7347	Intermediate Similarity	NPD2983	Phase 2
0.7347	Intermediate Similarity	NPD2982	Phase 2
0.7342	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6559	Discontinued
0.731	Intermediate Similarity	NPD5125	Phase 3
0.731	Intermediate Similarity	NPD5126	Approved
0.7292	Intermediate Similarity	NPD1548	Phase 1
0.7279	Intermediate Similarity	NPD2981	Phase 2
0.7273	Intermediate Similarity	NPD2801	Approved
0.7273	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7680	Approved
0.7225	Intermediate Similarity	NPD7074	Phase 3
0.7222	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1934	Approved
0.7211	Intermediate Similarity	NPD1091	Approved
0.7192	Intermediate Similarity	NPD4626	Approved
0.7186	Intermediate Similarity	NPD3882	Suspended
0.7179	Intermediate Similarity	NPD4108	Discontinued
0.7168	Intermediate Similarity	NPD7054	Approved
0.7161	Intermediate Similarity	NPD4097	Suspended
0.716	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7340	Approved
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4750	Phase 3
0.7134	Intermediate Similarity	NPD4005	Discontinued
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.7126	Intermediate Similarity	NPD7472	Approved
0.7125	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5691	Approved
0.7113	Intermediate Similarity	NPD7635	Approved
0.7102	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1611	Approved
0.7091	Intermediate Similarity	NPD7028	Phase 2
0.7089	Intermediate Similarity	NPD5762	Approved
0.7089	Intermediate Similarity	NPD7266	Discontinued
0.7089	Intermediate Similarity	NPD5763	Approved
0.7083	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5058	Phase 3
0.7076	Intermediate Similarity	NPD7229	Phase 3
0.7066	Intermediate Similarity	NPD5929	Approved
0.7063	Intermediate Similarity	NPD3892	Phase 2
0.7063	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1398	Phase 1
0.7044	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD228	Approved
0.7025	Intermediate Similarity	NPD2935	Discontinued
0.7018	Intermediate Similarity	NPD6959	Discontinued
0.7013	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3384	Approved
0.7006	Intermediate Similarity	NPD3382	Approved
0.7006	Intermediate Similarity	NPD7808	Phase 3
0.7006	Intermediate Similarity	NPD7549	Discontinued
0.7006	Intermediate Similarity	NPD3383	Approved
0.6989	Remote Similarity	NPD6797	Phase 2
0.6987	Remote Similarity	NPD3657	Discovery
0.6987	Remote Similarity	NPD5735	Approved
0.6981	Remote Similarity	NPD1375	Discontinued
0.6981	Remote Similarity	NPD3540	Phase 1
0.6978	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6671	Approved
0.6964	Remote Similarity	NPD2978	Approved
0.6964	Remote Similarity	NPD7819	Suspended
0.6964	Remote Similarity	NPD1465	Phase 2
0.6964	Remote Similarity	NPD2977	Approved
0.6954	Remote Similarity	NPD1283	Approved
0.6951	Remote Similarity	NPD6090	Discontinued
0.6949	Remote Similarity	NPD7251	Discontinued
0.6941	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2979	Phase 3
0.6923	Remote Similarity	NPD3817	Phase 2
0.6918	Remote Similarity	NPD3539	Phase 1
0.6918	Remote Similarity	NPD2438	Suspended
0.6901	Remote Similarity	NPD3022	Approved
0.6901	Remote Similarity	NPD3021	Approved
0.6897	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6166	Phase 2
0.6897	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4380	Phase 2
0.6886	Remote Similarity	NPD4675	Approved
0.6886	Remote Similarity	NPD4678	Approved
0.6879	Remote Similarity	NPD5711	Approved
0.6879	Remote Similarity	NPD5710	Approved
0.6879	Remote Similarity	NPD3787	Discontinued
0.6879	Remote Similarity	NPD5124	Phase 1
0.6879	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7124	Phase 2
0.6867	Remote Similarity	NPD422	Phase 1
0.6852	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4110	Phase 3
0.6852	Remote Similarity	NPD6331	Phase 2
0.6852	Remote Similarity	NPD3750	Approved
0.6851	Remote Similarity	NPD4663	Approved
0.6842	Remote Similarity	NPD4055	Discovery
0.6842	Remote Similarity	NPD8651	Approved
0.6839	Remote Similarity	NPD2970	Approved
0.6839	Remote Similarity	NPD2969	Approved
0.6835	Remote Similarity	NPD2157	Approved
0.6829	Remote Similarity	NPD1511	Approved
0.6829	Remote Similarity	NPD4357	Discontinued
0.6826	Remote Similarity	NPD7458	Discontinued
0.6824	Remote Similarity	NPD2560	Approved
0.6824	Remote Similarity	NPD2563	Approved
0.6821	Remote Similarity	NPD1247	Approved
0.6815	Remote Similarity	NPD2238	Phase 2
0.6815	Remote Similarity	NPD4140	Approved
0.6813	Remote Similarity	NPD6843	Phase 3
0.6813	Remote Similarity	NPD7906	Approved
0.6813	Remote Similarity	NPD6841	Approved
0.6813	Remote Similarity	NPD6842	Approved
0.6813	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5709	Phase 3
0.68	Remote Similarity	NPD2489	Approved
0.68	Remote Similarity	NPD27	Approved
0.6797	Remote Similarity	NPD3094	Phase 2
0.6795	Remote Similarity	NPD5110	Phase 2
0.6795	Remote Similarity	NPD7985	Registered
0.6795	Remote Similarity	NPD5109	Approved
0.6795	Remote Similarity	NPD5111	Phase 2
0.6792	Remote Similarity	NPD6111	Discontinued
0.679	Remote Similarity	NPD4237	Approved
0.679	Remote Similarity	NPD5177	Phase 3
0.679	Remote Similarity	NPD4236	Phase 3
0.6788	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3051	Approved
0.6779	Remote Similarity	NPD1651	Approved
0.6778	Remote Similarity	NPD7310	Approved
0.6778	Remote Similarity	NPD8313	Approved
0.6778	Remote Similarity	NPD4577	Approved
0.6778	Remote Similarity	NPD4578	Approved
0.6778	Remote Similarity	NPD7311	Approved
0.6778	Remote Similarity	NPD8312	Approved
0.6778	Remote Similarity	NPD7313	Approved
0.6778	Remote Similarity	NPD7312	Approved
0.6776	Remote Similarity	NPD5327	Phase 3
0.6772	Remote Similarity	NPD6355	Discontinued
0.677	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6005	Phase 3
0.677	Remote Similarity	NPD6002	Phase 3
0.677	Remote Similarity	NPD6004	Phase 3
0.6769	Remote Similarity	NPD7827	Phase 1
0.6765	Remote Similarity	NPD8455	Phase 2
0.6765	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4666	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