NPASS Compound

Structure

CID224623 OpenBabel06191716022D 41 48 0 0 1 0 0 0 0 0999 V2000 -3.7740 1.7097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6223 2.0205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5481 2.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5176 2.9854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0469 2.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0509 2.3734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3351 1.7319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.2580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5069 0.9929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3704 -0.6755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7453 0.2364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6471 2.9160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7795 1.6052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7379 1.7403 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5047 0.3154 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8404 0.9229 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3865 -0.8541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3856 2.1474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.2580 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7285 2.1464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3351 1.7319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7219 1.9188 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2841 2.0130 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6037 0.7493 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4464 1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4734 3.4793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9526 -1.7550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7923 3.0610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4445 3.1052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 2.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2429 2.2970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2689 2.1782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1957 1.0382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4464 0.3807 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9126 0.0265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7190 2.0774 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 1 13 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 22 1 0 0 0 0 8 25 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 25 1 0 0 0 0 12 23 1 0 0 0 0 12 30 1 0 0 0 0 13 18 1 0 0 0 0 14 23 1 1 0 0 0 14 26 1 0 0 0 0 15 26 1 6 0 0 0 15 37 1 0 0 0 0 16 28 1 1 0 0 0 16 38 1 0 0 0 0 17 31 2 0 0 0 0 17 39 1 0 0 0 0 18 32 2 0 0 0 0 18 40 1 0 0 0 0 19 22 1 1 0 0 0 19 28 1 0 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 20 33 2 0 0 0 0 21 27 1 0 0 0 0 21 34 2 0 0 0 0 22 2 1 6 0 0 0 23 3 1 1 0 0 0 23 37 1 0 0 0 0 24 28 1 6 0 0 0 24 35 1 0 0 0 0 25 27 1 6 0 0 0 25 41 1 0 0 0 0 26 11 1 1 0 0 0 26 39 1 0 0 0 0 27 36 1 1 0 0 0 28 40 1 1 0 0 0 29 21 1 6 0 0 0 29 38 1 0 0 0 0 29 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.21
Volume:	533.989
LogP:	1.479
LogD:	0.701
LogS:	-4.079
# Rotatable Bonds:	1
TPSA:	175.12
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	7.877
Fsp3:	0.793
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.464
MDCK Permeability:	4.584234193316661e-05
Pgp-inhibitor:	0.46
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.732
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.689
Plasma Protein Binding (PPB):	30.28392791748047%
Volume Distribution (VD):	0.636
Pgp-substrate:	43.63263702392578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.613
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.911
CYP3A4-substrate:	0.944

ADMET: Excretion

Clearance (CL):	5.315
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.98
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.932
Rat Oral Acute Toxicity:	0.484
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.929
Carcinogencity:	0.892
Eye Corrosion:	0.004
Eye Irritation:	0.025
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC224623

Natural Product ID:	NPC224623
*Common Name:**	Schisandilactone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ASWJDAOUCRGFEP-ZQUPJVRXSA-N
Standard InCHI:	InChI=1S/C29H34O12/c1-13-9-16-28(40-18(13)32)19-22(2,20(33)24(28,4)35)7-8-25-11-26-14(23(3,12-30)37-15(26)10-17(31)39-26)5-6-27(25,36)21(34)29(19,38-16)41-25/h9,14-16,19,30,35-36H,5-8,10-12H2,1-4H3/t14-,15+,16-,19+,22-,23-,24-,25-,26+,27+,28+,29-/m0/s1
SMILES:	OC[C@]1(C)O[C@H]2[C@@]3([C@H]1CC[C@@]1([C@@]4(C3)CC[C@]3([C@H]5[C@@](C1=O)(O4)O[C@@H]1[C@]5(OC(=O)C(=C1)C)[C@@](C3=O)(C)O)C)O)OC(=O)C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215350
PubChem CID:	46918729
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1002/cjoc.20010190319]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/j.tet.2008.10.079]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11395273]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[18536373]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	aerial parts	Erlang Mountain area of Sichuan Province, China	2007-SEP	PMID[19413342]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20681569]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9834	Veronica austriaca	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6903	Lecanora straminea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7128	Cynthia savignyi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7374	Seseli montanum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11167	Prunus ssiori	Species	Rosaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[511785]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	100000.0	nM	PMID[511785]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[511785]

☑ 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 NPC224623 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	372
0.1-0.2	2277
0.2-0.3	7238
0.3-0.4	13586
0.4-0.5	11387
0.5-0.6	6159
0.6-0.7	1543
0.7-0.8	112
0.8-0.85	13
0.85-0.9	2
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.959	High Similarity	NPC13071
0.9512	High Similarity	NPC469351
0.935	High Similarity	NPC172823
0.9268	High Similarity	NPC11732
0.918	High Similarity	NPC1538
0.9106	High Similarity	NPC144625
0.9098	High Similarity	NPC192309
0.9024	High Similarity	NPC186339
0.9024	High Similarity	NPC42747
0.8629	High Similarity	NPC163693
0.8629	High Similarity	NPC147635
0.8197	Intermediate Similarity	NPC182185
0.814	Intermediate Similarity	NPC129992
0.8115	Intermediate Similarity	NPC217041
0.8065	Intermediate Similarity	NPC98870
0.8033	Intermediate Similarity	NPC220773
0.8033	Intermediate Similarity	NPC278693
0.8031	Intermediate Similarity	NPC475401
0.8016	Intermediate Similarity	NPC277583
0.7984	Intermediate Similarity	NPC474750
0.7969	Intermediate Similarity	NPC477092
0.7953	Intermediate Similarity	NPC471145
0.7953	Intermediate Similarity	NPC475305
0.7953	Intermediate Similarity	NPC471146
0.7951	Intermediate Similarity	NPC469787
0.7951	Intermediate Similarity	NPC469788
0.7951	Intermediate Similarity	NPC290247
0.7886	Intermediate Similarity	NPC167044
0.7886	Intermediate Similarity	NPC10150
0.7869	Intermediate Similarity	NPC168890
0.7869	Intermediate Similarity	NPC228311
0.7869	Intermediate Similarity	NPC41674
0.7869	Intermediate Similarity	NPC469441
0.7868	Intermediate Similarity	NPC471234
0.7857	Intermediate Similarity	NPC209058
0.7823	Intermediate Similarity	NPC187876
0.7805	Intermediate Similarity	NPC26617
0.7805	Intermediate Similarity	NPC176756
0.7787	Intermediate Similarity	NPC472756
0.7778	Intermediate Similarity	NPC471570
0.776	Intermediate Similarity	NPC477103
0.7752	Intermediate Similarity	NPC475372
0.7752	Intermediate Similarity	NPC161060
0.7742	Intermediate Similarity	NPC329876
0.771	Intermediate Similarity	NPC471999
0.771	Intermediate Similarity	NPC470829
0.771	Intermediate Similarity	NPC472001
0.771	Intermediate Similarity	NPC472000
0.771	Intermediate Similarity	NPC473228
0.7705	Intermediate Similarity	NPC472755
0.7705	Intermediate Similarity	NPC475945
0.7705	Intermediate Similarity	NPC475871
0.7704	Intermediate Similarity	NPC475371
0.7704	Intermediate Similarity	NPC472770
0.7698	Intermediate Similarity	NPC475495
0.7692	Intermediate Similarity	NPC312536
0.7686	Intermediate Similarity	NPC171759
0.768	Intermediate Similarity	NPC477102
0.7674	Intermediate Similarity	NPC473656
0.7674	Intermediate Similarity	NPC36754
0.7674	Intermediate Similarity	NPC475323
0.7642	Intermediate Similarity	NPC472748
0.7642	Intermediate Similarity	NPC203659
0.7638	Intermediate Similarity	NPC473522
0.7638	Intermediate Similarity	NPC475277
0.7638	Intermediate Similarity	NPC477093
0.7623	Intermediate Similarity	NPC474747
0.7623	Intermediate Similarity	NPC472754
0.7619	Intermediate Similarity	NPC257240
0.7619	Intermediate Similarity	NPC471884
0.7615	Intermediate Similarity	NPC288679
0.7615	Intermediate Similarity	NPC13710
0.7594	Intermediate Similarity	NPC469352
0.7591	Intermediate Similarity	NPC472769
0.7581	Intermediate Similarity	NPC472751
0.7581	Intermediate Similarity	NPC472749
0.7581	Intermediate Similarity	NPC54737
0.7561	Intermediate Similarity	NPC475873
0.7561	Intermediate Similarity	NPC472747
0.7561	Intermediate Similarity	NPC472750
0.7561	Intermediate Similarity	NPC110989
0.7559	Intermediate Similarity	NPC287311
0.7541	Intermediate Similarity	NPC474742
0.7541	Intermediate Similarity	NPC472753
0.754	Intermediate Similarity	NPC139838
0.754	Intermediate Similarity	NPC59489
0.7536	Intermediate Similarity	NPC88668
0.752	Intermediate Similarity	NPC470192
0.7519	Intermediate Similarity	NPC471382
0.7519	Intermediate Similarity	NPC471380
0.7518	Intermediate Similarity	NPC473838
0.7518	Intermediate Similarity	NPC213634
0.7518	Intermediate Similarity	NPC475389
0.75	Intermediate Similarity	NPC100487
0.75	Intermediate Similarity	NPC474741
0.748	Intermediate Similarity	NPC49393
0.748	Intermediate Similarity	NPC475463
0.748	Intermediate Similarity	NPC320019
0.748	Intermediate Similarity	NPC86077
0.748	Intermediate Similarity	NPC225353
0.748	Intermediate Similarity	NPC105725
0.748	Intermediate Similarity	NPC324017
0.7464	Intermediate Similarity	NPC475139
0.7464	Intermediate Similarity	NPC180902
0.7463	Intermediate Similarity	NPC472768
0.7463	Intermediate Similarity	NPC471392
0.7462	Intermediate Similarity	NPC54739
0.746	Intermediate Similarity	NPC475960
0.746	Intermediate Similarity	NPC117604
0.7448	Intermediate Similarity	NPC194854
0.7448	Intermediate Similarity	NPC48813
0.7442	Intermediate Similarity	NPC106395
0.7442	Intermediate Similarity	NPC46269
0.744	Intermediate Similarity	NPC291643
0.744	Intermediate Similarity	NPC243998
0.744	Intermediate Similarity	NPC44004
0.744	Intermediate Similarity	NPC223450
0.7438	Intermediate Similarity	NPC311904
0.7438	Intermediate Similarity	NPC213947
0.7438	Intermediate Similarity	NPC170143
0.7438	Intermediate Similarity	NPC108475
0.7431	Intermediate Similarity	NPC471171
0.7424	Intermediate Similarity	NPC9674
0.7424	Intermediate Similarity	NPC19028
0.7419	Intermediate Similarity	NPC469350
0.7419	Intermediate Similarity	NPC473148
0.7413	Intermediate Similarity	NPC25887
0.7405	Intermediate Similarity	NPC475238
0.7398	Intermediate Similarity	NPC133907
0.7398	Intermediate Similarity	NPC477950
0.7398	Intermediate Similarity	NPC128733
0.7398	Intermediate Similarity	NPC150923
0.7398	Intermediate Similarity	NPC476270
0.7398	Intermediate Similarity	NPC110443
0.7398	Intermediate Similarity	NPC185141
0.7398	Intermediate Similarity	NPC15993
0.7398	Intermediate Similarity	NPC46998
0.7397	Intermediate Similarity	NPC475462
0.7397	Intermediate Similarity	NPC16729
0.7385	Intermediate Similarity	NPC67290
0.7385	Intermediate Similarity	NPC133677
0.7385	Intermediate Similarity	NPC138303
0.7372	Intermediate Similarity	NPC476091
0.7372	Intermediate Similarity	NPC311534
0.7372	Intermediate Similarity	NPC476078
0.7364	Intermediate Similarity	NPC76550
0.7364	Intermediate Similarity	NPC123855
0.7364	Intermediate Similarity	NPC138757
0.7361	Intermediate Similarity	NPC470426
0.736	Intermediate Similarity	NPC18433
0.736	Intermediate Similarity	NPC114365
0.736	Intermediate Similarity	NPC88890
0.736	Intermediate Similarity	NPC18044
0.736	Intermediate Similarity	NPC154962
0.736	Intermediate Similarity	NPC123070
0.736	Intermediate Similarity	NPC177518
0.736	Intermediate Similarity	NPC169089
0.736	Intermediate Similarity	NPC132304
0.7357	Intermediate Similarity	NPC475500
0.7357	Intermediate Similarity	NPC475154
0.7357	Intermediate Similarity	NPC473548
0.7357	Intermediate Similarity	NPC223356
0.7357	Intermediate Similarity	NPC471137
0.7357	Intermediate Similarity	NPC182266
0.7357	Intermediate Similarity	NPC471136
0.7357	Intermediate Similarity	NPC100017
0.7355	Intermediate Similarity	NPC476009
0.7355	Intermediate Similarity	NPC142529
0.7355	Intermediate Similarity	NPC91771
0.7355	Intermediate Similarity	NPC126156
0.7353	Intermediate Similarity	NPC217901
0.7353	Intermediate Similarity	NPC198714
0.7348	Intermediate Similarity	NPC475130
0.7348	Intermediate Similarity	NPC475309
0.7348	Intermediate Similarity	NPC474286
0.7344	Intermediate Similarity	NPC50223
0.7339	Intermediate Similarity	NPC471757
0.7339	Intermediate Similarity	NPC78127
0.7339	Intermediate Similarity	NPC149371
0.7338	Intermediate Similarity	NPC471855
0.7338	Intermediate Similarity	NPC254614
0.7338	Intermediate Similarity	NPC100390
0.7323	Intermediate Similarity	NPC308191
0.7319	Intermediate Similarity	NPC162495
0.7317	Intermediate Similarity	NPC280963
0.7313	Intermediate Similarity	NPC46570
0.7302	Intermediate Similarity	NPC469401
0.7302	Intermediate Similarity	NPC179891
0.7299	Intermediate Similarity	NPC42399
0.7299	Intermediate Similarity	NPC475273
0.7299	Intermediate Similarity	NPC473265
0.7299	Intermediate Similarity	NPC168849
0.7295	Intermediate Similarity	NPC477949
0.7295	Intermediate Similarity	NPC471150
0.7295	Intermediate Similarity	NPC474313
0.7293	Intermediate Similarity	NPC319570
0.7286	Intermediate Similarity	NPC168879
0.7286	Intermediate Similarity	NPC58029
0.728	Intermediate Similarity	NPC474775
0.728	Intermediate Similarity	NPC4620

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 NPC224623 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	2797
0.2-0.3	3943
0.3-0.4	1422
0.4-0.5	389
0.5-0.6	188
0.6-0.7	30
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7805	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6371	Approved
0.7426	Intermediate Similarity	NPD7078	Approved
0.7407	Intermediate Similarity	NPD7492	Approved
0.7368	Intermediate Similarity	NPD6054	Approved
0.736	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6616	Approved
0.7259	Intermediate Similarity	NPD6370	Approved
0.7246	Intermediate Similarity	NPD7736	Approved
0.7239	Intermediate Similarity	NPD6059	Approved
0.7185	Intermediate Similarity	NPD6015	Approved
0.7185	Intermediate Similarity	NPD6016	Approved
0.7174	Intermediate Similarity	NPD8293	Discontinued
0.7132	Intermediate Similarity	NPD5988	Approved
0.7111	Intermediate Similarity	NPD6319	Approved
0.7071	Intermediate Similarity	NPD7319	Approved
0.6992	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7507	Approved
0.697	Remote Similarity	NPD6053	Discontinued
0.6842	Remote Similarity	NPD6882	Approved
0.6794	Remote Similarity	NPD6686	Approved
0.6767	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6009	Approved
0.6761	Remote Similarity	NPD6033	Approved
0.6716	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6642	Remote Similarity	NPD6649	Approved
0.6642	Remote Similarity	NPD6650	Approved
0.6642	Remote Similarity	NPD7115	Discovery
0.6622	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6372	Approved
0.6617	Remote Similarity	NPD6373	Approved
0.6571	Remote Similarity	NPD8513	Phase 3
0.6552	Remote Similarity	NPD5956	Approved
0.6544	Remote Similarity	NPD4632	Approved
0.6541	Remote Similarity	NPD6899	Approved
0.6541	Remote Similarity	NPD7320	Approved
0.6541	Remote Similarity	NPD6881	Approved
0.6532	Remote Similarity	NPD46	Approved
0.6532	Remote Similarity	NPD6698	Approved
0.6515	Remote Similarity	NPD6675	Approved
0.6515	Remote Similarity	NPD6402	Approved
0.6515	Remote Similarity	NPD7128	Approved
0.6515	Remote Similarity	NPD5739	Approved
0.6508	Remote Similarity	NPD5282	Discontinued
0.6479	Remote Similarity	NPD8328	Phase 3
0.6475	Remote Similarity	NPD7328	Approved
0.6475	Remote Similarity	NPD7327	Approved
0.6466	Remote Similarity	NPD5697	Approved
0.6466	Remote Similarity	NPD6412	Phase 2
0.6454	Remote Similarity	NPD8033	Approved
0.6454	Remote Similarity	NPD8515	Approved
0.6454	Remote Similarity	NPD8269	Approved
0.6454	Remote Similarity	NPD8516	Approved
0.6454	Remote Similarity	NPD8268	Approved
0.6454	Remote Similarity	NPD8517	Approved
0.6454	Remote Similarity	NPD8267	Approved
0.6454	Remote Similarity	NPD8266	Approved
0.6454	Remote Similarity	NPD7503	Approved
0.6452	Remote Similarity	NPD1695	Approved
0.6444	Remote Similarity	NPD7290	Approved
0.6444	Remote Similarity	NPD4634	Approved
0.6444	Remote Similarity	NPD7102	Approved
0.6444	Remote Similarity	NPD6883	Approved
0.6434	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD7516	Approved
0.6397	Remote Similarity	NPD6617	Approved
0.6397	Remote Similarity	NPD8130	Phase 1
0.6397	Remote Similarity	NPD6847	Approved
0.6397	Remote Similarity	NPD6869	Approved
0.6395	Remote Similarity	NPD7260	Phase 2
0.6383	Remote Similarity	NPD8294	Approved
0.6383	Remote Similarity	NPD8377	Approved
0.637	Remote Similarity	NPD6012	Approved
0.637	Remote Similarity	NPD6014	Approved
0.637	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD7604	Phase 2
0.6357	Remote Similarity	NPD6084	Phase 2
0.6357	Remote Similarity	NPD6083	Phase 2
0.6351	Remote Similarity	NPD6845	Suspended
0.6349	Remote Similarity	NPD7983	Approved
0.6343	Remote Similarity	NPD5701	Approved
0.6338	Remote Similarity	NPD5983	Phase 2
0.6338	Remote Similarity	NPD8378	Approved
0.6338	Remote Similarity	NPD8335	Approved
0.6338	Remote Similarity	NPD8296	Approved
0.6338	Remote Similarity	NPD8380	Approved
0.6338	Remote Similarity	NPD8379	Approved
0.6308	Remote Similarity	NPD4225	Approved
0.6308	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6011	Approved
0.6276	Remote Similarity	NPD6336	Discontinued
0.6269	Remote Similarity	NPD6008	Approved
0.626	Remote Similarity	NPD5363	Approved
0.625	Remote Similarity	NPD7642	Approved
0.6233	Remote Similarity	NPD8074	Phase 3
0.621	Remote Similarity	NPD5786	Approved
0.6202	Remote Similarity	NPD5695	Phase 3
0.6176	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.617	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD7799	Discontinued
0.6159	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7838	Discovery
0.6111	Remote Similarity	NPD8444	Approved
0.6099	Remote Similarity	NPD6274	Approved
0.6084	Remote Similarity	NPD7101	Approved
0.6084	Remote Similarity	NPD7100	Approved
0.6077	Remote Similarity	NPD5210	Approved
0.6077	Remote Similarity	NPD4629	Approved
0.6071	Remote Similarity	NPD8133	Approved
0.6069	Remote Similarity	NPD8080	Discontinued
0.6066	Remote Similarity	NPD5369	Approved
0.6061	Remote Similarity	NPD7638	Approved
0.6045	Remote Similarity	NPD5211	Phase 2
0.6032	Remote Similarity	NPD4250	Approved
0.6032	Remote Similarity	NPD4251	Approved
0.6027	Remote Similarity	NPD7830	Approved
0.6027	Remote Similarity	NPD7829	Approved
0.6016	Remote Similarity	NPD4270	Approved
0.6016	Remote Similarity	NPD6435	Approved
0.6016	Remote Similarity	NPD4269	Approved
0.6015	Remote Similarity	NPD5285	Approved
0.6015	Remote Similarity	NPD7640	Approved
0.6015	Remote Similarity	NPD4696	Approved
0.6015	Remote Similarity	NPD5286	Approved
0.6015	Remote Similarity	NPD7639	Approved
0.6014	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD4755	Approved
0.5973	Remote Similarity	NPD8337	Approved
0.5973	Remote Similarity	NPD8336	Approved
0.597	Remote Similarity	NPD1700	Approved
0.5969	Remote Similarity	NPD5693	Phase 1
0.5968	Remote Similarity	NPD5362	Discontinued
0.5956	Remote Similarity	NPD5141	Approved
0.5952	Remote Similarity	NPD4249	Approved
0.5946	Remote Similarity	NPD8451	Approved
0.5944	Remote Similarity	NPD6317	Approved
0.5926	Remote Similarity	NPD5226	Approved
0.5926	Remote Similarity	NPD5224	Approved
0.5926	Remote Similarity	NPD5225	Approved
0.5926	Remote Similarity	NPD4633	Approved
0.5923	Remote Similarity	NPD5778	Approved
0.5923	Remote Similarity	NPD5779	Approved
0.5918	Remote Similarity	NPD6067	Discontinued
0.5909	Remote Similarity	NPD7839	Suspended
0.5906	Remote Similarity	NPD8448	Approved
0.5903	Remote Similarity	NPD7641	Discontinued
0.5903	Remote Similarity	NPD6314	Approved
0.5903	Remote Similarity	NPD6313	Approved
0.5896	Remote Similarity	NPD4700	Approved
0.589	Remote Similarity	NPD6909	Approved
0.589	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.589	Remote Similarity	NPD6908	Approved
0.5882	Remote Similarity	NPD5175	Approved
0.5882	Remote Similarity	NPD5174	Approved
0.5862	Remote Similarity	NPD4522	Approved
0.5854	Remote Similarity	NPD4252	Approved
0.5854	Remote Similarity	NPD5368	Approved
0.5852	Remote Similarity	NPD5344	Discontinued
0.5852	Remote Similarity	NPD5223	Approved
0.5846	Remote Similarity	NPD7637	Suspended
0.5827	Remote Similarity	NPD4730	Approved
0.5827	Remote Similarity	NPD4729	Approved
0.5817	Remote Similarity	NPD8338	Approved
0.5814	Remote Similarity	NPD6080	Approved
0.5814	Remote Similarity	NPD6673	Approved
0.5814	Remote Similarity	NPD4753	Phase 2
0.5814	Remote Similarity	NPD6904	Approved
0.5802	Remote Similarity	NPD6399	Phase 3
0.5797	Remote Similarity	NPD4767	Approved
0.5797	Remote Similarity	NPD4768	Approved
0.5789	Remote Similarity	NPD8390	Approved
0.5789	Remote Similarity	NPD8391	Approved
0.5789	Remote Similarity	NPD8392	Approved
0.5786	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD6921	Approved
0.5772	Remote Similarity	NPD8342	Approved
0.5772	Remote Similarity	NPD8340	Approved
0.5772	Remote Similarity	NPD8341	Approved
0.5772	Remote Similarity	NPD8299	Approved
0.576	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5248	Approved
0.5745	Remote Similarity	NPD5250	Approved
0.5745	Remote Similarity	NPD5247	Approved
0.5745	Remote Similarity	NPD5251	Approved
0.5745	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5249	Phase 3
0.5736	Remote Similarity	NPD5737	Approved
0.5736	Remote Similarity	NPD6672	Approved
0.5732	Remote Similarity	NPD6333	Approved
0.5732	Remote Similarity	NPD6334	Approved
0.5726	Remote Similarity	NPD4820	Approved
0.5726	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD4822	Approved
0.5726	Remote Similarity	NPD4819	Approved
0.5726	Remote Similarity	NPD4821	Approved

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