NPASS Compound

Structure

NPC475653 OpenBabel07101718322D 51 53 0 0 1 0 0 0 0 0999 V2000 6.1602 5.0324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4415 3.5400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2548 -1.8985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7852 5.7385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8632 -1.6531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1387 0.2435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0302 -2.1880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4628 1.5765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5849 -2.0614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4628 -2.1455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0302 1.6190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9331 1.3686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2325 1.6763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8129 0.5988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0776 -1.7769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5849 1.4924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9331 -1.9376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3040 2.6299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7414 -0.3549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4882 1.0138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5084 4.9086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7115 -0.8471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2160 0.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1677 -1.1127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0665 4.2461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0755 1.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3701 4.4937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4647 -1.3598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8566 4.7848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9347 -0.6994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0776 1.2079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4882 -1.5828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4861 3.1686 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7183 4.3699 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.1446 -0.1607 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7963 -0.2845 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8798 -0.7698 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.5690 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1677 0.5437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4147 4.1223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4882 -0.4576 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0079 1.5829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3478 2.7537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7897 3.4162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2829 -0.5757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6939 0.9587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4469 4.5372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2048 4.6610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8678 0.6692 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8798 -1.2706 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 27 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 29 2 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 15 2 0 0 0 0 10 17 2 0 0 0 0 11 16 1 0 0 0 0 12 20 2 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 28 1 0 0 0 0 18 33 1 0 0 0 0 19 37 1 0 0 0 0 20 39 1 0 0 0 0 21 27 1 0 0 0 0 21 34 1 0 0 0 0 22 28 2 0 0 0 0 23 31 1 0 0 0 0 23 35 1 0 0 0 0 24 32 1 0 0 0 0 24 38 1 0 0 0 0 25 29 1 0 0 0 0 25 48 1 0 0 0 0 26 41 1 0 0 0 0 26 42 1 0 0 0 0 29 34 1 0 0 0 0 30 5 1 1 0 0 0 30 35 1 0 0 0 0 30 36 1 0 0 0 0 31 16 1 1 0 0 0 31 49 1 0 0 0 0 32 17 1 1 0 0 0 32 50 1 0 0 0 0 33 40 1 0 0 0 0 33 43 1 6 0 0 0 34 44 1 0 0 0 0 35 45 1 6 0 0 0 36 22 1 1 0 0 0 36 49 1 0 0 0 0 37 41 1 1 0 0 0 37 50 1 0 0 0 0 38 41 1 1 0 0 0 38 51 1 0 0 0 0 39 46 2 0 0 0 0 39 51 1 0 0 0 0 40 47 2 0 0 0 0 40 48 1 0 0 0 0 41 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	712.42
Volume:	756.197
LogP:	4.666
LogD:	3.96
LogS:	-5.056
# Rotatable Bonds:	13
TPSA:	148.82
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.098
Synthetic Accessibility Score:	7.31
Fsp3:	0.634
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.953
MDCK Permeability:	2.225054231530521e-05
Pgp-inhibitor:	0.345
Pgp-substrate:	0.709
Human Intestinal Absorption (HIA):	0.563
20% Bioavailability (F20%):	0.19
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	94.1756362915039%
Volume Distribution (VD):	1.098
Pgp-substrate:	2.660330295562744%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.153
CYP2C19-substrate:	0.201
CYP2C9-inhibitor:	0.441
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	4.319
Half-life (T1/2):	0.652

ADMET: Toxicity

hERG Blockers:	0.347
Human Hepatotoxicity (H-HT):	0.987
Drug-inuced Liver Injury (DILI):	0.354
AMES Toxicity:	0.949
Rat Oral Acute Toxicity:	0.4
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.936
Carcinogencity:	0.579
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.763

Download Data

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

Natural Product: NPC475653

Natural Product ID:	NPC475653
*Common Name:**	Lasonolide C
IUPAC Name:	n.a.
Synonyms:	Lasonolide C
Standard InCHIKey:	LCKSAMKMISEHDA-YUYSQXCNSA-N
Standard InCHI:	InChI=1S/C41H60O10/c1-27(2)21-34(44)29(4)25-48-40(47)33(43)18-13-14-19-37-41(6,26-42)38-24-32(50-37)17-10-7-9-15-28(3)22-36-30(5)35(45)23-31(49-36)16-11-8-12-20-39(46)51-38/h8-15,17,20,22,27,30-38,42-45H,4,7,16,18-19,21,23-26H2,1-3,5-6H3/b11-8+,14-13-,15-9+,17-10+,20-12+,28-22-/t30-,31+,32-,33-,34?,35+,36-,37+,38-,41+/m1/s1
SMILES:	OC[C@@]1(C)[C@H](C/C=CC[C@H](C(=O)OCC(=C)C(CC(C)C)O)O)O[C@H]2C[C@H]1OC(=O)/C=C/C=C/C[C@H]1C[C@@H]([C@H]([C@@H](/C=C(C=CC/C=C/2)/C)O1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510681
PubChem CID:	11251102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO32865	forcepia sp.	Species	Coelosphaeridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332854]

☑ 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	=	130.0	nM	PMID[558632]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	380.0	nM	PMID[558632]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	IC50	=	1120.0	nM	PMID[558632]

☑ 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 NPC475653 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	203
0.1-0.2	990
0.2-0.3	3556
0.3-0.4	6266
0.4-0.5	15314
0.5-0.6	8648
0.6-0.7	6505
0.7-0.8	1156
0.8-0.85	52
0.85-0.9	2
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC120299
0.978	High Similarity	NPC255410
0.9681	High Similarity	NPC473596
0.967	High Similarity	NPC300710
0.8901	High Similarity	NPC199382
0.866	High Similarity	NPC475332
0.8557	High Similarity	NPC173329
0.8557	High Similarity	NPC288350
0.8438	Intermediate Similarity	NPC109406
0.8438	Intermediate Similarity	NPC159092
0.8333	Intermediate Similarity	NPC206679
0.8333	Intermediate Similarity	NPC476084
0.8333	Intermediate Similarity	NPC476075
0.8333	Intermediate Similarity	NPC114172
0.8333	Intermediate Similarity	NPC471324
0.8298	Intermediate Similarity	NPC313658
0.8298	Intermediate Similarity	NPC316138
0.8269	Intermediate Similarity	NPC193765
0.8247	Intermediate Similarity	NPC472195
0.8247	Intermediate Similarity	NPC472196
0.8247	Intermediate Similarity	NPC238090
0.8242	Intermediate Similarity	NPC8538
0.8242	Intermediate Similarity	NPC184208
0.8242	Intermediate Similarity	NPC315731
0.8229	Intermediate Similarity	NPC177668
0.8229	Intermediate Similarity	NPC3952
0.8224	Intermediate Similarity	NPC101965
0.8224	Intermediate Similarity	NPC101400
0.82	Intermediate Similarity	NPC65700
0.82	Intermediate Similarity	NPC161855
0.82	Intermediate Similarity	NPC203627
0.8191	Intermediate Similarity	NPC61527
0.819	Intermediate Similarity	NPC133625
0.8163	Intermediate Similarity	NPC469491
0.8163	Intermediate Similarity	NPC159698
0.8131	Intermediate Similarity	NPC98038
0.8131	Intermediate Similarity	NPC313921
0.8125	Intermediate Similarity	NPC133450
0.8119	Intermediate Similarity	NPC475053
0.8095	Intermediate Similarity	NPC473807
0.8085	Intermediate Similarity	NPC471494
0.8081	Intermediate Similarity	NPC272050
0.8077	Intermediate Similarity	NPC476740
0.8077	Intermediate Similarity	NPC472749
0.8077	Intermediate Similarity	NPC315070
0.8077	Intermediate Similarity	NPC472751
0.8077	Intermediate Similarity	NPC476738
0.8058	Intermediate Similarity	NPC309398
0.8056	Intermediate Similarity	NPC469496
0.8056	Intermediate Similarity	NPC469454
0.8056	Intermediate Similarity	NPC469463
0.8039	Intermediate Similarity	NPC475655
0.8039	Intermediate Similarity	NPC57586
0.8039	Intermediate Similarity	NPC475157
0.8039	Intermediate Similarity	NPC2313
0.8039	Intermediate Similarity	NPC471637
0.8039	Intermediate Similarity	NPC154132
0.802	Intermediate Similarity	NPC261377
0.802	Intermediate Similarity	NPC83895
0.802	Intermediate Similarity	NPC308567
0.802	Intermediate Similarity	NPC187761
0.802	Intermediate Similarity	NPC255592
0.8	Intermediate Similarity	NPC108682
0.8	Intermediate Similarity	NPC473291
0.8	Intermediate Similarity	NPC472263
0.8	Intermediate Similarity	NPC311163
0.8	Intermediate Similarity	NPC469959
0.8	Intermediate Similarity	NPC469957
0.7982	Intermediate Similarity	NPC265290
0.7982	Intermediate Similarity	NPC305044
0.7981	Intermediate Similarity	NPC472748
0.798	Intermediate Similarity	NPC256368
0.7979	Intermediate Similarity	NPC160517
0.7979	Intermediate Similarity	NPC186155
0.7979	Intermediate Similarity	NPC78673
0.7961	Intermediate Similarity	NPC201191
0.7957	Intermediate Similarity	NPC477385
0.7957	Intermediate Similarity	NPC477390
0.7921	Intermediate Similarity	NPC40812
0.7905	Intermediate Similarity	NPC469960
0.7905	Intermediate Similarity	NPC29389
0.7905	Intermediate Similarity	NPC93026
0.7905	Intermediate Similarity	NPC265502
0.7895	Intermediate Similarity	NPC11804
0.7885	Intermediate Similarity	NPC472755
0.7885	Intermediate Similarity	NPC474581
0.7885	Intermediate Similarity	NPC472747
0.7885	Intermediate Similarity	NPC197736
0.7885	Intermediate Similarity	NPC473816
0.7885	Intermediate Similarity	NPC472750
0.7885	Intermediate Similarity	NPC475367
0.7879	Intermediate Similarity	NPC478036
0.7879	Intermediate Similarity	NPC478037
0.7879	Intermediate Similarity	NPC476049
0.7872	Intermediate Similarity	NPC44261
0.787	Intermediate Similarity	NPC304180
0.787	Intermediate Similarity	NPC179798
0.7864	Intermediate Similarity	NPC197447
0.7864	Intermediate Similarity	NPC169365
0.7857	Intermediate Similarity	NPC313670
0.7826	Intermediate Similarity	NPC139712
0.7822	Intermediate Similarity	NPC472995
0.7812	Intermediate Similarity	NPC186332
0.7812	Intermediate Similarity	NPC47220
0.781	Intermediate Similarity	NPC475676
0.781	Intermediate Similarity	NPC220964
0.7802	Intermediate Similarity	NPC477203
0.78	Intermediate Similarity	NPC294293
0.7798	Intermediate Similarity	NPC317460
0.7798	Intermediate Similarity	NPC328074
0.7798	Intermediate Similarity	NPC321272
0.7798	Intermediate Similarity	NPC470025
0.7788	Intermediate Similarity	NPC472754
0.7778	Intermediate Similarity	NPC181298
0.7778	Intermediate Similarity	NPC5103
0.7768	Intermediate Similarity	NPC475130
0.7768	Intermediate Similarity	NPC474286
0.7745	Intermediate Similarity	NPC205143
0.7742	Intermediate Similarity	NPC470147
0.7742	Intermediate Similarity	NPC133226
0.7736	Intermediate Similarity	NPC82251
0.7732	Intermediate Similarity	NPC118077
0.7732	Intermediate Similarity	NPC475186
0.7727	Intermediate Similarity	NPC56448
0.7727	Intermediate Similarity	NPC470027
0.7723	Intermediate Similarity	NPC36954
0.7719	Intermediate Similarity	NPC470829
0.7719	Intermediate Similarity	NPC473228
0.7714	Intermediate Similarity	NPC4620
0.7714	Intermediate Similarity	NPC23584
0.7708	Intermediate Similarity	NPC242233
0.7706	Intermediate Similarity	NPC17791
0.7706	Intermediate Similarity	NPC297945
0.7706	Intermediate Similarity	NPC126897
0.7692	Intermediate Similarity	NPC477202
0.7692	Intermediate Similarity	NPC198992
0.7692	Intermediate Similarity	NPC472753
0.7692	Intermediate Similarity	NPC469880
0.7685	Intermediate Similarity	NPC15218
0.7685	Intermediate Similarity	NPC475274
0.7684	Intermediate Similarity	NPC161045
0.7679	Intermediate Similarity	NPC23046
0.7677	Intermediate Similarity	NPC473448
0.7677	Intermediate Similarity	NPC474761
0.7677	Intermediate Similarity	NPC476004
0.766	Intermediate Similarity	NPC112868
0.7647	Intermediate Similarity	NPC57664
0.7647	Intermediate Similarity	NPC473153
0.7642	Intermediate Similarity	NPC472756
0.7636	Intermediate Similarity	NPC241477
0.7636	Intermediate Similarity	NPC317687
0.7634	Intermediate Similarity	NPC470148
0.7634	Intermediate Similarity	NPC470149
0.7634	Intermediate Similarity	NPC180725
0.7629	Intermediate Similarity	NPC477387
0.7629	Intermediate Similarity	NPC208473
0.7629	Intermediate Similarity	NPC477389
0.7629	Intermediate Similarity	NPC164393
0.7624	Intermediate Similarity	NPC472198
0.7624	Intermediate Similarity	NPC71589
0.7619	Intermediate Similarity	NPC11956
0.7615	Intermediate Similarity	NPC316708
0.7611	Intermediate Similarity	NPC13710
0.76	Intermediate Similarity	NPC472199
0.76	Intermediate Similarity	NPC472197
0.7593	Intermediate Similarity	NPC233379
0.7593	Intermediate Similarity	NPC475263
0.7593	Intermediate Similarity	NPC474664
0.7593	Intermediate Similarity	NPC392
0.7593	Intermediate Similarity	NPC264819
0.7593	Intermediate Similarity	NPC14862
0.7593	Intermediate Similarity	NPC327286
0.7593	Intermediate Similarity	NPC177524
0.7593	Intermediate Similarity	NPC169888
0.7593	Intermediate Similarity	NPC219900
0.7593	Intermediate Similarity	NPC55972
0.7593	Intermediate Similarity	NPC470024
0.7576	Intermediate Similarity	NPC212598
0.757	Intermediate Similarity	NPC239961
0.757	Intermediate Similarity	NPC477125
0.7568	Intermediate Similarity	NPC473159
0.7568	Intermediate Similarity	NPC264153
0.7551	Intermediate Similarity	NPC86005
0.7551	Intermediate Similarity	NPC477959
0.7551	Intermediate Similarity	NPC477388
0.7551	Intermediate Similarity	NPC45409
0.7551	Intermediate Similarity	NPC477386
0.7545	Intermediate Similarity	NPC71680
0.7545	Intermediate Similarity	NPC317107
0.7545	Intermediate Similarity	NPC470026
0.7527	Intermediate Similarity	NPC248775
0.7526	Intermediate Similarity	NPC137033
0.7525	Intermediate Similarity	NPC320552
0.7525	Intermediate Similarity	NPC475912
0.7525	Intermediate Similarity	NPC205034
0.7525	Intermediate Similarity	NPC152778
0.7525	Intermediate Similarity	NPC162615
0.7525	Intermediate Similarity	NPC469692
0.7525	Intermediate Similarity	NPC469645
0.7525	Intermediate Similarity	NPC476300

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 NPC475653 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1160
0.2-0.3	3372
0.3-0.4	2716
0.4-0.5	1192
0.5-0.6	345
0.6-0.7	175
0.7-0.8	12
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8617	High Similarity	NPD7838	Discovery
0.8571	High Similarity	NPD8029	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD6698	Approved
0.8041	Intermediate Similarity	NPD46	Approved
0.7778	Intermediate Similarity	NPD7983	Approved
0.7706	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6686	Approved
0.75	Intermediate Similarity	NPD4225	Approved
0.7358	Intermediate Similarity	NPD5344	Discontinued
0.7339	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6648	Approved
0.7255	Intermediate Similarity	NPD7637	Suspended
0.7184	Intermediate Similarity	NPD5779	Approved
0.7184	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD6371	Approved
0.7143	Intermediate Similarity	NPD7839	Suspended
0.7103	Intermediate Similarity	NPD7639	Approved
0.7103	Intermediate Similarity	NPD7640	Approved
0.7009	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD7829	Approved
0.7	Intermediate Similarity	NPD7830	Approved
0.6975	Remote Similarity	NPD8513	Phase 3
0.6975	Remote Similarity	NPD8517	Approved
0.6975	Remote Similarity	NPD8515	Approved
0.6975	Remote Similarity	NPD8516	Approved
0.6975	Remote Similarity	NPD7503	Approved
0.6923	Remote Similarity	NPD6411	Approved
0.69	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7524	Approved
0.6833	Remote Similarity	NPD8033	Approved
0.6827	Remote Similarity	NPD5785	Approved
0.678	Remote Similarity	NPD7115	Discovery
0.675	Remote Similarity	NPD8294	Approved
0.675	Remote Similarity	NPD8377	Approved
0.6746	Remote Similarity	NPD7260	Phase 2
0.6731	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6101	Approved
0.6694	Remote Similarity	NPD8074	Phase 3
0.6694	Remote Similarity	NPD8379	Approved
0.6694	Remote Similarity	NPD8380	Approved
0.6694	Remote Similarity	NPD8296	Approved
0.6694	Remote Similarity	NPD8335	Approved
0.6694	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8039	Approved
0.6636	Remote Similarity	NPD5282	Discontinued
0.6634	Remote Similarity	NPD6695	Phase 3
0.6634	Remote Similarity	NPD6110	Phase 1
0.6634	Remote Similarity	NPD7154	Phase 3
0.6615	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8273	Phase 1
0.6613	Remote Similarity	NPD8451	Approved
0.6585	Remote Similarity	NPD8328	Phase 3
0.6583	Remote Similarity	NPD7327	Approved
0.6583	Remote Similarity	NPD7328	Approved
0.6581	Remote Similarity	NPD8297	Approved
0.6574	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.656	Remote Similarity	NPD8448	Approved
0.6538	Remote Similarity	NPD7750	Discontinued
0.6538	Remote Similarity	NPD4251	Approved
0.6538	Remote Similarity	NPD4250	Approved
0.6535	Remote Similarity	NPD5209	Approved
0.6535	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD8341	Approved
0.6532	Remote Similarity	NPD8342	Approved
0.6532	Remote Similarity	NPD8340	Approved
0.6532	Remote Similarity	NPD8299	Approved
0.6529	Remote Similarity	NPD7516	Approved
0.6522	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7632	Discontinued
0.65	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7505	Discontinued
0.648	Remote Similarity	NPD7507	Approved
0.6475	Remote Similarity	NPD6319	Approved
0.6466	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7641	Discontinued
0.6442	Remote Similarity	NPD4249	Approved
0.6435	Remote Similarity	NPD6412	Phase 2
0.6423	Remote Similarity	NPD8444	Approved
0.6406	Remote Similarity	NPD8391	Approved
0.6406	Remote Similarity	NPD8390	Approved
0.6406	Remote Similarity	NPD8392	Approved
0.64	Remote Similarity	NPD6929	Approved
0.6387	Remote Similarity	NPD8133	Approved
0.6387	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4756	Discovery
0.6364	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5363	Approved
0.6346	Remote Similarity	NPD1694	Approved
0.6346	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4822	Approved
0.6337	Remote Similarity	NPD7514	Phase 3
0.6337	Remote Similarity	NPD7332	Phase 2
0.6337	Remote Similarity	NPD4820	Approved
0.6337	Remote Similarity	NPD6931	Approved
0.6337	Remote Similarity	NPD6930	Phase 2
0.6337	Remote Similarity	NPD4821	Approved
0.6337	Remote Similarity	NPD4819	Approved
0.6328	Remote Similarity	NPD7319	Approved
0.6327	Remote Similarity	NPD8264	Approved
0.6311	Remote Similarity	NPD5362	Discontinued
0.6308	Remote Similarity	NPD6845	Suspended
0.6306	Remote Similarity	NPD6083	Phase 2
0.6306	Remote Similarity	NPD6084	Phase 2
0.6303	Remote Similarity	NPD6053	Discontinued
0.63	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4268	Approved
0.63	Remote Similarity	NPD4271	Approved
0.63	Remote Similarity	NPD7145	Approved
0.6281	Remote Similarity	NPD2629	Approved
0.6275	Remote Similarity	NPD6902	Approved
0.6271	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.623	Remote Similarity	NPD7500	Approved
0.6218	Remote Similarity	NPD6649	Approved
0.6218	Remote Similarity	NPD6650	Approved
0.6218	Remote Similarity	NPD8130	Phase 1
0.6207	Remote Similarity	NPD6640	Phase 3
0.62	Remote Similarity	NPD5776	Phase 2
0.62	Remote Similarity	NPD6925	Approved
0.619	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7642	Approved
0.6186	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7748	Approved
0.6167	Remote Similarity	NPD6882	Approved
0.6165	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5332	Approved
0.6154	Remote Similarity	NPD5697	Approved
0.6154	Remote Similarity	NPD5331	Approved
0.6147	Remote Similarity	NPD7087	Discontinued
0.6142	Remote Similarity	NPD7492	Approved
0.6134	Remote Similarity	NPD7102	Approved
0.6134	Remote Similarity	NPD7290	Approved
0.6134	Remote Similarity	NPD6883	Approved
0.6134	Remote Similarity	NPD6421	Discontinued
0.6132	Remote Similarity	NPD5279	Phase 3
0.6129	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5695	Phase 3
0.6124	Remote Similarity	NPD7736	Approved
0.6117	Remote Similarity	NPD4790	Discontinued
0.6111	Remote Similarity	NPD8080	Discontinued
0.6111	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6933	Approved
0.6098	Remote Similarity	NPD6009	Approved
0.6094	Remote Similarity	NPD6616	Approved
0.609	Remote Similarity	NPD8415	Approved
0.6083	Remote Similarity	NPD6869	Approved
0.6083	Remote Similarity	NPD6847	Approved
0.6083	Remote Similarity	NPD6617	Approved
0.608	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6054	Approved
0.6068	Remote Similarity	NPD5739	Approved
0.6068	Remote Similarity	NPD7128	Approved
0.6068	Remote Similarity	NPD6675	Approved
0.6068	Remote Similarity	NPD6402	Approved
0.6064	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD7604	Phase 2
0.6058	Remote Similarity	NPD4269	Approved
0.6058	Remote Similarity	NPD4270	Approved
0.605	Remote Similarity	NPD6373	Approved
0.605	Remote Similarity	NPD6012	Approved
0.605	Remote Similarity	NPD6014	Approved
0.605	Remote Similarity	NPD6372	Approved
0.605	Remote Similarity	NPD6013	Approved
0.6047	Remote Similarity	NPD7078	Approved
0.604	Remote Similarity	NPD6932	Approved
0.6038	Remote Similarity	NPD1696	Phase 3
0.6038	Remote Similarity	NPD6893	Approved
0.6034	Remote Similarity	NPD6647	Phase 2
0.6032	Remote Similarity	NPD6921	Approved
0.6032	Remote Similarity	NPD5983	Phase 2
0.6019	Remote Similarity	NPD4695	Discontinued
0.6019	Remote Similarity	NPD5737	Approved
0.6019	Remote Similarity	NPD6672	Approved
0.6018	Remote Similarity	NPD7902	Approved
0.6017	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7515	Phase 2
0.5984	Remote Similarity	NPD6370	Approved
0.5981	Remote Similarity	NPD5786	Approved
0.598	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6336	Discontinued
0.5968	Remote Similarity	NPD4198	Discontinued
0.5966	Remote Similarity	NPD7320	Approved
0.5966	Remote Similarity	NPD6011	Approved
0.5965	Remote Similarity	NPD5696	Approved
0.5963	Remote Similarity	NPD1695	Approved
0.5962	Remote Similarity	NPD6898	Phase 1
0.596	Remote Similarity	NPD4732	Discontinued
0.5957	Remote Similarity	NPD3197	Phase 1
0.5948	Remote Similarity	NPD5211	Phase 2
0.5946	Remote Similarity	NPD6399	Phase 3
0.5923	Remote Similarity	NPD8293	Discontinued
0.5914	Remote Similarity	NPD4192	Approved
0.5914	Remote Similarity	NPD4194	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