NPASS Compound

Structure

CID289670 OpenBabel06191716092D 39 43 0 0 1 0 0 0 0 0999 V2000 3.1429 -6.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5308 -5.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9356 1.4668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0871 -0.0015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4372 -3.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8485 2.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7245 1.9751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5458 -2.4799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5449 0.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7472 -4.5939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7900 -4.7977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0493 -3.6632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8479 1.4696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6965 0.9801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2411 -1.4675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2408 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6973 -1.9581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8488 -1.4685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2398 1.4675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8482 0.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4879 -5.7284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0875 0.9776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3943 -2.9361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3940 -1.9576 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6967 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3916 0.9784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6955 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8476 -0.4900 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6958 0.9791 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8482 1.4691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5455 -1.4680 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5452 -0.4891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8485 -0.4895 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3912 -0.0007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5650 -0.5026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8473 -1.4941 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 1.4683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 6 31 1 0 0 0 0 7 31 1 0 0 0 0 8 32 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 21 2 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 33 1 0 0 0 0 17 18 1 0 0 0 0 17 32 1 0 0 0 0 18 34 1 0 0 0 0 19 22 1 0 0 0 0 19 27 1 0 0 0 0 20 34 1 0 0 0 0 23 5 1 1 0 0 0 23 24 1 0 0 0 0 24 32 1 6 0 0 0 25 31 1 0 0 0 0 25 35 1 6 0 0 0 26 33 1 1 0 0 0 26 34 1 0 0 0 0 27 36 2 0 0 0 0 27 39 1 0 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 28 37 1 1 0 0 0 29 35 1 1 0 0 0 29 38 1 0 0 0 0 30 31 1 0 0 0 0 30 39 1 6 0 0 0 32 33 1 6 0 0 0 33 9 1 1 0 0 0 34 35 1 1 0 0 0 35 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.43
Volume:	601.022
LogP:	8.554
LogD:	6.227
LogS:	-7.262
# Rotatable Bonds:	8
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	5.937
Fsp3:	0.914
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.043
MDCK Permeability:	1.6823150872369297e-05
Pgp-inhibitor:	0.944
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	91.91940307617188%
Volume Distribution (VD):	1.167
Pgp-substrate:	1.7674392461776733%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.179
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	10.703
Half-life (T1/2):	0.049

ADMET: Toxicity

hERG Blockers:	0.875
Human Hepatotoxicity (H-HT):	0.484
Drug-inuced Liver Injury (DILI):	0.349
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.917
Carcinogencity:	0.113
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC289670

Natural Product ID:	NPC289670
*Common Name:**	YWDGWURPVXINEI-DYQOHTMLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YWDGWURPVXINEI-DYQOHTMLSA-N
Standard InCHI:	InChI=1S/C35H58O4/c1-21(2)11-10-12-23(5)24-15-16-33(9)26-14-13-25-31(6,7)30(39-27(36)19-22(3)4)28(37)29(38)35(25)20-34(26,35)18-17-32(24,33)8/h11,22-26,28-30,37-38H,10,12-20H2,1-9H3/t23-,24-,25+,26+,28-,29+,30+,32-,33+,34+,35-/m1/s1
SMILES:	CC(CC(=O)O[C@H]1[C@H](O)[C@H](O)[C@]23[C@H](C1(C)C)CC[C@@H]1[C@@]3(C2)CC[C@]2([C@@]1(C)CC[C@@H]2[C@@H](CCC=C(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255650
PubChem CID:	24770662
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	roots	northern Saudi desert	n.a.	PMID[10924184]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18177010]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9883	Allium giganteum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6022	Cytisus supinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8985	Gazania rigens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24891	Elmerina caryae	Species	Aporpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5284	Ramalina hierrensis	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1586	Gorgonocephalus chilensis	Species	Gorgonocephalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5886	Fossombronia alaskana	Species	Fossombroniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8810	Pinus austriaca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29336	Corynandra chelidonii	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10085	Aspergillus varians	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9036	Dipteryx lacunifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2328	Lagochilus setulosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4463	Cytisus canariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9639	Prunus puddum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25831	Siphonoglossa sessilis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3693	Calpurnia aurea	Species	Fabaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	28400.0	nM	PMID[542024]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[542024]

☑ 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 NPC289670 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	206
0.1-0.2	1361
0.2-0.3	4934
0.3-0.4	12227
0.4-0.5	9884
0.5-0.6	5476
0.6-0.7	5232
0.7-0.8	3201
0.8-0.85	160
0.85-0.9	13
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9785	High Similarity	NPC102426
0.9785	High Similarity	NPC300179
0.8969	High Similarity	NPC119036
0.8788	High Similarity	NPC155974
0.8763	High Similarity	NPC471903
0.8737	High Similarity	NPC219516
0.8687	High Similarity	NPC208358
0.8673	High Similarity	NPC475032
0.8673	High Similarity	NPC475033
0.866	High Similarity	NPC279974
0.8614	High Similarity	NPC474124
0.8602	High Similarity	NPC269058
0.8602	High Similarity	NPC71520
0.86	High Similarity	NPC476132
0.86	High Similarity	NPC475617
0.8586	High Similarity	NPC477876
0.8586	High Similarity	NPC470067
0.8586	High Similarity	NPC470068
0.8586	High Similarity	NPC470066
0.8586	High Similarity	NPC477875
0.8571	High Similarity	NPC276103
0.8571	High Similarity	NPC54248
0.8571	High Similarity	NPC327788
0.8515	High Similarity	NPC475344
0.8515	High Similarity	NPC476471
0.85	High Similarity	NPC167974
0.85	High Similarity	NPC476195
0.85	High Similarity	NPC94906
0.85	High Similarity	NPC254567
0.85	High Similarity	NPC474571
0.8462	Intermediate Similarity	NPC88701
0.8462	Intermediate Similarity	NPC472218
0.8462	Intermediate Similarity	NPC472217
0.8462	Intermediate Similarity	NPC472219
0.8447	Intermediate Similarity	NPC473199
0.8447	Intermediate Similarity	NPC477877
0.8438	Intermediate Similarity	NPC10274
0.8431	Intermediate Similarity	NPC222153
0.8431	Intermediate Similarity	NPC473523
0.8416	Intermediate Similarity	NPC470054
0.8416	Intermediate Similarity	NPC96784
0.8416	Intermediate Similarity	NPC235920
0.84	Intermediate Similarity	NPC472028
0.8396	Intermediate Similarity	NPC263827
0.8396	Intermediate Similarity	NPC250481
0.8396	Intermediate Similarity	NPC285410
0.8387	Intermediate Similarity	NPC299963
0.8384	Intermediate Similarity	NPC253115
0.8384	Intermediate Similarity	NPC169270
0.8384	Intermediate Similarity	NPC292718
0.8384	Intermediate Similarity	NPC88009
0.8384	Intermediate Similarity	NPC306797
0.8384	Intermediate Similarity	NPC111834
0.8384	Intermediate Similarity	NPC304899
0.8381	Intermediate Similarity	NPC472216
0.8381	Intermediate Similarity	NPC154085
0.8381	Intermediate Similarity	NPC51925
0.8381	Intermediate Similarity	NPC5475
0.8381	Intermediate Similarity	NPC173905
0.8381	Intermediate Similarity	NPC284828
0.8381	Intermediate Similarity	NPC296761
0.8381	Intermediate Similarity	NPC125361
0.8381	Intermediate Similarity	NPC43976
0.8365	Intermediate Similarity	NPC234160
0.8351	Intermediate Similarity	NPC189520
0.835	Intermediate Similarity	NPC31430
0.835	Intermediate Similarity	NPC85593
0.835	Intermediate Similarity	NPC473543
0.835	Intermediate Similarity	NPC471293
0.8333	Intermediate Similarity	NPC124544
0.8333	Intermediate Similarity	NPC271980
0.8333	Intermediate Similarity	NPC470053
0.8333	Intermediate Similarity	NPC193934
0.8317	Intermediate Similarity	NPC473510
0.8317	Intermediate Similarity	NPC230546
0.8302	Intermediate Similarity	NPC472215
0.8302	Intermediate Similarity	NPC101450
0.8302	Intermediate Similarity	NPC472214
0.83	Intermediate Similarity	NPC474994
0.83	Intermediate Similarity	NPC210337
0.83	Intermediate Similarity	NPC476878
0.83	Intermediate Similarity	NPC476040
0.83	Intermediate Similarity	NPC476879
0.83	Intermediate Similarity	NPC274793
0.83	Intermediate Similarity	NPC476021
0.8286	Intermediate Similarity	NPC258323
0.8286	Intermediate Similarity	NPC472988
0.8286	Intermediate Similarity	NPC38217
0.8283	Intermediate Similarity	NPC241047
0.828	Intermediate Similarity	NPC139206
0.828	Intermediate Similarity	NPC113978
0.8273	Intermediate Similarity	NPC239293
0.8269	Intermediate Similarity	NPC472655
0.8252	Intermediate Similarity	NPC475334
0.8252	Intermediate Similarity	NPC473694
0.8252	Intermediate Similarity	NPC218513
0.8252	Intermediate Similarity	NPC312900
0.8252	Intermediate Similarity	NPC475623
0.8252	Intermediate Similarity	NPC55954
0.8247	Intermediate Similarity	NPC471896
0.8235	Intermediate Similarity	NPC477053
0.8235	Intermediate Similarity	NPC75941
0.8235	Intermediate Similarity	NPC477051
0.8235	Intermediate Similarity	NPC477052
0.8224	Intermediate Similarity	NPC65167
0.8224	Intermediate Similarity	NPC470076
0.8218	Intermediate Similarity	NPC247233
0.8218	Intermediate Similarity	NPC234287
0.8218	Intermediate Similarity	NPC280825
0.8211	Intermediate Similarity	NPC474970
0.8208	Intermediate Similarity	NPC310546
0.8208	Intermediate Similarity	NPC218853
0.82	Intermediate Similarity	NPC230151
0.82	Intermediate Similarity	NPC475178
0.819	Intermediate Similarity	NPC59530
0.8182	Intermediate Similarity	NPC474922
0.8182	Intermediate Similarity	NPC277399
0.8173	Intermediate Similarity	NPC473577
0.8173	Intermediate Similarity	NPC288502
0.8173	Intermediate Similarity	NPC470043
0.8173	Intermediate Similarity	NPC470059
0.8173	Intermediate Similarity	NPC475331
0.8173	Intermediate Similarity	NPC475335
0.8173	Intermediate Similarity	NPC470057
0.8173	Intermediate Similarity	NPC181104
0.8173	Intermediate Similarity	NPC121518
0.8173	Intermediate Similarity	NPC470060
0.8173	Intermediate Similarity	NPC475585
0.8173	Intermediate Similarity	NPC301787
0.8173	Intermediate Similarity	NPC474550
0.8173	Intermediate Similarity	NPC201144
0.8173	Intermediate Similarity	NPC470061
0.8173	Intermediate Similarity	NPC470064
0.8173	Intermediate Similarity	NPC80809
0.8173	Intermediate Similarity	NPC470058
0.8173	Intermediate Similarity	NPC470062
0.8173	Intermediate Similarity	NPC103298
0.8172	Intermediate Similarity	NPC472504
0.8163	Intermediate Similarity	NPC275671
0.8163	Intermediate Similarity	NPC210268
0.8155	Intermediate Similarity	NPC471119
0.8155	Intermediate Similarity	NPC296879
0.8155	Intermediate Similarity	NPC477054
0.8148	Intermediate Similarity	NPC470063
0.8148	Intermediate Similarity	NPC280782
0.8144	Intermediate Similarity	NPC475921
0.8144	Intermediate Similarity	NPC474704
0.8137	Intermediate Similarity	NPC317019
0.8137	Intermediate Similarity	NPC7341
0.8137	Intermediate Similarity	NPC180733
0.8137	Intermediate Similarity	NPC37047
0.8137	Intermediate Similarity	NPC251680
0.8137	Intermediate Similarity	NPC473200
0.8137	Intermediate Similarity	NPC41971
0.8131	Intermediate Similarity	NPC129340
0.8113	Intermediate Similarity	NPC163216
0.8113	Intermediate Similarity	NPC295389
0.81	Intermediate Similarity	NPC469329
0.81	Intermediate Similarity	NPC30677
0.81	Intermediate Similarity	NPC263135
0.81	Intermediate Similarity	NPC180557
0.81	Intermediate Similarity	NPC37787
0.81	Intermediate Similarity	NPC288906
0.81	Intermediate Similarity	NPC473415
0.81	Intermediate Similarity	NPC474727
0.8095	Intermediate Similarity	NPC186668
0.8095	Intermediate Similarity	NPC470055
0.8095	Intermediate Similarity	NPC165405
0.8095	Intermediate Similarity	NPC60315
0.8095	Intermediate Similarity	NPC278628
0.8095	Intermediate Similarity	NPC222833
0.8095	Intermediate Similarity	NPC470056
0.8095	Intermediate Similarity	NPC231530
0.8095	Intermediate Similarity	NPC475290
0.8091	Intermediate Similarity	NPC244127
0.8081	Intermediate Similarity	NPC476304
0.8081	Intermediate Similarity	NPC477855
0.8081	Intermediate Similarity	NPC291373
0.8077	Intermediate Similarity	NPC10232
0.8077	Intermediate Similarity	NPC16573
0.8077	Intermediate Similarity	NPC187302
0.8077	Intermediate Similarity	NPC189588
0.8077	Intermediate Similarity	NPC196471
0.8077	Intermediate Similarity	NPC97487
0.8073	Intermediate Similarity	NPC144068
0.8061	Intermediate Similarity	NPC473269
0.8061	Intermediate Similarity	NPC111585
0.8061	Intermediate Similarity	NPC123252
0.8061	Intermediate Similarity	NPC219937
0.8061	Intermediate Similarity	NPC175628
0.8061	Intermediate Similarity	NPC194485
0.8061	Intermediate Similarity	NPC53890
0.8061	Intermediate Similarity	NPC148414
0.8058	Intermediate Similarity	NPC472023
0.8058	Intermediate Similarity	NPC49532
0.8058	Intermediate Similarity	NPC476897
0.8058	Intermediate Similarity	NPC309425
0.8058	Intermediate Similarity	NPC129372
0.8058	Intermediate Similarity	NPC88000
0.8058	Intermediate Similarity	NPC4831

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 NPC289670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1602
0.2-0.3	4148
0.3-0.4	2179
0.4-0.5	561
0.5-0.6	221
0.6-0.7	212
0.7-0.8	55
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8218	Intermediate Similarity	NPD7638	Approved
0.8137	Intermediate Similarity	NPD7640	Approved
0.8137	Intermediate Similarity	NPD7639	Approved
0.7719	Intermediate Similarity	NPD7516	Approved
0.7632	Intermediate Similarity	NPD7328	Approved
0.7632	Intermediate Similarity	NPD7327	Approved
0.7624	Intermediate Similarity	NPD8035	Phase 2
0.7624	Intermediate Similarity	NPD8034	Phase 2
0.7586	Intermediate Similarity	NPD8335	Approved
0.7586	Intermediate Similarity	NPD8379	Approved
0.7586	Intermediate Similarity	NPD8378	Approved
0.7586	Intermediate Similarity	NPD8380	Approved
0.7586	Intermediate Similarity	NPD8296	Approved
0.7579	Intermediate Similarity	NPD7525	Registered
0.7576	Intermediate Similarity	NPD7524	Approved
0.7551	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6399	Phase 3
0.7545	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8294	Approved
0.75	Intermediate Similarity	NPD8377	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.7477	Intermediate Similarity	NPD7632	Discontinued
0.7476	Intermediate Similarity	NPD7748	Approved
0.7451	Intermediate Similarity	NPD7637	Suspended
0.7436	Intermediate Similarity	NPD8033	Approved
0.7434	Intermediate Similarity	NPD4632	Approved
0.7431	Intermediate Similarity	NPD6402	Approved
0.7431	Intermediate Similarity	NPD5739	Approved
0.7431	Intermediate Similarity	NPD7128	Approved
0.7431	Intermediate Similarity	NPD6675	Approved
0.7391	Intermediate Similarity	NPD7115	Discovery
0.7387	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6412	Phase 2
0.7358	Intermediate Similarity	NPD4225	Approved
0.735	Intermediate Similarity	NPD6319	Approved
0.7333	Intermediate Similarity	NPD7507	Approved
0.7311	Intermediate Similarity	NPD7604	Phase 2
0.7297	Intermediate Similarity	NPD7320	Approved
0.7297	Intermediate Similarity	NPD6881	Approved
0.7297	Intermediate Similarity	NPD6899	Approved
0.7295	Intermediate Similarity	NPD7319	Approved
0.7282	Intermediate Similarity	NPD7515	Phase 2
0.7281	Intermediate Similarity	NPD8133	Approved
0.7273	Intermediate Similarity	NPD4786	Approved
0.7264	Intermediate Similarity	NPD7902	Approved
0.7264	Intermediate Similarity	NPD6083	Phase 2
0.7264	Intermediate Similarity	NPD6084	Phase 2
0.7257	Intermediate Similarity	NPD8130	Phase 1
0.7255	Intermediate Similarity	NPD5328	Approved
0.7232	Intermediate Similarity	NPD6373	Approved
0.7232	Intermediate Similarity	NPD6372	Approved
0.7213	Intermediate Similarity	NPD7736	Approved
0.7207	Intermediate Similarity	NPD5701	Approved
0.7207	Intermediate Similarity	NPD5697	Approved
0.7188	Intermediate Similarity	NPD6114	Approved
0.7188	Intermediate Similarity	NPD6697	Approved
0.7188	Intermediate Similarity	NPD6118	Approved
0.7188	Intermediate Similarity	NPD6115	Approved
0.7172	Intermediate Similarity	NPD6695	Phase 3
0.7168	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7290	Approved
0.7168	Intermediate Similarity	NPD7102	Approved
0.7168	Intermediate Similarity	NPD6883	Approved
0.7143	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6686	Approved
0.7131	Intermediate Similarity	NPD8293	Discontinued
0.7129	Intermediate Similarity	NPD3618	Phase 1
0.7117	Intermediate Similarity	NPD6008	Approved
0.7115	Intermediate Similarity	NPD6079	Approved
0.7113	Intermediate Similarity	NPD7645	Phase 2
0.7107	Intermediate Similarity	NPD7492	Approved
0.7105	Intermediate Similarity	NPD6869	Approved
0.7105	Intermediate Similarity	NPD6617	Approved
0.7105	Intermediate Similarity	NPD6649	Approved
0.7105	Intermediate Similarity	NPD6847	Approved
0.7105	Intermediate Similarity	NPD6650	Approved
0.71	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6009	Approved
0.708	Intermediate Similarity	NPD6014	Approved
0.708	Intermediate Similarity	NPD6013	Approved
0.708	Intermediate Similarity	NPD6012	Approved
0.7075	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3667	Approved
0.7064	Intermediate Similarity	NPD5344	Discontinued
0.7059	Intermediate Similarity	NPD6059	Approved
0.7059	Intermediate Similarity	NPD7750	Discontinued
0.7059	Intermediate Similarity	NPD6054	Approved
0.7053	Intermediate Similarity	NPD7339	Approved
0.7053	Intermediate Similarity	NPD6942	Approved
0.7049	Intermediate Similarity	NPD6616	Approved
0.7043	Intermediate Similarity	NPD6882	Approved
0.7025	Intermediate Similarity	NPD8328	Phase 3
0.7	Intermediate Similarity	NPD7503	Approved
0.7	Intermediate Similarity	NPD5983	Phase 2
0.6992	Remote Similarity	NPD7078	Approved
0.6991	Remote Similarity	NPD6011	Approved
0.699	Remote Similarity	NPD6672	Approved
0.699	Remote Similarity	NPD5737	Approved
0.699	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7900	Approved
0.6979	Remote Similarity	NPD6117	Approved
0.6961	Remote Similarity	NPD5330	Approved
0.6961	Remote Similarity	NPD7521	Approved
0.6961	Remote Similarity	NPD6684	Approved
0.6961	Remote Similarity	NPD7146	Approved
0.6961	Remote Similarity	NPD7334	Approved
0.6961	Remote Similarity	NPD6409	Approved
0.6957	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4755	Approved
0.6942	Remote Similarity	NPD6370	Approved
0.6939	Remote Similarity	NPD6929	Approved
0.6916	Remote Similarity	NPD5695	Phase 3
0.6911	Remote Similarity	NPD6336	Discontinued
0.6907	Remote Similarity	NPD6116	Phase 1
0.6903	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4202	Approved
0.6881	Remote Similarity	NPD5696	Approved
0.687	Remote Similarity	NPD4634	Approved
0.6869	Remote Similarity	NPD6931	Approved
0.6869	Remote Similarity	NPD6930	Phase 2
0.686	Remote Similarity	NPD6015	Approved
0.686	Remote Similarity	NPD6016	Approved
0.6852	Remote Similarity	NPD5221	Approved
0.6852	Remote Similarity	NPD4697	Phase 3
0.6852	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5222	Approved
0.6827	Remote Similarity	NPD6903	Approved
0.6818	Remote Similarity	NPD5285	Approved
0.6818	Remote Similarity	NPD5286	Approved
0.6818	Remote Similarity	NPD4700	Approved
0.6818	Remote Similarity	NPD4696	Approved
0.6804	Remote Similarity	NPD6933	Approved
0.6804	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5988	Approved
0.68	Remote Similarity	NPD6902	Approved
0.6789	Remote Similarity	NPD5173	Approved
0.6771	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3666	Approved
0.6765	Remote Similarity	NPD3133	Approved
0.6765	Remote Similarity	NPD3665	Phase 1
0.6762	Remote Similarity	NPD4753	Phase 2
0.6762	Remote Similarity	NPD6051	Approved
0.6735	Remote Similarity	NPD6925	Approved
0.6735	Remote Similarity	NPD5776	Phase 2
0.6735	Remote Similarity	NPD6932	Approved
0.6723	Remote Similarity	NPD6274	Approved
0.6723	Remote Similarity	NPD6868	Approved
0.6702	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5225	Approved
0.6696	Remote Similarity	NPD5211	Phase 2
0.6696	Remote Similarity	NPD5224	Approved
0.6696	Remote Similarity	NPD5226	Approved
0.6696	Remote Similarity	NPD4633	Approved
0.6694	Remote Similarity	NPD7100	Approved
0.6694	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6637	Remote Similarity	NPD5174	Approved
0.6637	Remote Similarity	NPD5175	Approved
0.6636	Remote Similarity	NPD6411	Approved
0.6636	Remote Similarity	NPD7087	Discontinued
0.6635	Remote Similarity	NPD6098	Approved
0.6613	Remote Similarity	NPD6067	Discontinued
0.6612	Remote Similarity	NPD6335	Approved
0.6607	Remote Similarity	NPD4159	Approved
0.6607	Remote Similarity	NPD5223	Approved
0.6604	Remote Similarity	NPD6904	Approved
0.6604	Remote Similarity	NPD6673	Approved
0.6604	Remote Similarity	NPD6080	Approved
0.6602	Remote Similarity	NPD3668	Phase 3
0.66	Remote Similarity	NPD6683	Phase 2
0.6598	Remote Similarity	NPD6926	Approved
0.6598	Remote Similarity	NPD6924	Approved
0.6585	Remote Similarity	NPD6908	Approved
0.6585	Remote Similarity	NPD6909	Approved
0.6579	Remote Similarity	NPD5141	Approved
0.6571	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7838	Discovery
0.6542	Remote Similarity	NPD46	Approved
0.6542	Remote Similarity	NPD6698	Approved
0.6538	Remote Similarity	NPD6893	Approved
0.6535	Remote Similarity	NPD7514	Phase 3
0.6535	Remote Similarity	NPD6033	Approved
0.6529	Remote Similarity	NPD6317	Approved
0.6522	Remote Similarity	NPD4767	Approved
0.6522	Remote Similarity	NPD4768	Approved
0.6505	Remote Similarity	NPD4788	Approved
0.6491	Remote Similarity	NPD4754	Approved
0.6476	Remote Similarity	NPD5279	Phase 3
0.6475	Remote Similarity	NPD6314	Approved
0.6475	Remote Similarity	NPD6313	Approved
0.6471	Remote Similarity	NPD6053	Discontinued
0.6455	Remote Similarity	NPD5210	Approved
0.6455	Remote Similarity	NPD4629	Approved
0.6452	Remote Similarity	NPD6921	Approved
0.6449	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6101	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