NPASS Compound

Structure

CID230677 OpenBabel06191716022D 31 34 0 0 1 0 0 0 0 0999 V2000 -4.9977 -0.7047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8661 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6563 -5.1812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3836 -3.9402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -2.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5969 -5.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5369 -0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6910 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0737 -2.9277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0734 -1.9517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -2.9287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3441 -0.3527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0693 -1.0060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2295 -4.3918 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5372 -1.4641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2293 -3.4162 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3831 -1.9522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6915 -1.9527 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8453 -0.4880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8450 -0.4885 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4157 -0.6541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3834 -2.9282 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8456 -1.4646 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1998 -4.4935 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6905 -0.0007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2125 -1.6088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 8 22 2 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 17 3 1 1 0 0 0 17 19 1 0 0 0 0 17 28 1 0 0 0 0 18 7 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 26 1 6 0 0 0 20 26 1 6 0 0 0 21 27 1 6 0 0 0 22 25 1 0 0 0 0 22 27 1 0 0 0 0 23 25 1 0 0 0 0 23 29 1 6 0 0 0 24 29 2 3 0 0 0 24 30 1 0 0 0 0 25 31 2 0 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.32
Volume:	470.35
LogP:	4.072
LogD:	3.868
LogS:	-5.184
# Rotatable Bonds:	5
TPSA:	58.53
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	4.915
Fsp3:	0.815
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.98
MDCK Permeability:	1.8982449546456337e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.439

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	95.23748016357422%
Volume Distribution (VD):	0.864
Pgp-substrate:	1.6799449920654297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.452
CYP2C19-inhibitor:	0.216
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.235
CYP2C9-substrate:	0.287
CYP2D6-inhibitor:	0.361
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.484

ADMET: Excretion

Clearance (CL):	6.096
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.472
Human Hepatotoxicity (H-HT):	0.375
Drug-inuced Liver Injury (DILI):	0.165
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.515
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.11
Carcinogencity:	0.128
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC230677

Natural Product ID:	NPC230677
*Common Name:**	Epipachysamine-E-5-En-4-One
IUPAC Name:	N-[(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-[(1S)-1-(methylamino)ethyl]-4-oxo-1,2,3,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]-3-methylbut-2-enamide
Synonyms:
Standard InCHIKey:	CLUQFEVBBPGSGA-FXLGMTMQSA-N
Standard InCHI:	InChI=1S/C27H42N2O2/c1-16(2)15-24(30)29-23-12-14-27(5)21-11-13-26(4)19(17(3)28-6)9-10-20(26)18(21)7-8-22(27)25(23)31/h8,15,17-21,23,28H,7,9-14H2,1-6H3,(H,29,30)/t17-,18-,19+,20-,21-,23-,26+,27+/m0/s1
SMILES:	CC(=CC(=N[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC=C2C1=O)[C@H](C)NC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496259
PubChem CID:	44587247
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930771]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17827771]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18681480]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18681480]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19818612]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4160	Cephalosporium polyaleurum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11838	Euphorbia regis-jubae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7351	Uncaria pteropoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18213	Strychnos variabilis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10911	Euphorbia peplis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2332	Plantago serraria	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13128	Crotalaria rosenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9527	Dendrodoa grossularia	Species	Styelidae	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
MIC	1
Others	1

Activity Type	# Activity
Individual Protein	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	9900.0	nM	PMID[496396]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	=	600.0	nM	PMID[496396]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	9.0	mm	PMID[496396]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	568100.0	nM	PMID[496396]

☑ 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 NPC230677 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	95
0.1-0.2	836
0.2-0.3	10281
0.3-0.4	17826
0.4-0.5	10306
0.5-0.6	2967
0.6-0.7	344
0.7-0.8	35
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9126	High Similarity	NPC175585
0.91	High Similarity	NPC152718
0.8911	High Similarity	NPC226509
0.8738	High Similarity	NPC469958
0.8058	Intermediate Similarity	NPC247220
0.8039	Intermediate Similarity	NPC476754
0.7981	Intermediate Similarity	NPC184033
0.7941	Intermediate Similarity	NPC476753
0.7941	Intermediate Similarity	NPC476752
0.7938	Intermediate Similarity	NPC21667
0.7905	Intermediate Similarity	NPC140685
0.7685	Intermediate Similarity	NPC58200
0.7647	Intermediate Similarity	NPC249312
0.76	Intermediate Similarity	NPC311769
0.76	Intermediate Similarity	NPC152684
0.76	Intermediate Similarity	NPC182106
0.7477	Intermediate Similarity	NPC167419
0.7431	Intermediate Similarity	NPC34193
0.7379	Intermediate Similarity	NPC259252
0.7353	Intermediate Similarity	NPC166458
0.72	Intermediate Similarity	NPC257962
0.7193	Intermediate Similarity	NPC24596
0.7168	Intermediate Similarity	NPC233256
0.7168	Intermediate Similarity	NPC195841
0.7167	Intermediate Similarity	NPC35037
0.7143	Intermediate Similarity	NPC98765
0.7129	Intermediate Similarity	NPC472239
0.7117	Intermediate Similarity	NPC474001
0.7087	Intermediate Similarity	NPC24733
0.708	Intermediate Similarity	NPC119329
0.7069	Intermediate Similarity	NPC328052
0.7054	Intermediate Similarity	NPC471083
0.7018	Intermediate Similarity	NPC185929
0.6961	Remote Similarity	NPC472867
0.6961	Remote Similarity	NPC3511
0.6961	Remote Similarity	NPC142253
0.6949	Remote Similarity	NPC124358
0.6931	Remote Similarity	NPC12035
0.6923	Remote Similarity	NPC72688
0.6923	Remote Similarity	NPC72753
0.6907	Remote Similarity	NPC303613
0.6907	Remote Similarity	NPC474228
0.6903	Remote Similarity	NPC50815
0.6863	Remote Similarity	NPC152039
0.6863	Remote Similarity	NPC329782
0.6863	Remote Similarity	NPC118329
0.6842	Remote Similarity	NPC474563
0.6827	Remote Similarity	NPC178025
0.6827	Remote Similarity	NPC181743
0.6827	Remote Similarity	NPC87552
0.6827	Remote Similarity	NPC16287
0.681	Remote Similarity	NPC244982
0.681	Remote Similarity	NPC476756
0.68	Remote Similarity	NPC91665
0.6796	Remote Similarity	NPC283277
0.6796	Remote Similarity	NPC472312
0.6796	Remote Similarity	NPC215474
0.6772	Remote Similarity	NPC317654
0.6772	Remote Similarity	NPC96010
0.6762	Remote Similarity	NPC8571
0.6762	Remote Similarity	NPC60350
0.6754	Remote Similarity	NPC247060
0.6735	Remote Similarity	NPC251705
0.6731	Remote Similarity	NPC41539
0.6726	Remote Similarity	NPC128698
0.6726	Remote Similarity	NPC239768
0.6724	Remote Similarity	NPC55462
0.6723	Remote Similarity	NPC66862
0.6701	Remote Similarity	NPC251929
0.6701	Remote Similarity	NPC282593
0.6701	Remote Similarity	NPC35734
0.6701	Remote Similarity	NPC307176
0.6701	Remote Similarity	NPC159577
0.6701	Remote Similarity	NPC265782
0.6701	Remote Similarity	NPC2634
0.67	Remote Similarity	NPC69408
0.6696	Remote Similarity	NPC90538
0.6694	Remote Similarity	NPC176336
0.6667	Remote Similarity	NPC255021
0.6667	Remote Similarity	NPC309852
0.6667	Remote Similarity	NPC80834
0.6667	Remote Similarity	NPC211322
0.6667	Remote Similarity	NPC469968
0.6636	Remote Similarity	NPC476293
0.6635	Remote Similarity	NPC469804
0.6635	Remote Similarity	NPC469805
0.6633	Remote Similarity	NPC21773
0.6633	Remote Similarity	NPC305501
0.6633	Remote Similarity	NPC115023
0.6633	Remote Similarity	NPC234707
0.6633	Remote Similarity	NPC54123
0.6618	Remote Similarity	NPC153007
0.661	Remote Similarity	NPC307903
0.661	Remote Similarity	NPC140251
0.6604	Remote Similarity	NPC147513
0.6604	Remote Similarity	NPC472940
0.6604	Remote Similarity	NPC472931
0.66	Remote Similarity	NPC293803
0.6598	Remote Similarity	NPC139397
0.6571	Remote Similarity	NPC3856
0.6571	Remote Similarity	NPC279639
0.6566	Remote Similarity	NPC470045
0.6566	Remote Similarity	NPC470044
0.6562	Remote Similarity	NPC237286
0.6549	Remote Similarity	NPC474164
0.6542	Remote Similarity	NPC157479
0.6538	Remote Similarity	NPC4166
0.6532	Remote Similarity	NPC474006
0.6531	Remote Similarity	NPC260040
0.6514	Remote Similarity	NPC473999
0.6514	Remote Similarity	NPC309603
0.6514	Remote Similarity	NPC262043
0.65	Remote Similarity	NPC476904
0.6495	Remote Similarity	NPC20610
0.6486	Remote Similarity	NPC474736
0.6481	Remote Similarity	NPC136948
0.6481	Remote Similarity	NPC43308
0.6476	Remote Similarity	NPC469799
0.6476	Remote Similarity	NPC311092
0.6476	Remote Similarity	NPC469806
0.6476	Remote Similarity	NPC320514
0.6476	Remote Similarity	NPC224072
0.6466	Remote Similarity	NPC176012
0.6465	Remote Similarity	NPC110615
0.6462	Remote Similarity	NPC471586
0.6462	Remote Similarity	NPC478136
0.6455	Remote Similarity	NPC84171
0.6455	Remote Similarity	NPC48010
0.6449	Remote Similarity	NPC29447
0.6449	Remote Similarity	NPC471224
0.6446	Remote Similarity	NPC79238
0.6442	Remote Similarity	NPC469797
0.6442	Remote Similarity	NPC469798
0.6442	Remote Similarity	NPC250632
0.6442	Remote Similarity	NPC474509
0.6441	Remote Similarity	NPC36497
0.6436	Remote Similarity	NPC255650
0.6436	Remote Similarity	NPC476346
0.6435	Remote Similarity	NPC275686
0.6435	Remote Similarity	NPC135799
0.6429	Remote Similarity	NPC182815
0.641	Remote Similarity	NPC474583
0.6408	Remote Similarity	NPC82635
0.6408	Remote Similarity	NPC470052
0.64	Remote Similarity	NPC109576
0.64	Remote Similarity	NPC56747
0.64	Remote Similarity	NPC180015
0.64	Remote Similarity	NPC130016
0.6396	Remote Similarity	NPC475806
0.6396	Remote Similarity	NPC473998
0.6396	Remote Similarity	NPC23217
0.6387	Remote Similarity	NPC25340
0.6387	Remote Similarity	NPC169375
0.6381	Remote Similarity	NPC474122
0.6379	Remote Similarity	NPC77703
0.6373	Remote Similarity	NPC7214
0.6364	Remote Similarity	NPC472313
0.6364	Remote Similarity	NPC472359
0.6364	Remote Similarity	NPC478139
0.6356	Remote Similarity	NPC475239
0.6355	Remote Similarity	NPC214043
0.6355	Remote Similarity	NPC85774
0.6355	Remote Similarity	NPC164577
0.6346	Remote Similarity	NPC170793
0.6346	Remote Similarity	NPC90965
0.6337	Remote Similarity	NPC329866
0.6337	Remote Similarity	NPC474797
0.6337	Remote Similarity	NPC474796
0.633	Remote Similarity	NPC93778
0.6325	Remote Similarity	NPC476755
0.6325	Remote Similarity	NPC469598
0.6321	Remote Similarity	NPC477581
0.6321	Remote Similarity	NPC39966
0.6321	Remote Similarity	NPC193347
0.6321	Remote Similarity	NPC477583
0.6311	Remote Similarity	NPC474459
0.6303	Remote Similarity	NPC476328
0.63	Remote Similarity	NPC470078
0.63	Remote Similarity	NPC21944
0.63	Remote Similarity	NPC265789
0.63	Remote Similarity	NPC133253
0.6296	Remote Similarity	NPC469948
0.6296	Remote Similarity	NPC474083
0.629	Remote Similarity	NPC476814
0.629	Remote Similarity	NPC476813
0.6286	Remote Similarity	NPC472478
0.6283	Remote Similarity	NPC8993
0.6283	Remote Similarity	NPC477290
0.6275	Remote Similarity	NPC473171
0.6275	Remote Similarity	NPC469803
0.6273	Remote Similarity	NPC117122
0.6271	Remote Similarity	NPC45365
0.6271	Remote Similarity	NPC293299
0.6262	Remote Similarity	NPC97913
0.6262	Remote Similarity	NPC477584
0.626	Remote Similarity	NPC474452
0.626	Remote Similarity	NPC56796
0.625	Remote Similarity	NPC204341
0.6239	Remote Similarity	NPC474732
0.6239	Remote Similarity	NPC474733

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 NPC230677 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	84
0.1-0.2	398
0.2-0.3	2504
0.3-0.4	4605
0.4-0.5	1275
0.5-0.6	239
0.6-0.7	44
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8039	Intermediate Similarity	NPD5769	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6404	Discontinued
0.6893	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5771	Approved
0.6719	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4747	Approved
0.6701	Remote Similarity	NPD4691	Approved
0.6598	Remote Similarity	NPD4137	Phase 3
0.65	Remote Similarity	NPD5733	Approved
0.65	Remote Similarity	NPD4058	Approved
0.6496	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6914	Discontinued
0.6378	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4687	Approved
0.6321	Remote Similarity	NPD4221	Approved
0.6321	Remote Similarity	NPD4223	Phase 3
0.63	Remote Similarity	NPD5276	Approved
0.6296	Remote Similarity	NPD5329	Approved
0.6204	Remote Similarity	NPD4197	Approved
0.6202	Remote Similarity	NPD7623	Phase 3
0.6202	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7333	Discontinued
0.6162	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6079	Approved
0.6095	Remote Similarity	NPD4777	Suspended
0.6095	Remote Similarity	NPD4776	Phase 2
0.6091	Remote Similarity	NPD4688	Approved
0.6091	Remote Similarity	NPD4693	Phase 3
0.6091	Remote Similarity	NPD4690	Approved
0.6091	Remote Similarity	NPD4138	Approved
0.6091	Remote Similarity	NPD4519	Discontinued
0.6091	Remote Similarity	NPD4623	Approved
0.6091	Remote Similarity	NPD4689	Approved
0.6091	Remote Similarity	NPD5690	Phase 2
0.6091	Remote Similarity	NPD5205	Approved
0.6075	Remote Similarity	NPD8028	Phase 2
0.6071	Remote Similarity	NPD5328	Approved
0.6055	Remote Similarity	NPD3666	Approved
0.6055	Remote Similarity	NPD3665	Phase 1
0.6055	Remote Similarity	NPD4786	Approved
0.6055	Remote Similarity	NPD3133	Approved
0.604	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6939	Phase 2
0.6018	Remote Similarity	NPD4096	Approved
0.6015	Remote Similarity	NPD7746	Phase 1
0.6015	Remote Similarity	NPD7747	Phase 1
0.5946	Remote Similarity	NPD3618	Phase 1
0.5946	Remote Similarity	NPD5280	Approved
0.5946	Remote Similarity	NPD4694	Approved
0.5946	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD1402	Approved
0.5943	Remote Similarity	NPD3617	Approved
0.5929	Remote Similarity	NPD4753	Phase 2
0.5888	Remote Similarity	NPD4195	Approved
0.5877	Remote Similarity	NPD6934	Discontinued
0.5872	Remote Similarity	NPD3667	Approved
0.5841	Remote Similarity	NPD5737	Approved
0.5841	Remote Similarity	NPD6672	Approved
0.5833	Remote Similarity	NPD4695	Discontinued
0.5825	Remote Similarity	NPD5365	Phase 2
0.5812	Remote Similarity	NPD5210	Approved
0.5812	Remote Similarity	NPD4629	Approved
0.5804	Remote Similarity	NPD7521	Approved
0.5804	Remote Similarity	NPD5279	Phase 3
0.5804	Remote Similarity	NPD6409	Approved
0.5804	Remote Similarity	NPD7334	Approved
0.5804	Remote Similarity	NPD7146	Approved
0.5804	Remote Similarity	NPD6684	Approved
0.5804	Remote Similarity	NPD5330	Approved
0.5794	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6080	Approved
0.5789	Remote Similarity	NPD6673	Approved
0.5789	Remote Similarity	NPD6904	Approved
0.5785	Remote Similarity	NPD5211	Phase 2
0.5776	Remote Similarity	NPD4202	Approved
0.5763	Remote Similarity	NPD5221	Approved
0.5763	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD5222	Approved
0.5758	Remote Similarity	NPD6909	Approved
0.5758	Remote Similarity	NPD6908	Approved
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD6420	Discontinued
0.5714	Remote Similarity	NPD6084	Phase 2
0.5714	Remote Similarity	NPD5173	Approved
0.5702	Remote Similarity	NPD4723	Approved
0.5702	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5208	Approved
0.5702	Remote Similarity	NPD4722	Approved
0.5702	Remote Similarity	NPD6903	Approved
0.5691	Remote Similarity	NPD5141	Approved
0.569	Remote Similarity	NPD5693	Phase 1
0.569	Remote Similarity	NPD5281	Approved
0.569	Remote Similarity	NPD5284	Approved
0.5676	Remote Similarity	NPD4788	Approved
0.5664	Remote Similarity	NPD6098	Approved
0.5641	Remote Similarity	NPD6399	Phase 3
0.563	Remote Similarity	NPD7614	Phase 1
0.563	Remote Similarity	NPD4697	Phase 3
0.5625	Remote Similarity	NPD3668	Phase 3
0.562	Remote Similarity	NPD5285	Approved
0.562	Remote Similarity	NPD4696	Approved
0.562	Remote Similarity	NPD5286	Approved
0.561	Remote Similarity	NPD2259	Approved
0.561	Remote Similarity	NPD2258	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