NPASS Compound

Structure

CID300179 OpenBabel06191716102D 36 40 0 0 1 0 0 0 0 0999 V2000 -3.1380 6.4454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5284 5.9229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4334 3.1350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2331 -1.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -2.4771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7218 -1.9720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5418 2.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5410 -0.5220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7413 4.5867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7857 4.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0430 3.6574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8466 -1.4673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6938 -0.9785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2344 1.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2341 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6946 1.9550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8475 1.4662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8469 -0.4893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4840 5.7195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3890 2.9315 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3863 -0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3887 1.9545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9780 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6941 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6929 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8463 0.4893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6932 -0.9776 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8469 -1.4668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5415 1.4657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5413 0.4883 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8472 0.4888 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 3.3859 0.0007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5610 0.5019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 1.4918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5400 -1.4660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 4 21 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 31 1 0 0 0 0 18 31 1 0 0 0 0 20 3 1 1 0 0 0 20 22 1 0 0 0 0 21 33 2 0 0 0 0 21 36 1 0 0 0 0 22 29 1 6 0 0 0 23 28 1 0 0 0 0 23 32 1 6 0 0 0 24 30 1 1 0 0 0 24 31 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 25 34 1 1 0 0 0 26 32 1 1 0 0 0 26 35 1 0 0 0 0 27 28 1 0 0 0 0 27 36 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 31 32 1 1 0 0 0 32 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.39
Volume:	549.134
LogP:	7.692
LogD:	5.353
LogS:	-6.364
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.326
Synthetic Accessibility Score:	5.881
Fsp3:	0.906
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:	-5.07
MDCK Permeability:	1.1339304364810232e-05
Pgp-inhibitor:	0.96
Pgp-substrate:	0.071
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	93.06407165527344%
Volume Distribution (VD):	1.331
Pgp-substrate:	2.305906057357788%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.149
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.193
CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.701
CYP3A4-substrate:	0.374

ADMET: Excretion

Clearance (CL):	4.425
Half-life (T1/2):	0.08

ADMET: Toxicity

hERG Blockers:	0.79
Human Hepatotoxicity (H-HT):	0.569
Drug-inuced Liver Injury (DILI):	0.442
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.919
Carcinogencity:	0.127
Eye Corrosion:	0.008
Eye Irritation:	0.016
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC300179

Natural Product ID:	NPC300179
*Common Name:**	ZXSOZQFDXGTVED-ALLDTQKISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZXSOZQFDXGTVED-ALLDTQKISA-N
Standard InCHI:	InChI=1S/C32H52O4/c1-19(2)10-9-11-20(3)22-14-15-30(8)24-13-12-23-28(5,6)27(36-21(4)33)25(34)26(35)32(23)18-31(24,32)17-16-29(22,30)7/h10,20,22-27,34-35H,9,11-18H2,1-8H3/t20-,22-,23+,24+,25-,26+,27+,29-,30+,31+,32-/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@H]([C@@H]([C@@H]([C@]54C[C@@]35CC[C@]12C)O)O)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256313
PubChem CID:	24770658
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]
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]
NPO7260	Angelica genuflexa	Species	Apiaceae	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]
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]
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]
NPO24891	Elmerina caryae	Species	Aporpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	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]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9036	Dipteryx lacunifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10085	Aspergillus varians	Species	Aspergillaceae	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]

☑ 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	=	15400.0	nM	PMID[509011]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	20700.0	nM	PMID[509011]

☑ 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 NPC300179 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	204
0.1-0.2	1477
0.2-0.3	5227
0.3-0.4	13202
0.4-0.5	9084
0.5-0.6	5367
0.6-0.7	5161
0.7-0.8	2792
0.8-0.85	161
0.85-0.9	17
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC102426
0.9785	High Similarity	NPC289670
0.8969	High Similarity	NPC155974
0.8947	High Similarity	NPC471903
0.8925	High Similarity	NPC219516
0.8866	High Similarity	NPC208358
0.8854	High Similarity	NPC475033
0.8854	High Similarity	NPC475032
0.8791	High Similarity	NPC71520
0.8791	High Similarity	NPC269058
0.8788	High Similarity	NPC474124
0.8776	High Similarity	NPC475617
0.8763	High Similarity	NPC119036
0.8763	High Similarity	NPC477875
0.8763	High Similarity	NPC470066
0.8763	High Similarity	NPC470067
0.8763	High Similarity	NPC470068
0.8763	High Similarity	NPC477876
0.875	High Similarity	NPC54248
0.875	High Similarity	NPC276103
0.8687	High Similarity	NPC475344
0.8687	High Similarity	NPC476471
0.8673	High Similarity	NPC474571
0.8673	High Similarity	NPC254567
0.8617	High Similarity	NPC10274
0.8614	High Similarity	NPC473199
0.86	High Similarity	NPC473523
0.8586	High Similarity	NPC235920
0.8586	High Similarity	NPC96784
0.8586	High Similarity	NPC470054
0.8571	High Similarity	NPC299963
0.8557	High Similarity	NPC306797
0.8557	High Similarity	NPC169270
0.8557	High Similarity	NPC253115
0.8557	High Similarity	NPC304899
0.8557	High Similarity	NPC111834
0.8557	High Similarity	NPC88009
0.8557	High Similarity	NPC292718
0.8544	High Similarity	NPC43976
0.8544	High Similarity	NPC296761
0.8544	High Similarity	NPC154085
0.8544	High Similarity	NPC125361
0.8544	High Similarity	NPC51925
0.8529	High Similarity	NPC234160
0.8515	High Similarity	NPC85593
0.8515	High Similarity	NPC31430
0.8515	High Similarity	NPC473543
0.85	High Similarity	NPC470053
0.8485	Intermediate Similarity	NPC230546
0.8485	Intermediate Similarity	NPC473510
0.8469	Intermediate Similarity	NPC274793
0.8469	Intermediate Similarity	NPC210337
0.8469	Intermediate Similarity	NPC476040
0.8469	Intermediate Similarity	NPC474994
0.8469	Intermediate Similarity	NPC476021
0.8462	Intermediate Similarity	NPC113978
0.8462	Intermediate Similarity	NPC139206
0.8454	Intermediate Similarity	NPC279974
0.8454	Intermediate Similarity	NPC241047
0.8447	Intermediate Similarity	NPC472988
0.8447	Intermediate Similarity	NPC38217
0.84	Intermediate Similarity	NPC476132
0.8387	Intermediate Similarity	NPC474970
0.8384	Intermediate Similarity	NPC280825
0.8384	Intermediate Similarity	NPC247233
0.8384	Intermediate Similarity	NPC234287
0.8381	Intermediate Similarity	NPC65167
0.8367	Intermediate Similarity	NPC327788
0.8367	Intermediate Similarity	NPC475178
0.8352	Intermediate Similarity	NPC472504
0.8351	Intermediate Similarity	NPC474922
0.8333	Intermediate Similarity	NPC470061
0.8333	Intermediate Similarity	NPC470062
0.8333	Intermediate Similarity	NPC470064
0.8333	Intermediate Similarity	NPC275671
0.8333	Intermediate Similarity	NPC470058
0.8333	Intermediate Similarity	NPC470043
0.8333	Intermediate Similarity	NPC470057
0.8333	Intermediate Similarity	NPC470059
0.8333	Intermediate Similarity	NPC210268
0.8333	Intermediate Similarity	NPC470060
0.83	Intermediate Similarity	NPC167974
0.83	Intermediate Similarity	NPC476195
0.83	Intermediate Similarity	NPC317019
0.83	Intermediate Similarity	NPC473200
0.83	Intermediate Similarity	NPC94906
0.83	Intermediate Similarity	NPC7341
0.8269	Intermediate Similarity	NPC88701
0.8269	Intermediate Similarity	NPC472218
0.8269	Intermediate Similarity	NPC472217
0.8269	Intermediate Similarity	NPC472219
0.8252	Intermediate Similarity	NPC470056
0.8252	Intermediate Similarity	NPC165405
0.8252	Intermediate Similarity	NPC186668
0.8252	Intermediate Similarity	NPC477877
0.8252	Intermediate Similarity	NPC470055
0.8235	Intermediate Similarity	NPC10232
0.8235	Intermediate Similarity	NPC196471
0.8235	Intermediate Similarity	NPC16573
0.8235	Intermediate Similarity	NPC222153
0.8235	Intermediate Similarity	NPC187302
0.8235	Intermediate Similarity	NPC97487
0.8235	Intermediate Similarity	NPC189588
0.8229	Intermediate Similarity	NPC219937
0.8229	Intermediate Similarity	NPC194485
0.8229	Intermediate Similarity	NPC123252
0.8229	Intermediate Similarity	NPC53890
0.8229	Intermediate Similarity	NPC473269
0.8224	Intermediate Similarity	NPC144068
0.8218	Intermediate Similarity	NPC160734
0.8218	Intermediate Similarity	NPC129372
0.8218	Intermediate Similarity	NPC309425
0.8218	Intermediate Similarity	NPC4831
0.8218	Intermediate Similarity	NPC49532
0.8218	Intermediate Similarity	NPC472023
0.8218	Intermediate Similarity	NPC88000
0.8218	Intermediate Similarity	NPC47566
0.8211	Intermediate Similarity	NPC473436
0.8208	Intermediate Similarity	NPC250481
0.8208	Intermediate Similarity	NPC114188
0.8208	Intermediate Similarity	NPC285410
0.8208	Intermediate Similarity	NPC470076
0.8208	Intermediate Similarity	NPC263827
0.82	Intermediate Similarity	NPC472028
0.8191	Intermediate Similarity	NPC94462
0.8191	Intermediate Similarity	NPC125399
0.819	Intermediate Similarity	NPC284828
0.819	Intermediate Similarity	NPC173905
0.819	Intermediate Similarity	NPC472216
0.819	Intermediate Similarity	NPC5475
0.8163	Intermediate Similarity	NPC215700
0.8163	Intermediate Similarity	NPC211238
0.8155	Intermediate Similarity	NPC273879
0.8155	Intermediate Similarity	NPC165033
0.8155	Intermediate Similarity	NPC471293
0.8144	Intermediate Similarity	NPC130840
0.8144	Intermediate Similarity	NPC234335
0.8144	Intermediate Similarity	NPC189520
0.8137	Intermediate Similarity	NPC154452
0.8137	Intermediate Similarity	NPC271980
0.8137	Intermediate Similarity	NPC136816
0.8137	Intermediate Similarity	NPC124544
0.8137	Intermediate Similarity	NPC159036
0.8137	Intermediate Similarity	NPC288694
0.8137	Intermediate Similarity	NPC312553
0.8137	Intermediate Similarity	NPC193934
0.8125	Intermediate Similarity	NPC109744
0.8113	Intermediate Similarity	NPC472214
0.8113	Intermediate Similarity	NPC472215
0.8113	Intermediate Similarity	NPC101450
0.8105	Intermediate Similarity	NPC474657
0.8105	Intermediate Similarity	NPC186145
0.81	Intermediate Similarity	NPC278939
0.81	Intermediate Similarity	NPC476878
0.81	Intermediate Similarity	NPC51499
0.81	Intermediate Similarity	NPC476879
0.81	Intermediate Similarity	NPC316604
0.81	Intermediate Similarity	NPC473555
0.81	Intermediate Similarity	NPC471770
0.8095	Intermediate Similarity	NPC7213
0.8095	Intermediate Similarity	NPC258323
0.8091	Intermediate Similarity	NPC239293
0.8077	Intermediate Similarity	NPC472655
0.8065	Intermediate Similarity	NPC473742
0.8065	Intermediate Similarity	NPC85095
0.8065	Intermediate Similarity	NPC211135
0.8065	Intermediate Similarity	NPC207013
0.8065	Intermediate Similarity	NPC5280
0.8065	Intermediate Similarity	NPC216420
0.8061	Intermediate Similarity	NPC307776
0.8061	Intermediate Similarity	NPC26046
0.8061	Intermediate Similarity	NPC476304
0.8061	Intermediate Similarity	NPC473678
0.8058	Intermediate Similarity	NPC31907
0.8058	Intermediate Similarity	NPC114874
0.8058	Intermediate Similarity	NPC155010
0.8058	Intermediate Similarity	NPC472252
0.8058	Intermediate Similarity	NPC120123
0.8058	Intermediate Similarity	NPC473020
0.8058	Intermediate Similarity	NPC8039
0.8058	Intermediate Similarity	NPC473694
0.8058	Intermediate Similarity	NPC218513
0.8058	Intermediate Similarity	NPC472821
0.8058	Intermediate Similarity	NPC211879
0.8058	Intermediate Similarity	NPC189852
0.8058	Intermediate Similarity	NPC474575
0.8058	Intermediate Similarity	NPC55954
0.8058	Intermediate Similarity	NPC131479
0.8058	Intermediate Similarity	NPC475334
0.8058	Intermediate Similarity	NPC473198
0.8058	Intermediate Similarity	NPC157659
0.8058	Intermediate Similarity	NPC312900
0.8058	Intermediate Similarity	NPC286969
0.8058	Intermediate Similarity	NPC281378
0.8058	Intermediate Similarity	NPC245280
0.8058	Intermediate Similarity	NPC475623
0.8058	Intermediate Similarity	NPC16520
0.8058	Intermediate Similarity	NPC213190
0.8041	Intermediate Similarity	NPC475751
0.8041	Intermediate Similarity	NPC471896

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 NPC300179 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	1692
0.2-0.3	4215
0.3-0.4	2100
0.4-0.5	512
0.5-0.6	216
0.6-0.7	207
0.7-0.8	39
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
0.802	Intermediate Similarity	NPD7638	Approved
0.7941	Intermediate Similarity	NPD7640	Approved
0.7941	Intermediate Similarity	NPD7639	Approved
0.7857	Intermediate Similarity	NPD7516	Approved
0.7768	Intermediate Similarity	NPD7327	Approved
0.7768	Intermediate Similarity	NPD7328	Approved
0.7742	Intermediate Similarity	NPD7525	Registered
0.7732	Intermediate Similarity	NPD7524	Approved
0.7719	Intermediate Similarity	NPD8380	Approved
0.7719	Intermediate Similarity	NPD8335	Approved
0.7719	Intermediate Similarity	NPD8379	Approved
0.7719	Intermediate Similarity	NPD8296	Approved
0.7719	Intermediate Similarity	NPD8378	Approved
0.7632	Intermediate Similarity	NPD8294	Approved
0.7632	Intermediate Similarity	NPD8377	Approved
0.7565	Intermediate Similarity	NPD8033	Approved
0.7426	Intermediate Similarity	NPD8035	Phase 2
0.7426	Intermediate Similarity	NPD8034	Phase 2
0.7364	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6399	Phase 3
0.7347	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8297	Approved
0.732	Intermediate Similarity	NPD6695	Phase 3
0.729	Intermediate Similarity	NPD7632	Discontinued
0.7282	Intermediate Similarity	NPD7748	Approved
0.7263	Intermediate Similarity	NPD7645	Phase 2
0.7257	Intermediate Similarity	NPD4632	Approved
0.7255	Intermediate Similarity	NPD7637	Suspended
0.7248	Intermediate Similarity	NPD7128	Approved
0.7248	Intermediate Similarity	NPD6675	Approved
0.7248	Intermediate Similarity	NPD6402	Approved
0.7248	Intermediate Similarity	NPD5739	Approved
0.7245	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7115	Discovery
0.7207	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7339	Approved
0.7204	Intermediate Similarity	NPD6942	Approved
0.72	Intermediate Similarity	NPD7750	Discontinued
0.7196	Intermediate Similarity	NPD5344	Discontinued
0.7182	Intermediate Similarity	NPD6412	Phase 2
0.7179	Intermediate Similarity	NPD6319	Approved
0.717	Intermediate Similarity	NPD4225	Approved
0.7167	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.7131	Intermediate Similarity	NPD7319	Approved
0.7119	Intermediate Similarity	NPD7503	Approved
0.7117	Intermediate Similarity	NPD7320	Approved
0.7117	Intermediate Similarity	NPD6899	Approved
0.7117	Intermediate Similarity	NPD6881	Approved
0.7105	Intermediate Similarity	NPD8133	Approved
0.7087	Intermediate Similarity	NPD7515	Phase 2
0.7083	Intermediate Similarity	NPD6929	Approved
0.708	Intermediate Similarity	NPD8130	Phase 1
0.7075	Intermediate Similarity	NPD6084	Phase 2
0.7075	Intermediate Similarity	NPD6083	Phase 2
0.7075	Intermediate Similarity	NPD7902	Approved
0.7071	Intermediate Similarity	NPD4786	Approved
0.7059	Intermediate Similarity	NPD5328	Approved
0.7054	Intermediate Similarity	NPD6372	Approved
0.7054	Intermediate Similarity	NPD6373	Approved
0.7049	Intermediate Similarity	NPD7736	Approved
0.7027	Intermediate Similarity	NPD5697	Approved
0.7027	Intermediate Similarity	NPD5701	Approved
0.701	Intermediate Similarity	NPD6931	Approved
0.701	Intermediate Similarity	NPD6930	Phase 2
0.6991	Remote Similarity	NPD7102	Approved
0.6991	Remote Similarity	NPD6883	Approved
0.6991	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7290	Approved
0.6979	Remote Similarity	NPD6114	Approved
0.6979	Remote Similarity	NPD6115	Approved
0.6979	Remote Similarity	NPD6697	Approved
0.6979	Remote Similarity	NPD6118	Approved
0.6967	Remote Similarity	NPD8293	Discontinued
0.6964	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6686	Approved
0.6947	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6933	Approved
0.6942	Remote Similarity	NPD7492	Approved
0.6939	Remote Similarity	NPD6902	Approved
0.6937	Remote Similarity	NPD6008	Approved
0.6931	Remote Similarity	NPD3618	Phase 1
0.693	Remote Similarity	NPD6869	Approved
0.693	Remote Similarity	NPD6847	Approved
0.693	Remote Similarity	NPD6617	Approved
0.693	Remote Similarity	NPD6650	Approved
0.693	Remote Similarity	NPD6649	Approved
0.6923	Remote Similarity	NPD6009	Approved
0.6923	Remote Similarity	NPD6079	Approved
0.6903	Remote Similarity	NPD6012	Approved
0.6903	Remote Similarity	NPD6013	Approved
0.6903	Remote Similarity	NPD6014	Approved
0.6893	Remote Similarity	NPD6051	Approved
0.6891	Remote Similarity	NPD6059	Approved
0.6891	Remote Similarity	NPD6054	Approved
0.6887	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6616	Approved
0.6875	Remote Similarity	NPD6932	Approved
0.6875	Remote Similarity	NPD6925	Approved
0.6875	Remote Similarity	NPD5776	Phase 2
0.687	Remote Similarity	NPD6882	Approved
0.6869	Remote Similarity	NPD3667	Approved
0.686	Remote Similarity	NPD8328	Phase 3
0.6848	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5983	Phase 2
0.6829	Remote Similarity	NPD7078	Approved
0.6814	Remote Similarity	NPD6011	Approved
0.6804	Remote Similarity	NPD7145	Approved
0.6796	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6672	Approved
0.6796	Remote Similarity	NPD5737	Approved
0.6792	Remote Similarity	NPD7900	Approved
0.6792	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6648	Approved
0.6783	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6370	Approved
0.6771	Remote Similarity	NPD6117	Approved
0.6765	Remote Similarity	NPD6684	Approved
0.6765	Remote Similarity	NPD7334	Approved
0.6765	Remote Similarity	NPD7146	Approved
0.6765	Remote Similarity	NPD6409	Approved
0.6765	Remote Similarity	NPD5330	Approved
0.6765	Remote Similarity	NPD7521	Approved
0.6762	Remote Similarity	NPD7087	Discontinued
0.6759	Remote Similarity	NPD4755	Approved
0.6748	Remote Similarity	NPD6336	Discontinued
0.6737	Remote Similarity	NPD6926	Approved
0.6737	Remote Similarity	NPD6924	Approved
0.6735	Remote Similarity	NPD6683	Phase 2
0.6729	Remote Similarity	NPD5695	Phase 3
0.6727	Remote Similarity	NPD4159	Approved
0.6726	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6116	Phase 1
0.6699	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4202	Approved
0.6697	Remote Similarity	NPD5696	Approved
0.6696	Remote Similarity	NPD4634	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6694	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5222	Approved
0.6639	Remote Similarity	NPD5988	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6635	Remote Similarity	NPD6903	Approved
0.6606	Remote Similarity	NPD5173	Approved
0.6571	Remote Similarity	NPD4753	Phase 2
0.6569	Remote Similarity	NPD3133	Approved
0.6569	Remote Similarity	NPD3666	Approved
0.6569	Remote Similarity	NPD3665	Phase 1
0.6562	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6274	Approved
0.6555	Remote Similarity	NPD6868	Approved
0.6542	Remote Similarity	NPD8171	Discontinued
0.6529	Remote Similarity	NPD7101	Approved
0.6529	Remote Similarity	NPD7100	Approved
0.6526	Remote Similarity	NPD7152	Approved
0.6526	Remote Similarity	NPD7151	Approved
0.6526	Remote Similarity	NPD4243	Approved
0.6526	Remote Similarity	NPD7150	Approved
0.6518	Remote Similarity	NPD5224	Approved
0.6518	Remote Similarity	NPD5211	Phase 2
0.6518	Remote Similarity	NPD5225	Approved
0.6518	Remote Similarity	NPD5226	Approved
0.6518	Remote Similarity	NPD4633	Approved
0.6509	Remote Similarity	NPD7838	Discovery
0.6509	Remote Similarity	NPD3168	Discontinued
0.65	Remote Similarity	NPD7332	Phase 2
0.6489	Remote Similarity	NPD6922	Approved
0.6489	Remote Similarity	NPD6923	Approved
0.6481	Remote Similarity	NPD6001	Approved
0.646	Remote Similarity	NPD5175	Approved
0.646	Remote Similarity	NPD5174	Approved
0.6452	Remote Similarity	NPD6067	Discontinued
0.6449	Remote Similarity	NPD6411	Approved
0.6446	Remote Similarity	NPD6335	Approved
0.6442	Remote Similarity	NPD6098	Approved
0.6436	Remote Similarity	NPD6898	Phase 1
0.6429	Remote Similarity	NPD5223	Approved
0.6423	Remote Similarity	NPD6908	Approved
0.6423	Remote Similarity	NPD6909	Approved
0.6421	Remote Similarity	NPD7143	Approved
0.6421	Remote Similarity	NPD7144	Approved
0.6415	Remote Similarity	NPD6904	Approved
0.6415	Remote Similarity	NPD6080	Approved
0.6415	Remote Similarity	NPD6673	Approved
0.6408	Remote Similarity	NPD3668	Phase 3
0.6404	Remote Similarity	NPD5141	Approved
0.64	Remote Similarity	NPD4195	Approved
0.6392	Remote Similarity	NPD4785	Approved
0.6392	Remote Similarity	NPD4784	Approved
0.6378	Remote Similarity	NPD6033	Approved
0.6364	Remote Similarity	NPD6317	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