NPASS Compound

Structure

NPC475463 OpenBabel07101718292D 41 46 0 0 1 0 0 0 0 0999 V2000 -10.6234 -1.4963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4826 -2.8225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0521 -4.9984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0585 -1.9554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7813 -1.2644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2317 -2.2227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6034 -2.0191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5783 -2.2417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0922 -0.6182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2262 -0.1182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8438 -1.5895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4286 -3.2008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3145 1.3748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5783 0.0053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7098 -1.0895 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8135 -2.0794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0740 -4.7905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8353 -2.2873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0922 -1.6182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1007 -0.9204 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1695 -1.1182 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3601 -1.6182 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4341 -3.0963 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3054 1.2406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1225 -1.1283 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5019 -0.1114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1786 -0.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2262 -2.1182 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3601 -0.6182 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6034 -0.2172 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8806 0.4739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4048 -5.5337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9965 1.9634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4534 -0.3852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1710 0.6317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7968 -1.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1578 1.1649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7650 -3.8395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5074 -0.0069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4840 0.2567 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 17 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 29 1 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 13 31 1 0 0 0 0 14 29 1 0 0 0 0 14 30 1 0 0 0 0 15 1 1 6 0 0 0 15 26 1 0 0 0 0 16 2 1 6 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 32 2 0 0 0 0 17 38 1 0 0 0 0 18 19 2 0 0 0 0 19 28 1 0 0 0 0 20 25 1 6 0 0 0 20 39 1 0 0 0 0 21 27 1 0 0 0 0 21 30 1 6 0 0 0 22 28 1 1 0 0 0 22 29 1 0 0 0 0 23 28 1 1 0 0 0 23 38 1 0 0 0 0 24 33 2 0 0 0 0 24 40 1 0 0 0 0 25 34 1 1 0 0 0 26 35 2 0 0 0 0 26 39 1 0 0 0 0 27 41 1 0 0 0 0 28 6 1 6 0 0 0 29 36 1 1 0 0 0 30 31 1 6 0 0 0 30 40 1 0 0 0 0 31 37 1 6 0 0 0 31 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.29
Volume:	570.75
LogP:	2.665
LogD:	1.442
LogS:	-4.146
# Rotatable Bonds:	5
TPSA:	148.82
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.259
Synthetic Accessibility Score:	6.342
Fsp3:	0.839
Lipinski Rule-of-5:	Accepted
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:	-5.256
MDCK Permeability:	7.511912554036826e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.875
Human Intestinal Absorption (HIA):	0.099
20% Bioavailability (F20%):	0.514
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.437
Plasma Protein Binding (PPB):	64.24532318115234%
Volume Distribution (VD):	0.738
Pgp-substrate:	33.196388244628906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.497
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.643
CYP3A4-substrate:	0.433

ADMET: Excretion

Clearance (CL):	7.844
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.652
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.347
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.225
Carcinogencity:	0.882
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC475463

Natural Product ID:	NPC475463
*Common Name:**	Kadcoccilactone F
IUPAC Name:	n.a.
Synonyms:	Kadcoccilactone F
Standard InCHIKey:	AUPPZHFOVAGCDF-DAVIGNLWSA-N
Standard InCHI:	InChI=1S/C31H44O10/c1-15-11-20(39-26(15)35)25(34)16(2)18-12-23(38-17(3)32)28(6)19(18)9-10-29(36)14-30-21(7-8-22(28)29)27(4,5)41-31(30,37)13-24(33)40-30/h15-16,20-23,25,34,36-37H,7-14H2,1-6H3/t15-,16-,20-,21-,22-,23-,25-,28-,29-,30+,31+/m0/s1
SMILES:	CC(=O)O[C@H]1CC(=C2[C@@]1(C)[C@@H]1CC[C@@H]3[C@@]4(C[C@]1(CC2)O)OC(=O)C[C@]4(OC3(C)C)O)[C@@H]([C@@H]([C@@H]1C[C@@H](C(=O)O1)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506113
PubChem CID:	24970813
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18027905]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271558]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	roots	n.a.	n.a.	PMID[18491866]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590312]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24299567]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214125]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[27704807]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO912	Kadsura coccinea	Species	Schisandraceae	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	5
Others	1

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[541892]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[541892]
NPT81	Cell Line	A549	Homo sapiens	IC	>	100.0	ug ml-1	PMID[541892]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[541892]

☑ 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 NPC475463 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	273
0.1-0.2	1848
0.2-0.3	6347
0.3-0.4	12836
0.4-0.5	9113
0.5-0.6	7430
0.6-0.7	4505
0.7-0.8	339
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8136	Intermediate Similarity	NPC129992
0.8087	Intermediate Similarity	NPC475323
0.8036	Intermediate Similarity	NPC250956
0.8	Intermediate Similarity	NPC472655
0.8	Intermediate Similarity	NPC470587
0.7946	Intermediate Similarity	NPC218853
0.7931	Intermediate Similarity	NPC475238
0.7909	Intermediate Similarity	NPC473526
0.7909	Intermediate Similarity	NPC473701
0.7845	Intermediate Similarity	NPC277583
0.7833	Intermediate Similarity	NPC186339
0.7833	Intermediate Similarity	NPC469352
0.7807	Intermediate Similarity	NPC472003
0.7788	Intermediate Similarity	NPC273433
0.7778	Intermediate Similarity	NPC473656
0.7768	Intermediate Similarity	NPC112780
0.7731	Intermediate Similarity	NPC329008
0.7731	Intermediate Similarity	NPC317635
0.7727	Intermediate Similarity	NPC474709
0.7719	Intermediate Similarity	NPC48305
0.7719	Intermediate Similarity	NPC470065
0.7719	Intermediate Similarity	NPC474923
0.7712	Intermediate Similarity	NPC475372
0.7699	Intermediate Similarity	NPC469845
0.7686	Intermediate Similarity	NPC471392
0.7679	Intermediate Similarity	NPC166079
0.7664	Intermediate Similarity	NPC292178
0.7664	Intermediate Similarity	NPC86893
0.7658	Intermediate Similarity	NPC474775
0.7647	Intermediate Similarity	NPC312536
0.7632	Intermediate Similarity	NPC42662
0.7623	Intermediate Similarity	NPC144625
0.7611	Intermediate Similarity	NPC59530
0.7611	Intermediate Similarity	NPC293512
0.7607	Intermediate Similarity	NPC123117
0.7607	Intermediate Similarity	NPC117712
0.7589	Intermediate Similarity	NPC100078
0.7589	Intermediate Similarity	NPC471293
0.7581	Intermediate Similarity	NPC188291
0.757	Intermediate Similarity	NPC240617
0.7568	Intermediate Similarity	NPC213528
0.7568	Intermediate Similarity	NPC244969
0.7563	Intermediate Similarity	NPC297179
0.7563	Intermediate Similarity	NPC106644
0.7561	Intermediate Similarity	NPC47113
0.7561	Intermediate Similarity	NPC174367
0.7545	Intermediate Similarity	NPC473146
0.7544	Intermediate Similarity	NPC94377
0.7544	Intermediate Similarity	NPC258323
0.7542	Intermediate Similarity	NPC207217
0.7523	Intermediate Similarity	NPC254121
0.7522	Intermediate Similarity	NPC306776
0.7522	Intermediate Similarity	NPC252234
0.752	Intermediate Similarity	NPC475371
0.752	Intermediate Similarity	NPC13071
0.75	Intermediate Similarity	NPC471005
0.75	Intermediate Similarity	NPC69171
0.75	Intermediate Similarity	NPC474165
0.75	Intermediate Similarity	NPC55954
0.75	Intermediate Similarity	NPC218513
0.75	Intermediate Similarity	NPC2757
0.748	Intermediate Similarity	NPC224623
0.7479	Intermediate Similarity	NPC476713
0.7479	Intermediate Similarity	NPC470171
0.7479	Intermediate Similarity	NPC476712
0.7478	Intermediate Similarity	NPC477070
0.7478	Intermediate Similarity	NPC477069
0.7477	Intermediate Similarity	NPC98225
0.746	Intermediate Similarity	NPC475389
0.746	Intermediate Similarity	NPC473838
0.7458	Intermediate Similarity	NPC471382
0.7458	Intermediate Similarity	NPC472274
0.7458	Intermediate Similarity	NPC471380
0.7456	Intermediate Similarity	NPC176756
0.7455	Intermediate Similarity	NPC274695
0.7438	Intermediate Similarity	NPC241192
0.7436	Intermediate Similarity	NPC23967
0.7436	Intermediate Similarity	NPC473877
0.7436	Intermediate Similarity	NPC234042
0.7436	Intermediate Similarity	NPC152117
0.7436	Intermediate Similarity	NPC269530
0.7434	Intermediate Similarity	NPC475036
0.7434	Intermediate Similarity	NPC65523
0.7434	Intermediate Similarity	NPC203659
0.7431	Intermediate Similarity	NPC475304
0.7419	Intermediate Similarity	NPC217901
0.7417	Intermediate Similarity	NPC204552
0.7417	Intermediate Similarity	NPC188667
0.7417	Intermediate Similarity	NPC161060
0.7414	Intermediate Similarity	NPC475134
0.7414	Intermediate Similarity	NPC475563
0.7414	Intermediate Similarity	NPC90630
0.7414	Intermediate Similarity	NPC475243
0.7414	Intermediate Similarity	NPC5284
0.7414	Intermediate Similarity	NPC101450
0.7414	Intermediate Similarity	NPC235014
0.7411	Intermediate Similarity	NPC225353
0.7411	Intermediate Similarity	NPC183571
0.7411	Intermediate Similarity	NPC296879
0.7411	Intermediate Similarity	NPC471119
0.7402	Intermediate Similarity	NPC475139
0.7402	Intermediate Similarity	NPC180902
0.7398	Intermediate Similarity	NPC1538
0.7398	Intermediate Similarity	NPC469382
0.7395	Intermediate Similarity	NPC16081
0.7395	Intermediate Similarity	NPC476710
0.7395	Intermediate Similarity	NPC134869
0.7395	Intermediate Similarity	NPC470628
0.7395	Intermediate Similarity	NPC173686
0.7395	Intermediate Similarity	NPC259306
0.7395	Intermediate Similarity	NPC138372
0.7395	Intermediate Similarity	NPC106228
0.7395	Intermediate Similarity	NPC235539
0.7395	Intermediate Similarity	NPC474046
0.7395	Intermediate Similarity	NPC152199
0.7395	Intermediate Similarity	NPC476711
0.7391	Intermediate Similarity	NPC255082
0.7391	Intermediate Similarity	NPC167044
0.7391	Intermediate Similarity	NPC94942
0.7387	Intermediate Similarity	NPC475877
0.7387	Intermediate Similarity	NPC474718
0.7377	Intermediate Similarity	NPC477046
0.7377	Intermediate Similarity	NPC472401
0.7377	Intermediate Similarity	NPC102822
0.7373	Intermediate Similarity	NPC102619
0.7373	Intermediate Similarity	NPC473535
0.7373	Intermediate Similarity	NPC255017
0.7373	Intermediate Similarity	NPC52634
0.7373	Intermediate Similarity	NPC194273
0.7368	Intermediate Similarity	NPC471333
0.7368	Intermediate Similarity	NPC168890
0.7368	Intermediate Similarity	NPC469401
0.7368	Intermediate Similarity	NPC471332
0.7364	Intermediate Similarity	NPC263674
0.7364	Intermediate Similarity	NPC261372
0.7364	Intermediate Similarity	NPC58267
0.736	Intermediate Similarity	NPC168849
0.736	Intermediate Similarity	NPC298841
0.736	Intermediate Similarity	NPC475273
0.736	Intermediate Similarity	NPC11732
0.7358	Intermediate Similarity	NPC471222
0.7358	Intermediate Similarity	NPC77001
0.7358	Intermediate Similarity	NPC253618
0.7355	Intermediate Similarity	NPC230513
0.7355	Intermediate Similarity	NPC19028
0.7355	Intermediate Similarity	NPC9674
0.7355	Intermediate Similarity	NPC477071
0.7355	Intermediate Similarity	NPC161065
0.7355	Intermediate Similarity	NPC178548
0.7355	Intermediate Similarity	NPC469380
0.7355	Intermediate Similarity	NPC42673
0.7355	Intermediate Similarity	NPC258592
0.735	Intermediate Similarity	NPC287311
0.735	Intermediate Similarity	NPC475480
0.735	Intermediate Similarity	NPC477073
0.735	Intermediate Similarity	NPC157476
0.735	Intermediate Similarity	NPC475668
0.735	Intermediate Similarity	NPC272242
0.735	Intermediate Similarity	NPC473921
0.7345	Intermediate Similarity	NPC159533
0.7345	Intermediate Similarity	NPC110989
0.7345	Intermediate Similarity	NPC140723
0.7344	Intermediate Similarity	NPC88668
0.7339	Intermediate Similarity	NPC30677
0.7339	Intermediate Similarity	NPC180557
0.7339	Intermediate Similarity	NPC469379
0.7339	Intermediate Similarity	NPC469329
0.7339	Intermediate Similarity	NPC37787
0.7339	Intermediate Similarity	NPC473415
0.7339	Intermediate Similarity	NPC86346
0.7339	Intermediate Similarity	NPC75856
0.7333	Intermediate Similarity	NPC122033
0.7333	Intermediate Similarity	NPC470854
0.7333	Intermediate Similarity	NPC36754
0.7333	Intermediate Similarity	NPC470775
0.7333	Intermediate Similarity	NPC176513
0.7333	Intermediate Similarity	NPC474654
0.7333	Intermediate Similarity	NPC287343
0.7333	Intermediate Similarity	NPC97908
0.7328	Intermediate Similarity	NPC475588
0.7328	Intermediate Similarity	NPC143706
0.7328	Intermediate Similarity	NPC217041
0.7328	Intermediate Similarity	NPC472534
0.7323	Intermediate Similarity	NPC469351
0.7321	Intermediate Similarity	NPC73385
0.7321	Intermediate Similarity	NPC67296
0.7317	Intermediate Similarity	NPC192309
0.7317	Intermediate Similarity	NPC19464
0.7315	Intermediate Similarity	NPC475788
0.7311	Intermediate Similarity	NPC45218
0.7311	Intermediate Similarity	NPC474906
0.7311	Intermediate Similarity	NPC323821
0.7311	Intermediate Similarity	NPC469877
0.7311	Intermediate Similarity	NPC116024
0.7311	Intermediate Similarity	NPC243354
0.7311	Intermediate Similarity	NPC268238
0.7311	Intermediate Similarity	NPC470919
0.7311	Intermediate Similarity	NPC18547
0.7311	Intermediate Similarity	NPC143268
0.7308	Intermediate Similarity	NPC477236

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 NPC475463 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	2502
0.2-0.3	3910
0.3-0.4	1664
0.4-0.5	449
0.5-0.6	282
0.6-0.7	76
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
0.7333	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7078	Approved
0.72	Intermediate Similarity	NPD7492	Approved
0.7154	Intermediate Similarity	NPD6054	Approved
0.7154	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD6616	Approved
0.7109	Intermediate Similarity	NPD7319	Approved
0.7087	Intermediate Similarity	NPD8293	Discontinued
0.704	Intermediate Similarity	NPD6370	Approved
0.7034	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7736	Approved
0.7016	Intermediate Similarity	NPD6319	Approved
0.7008	Intermediate Similarity	NPD7507	Approved
0.6983	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6371	Approved
0.696	Remote Similarity	NPD6016	Approved
0.696	Remote Similarity	NPD6015	Approved
0.6905	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1700	Approved
0.685	Remote Similarity	NPD8328	Phase 3
0.6807	Remote Similarity	NPD6686	Approved
0.6807	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6008	Approved
0.6757	Remote Similarity	NPD7983	Approved
0.675	Remote Similarity	NPD6372	Approved
0.675	Remote Similarity	NPD6373	Approved
0.6723	Remote Similarity	NPD6412	Phase 2
0.6721	Remote Similarity	NPD8297	Approved
0.6721	Remote Similarity	NPD6882	Approved
0.6696	Remote Similarity	NPD4225	Approved
0.6693	Remote Similarity	NPD8515	Approved
0.6693	Remote Similarity	NPD8516	Approved
0.6693	Remote Similarity	NPD8517	Approved
0.6693	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6641	Remote Similarity	NPD6033	Approved
0.664	Remote Similarity	NPD6009	Approved
0.6639	Remote Similarity	NPD6650	Approved
0.6639	Remote Similarity	NPD6402	Approved
0.6639	Remote Similarity	NPD7128	Approved
0.6639	Remote Similarity	NPD5739	Approved
0.6639	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD6675	Approved
0.6637	Remote Similarity	NPD5282	Discontinued
0.6612	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6411	Approved
0.6557	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5779	Approved
0.6549	Remote Similarity	NPD5778	Approved
0.6532	Remote Similarity	NPD8133	Approved
0.6529	Remote Similarity	NPD6881	Approved
0.6529	Remote Similarity	NPD6899	Approved
0.6508	Remote Similarity	NPD7115	Discovery
0.6457	Remote Similarity	NPD7327	Approved
0.6457	Remote Similarity	NPD7328	Approved
0.6452	Remote Similarity	NPD6053	Discontinued
0.6446	Remote Similarity	NPD5697	Approved
0.6446	Remote Similarity	NPD5701	Approved
0.6439	Remote Similarity	NPD8074	Phase 3
0.6434	Remote Similarity	NPD8033	Approved
0.6429	Remote Similarity	NPD1695	Approved
0.6429	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6101	Approved
0.6423	Remote Similarity	NPD7290	Approved
0.6423	Remote Similarity	NPD7102	Approved
0.6423	Remote Similarity	NPD6883	Approved
0.6423	Remote Similarity	NPD4634	Approved
0.6417	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7638	Approved
0.6406	Remote Similarity	NPD7516	Approved
0.6404	Remote Similarity	NPD6399	Phase 3
0.6378	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6698	Approved
0.6372	Remote Similarity	NPD46	Approved
0.6371	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6869	Approved
0.6371	Remote Similarity	NPD6847	Approved
0.6371	Remote Similarity	NPD6617	Approved
0.6371	Remote Similarity	NPD8130	Phase 1
0.6357	Remote Similarity	NPD8377	Approved
0.6357	Remote Similarity	NPD8294	Approved
0.6356	Remote Similarity	NPD7639	Approved
0.6356	Remote Similarity	NPD7640	Approved
0.6341	Remote Similarity	NPD6013	Approved
0.6341	Remote Similarity	NPD6014	Approved
0.6341	Remote Similarity	NPD6012	Approved
0.6336	Remote Similarity	NPD7604	Phase 2
0.6311	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD8269	Approved
0.6308	Remote Similarity	NPD8296	Approved
0.6308	Remote Similarity	NPD8380	Approved
0.6308	Remote Similarity	NPD5983	Phase 2
0.6308	Remote Similarity	NPD8335	Approved
0.6308	Remote Similarity	NPD8379	Approved
0.6308	Remote Similarity	NPD8378	Approved
0.6308	Remote Similarity	NPD8267	Approved
0.6308	Remote Similarity	NPD6921	Approved
0.6308	Remote Similarity	NPD8268	Approved
0.6308	Remote Similarity	NPD8266	Approved
0.6296	Remote Similarity	NPD5369	Approved
0.626	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD7632	Discontinued
0.6241	Remote Similarity	NPD6336	Discontinued
0.624	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6435	Approved
0.6239	Remote Similarity	NPD7839	Suspended
0.6212	Remote Similarity	NPD6067	Discontinued
0.6186	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD4755	Approved
0.6186	Remote Similarity	NPD6084	Phase 2
0.6183	Remote Similarity	NPD7503	Approved
0.6183	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD8034	Phase 2
0.6174	Remote Similarity	NPD8035	Phase 2
0.6174	Remote Similarity	NPD7637	Suspended
0.6161	Remote Similarity	NPD5786	Approved
0.6154	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD8080	Discontinued
0.6106	Remote Similarity	NPD4251	Approved
0.6106	Remote Similarity	NPD4250	Approved
0.6083	Remote Similarity	NPD4696	Approved
0.6083	Remote Similarity	NPD5285	Approved
0.6083	Remote Similarity	NPD5286	Approved
0.6083	Remote Similarity	NPD4700	Approved
0.6078	Remote Similarity	NPD229	Approved
0.6061	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5956	Approved
0.6055	Remote Similarity	NPD5368	Approved
0.605	Remote Similarity	NPD7902	Approved
0.6047	Remote Similarity	NPD6274	Approved
0.6036	Remote Similarity	NPD7154	Phase 3
0.6036	Remote Similarity	NPD5362	Discontinued
0.6033	Remote Similarity	NPD5344	Discontinued
0.6031	Remote Similarity	NPD7100	Approved
0.6031	Remote Similarity	NPD7101	Approved
0.6018	Remote Similarity	NPD4249	Approved
0.6017	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD5328	Approved
0.5984	Remote Similarity	NPD5211	Phase 2
0.5984	Remote Similarity	NPD4633	Approved
0.5984	Remote Similarity	NPD5224	Approved
0.5984	Remote Similarity	NPD5225	Approved
0.5984	Remote Similarity	NPD5226	Approved
0.5971	Remote Similarity	NPD6845	Suspended
0.5968	Remote Similarity	NPD4767	Approved
0.5968	Remote Similarity	NPD4768	Approved
0.5965	Remote Similarity	NPD7524	Approved
0.5954	Remote Similarity	NPD6335	Approved
0.5948	Remote Similarity	NPD5785	Approved
0.5946	Remote Similarity	NPD4270	Approved
0.5946	Remote Similarity	NPD4269	Approved
0.594	Remote Similarity	NPD6909	Approved
0.594	Remote Similarity	NPD6908	Approved
0.5935	Remote Similarity	NPD5175	Approved
0.5935	Remote Similarity	NPD5174	Approved
0.5932	Remote Similarity	NPD7748	Approved
0.5929	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD8342	Approved
0.5926	Remote Similarity	NPD8299	Approved
0.5926	Remote Similarity	NPD8341	Approved
0.5926	Remote Similarity	NPD8340	Approved
0.5915	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6903	Approved
0.5902	Remote Similarity	NPD5223	Approved
0.5897	Remote Similarity	NPD7515	Phase 2
0.5897	Remote Similarity	NPD6079	Approved
0.5893	Remote Similarity	NPD3669	Approved
0.5893	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5141	Approved
0.5882	Remote Similarity	NPD8451	Approved
0.5878	Remote Similarity	NPD6317	Approved
0.5877	Remote Similarity	NPD7146	Approved
0.5877	Remote Similarity	NPD3618	Phase 1
0.5877	Remote Similarity	NPD7334	Approved
0.5877	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6684	Approved
0.5877	Remote Similarity	NPD6409	Approved
0.5877	Remote Similarity	NPD7521	Approved
0.5877	Remote Similarity	NPD5330	Approved
0.5873	Remote Similarity	NPD4730	Approved
0.5873	Remote Similarity	NPD4729	Approved
0.5872	Remote Similarity	NPD4802	Phase 2
0.5872	Remote Similarity	NPD6118	Approved
0.5872	Remote Similarity	NPD6114	Approved
0.5872	Remote Similarity	NPD6115	Approved
0.5872	Remote Similarity	NPD6697	Approved
0.5872	Remote Similarity	NPD4238	Approved
0.5868	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD1779	Approved
0.5856	Remote Similarity	NPD1780	Approved
0.5852	Remote Similarity	NPD7642	Approved
0.5852	Remote Similarity	NPD7122	Discontinued
0.5847	Remote Similarity	NPD4202	Approved
0.5841	Remote Similarity	NPD7338	Clinical (unspecified phase)

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