NPASS Compound

Structure

CID13071 OpenBabel06191715342D 41 47 0 0 1 0 0 0 0 0999 V2000 -5.2922 -0.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4804 -3.8738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4774 -3.8738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2024 1.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0799 2.3951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4515 0.8017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0954 0.1492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5298 -0.2293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3790 -2.7936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7206 -0.7278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0155 -0.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4684 0.1071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5921 -2.3234 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2373 -2.4715 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4373 -1.5997 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9199 0.5595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9789 -0.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4690 -1.4150 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4464 -1.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4386 1.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0974 0.1319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8983 1.6017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9789 -3.0103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4639 0.7945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8003 1.4381 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1025 -0.7524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5206 -1.5997 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9233 0.5296 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0903 -0.7697 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2400 -2.8727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9789 0.8081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8148 -2.3133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2273 1.7136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4657 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7689 1.6744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4475 -0.3185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9271 -1.2486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4816 1.3833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7206 -2.4715 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2373 -0.7278 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 2 23 1 0 0 0 0 3 23 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 24 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 26 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 30 1 1 0 0 0 14 23 1 0 0 0 0 14 27 1 6 0 0 0 15 27 1 1 0 0 0 15 39 1 0 0 0 0 16 8 1 6 0 0 0 16 28 1 0 0 0 0 16 38 1 0 0 0 0 17 31 2 0 0 0 0 17 40 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 29 1 0 0 0 0 19 32 2 0 0 0 0 20 33 2 0 0 0 0 20 38 1 0 0 0 0 21 24 1 1 0 0 0 21 28 1 0 0 0 0 21 29 1 0 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 22 34 2 0 0 0 0 23 39 1 0 0 0 0 24 4 1 6 0 0 0 25 28 1 6 0 0 0 25 35 1 0 0 0 0 26 7 1 6 0 0 0 26 41 1 0 0 0 0 27 11 1 6 0 0 0 27 40 1 0 0 0 0 28 36 1 6 0 0 0 29 37 1 1 0 0 0 29 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.22
Volume:	542.545
LogP:	1.82
LogD:	0.792
LogS:	-3.776
# Rotatable Bonds:	1
TPSA:	193.19
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	7.492
Fsp3:	0.759
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:	-5.893
MDCK Permeability:	5.2673414757009596e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.599
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.299
Plasma Protein Binding (PPB):	68.18152618408203%
Volume Distribution (VD):	0.541
Pgp-substrate:	24.16565704345703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.991
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.399
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.528
CYP3A4-substrate:	0.607

ADMET: Excretion

Clearance (CL):	4.984
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.591
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.168
Carcinogencity:	0.902
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC13071

Natural Product ID:	NPC13071
*Common Name:**	Schisandilactone F
IUPAC Name:	n.a.
Synonyms:	Schisandilactone F
Standard InCHIKey:	ZQMIOJYHXMZMSW-VCRLAHENSA-N
Standard InCHI:	InChI=1S/C29H36O12/c1-12-8-16(38-20(12)33)28(36)21-24(4,22(34)25(28,5)35)6-7-26-11-27-14(23(2,3)39-15(27)10-17(31)40-27)9-13(30)18(26)19(32)29(21,37)41-26/h8,13-16,18,21,30,35-37H,6-7,9-11H2,1-5H3/t13-,14+,15-,16+,18+,21-,24+,25+,26+,27-,28+,29-/m1/s1
SMILES:	CC1=C[C@@H]([C@@]2([C@H]3[C@](C)(CC[C@]45C[C@@]67[C@@H](C[C@H]([C@H]4C(=O)[C@@]3(O)O5)O)C(C)(C)O[C@@H]6CC(=O)O7)C(=O)[C@]2(C)O)O)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215355
PubChem CID:	46918831
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]
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[489679]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	100000.0	nM	PMID[489679]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[489679]

☑ 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 NPC13071 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	359
0.1-0.2	2244
0.2-0.3	7139
0.3-0.4	13380
0.4-0.5	11305
0.5-0.6	6173
0.6-0.7	1883
0.7-0.8	188
0.8-0.85	15
0.85-0.9	4
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.959	High Similarity	NPC224623
0.9576	High Similarity	NPC1538
0.9496	High Similarity	NPC144625
0.9492	High Similarity	NPC192309
0.9412	High Similarity	NPC42747
0.9268	High Similarity	NPC469351
0.9262	High Similarity	NPC172823
0.9024	High Similarity	NPC11732
0.878	High Similarity	NPC186339
0.8689	High Similarity	NPC147635
0.8689	High Similarity	NPC163693
0.8333	Intermediate Similarity	NPC129992
0.8226	Intermediate Similarity	NPC475401
0.816	Intermediate Similarity	NPC477092
0.8145	Intermediate Similarity	NPC475305
0.8083	Intermediate Similarity	NPC220773
0.8083	Intermediate Similarity	NPC278693
0.8049	Intermediate Similarity	NPC209058
0.8045	Intermediate Similarity	NPC471234
0.8	Intermediate Similarity	NPC26617
0.7983	Intermediate Similarity	NPC472756
0.7951	Intermediate Similarity	NPC477103
0.7951	Intermediate Similarity	NPC182185
0.7937	Intermediate Similarity	NPC161060
0.792	Intermediate Similarity	NPC277583
0.7917	Intermediate Similarity	NPC168890
0.7899	Intermediate Similarity	NPC475871
0.7899	Intermediate Similarity	NPC475945
0.7899	Intermediate Similarity	NPC472755
0.7891	Intermediate Similarity	NPC471999
0.7891	Intermediate Similarity	NPC472001
0.7891	Intermediate Similarity	NPC472000
0.7886	Intermediate Similarity	NPC475495
0.7886	Intermediate Similarity	NPC474750
0.7881	Intermediate Similarity	NPC171759
0.7879	Intermediate Similarity	NPC472770
0.7879	Intermediate Similarity	NPC475371
0.7869	Intermediate Similarity	NPC217041
0.7869	Intermediate Similarity	NPC477102
0.7857	Intermediate Similarity	NPC471145
0.7857	Intermediate Similarity	NPC475323
0.7857	Intermediate Similarity	NPC36754
0.7857	Intermediate Similarity	NPC471146
0.7833	Intermediate Similarity	NPC203659
0.7823	Intermediate Similarity	NPC473522
0.7823	Intermediate Similarity	NPC475277
0.7823	Intermediate Similarity	NPC477093
0.7823	Intermediate Similarity	NPC98870
0.7815	Intermediate Similarity	NPC474747
0.7815	Intermediate Similarity	NPC472754
0.7805	Intermediate Similarity	NPC471884
0.7805	Intermediate Similarity	NPC257240
0.7787	Intermediate Similarity	NPC10150
0.7769	Intermediate Similarity	NPC469352
0.7769	Intermediate Similarity	NPC54737
0.7769	Intermediate Similarity	NPC41674
0.7769	Intermediate Similarity	NPC228311
0.7769	Intermediate Similarity	NPC469441
0.7761	Intermediate Similarity	NPC472769
0.775	Intermediate Similarity	NPC475873
0.775	Intermediate Similarity	NPC110989
0.7742	Intermediate Similarity	NPC287311
0.7731	Intermediate Similarity	NPC472753
0.7731	Intermediate Similarity	NPC477950
0.7731	Intermediate Similarity	NPC474742
0.7724	Intermediate Similarity	NPC59489
0.7724	Intermediate Similarity	NPC187876
0.7724	Intermediate Similarity	NPC139838
0.7705	Intermediate Similarity	NPC469787
0.7705	Intermediate Similarity	NPC469788
0.7705	Intermediate Similarity	NPC470192
0.7705	Intermediate Similarity	NPC290247
0.7698	Intermediate Similarity	NPC471380
0.7698	Intermediate Similarity	NPC471382
0.7686	Intermediate Similarity	NPC474741
0.7686	Intermediate Similarity	NPC100487
0.7686	Intermediate Similarity	NPC472748
0.768	Intermediate Similarity	NPC471570
0.7667	Intermediate Similarity	NPC86077
0.7667	Intermediate Similarity	NPC324017
0.7667	Intermediate Similarity	NPC49393
0.7667	Intermediate Similarity	NPC105725
0.7667	Intermediate Similarity	NPC320019
0.7667	Intermediate Similarity	NPC225353
0.7656	Intermediate Similarity	NPC475372
0.7642	Intermediate Similarity	NPC167044
0.7642	Intermediate Similarity	NPC117604
0.7642	Intermediate Similarity	NPC329876
0.7634	Intermediate Similarity	NPC472768
0.7627	Intermediate Similarity	NPC213947
0.7627	Intermediate Similarity	NPC108475
0.7627	Intermediate Similarity	NPC170143
0.7627	Intermediate Similarity	NPC477949
0.7627	Intermediate Similarity	NPC311904
0.7623	Intermediate Similarity	NPC472751
0.7623	Intermediate Similarity	NPC223450
0.7623	Intermediate Similarity	NPC243998
0.7623	Intermediate Similarity	NPC44004
0.7623	Intermediate Similarity	NPC472749
0.7619	Intermediate Similarity	NPC106395
0.7619	Intermediate Similarity	NPC46269
0.7615	Intermediate Similarity	NPC470829
0.7615	Intermediate Similarity	NPC473228
0.7603	Intermediate Similarity	NPC472747
0.7603	Intermediate Similarity	NPC472750
0.7597	Intermediate Similarity	NPC9674
0.7597	Intermediate Similarity	NPC312536
0.7597	Intermediate Similarity	NPC19028
0.7583	Intermediate Similarity	NPC15993
0.7583	Intermediate Similarity	NPC150923
0.7583	Intermediate Similarity	NPC476270
0.7583	Intermediate Similarity	NPC133907
0.7583	Intermediate Similarity	NPC128733
0.7583	Intermediate Similarity	NPC110443
0.7583	Intermediate Similarity	NPC46998
0.7583	Intermediate Similarity	NPC185141
0.7581	Intermediate Similarity	NPC38154
0.7578	Intermediate Similarity	NPC475238
0.7578	Intermediate Similarity	NPC473656
0.7574	Intermediate Similarity	NPC88668
0.7571	Intermediate Similarity	NPC25887
0.7561	Intermediate Similarity	NPC176756
0.7559	Intermediate Similarity	NPC138303
0.7559	Intermediate Similarity	NPC67290
0.7559	Intermediate Similarity	NPC133677
0.7542	Intermediate Similarity	NPC476009
0.7542	Intermediate Similarity	NPC126156
0.7542	Intermediate Similarity	NPC91771
0.7542	Intermediate Similarity	NPC142529
0.754	Intermediate Similarity	NPC138757
0.754	Intermediate Similarity	NPC76550
0.754	Intermediate Similarity	NPC123855
0.7521	Intermediate Similarity	NPC471757
0.7521	Intermediate Similarity	NPC78127
0.7521	Intermediate Similarity	NPC149371
0.752	Intermediate Similarity	NPC475463
0.7519	Intermediate Similarity	NPC288679
0.7519	Intermediate Similarity	NPC13710
0.75	Intermediate Similarity	NPC54739
0.75	Intermediate Similarity	NPC308191
0.7483	Intermediate Similarity	NPC194854
0.7483	Intermediate Similarity	NPC48813
0.748	Intermediate Similarity	NPC291643
0.748	Intermediate Similarity	NPC179891
0.7479	Intermediate Similarity	NPC474313
0.7479	Intermediate Similarity	NPC471150
0.7465	Intermediate Similarity	NPC471171
0.7458	Intermediate Similarity	NPC163228
0.7458	Intermediate Similarity	NPC475900
0.7445	Intermediate Similarity	NPC58029
0.7438	Intermediate Similarity	NPC47880
0.7431	Intermediate Similarity	NPC16729
0.7431	Intermediate Similarity	NPC475462
0.7426	Intermediate Similarity	NPC473838
0.7426	Intermediate Similarity	NPC213634
0.7426	Intermediate Similarity	NPC476855
0.7426	Intermediate Similarity	NPC475389
0.7426	Intermediate Similarity	NPC476852
0.7419	Intermediate Similarity	NPC477513
0.7419	Intermediate Similarity	NPC204884
0.7417	Intermediate Similarity	NPC54843
0.7417	Intermediate Similarity	NPC471144
0.7417	Intermediate Similarity	NPC470188
0.7407	Intermediate Similarity	NPC311534
0.7405	Intermediate Similarity	NPC472004
0.7395	Intermediate Similarity	NPC18019
0.7395	Intermediate Similarity	NPC24956
0.7394	Intermediate Similarity	NPC470426
0.7385	Intermediate Similarity	NPC474286
0.7385	Intermediate Similarity	NPC475130
0.7381	Intermediate Similarity	NPC50223
0.7381	Intermediate Similarity	NPC206595
0.7377	Intermediate Similarity	NPC118405
0.7376	Intermediate Similarity	NPC476825
0.7373	Intermediate Similarity	NPC473331
0.7372	Intermediate Similarity	NPC34963
0.7372	Intermediate Similarity	NPC475139
0.7372	Intermediate Similarity	NPC180902
0.7368	Intermediate Similarity	NPC471392
0.7364	Intermediate Similarity	NPC170692
0.7364	Intermediate Similarity	NPC138372
0.7364	Intermediate Similarity	NPC106228
0.7364	Intermediate Similarity	NPC255450
0.736	Intermediate Similarity	NPC475960
0.7355	Intermediate Similarity	NPC471381
0.7355	Intermediate Similarity	NPC280963
0.7355	Intermediate Similarity	NPC186861
0.7355	Intermediate Similarity	NPC70865
0.7353	Intermediate Similarity	NPC476851
0.7353	Intermediate Similarity	NPC231529
0.7353	Intermediate Similarity	NPC476854
0.7353	Intermediate Similarity	NPC470851
0.7353	Intermediate Similarity	NPC35109
0.7339	Intermediate Similarity	NPC252234
0.7339	Intermediate Similarity	NPC475217
0.7333	Intermediate Similarity	NPC328562
0.7333	Intermediate Similarity	NPC323421
0.7333	Intermediate Similarity	NPC473265
0.7333	Intermediate Similarity	NPC161493
0.7333	Intermediate Similarity	NPC287423

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 NPC13071 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	2819
0.2-0.3	3885
0.3-0.4	1428
0.4-0.5	391
0.5-0.6	203
0.6-0.7	31
0.7-0.8	3
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
0.8	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6371	Approved
0.7333	Intermediate Similarity	NPD7078	Approved
0.7313	Intermediate Similarity	NPD7492	Approved
0.7273	Intermediate Similarity	NPD6054	Approved
0.7259	Intermediate Similarity	NPD6616	Approved
0.7258	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6370	Approved
0.7153	Intermediate Similarity	NPD7736	Approved
0.7143	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD6059	Approved
0.7101	Intermediate Similarity	NPD7319	Approved
0.709	Intermediate Similarity	NPD6015	Approved
0.709	Intermediate Similarity	NPD6016	Approved
0.708	Intermediate Similarity	NPD8293	Discontinued
0.7037	Intermediate Similarity	NPD5988	Approved
0.7007	Intermediate Similarity	NPD7507	Approved
0.687	Remote Similarity	NPD6053	Discontinued
0.6833	Remote Similarity	NPD5785	Approved
0.6822	Remote Similarity	NPD6686	Approved
0.6742	Remote Similarity	NPD6882	Approved
0.6742	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6641	Remote Similarity	NPD6373	Approved
0.6641	Remote Similarity	NPD6372	Approved
0.6612	Remote Similarity	NPD1695	Approved
0.6567	Remote Similarity	NPD4632	Approved
0.6565	Remote Similarity	NPD7320	Approved
0.6565	Remote Similarity	NPD6881	Approved
0.6565	Remote Similarity	NPD6899	Approved
0.6557	Remote Similarity	NPD6698	Approved
0.6557	Remote Similarity	NPD46	Approved
0.6544	Remote Similarity	NPD7115	Discovery
0.6541	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6532	Remote Similarity	NPD5282	Discontinued
0.6531	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD7983	Approved
0.6496	Remote Similarity	NPD7327	Approved
0.6496	Remote Similarity	NPD7328	Approved
0.6489	Remote Similarity	NPD5697	Approved
0.6475	Remote Similarity	NPD8033	Approved
0.6466	Remote Similarity	NPD4634	Approved
0.6466	Remote Similarity	NPD6883	Approved
0.6466	Remote Similarity	NPD7290	Approved
0.6466	Remote Similarity	NPD7102	Approved
0.6458	Remote Similarity	NPD5956	Approved
0.6457	Remote Similarity	NPD5696	Approved
0.6449	Remote Similarity	NPD7516	Approved
0.6418	Remote Similarity	NPD6617	Approved
0.6418	Remote Similarity	NPD8130	Phase 1
0.6418	Remote Similarity	NPD6847	Approved
0.6418	Remote Similarity	NPD6869	Approved
0.6417	Remote Similarity	NPD5363	Approved
0.6414	Remote Similarity	NPD7260	Phase 2
0.6403	Remote Similarity	NPD8294	Approved
0.6403	Remote Similarity	NPD8377	Approved
0.6391	Remote Similarity	NPD6012	Approved
0.6391	Remote Similarity	NPD6014	Approved
0.6391	Remote Similarity	NPD6013	Approved
0.6383	Remote Similarity	NPD7604	Phase 2
0.6383	Remote Similarity	NPD8328	Phase 3
0.6378	Remote Similarity	NPD6083	Phase 2
0.6378	Remote Similarity	NPD6084	Phase 2
0.637	Remote Similarity	NPD6845	Suspended
0.6364	Remote Similarity	NPD5786	Approved
0.6364	Remote Similarity	NPD6412	Phase 2
0.6364	Remote Similarity	NPD5701	Approved
0.6357	Remote Similarity	NPD8379	Approved
0.6357	Remote Similarity	NPD8515	Approved
0.6357	Remote Similarity	NPD8378	Approved
0.6357	Remote Similarity	NPD5983	Phase 2
0.6357	Remote Similarity	NPD8517	Approved
0.6357	Remote Similarity	NPD8296	Approved
0.6357	Remote Similarity	NPD8380	Approved
0.6357	Remote Similarity	NPD8516	Approved
0.6357	Remote Similarity	NPD8513	Phase 3
0.6357	Remote Similarity	NPD8335	Approved
0.6328	Remote Similarity	NPD4225	Approved
0.6316	Remote Similarity	NPD6011	Approved
0.6294	Remote Similarity	NPD6336	Discontinued
0.629	Remote Similarity	NPD7838	Discovery
0.6288	Remote Similarity	NPD6008	Approved
0.6241	Remote Similarity	NPD8267	Approved
0.6241	Remote Similarity	NPD8266	Approved
0.6241	Remote Similarity	NPD8268	Approved
0.6241	Remote Similarity	NPD7503	Approved
0.6241	Remote Similarity	NPD8269	Approved
0.622	Remote Similarity	NPD5695	Phase 3
0.6218	Remote Similarity	NPD5369	Approved
0.6202	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD4250	Approved
0.6179	Remote Similarity	NPD4251	Approved
0.6176	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4269	Approved
0.6167	Remote Similarity	NPD4270	Approved
0.6167	Remote Similarity	NPD6435	Approved
0.6154	Remote Similarity	NPD7642	Approved
0.6148	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD8074	Phase 3
0.6116	Remote Similarity	NPD5362	Discontinued
0.6115	Remote Similarity	NPD6274	Approved
0.6099	Remote Similarity	NPD7101	Approved
0.6099	Remote Similarity	NPD7100	Approved
0.6098	Remote Similarity	NPD4249	Approved
0.6094	Remote Similarity	NPD5210	Approved
0.6094	Remote Similarity	NPD4629	Approved
0.6084	Remote Similarity	NPD8080	Discontinued
0.6082	Remote Similarity	NPD7799	Discontinued
0.6077	Remote Similarity	NPD7638	Approved
0.6071	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5211	Phase 2
0.6031	Remote Similarity	NPD7640	Approved
0.6031	Remote Similarity	NPD4696	Approved
0.6031	Remote Similarity	NPD5285	Approved
0.6031	Remote Similarity	NPD7639	Approved
0.6031	Remote Similarity	NPD5286	Approved
0.6028	Remote Similarity	NPD6335	Approved
0.6014	Remote Similarity	NPD8444	Approved
0.6014	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD4755	Approved
0.5985	Remote Similarity	NPD1700	Approved
0.5984	Remote Similarity	NPD5693	Phase 1
0.5971	Remote Similarity	NPD8133	Approved
0.597	Remote Similarity	NPD5141	Approved
0.5957	Remote Similarity	NPD6317	Approved
0.594	Remote Similarity	NPD5225	Approved
0.594	Remote Similarity	NPD5226	Approved
0.594	Remote Similarity	NPD4633	Approved
0.594	Remote Similarity	NPD5224	Approved
0.5938	Remote Similarity	NPD5779	Approved
0.5938	Remote Similarity	NPD5778	Approved
0.5931	Remote Similarity	NPD7829	Approved
0.5931	Remote Similarity	NPD7830	Approved
0.5923	Remote Similarity	NPD7839	Suspended
0.5915	Remote Similarity	NPD6314	Approved
0.5915	Remote Similarity	NPD6313	Approved
0.5912	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4700	Approved
0.5903	Remote Similarity	NPD6909	Approved
0.5903	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5903	Remote Similarity	NPD6908	Approved
0.5902	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD5174	Approved
0.5896	Remote Similarity	NPD5175	Approved
0.5878	Remote Similarity	NPD8336	Approved
0.5878	Remote Similarity	NPD8337	Approved
0.5874	Remote Similarity	NPD4522	Approved
0.587	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD4820	Approved
0.5868	Remote Similarity	NPD4819	Approved
0.5868	Remote Similarity	NPD4821	Approved
0.5868	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD4822	Approved
0.5865	Remote Similarity	NPD5344	Discontinued
0.5865	Remote Similarity	NPD5223	Approved
0.5859	Remote Similarity	NPD7637	Suspended
0.585	Remote Similarity	NPD8451	Approved
0.5844	Remote Similarity	NPD6333	Approved
0.5844	Remote Similarity	NPD6334	Approved
0.5839	Remote Similarity	NPD4730	Approved
0.5839	Remote Similarity	NPD4729	Approved
0.5833	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD2204	Approved
0.5827	Remote Similarity	NPD6673	Approved
0.5827	Remote Similarity	NPD4753	Phase 2
0.5827	Remote Similarity	NPD6904	Approved
0.5827	Remote Similarity	NPD6080	Approved
0.5822	Remote Similarity	NPD6067	Discontinued
0.582	Remote Similarity	NPD4790	Discontinued
0.5814	Remote Similarity	NPD6399	Phase 3
0.5811	Remote Similarity	NPD8448	Approved
0.5809	Remote Similarity	NPD4768	Approved
0.5809	Remote Similarity	NPD4767	Approved
0.5804	Remote Similarity	NPD7641	Discontinued
0.5793	Remote Similarity	NPD6921	Approved
0.5755	Remote Similarity	NPD5250	Approved
0.5755	Remote Similarity	NPD5247	Approved
0.5755	Remote Similarity	NPD5249	Phase 3
0.5755	Remote Similarity	NPD5251	Approved
0.5755	Remote Similarity	NPD5248	Approved
0.5748	Remote Similarity	NPD5737	Approved
0.5748	Remote Similarity	NPD6672	Approved
0.5736	Remote Similarity	NPD6050	Approved
0.5736	Remote Similarity	NPD6411	Approved
0.5726	Remote Similarity	NPD7154	Phase 3
0.5726	Remote Similarity	NPD5332	Approved
0.5726	Remote Similarity	NPD5331	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