NPASS Compound

Structure

CID144625 OpenBabel06191715502D 41 47 0 0 1 0 0 0 0 0999 V2000 -5.3811 0.0971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4800 3.8769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2018 -1.4920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7713 -1.6758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5923 2.3253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3799 2.7958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7028 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7233 0.7284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0960 -0.1493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0169 0.8353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4821 3.8769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3923 0.2311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4692 1.4161 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8038 -0.0572 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2388 2.4735 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4516 -0.8024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4398 1.6009 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9811 0.1891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9251 -0.5301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0985 -0.1320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4469 1.4234 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9195 1.1098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8992 -1.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9811 3.0127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4645 -0.7951 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8019 -1.4392 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1032 0.7530 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5223 1.6009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0914 0.7704 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9811 4.7410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8200 -1.6934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9811 -0.8087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8154 2.3144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3524 2.0088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4663 -2.5020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0817 -2.3970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9282 1.2492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9377 0.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7233 2.4735 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2388 0.7284 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 12 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 8 17 1 0 0 0 0 8 18 1 0 0 0 0 9 16 1 0 0 0 0 10 27 1 0 0 0 0 11 24 1 0 0 0 0 11 30 1 0 0 0 0 12 22 1 0 0 0 0 13 21 1 0 0 0 0 13 27 1 1 0 0 0 14 7 1 6 0 0 0 14 19 1 0 0 0 0 14 38 1 0 0 0 0 15 24 1 1 0 0 0 15 28 1 0 0 0 0 16 25 1 0 0 0 0 16 31 2 0 0 0 0 17 28 1 6 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 20 1 0 0 0 0 19 26 1 6 0 0 0 20 25 1 6 0 0 0 20 29 1 0 0 0 0 21 29 1 6 0 0 0 21 33 1 0 0 0 0 22 34 2 0 0 0 0 22 38 1 0 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 23 35 2 0 0 0 0 24 2 1 1 0 0 0 24 39 1 0 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 26 36 1 0 0 0 0 27 9 1 1 0 0 0 27 41 1 0 0 0 0 28 10 1 1 0 0 0 28 40 1 0 0 0 0 29 37 1 6 0 0 0 29 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.22
Volume:	542.545
LogP:	0.931
LogD:	0.091
LogS:	-3.556
# Rotatable Bonds:	2
TPSA:	193.19
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.24
Synthetic Accessibility Score:	7.479
Fsp3:	0.759
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.605
MDCK Permeability:	1.5230326425808016e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.851
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.329
Plasma Protein Binding (PPB):	69.60811614990234%
Volume Distribution (VD):	0.506
Pgp-substrate:	23.107868194580078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.302
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.503
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	4.289
Half-life (T1/2):	0.726

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.771
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.515
Skin Sensitization:	0.191
Carcinogencity:	0.645
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC144625

Natural Product ID:	NPC144625
*Common Name:**	Schisandilactone E
IUPAC Name:	n.a.
Synonyms:	Schisandilactone E
Standard InCHIKey:	WCKMMTKBFVRBSL-OOMVBABASA-N
Standard InCHI:	InChI=1S/C29H36O12/c1-12-7-14(38-22(12)34)19-20-25(3,23(35)26(19,4)36)16(31)9-27-10-28-15(6-5-13(27)21(33)29(20,37)41-27)24(2,11-30)39-17(28)8-18(32)40-28/h7,13-15,17,19-21,30,33,36-37H,5-6,8-11H2,1-4H3/t13-,14+,15+,17-,19-,20+,21-,24+,25+,26-,27+,28-,29+/m1/s1
SMILES:	CC1=C[C@@H]([C@@H]2[C@H]3[C@](C)(C(=O)C[C@]45C[C@@]67[C@@H](CC[C@@H]4[C@H]([C@@]3(O)O5)O)[C@](C)(CO)O[C@@H]6CC(=O)O7)C(=O)[C@]2(C)O)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215354
PubChem CID:	46918830
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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]
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]
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]

☑ 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[546549]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	100000.0	nM	PMID[546549]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[546549]

☑ 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 NPC144625 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	338
0.1-0.2	2172
0.2-0.3	7116
0.3-0.4	13238
0.4-0.5	11009
0.5-0.6	6546
0.6-0.7	2058
0.7-0.8	194
0.8-0.85	18
0.85-0.9	3
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9496	High Similarity	NPC13071
0.9402	High Similarity	NPC1538
0.9316	High Similarity	NPC192309
0.9106	High Similarity	NPC224623
0.9076	High Similarity	NPC42747
0.8934	High Similarity	NPC172823
0.879	High Similarity	NPC469351
0.8699	High Similarity	NPC11732
0.8455	Intermediate Similarity	NPC129992
0.8455	Intermediate Similarity	NPC186339
0.8361	Intermediate Similarity	NPC147635
0.8361	Intermediate Similarity	NPC163693
0.8167	Intermediate Similarity	NPC209058
0.812	Intermediate Similarity	NPC26617
0.8067	Intermediate Similarity	NPC477103
0.8049	Intermediate Similarity	NPC161060
0.8049	Intermediate Similarity	NPC475401
0.8033	Intermediate Similarity	NPC277583
0.8017	Intermediate Similarity	NPC110989
0.8017	Intermediate Similarity	NPC475945
0.8017	Intermediate Similarity	NPC475871
0.8	Intermediate Similarity	NPC474750
0.8	Intermediate Similarity	NPC171759
0.8	Intermediate Similarity	NPC477950
0.7984	Intermediate Similarity	NPC477092
0.7983	Intermediate Similarity	NPC477102
0.7967	Intermediate Similarity	NPC475323
0.7967	Intermediate Similarity	NPC36754
0.7967	Intermediate Similarity	NPC475305
0.7966	Intermediate Similarity	NPC176756
0.7949	Intermediate Similarity	NPC203659
0.7931	Intermediate Similarity	NPC474747
0.7931	Intermediate Similarity	NPC225353
0.7917	Intermediate Similarity	NPC471884
0.7917	Intermediate Similarity	NPC257240
0.7899	Intermediate Similarity	NPC167044
0.7899	Intermediate Similarity	NPC10150
0.7895	Intermediate Similarity	NPC477949
0.7881	Intermediate Similarity	NPC168890
0.7879	Intermediate Similarity	NPC471234
0.7874	Intermediate Similarity	NPC469352
0.7863	Intermediate Similarity	NPC472755
0.7851	Intermediate Similarity	NPC287311
0.7846	Intermediate Similarity	NPC475371
0.7845	Intermediate Similarity	NPC474742
0.784	Intermediate Similarity	NPC19028
0.784	Intermediate Similarity	NPC9674
0.7833	Intermediate Similarity	NPC187876
0.7823	Intermediate Similarity	NPC471146
0.7823	Intermediate Similarity	NPC471145
0.7807	Intermediate Similarity	NPC126156
0.7805	Intermediate Similarity	NPC471380
0.7805	Intermediate Similarity	NPC471382
0.7803	Intermediate Similarity	NPC88668
0.7797	Intermediate Similarity	NPC474741
0.7797	Intermediate Similarity	NPC100487
0.7778	Intermediate Similarity	NPC86077
0.7778	Intermediate Similarity	NPC472754
0.776	Intermediate Similarity	NPC13710
0.776	Intermediate Similarity	NPC475372
0.775	Intermediate Similarity	NPC220773
0.775	Intermediate Similarity	NPC278693
0.7739	Intermediate Similarity	NPC213947
0.7739	Intermediate Similarity	NPC108475
0.7739	Intermediate Similarity	NPC170143
0.7731	Intermediate Similarity	NPC243998
0.7731	Intermediate Similarity	NPC223450
0.7731	Intermediate Similarity	NPC54737
0.7724	Intermediate Similarity	NPC46269
0.7724	Intermediate Similarity	NPC106395
0.7717	Intermediate Similarity	NPC471999
0.7717	Intermediate Similarity	NPC472001
0.7717	Intermediate Similarity	NPC472000
0.7717	Intermediate Similarity	NPC470829
0.7717	Intermediate Similarity	NPC473228
0.771	Intermediate Similarity	NPC472770
0.7705	Intermediate Similarity	NPC475495
0.7698	Intermediate Similarity	NPC312536
0.7692	Intermediate Similarity	NPC472753
0.7686	Intermediate Similarity	NPC139838
0.7686	Intermediate Similarity	NPC59489
0.7686	Intermediate Similarity	NPC217041
0.768	Intermediate Similarity	NPC473656
0.7661	Intermediate Similarity	NPC67290
0.7661	Intermediate Similarity	NPC133677
0.7661	Intermediate Similarity	NPC138303
0.7652	Intermediate Similarity	NPC476009
0.7652	Intermediate Similarity	NPC91771
0.7652	Intermediate Similarity	NPC142529
0.7647	Intermediate Similarity	NPC472748
0.7647	Intermediate Similarity	NPC472756
0.7642	Intermediate Similarity	NPC76550
0.7642	Intermediate Similarity	NPC475277
0.7642	Intermediate Similarity	NPC123855
0.7642	Intermediate Similarity	NPC471570
0.7642	Intermediate Similarity	NPC138757
0.7642	Intermediate Similarity	NPC473522
0.7642	Intermediate Similarity	NPC477093
0.7638	Intermediate Similarity	NPC472004
0.7627	Intermediate Similarity	NPC49393
0.7627	Intermediate Similarity	NPC105725
0.7627	Intermediate Similarity	NPC149371
0.7623	Intermediate Similarity	NPC182185
0.7623	Intermediate Similarity	NPC475463
0.7619	Intermediate Similarity	NPC288679
0.7607	Intermediate Similarity	NPC280963
0.7603	Intermediate Similarity	NPC308191
0.76	Intermediate Similarity	NPC138372
0.76	Intermediate Similarity	NPC106228
0.7597	Intermediate Similarity	NPC472768
0.7594	Intermediate Similarity	NPC472769
0.7586	Intermediate Similarity	NPC311904
0.7586	Intermediate Similarity	NPC474313
0.7583	Intermediate Similarity	NPC41674
0.7583	Intermediate Similarity	NPC228311
0.7583	Intermediate Similarity	NPC472751
0.7583	Intermediate Similarity	NPC179891
0.7583	Intermediate Similarity	NPC469441
0.7583	Intermediate Similarity	NPC291643
0.7583	Intermediate Similarity	NPC472749
0.7565	Intermediate Similarity	NPC163228
0.7565	Intermediate Similarity	NPC475900
0.7563	Intermediate Similarity	NPC475873
0.7563	Intermediate Similarity	NPC472747
0.7563	Intermediate Similarity	NPC472750
0.7542	Intermediate Similarity	NPC47880
0.7542	Intermediate Similarity	NPC150923
0.7542	Intermediate Similarity	NPC185141
0.7542	Intermediate Similarity	NPC128733
0.7542	Intermediate Similarity	NPC110443
0.7542	Intermediate Similarity	NPC133907
0.7542	Intermediate Similarity	NPC46998
0.7542	Intermediate Similarity	NPC475099
0.7541	Intermediate Similarity	NPC475588
0.7541	Intermediate Similarity	NPC38154
0.754	Intermediate Similarity	NPC475238
0.7536	Intermediate Similarity	NPC25887
0.7521	Intermediate Similarity	NPC290247
0.7521	Intermediate Similarity	NPC470188
0.7521	Intermediate Similarity	NPC470192
0.7521	Intermediate Similarity	NPC469787
0.7521	Intermediate Similarity	NPC204884
0.7521	Intermediate Similarity	NPC471144
0.7521	Intermediate Similarity	NPC469788
0.752	Intermediate Similarity	NPC178289
0.7519	Intermediate Similarity	NPC473838
0.7519	Intermediate Similarity	NPC475389
0.75	Intermediate Similarity	NPC24956
0.75	Intermediate Similarity	NPC98870
0.75	Intermediate Similarity	NPC18019
0.75	Intermediate Similarity	NPC311534
0.748	Intermediate Similarity	NPC50223
0.748	Intermediate Similarity	NPC475309
0.7478	Intermediate Similarity	NPC473331
0.7463	Intermediate Similarity	NPC475139
0.7463	Intermediate Similarity	NPC180902
0.7463	Intermediate Similarity	NPC34963
0.7459	Intermediate Similarity	NPC117604
0.7459	Intermediate Similarity	NPC475960
0.7459	Intermediate Similarity	NPC329876
0.7444	Intermediate Similarity	NPC470851
0.7444	Intermediate Similarity	NPC231529
0.7444	Intermediate Similarity	NPC35109
0.7438	Intermediate Similarity	NPC44004
0.7438	Intermediate Similarity	NPC475217
0.7438	Intermediate Similarity	NPC252234
0.7436	Intermediate Similarity	NPC471150
0.7436	Intermediate Similarity	NPC161493
0.7429	Intermediate Similarity	NPC471171
0.7424	Intermediate Similarity	NPC471357
0.7424	Intermediate Similarity	NPC146456
0.7424	Intermediate Similarity	NPC117702
0.7424	Intermediate Similarity	NPC287423
0.7424	Intermediate Similarity	NPC469757
0.7417	Intermediate Similarity	NPC474775
0.7417	Intermediate Similarity	NPC4620
0.7417	Intermediate Similarity	NPC473148
0.7414	Intermediate Similarity	NPC36954
0.7414	Intermediate Similarity	NPC52044
0.7414	Intermediate Similarity	NPC37408
0.7414	Intermediate Similarity	NPC67584
0.7407	Intermediate Similarity	NPC58029
0.7407	Intermediate Similarity	NPC469673
0.7402	Intermediate Similarity	NPC239273
0.7398	Intermediate Similarity	NPC47951
0.7391	Intermediate Similarity	NPC81419
0.7391	Intermediate Similarity	NPC308656
0.7391	Intermediate Similarity	NPC200237
0.7391	Intermediate Similarity	NPC473263
0.7391	Intermediate Similarity	NPC60386
0.7391	Intermediate Similarity	NPC476300
0.7391	Intermediate Similarity	NPC153590
0.7391	Intermediate Similarity	NPC473234
0.7391	Intermediate Similarity	NPC473273
0.7391	Intermediate Similarity	NPC179746
0.7388	Intermediate Similarity	NPC196921
0.7388	Intermediate Similarity	NPC213634
0.7388	Intermediate Similarity	NPC279478
0.7388	Intermediate Similarity	NPC241935
0.7388	Intermediate Similarity	NPC220757

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 NPC144625 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	2814
0.2-0.3	3884
0.3-0.4	1435
0.4-0.5	379
0.5-0.6	231
0.6-0.7	37
0.7-0.8	1
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
0.812	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6371	Approved
0.7313	Intermediate Similarity	NPD7319	Approved
0.7293	Intermediate Similarity	NPD7078	Approved
0.7273	Intermediate Similarity	NPD7492	Approved
0.7265	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6054	Approved
0.7218	Intermediate Similarity	NPD7507	Approved
0.7218	Intermediate Similarity	NPD6616	Approved
0.7121	Intermediate Similarity	NPD6370	Approved
0.7111	Intermediate Similarity	NPD7736	Approved
0.7099	Intermediate Similarity	NPD6319	Approved
0.7099	Intermediate Similarity	NPD6059	Approved
0.7073	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6015	Approved
0.7045	Intermediate Similarity	NPD6016	Approved
0.704	Intermediate Similarity	NPD6686	Approved
0.7037	Intermediate Similarity	NPD8293	Discontinued
0.6992	Remote Similarity	NPD5988	Approved
0.6953	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD5785	Approved
0.6822	Remote Similarity	NPD8297	Approved
0.6822	Remote Similarity	NPD6882	Approved
0.6769	Remote Similarity	NPD4632	Approved
0.6744	Remote Similarity	NPD6649	Approved
0.6744	Remote Similarity	NPD6650	Approved
0.6742	Remote Similarity	NPD6009	Approved
0.6719	Remote Similarity	NPD6373	Approved
0.6719	Remote Similarity	NPD6372	Approved
0.6695	Remote Similarity	NPD1695	Approved
0.6692	Remote Similarity	NPD7328	Approved
0.6692	Remote Similarity	NPD7327	Approved
0.6642	Remote Similarity	NPD7516	Approved
0.6641	Remote Similarity	NPD6881	Approved
0.6641	Remote Similarity	NPD7320	Approved
0.6641	Remote Similarity	NPD6899	Approved
0.6639	Remote Similarity	NPD6698	Approved
0.6639	Remote Similarity	NPD46	Approved
0.6619	Remote Similarity	NPD6033	Approved
0.6617	Remote Similarity	NPD7115	Discovery
0.6615	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6675	Approved
0.6614	Remote Similarity	NPD7128	Approved
0.6614	Remote Similarity	NPD6402	Approved
0.6614	Remote Similarity	NPD5739	Approved
0.6612	Remote Similarity	NPD5282	Discontinued
0.6593	Remote Similarity	NPD8377	Approved
0.6593	Remote Similarity	NPD8294	Approved
0.6583	Remote Similarity	NPD7983	Approved
0.6562	Remote Similarity	NPD5697	Approved
0.6562	Remote Similarity	NPD6412	Phase 2
0.6544	Remote Similarity	NPD8296	Approved
0.6544	Remote Similarity	NPD8380	Approved
0.6544	Remote Similarity	NPD8378	Approved
0.6544	Remote Similarity	NPD8033	Approved
0.6544	Remote Similarity	NPD8379	Approved
0.6544	Remote Similarity	NPD8335	Approved
0.6538	Remote Similarity	NPD6883	Approved
0.6538	Remote Similarity	NPD7102	Approved
0.6538	Remote Similarity	NPD4634	Approved
0.6538	Remote Similarity	NPD7290	Approved
0.6496	Remote Similarity	NPD5363	Approved
0.6489	Remote Similarity	NPD6617	Approved
0.6489	Remote Similarity	NPD6847	Approved
0.6489	Remote Similarity	NPD8130	Phase 1
0.6489	Remote Similarity	NPD6869	Approved
0.6483	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6013	Approved
0.6462	Remote Similarity	NPD6012	Approved
0.6462	Remote Similarity	NPD6014	Approved
0.6452	Remote Similarity	NPD6084	Phase 2
0.6452	Remote Similarity	NPD6083	Phase 2
0.6449	Remote Similarity	NPD7604	Phase 2
0.6449	Remote Similarity	NPD8328	Phase 3
0.6441	Remote Similarity	NPD5786	Approved
0.6434	Remote Similarity	NPD5701	Approved
0.6423	Remote Similarity	NPD7503	Approved
0.6423	Remote Similarity	NPD5983	Phase 2
0.6423	Remote Similarity	NPD8517	Approved
0.6423	Remote Similarity	NPD8516	Approved
0.6423	Remote Similarity	NPD8515	Approved
0.6423	Remote Similarity	NPD8513	Phase 3
0.6408	Remote Similarity	NPD5956	Approved
0.64	Remote Similarity	NPD4225	Approved
0.6385	Remote Similarity	NPD6011	Approved
0.6385	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6435	Approved
0.6364	Remote Similarity	NPD7838	Discovery
0.6357	Remote Similarity	NPD6336	Discontinued
0.6357	Remote Similarity	NPD6008	Approved
0.6356	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8269	Approved
0.6304	Remote Similarity	NPD8267	Approved
0.6304	Remote Similarity	NPD8266	Approved
0.6304	Remote Similarity	NPD8268	Approved
0.6293	Remote Similarity	NPD5369	Approved
0.629	Remote Similarity	NPD5695	Phase 3
0.627	Remote Similarity	NPD5696	Approved
0.627	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD7260	Phase 2
0.625	Remote Similarity	NPD5211	Phase 2
0.6241	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4270	Approved
0.6239	Remote Similarity	NPD4269	Approved
0.622	Remote Similarity	NPD5286	Approved
0.622	Remote Similarity	NPD5285	Approved
0.622	Remote Similarity	NPD4696	Approved
0.622	Remote Similarity	NPD7640	Approved
0.622	Remote Similarity	NPD7639	Approved
0.6218	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7642	Approved
0.6207	Remote Similarity	NPD6845	Suspended
0.6207	Remote Similarity	NPD5368	Approved
0.6197	Remote Similarity	NPD8074	Phase 3
0.619	Remote Similarity	NPD4755	Approved
0.6187	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5362	Discontinued
0.6176	Remote Similarity	NPD6274	Approved
0.6167	Remote Similarity	NPD4249	Approved
0.6159	Remote Similarity	NPD7101	Approved
0.6159	Remote Similarity	NPD7100	Approved
0.6154	Remote Similarity	NPD5141	Approved
0.6148	Remote Similarity	NPD8133	Approved
0.6124	Remote Similarity	NPD5224	Approved
0.6124	Remote Similarity	NPD4633	Approved
0.6124	Remote Similarity	NPD5226	Approved
0.6124	Remote Similarity	NPD5225	Approved
0.6102	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD4700	Approved
0.609	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6335	Approved
0.6077	Remote Similarity	NPD5175	Approved
0.6077	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD4252	Approved
0.6048	Remote Similarity	NPD5693	Phase 1
0.6047	Remote Similarity	NPD1700	Approved
0.6047	Remote Similarity	NPD5223	Approved
0.6045	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD5210	Approved
0.6032	Remote Similarity	NPD4629	Approved
0.6028	Remote Similarity	NPD8080	Discontinued
0.6016	Remote Similarity	NPD4753	Phase 2
0.6015	Remote Similarity	NPD4729	Approved
0.6015	Remote Similarity	NPD4730	Approved
0.6014	Remote Similarity	NPD6317	Approved
0.6014	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5778	Approved
0.5986	Remote Similarity	NPD7830	Approved
0.5986	Remote Similarity	NPD7829	Approved
0.5985	Remote Similarity	NPD4767	Approved
0.5985	Remote Similarity	NPD4768	Approved
0.5984	Remote Similarity	NPD7839	Suspended
0.5971	Remote Similarity	NPD6314	Approved
0.5971	Remote Similarity	NPD6313	Approved
0.5957	Remote Similarity	NPD6921	Approved
0.5957	Remote Similarity	NPD6908	Approved
0.5957	Remote Similarity	NPD6909	Approved
0.5957	Remote Similarity	NPD8444	Approved
0.5941	Remote Similarity	NPD7799	Discontinued
0.5932	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD4821	Approved
0.5932	Remote Similarity	NPD4819	Approved
0.5932	Remote Similarity	NPD4820	Approved
0.5932	Remote Similarity	NPD4822	Approved
0.5929	Remote Similarity	NPD4522	Approved
0.5926	Remote Similarity	NPD5248	Approved
0.5926	Remote Similarity	NPD5247	Approved
0.5926	Remote Similarity	NPD5249	Phase 3
0.5926	Remote Similarity	NPD5250	Approved
0.5926	Remote Similarity	NPD5251	Approved
0.5923	Remote Similarity	NPD5344	Discontinued
0.592	Remote Similarity	NPD7637	Suspended
0.5906	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5903	Remote Similarity	NPD8451	Approved
0.5896	Remote Similarity	NPD5128	Approved
0.5894	Remote Similarity	NPD6334	Approved
0.5894	Remote Similarity	NPD6333	Approved
0.5887	Remote Similarity	NPD6673	Approved
0.5887	Remote Similarity	NPD6904	Approved
0.5887	Remote Similarity	NPD6080	Approved
0.5882	Remote Similarity	NPD4790	Discontinued
0.5874	Remote Similarity	NPD6067	Discontinued
0.5873	Remote Similarity	NPD6399	Phase 3
0.5862	Remote Similarity	NPD8448	Approved
0.5857	Remote Similarity	NPD7641	Discontinued
0.5845	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5209	Approved
0.5833	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4754	Approved
0.5822	Remote Similarity	NPD8337	Approved
0.5822	Remote Similarity	NPD8336	Approved
0.5821	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.582	Remote Similarity	NPD1694	Approved
0.5806	Remote Similarity	NPD5737	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