NPASS Compound

Structure

CID246303 OpenBabel06191716042D 44 46 0 0 1 0 0 0 0 0999 V2000 -2.2277 3.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3631 0.4920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2809 -3.5459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5397 -2.5799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2723 4.2313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0810 -1.1273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0937 0.1333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1383 1.9993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6383 0.1333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2277 3.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0702 -0.2151 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2723 2.4993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2423 -0.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5937 -0.7328 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1383 -0.7328 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7177 -3.5982 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7277 4.2313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7723 3.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7277 2.4993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0761 -2.6646 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7277 -1.2328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8454 -1.4399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0420 -2.4058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3513 -1.0367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0361 0.0437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5937 1.9993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2946 0.4160 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8113 -1.1811 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3008 -1.4399 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2723 -1.2328 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2990 -2.0353 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0286 -2.1259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2624 -4.4369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2277 5.0974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7723 3.3653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9865 -2.1987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5866 -2.4058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7491 -3.1129 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4874 -0.4920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2949 1.0096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7432 -0.6634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3008 2.7064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0937 1.1333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6383 1.1333 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 3 4 1 0 0 0 0 3 16 1 0 0 0 0 4 31 1 0 0 0 0 5 17 2 0 0 0 0 5 18 1 0 0 0 0 6 13 1 0 0 0 0 6 32 1 0 0 0 0 7 14 1 0 0 0 0 7 43 1 0 0 0 0 8 12 1 0 0 0 0 8 44 1 0 0 0 0 9 15 1 0 0 0 0 9 44 1 0 0 0 0 10 17 1 0 0 0 0 10 19 2 0 0 0 0 11 2 1 1 0 0 0 11 25 1 0 0 0 0 11 28 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 24 1 0 0 0 0 13 27 1 6 0 0 0 14 21 1 0 0 0 0 14 29 1 1 0 0 0 15 22 1 1 0 0 0 15 30 1 0 0 0 0 16 20 1 0 0 0 0 16 33 1 1 0 0 0 17 34 1 0 0 0 0 18 35 1 0 0 0 0 19 26 1 0 0 0 0 20 23 1 1 0 0 0 20 31 1 0 0 0 0 21 30 2 3 0 0 0 21 36 1 0 0 0 0 22 28 2 3 0 0 0 22 37 1 0 0 0 0 23 29 2 3 0 0 0 23 38 1 0 0 0 0 24 31 1 0 0 0 0 24 39 2 0 0 0 0 25 40 2 0 0 0 0 25 41 1 0 0 0 0 26 42 2 0 0 0 0 26 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	641.2
Volume:	587.83
LogP:	-1.249
LogD:	-0.32
LogS:	-1.408
# Rotatable Bonds:	10
TPSA:	278.15
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	3
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.132
Synthetic Accessibility Score:	5.19
Fsp3:	0.538
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.838
MDCK Permeability:	2.0121215129620396e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.903
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	20.246864318847656%
Volume Distribution (VD):	0.277
Pgp-substrate:	66.9180679321289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.135
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.686
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.493
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.158
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC246303

Natural Product ID:	NPC246303
*Common Name:**	(S)-2-((4R,7S)-7-((2S,3R)-1-((S)-2-Amino-3-Hydroxypropanoyl)-3-Hydroxypyrrolidine-2-Carboxamido)-12,14-Dihydroxy-11-Methyl-6,10-Dioxo-1,3,4,5,6,7,8,10-Octahydrobenzo[J][1,8,5]Oxathiaazacyclododecine-4-Carboxamido)Propanoic Acid
IUPAC Name:	(2S)-2-[[(5R,8S)-8-[[(2S,3R)-1-[(2S)-2-amino-3-hydroxypropanoyl]-3-hydroxypyrrolidine-2-carbonyl]amino]-14,16-dihydroxy-13-methyl-7,11-dioxo-10-oxa-3-thia-6-azabicyclo[10.4.0]hexadeca-1(16),12,14-triene-5-carbonyl]amino]propanoic acid
Synonyms:	Ro-091437
Standard InCHIKey:	HMHQWJDFNVJCHA-BTZKOOKSSA-N
Standard InCHI:	InChI=1S/C26H35N5O12S/c1-10-17(34)5-18(35)12-8-44-9-15(22(37)28-11(2)25(40)41)30-21(36)14(7-43-26(42)19(10)12)29-23(38)20-16(33)3-4-31(20)24(39)13(27)6-32/h5,11,13-16,20,32-35H,3-4,6-9,27H2,1-2H3,(H,28,37)(H,29,38)(H,30,36)(H,40,41)/t11-,13-,14-,15-,16+,20-/m0/s1
SMILES:	OC[C@@H](C(=O)N1CC[C@H]([C@H]1C(=N[C@H]1COC(=O)c2c(C)c(O)cc(c2CSC[C@H](N=C1O)C(=N[C@H](C(=O)O)C)O)O)O)O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL431453
PubChem CID:	164470
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO4731	Streptomyces filipinensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[5453318]
NPO3820	Juglans cathayensis	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4731	Streptomyces filipinensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5675	Siphonaria grisea	Species	Chytriomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9183	Amycolatopsis tolypomycina	Species	Pseudonocardiaceae	Bacteria	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	1
Others	1

Activity Type	# Activity
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5484	Protein Complex	DNA gyrase	Staphylococcus aureus	MNEC	=	0.05	ug ml-1	PMID[463072]
NPT2	Others	Unspecified		IC50	=	70.0	nM	PMID[463073]

☑ 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 NPC246303 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	239
0.1-0.2	1306
0.2-0.3	4895
0.3-0.4	12274
0.4-0.5	7917
0.5-0.6	14510
0.6-0.7	1492
0.7-0.8	63
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7525	Intermediate Similarity	NPC59827
0.7525	Intermediate Similarity	NPC184933
0.7476	Intermediate Similarity	NPC476662
0.7427	Intermediate Similarity	NPC476661
0.7415	Intermediate Similarity	NPC477527
0.7337	Intermediate Similarity	NPC477816
0.733	Intermediate Similarity	NPC477552
0.733	Intermediate Similarity	NPC477550
0.7313	Intermediate Similarity	NPC329731
0.7313	Intermediate Similarity	NPC4910
0.73	Intermediate Similarity	NPC299806
0.7291	Intermediate Similarity	NPC477526
0.726	Intermediate Similarity	NPC477551
0.7245	Intermediate Similarity	NPC471165
0.7236	Intermediate Similarity	NPC477637
0.7231	Intermediate Similarity	NPC328494
0.719	Intermediate Similarity	NPC286135
0.7179	Intermediate Similarity	NPC475123
0.7179	Intermediate Similarity	NPC475204
0.7158	Intermediate Similarity	NPC326349
0.7158	Intermediate Similarity	NPC323336
0.7157	Intermediate Similarity	NPC283207
0.7149	Intermediate Similarity	NPC478008
0.7136	Intermediate Similarity	NPC328763
0.7136	Intermediate Similarity	NPC475421
0.7103	Intermediate Similarity	NPC478005
0.7092	Intermediate Similarity	NPC46009
0.7077	Intermediate Similarity	NPC209463
0.7071	Intermediate Similarity	NPC26108
0.7071	Intermediate Similarity	NPC158277
0.7062	Intermediate Similarity	NPC63931
0.7059	Intermediate Similarity	NPC478007
0.7056	Intermediate Similarity	NPC89831
0.704	Intermediate Similarity	NPC252156
0.703	Intermediate Similarity	NPC470903
0.703	Intermediate Similarity	NPC167763
0.703	Intermediate Similarity	NPC470112
0.703	Intermediate Similarity	NPC99723
0.702	Intermediate Similarity	NPC137627
0.702	Intermediate Similarity	NPC306804
0.7019	Intermediate Similarity	NPC477632
0.7019	Intermediate Similarity	NPC477638
0.7	Intermediate Similarity	NPC323662
0.699	Remote Similarity	NPC209865
0.6985	Remote Similarity	NPC476227
0.698	Remote Similarity	NPC309692
0.6971	Remote Similarity	NPC314083
0.6963	Remote Similarity	NPC244509
0.6939	Remote Similarity	NPC61004
0.6931	Remote Similarity	NPC153554
0.6923	Remote Similarity	NPC477631
0.6919	Remote Similarity	NPC40234
0.6919	Remote Similarity	NPC196091
0.6908	Remote Similarity	NPC240130
0.6908	Remote Similarity	NPC477636
0.6908	Remote Similarity	NPC61332
0.6905	Remote Similarity	NPC477639
0.6888	Remote Similarity	NPC472923
0.6882	Remote Similarity	NPC275356
0.6881	Remote Similarity	NPC269750
0.6881	Remote Similarity	NPC221792
0.6881	Remote Similarity	NPC194671
0.6878	Remote Similarity	NPC476444
0.6872	Remote Similarity	NPC204580
0.6866	Remote Similarity	NPC50016
0.6866	Remote Similarity	NPC129578
0.686	Remote Similarity	NPC329790
0.6857	Remote Similarity	NPC471563
0.6856	Remote Similarity	NPC213224
0.6856	Remote Similarity	NPC244336
0.6852	Remote Similarity	NPC314946
0.6852	Remote Similarity	NPC80472
0.685	Remote Similarity	NPC273755
0.6849	Remote Similarity	NPC131258
0.6842	Remote Similarity	NPC473491
0.684	Remote Similarity	NPC83019
0.6832	Remote Similarity	NPC117713
0.6832	Remote Similarity	NPC292213
0.6829	Remote Similarity	NPC473562
0.6825	Remote Similarity	NPC329295
0.6823	Remote Similarity	NPC39431
0.6821	Remote Similarity	NPC55092
0.6821	Remote Similarity	NPC275837
0.6818	Remote Similarity	NPC294516
0.6818	Remote Similarity	NPC107938
0.6818	Remote Similarity	NPC328649
0.6816	Remote Similarity	NPC155506
0.6816	Remote Similarity	NPC159767
0.6814	Remote Similarity	NPC329816
0.6814	Remote Similarity	NPC473404
0.6812	Remote Similarity	NPC94862
0.681	Remote Similarity	NPC94499
0.6809	Remote Similarity	NPC472605
0.6809	Remote Similarity	NPC472604
0.6798	Remote Similarity	NPC314987
0.6796	Remote Similarity	NPC315542
0.6788	Remote Similarity	NPC476268
0.6784	Remote Similarity	NPC280022
0.6771	Remote Similarity	NPC166583
0.6771	Remote Similarity	NPC56685
0.6771	Remote Similarity	NPC262166
0.6771	Remote Similarity	NPC53362
0.6766	Remote Similarity	NPC248670
0.6755	Remote Similarity	NPC472600
0.6755	Remote Similarity	NPC472601
0.6753	Remote Similarity	NPC179178
0.6746	Remote Similarity	NPC29531
0.6746	Remote Similarity	NPC469437
0.6741	Remote Similarity	NPC313582
0.6738	Remote Similarity	NPC212693
0.6738	Remote Similarity	NPC94248
0.6737	Remote Similarity	NPC471731
0.6736	Remote Similarity	NPC68967
0.6736	Remote Similarity	NPC133864
0.6734	Remote Similarity	NPC473502
0.6733	Remote Similarity	NPC279871
0.6731	Remote Similarity	NPC295531
0.6729	Remote Similarity	NPC42286
0.672	Remote Similarity	NPC472603
0.672	Remote Similarity	NPC81026
0.6719	Remote Similarity	NPC473023
0.6718	Remote Similarity	NPC200773
0.6718	Remote Similarity	NPC240768
0.6716	Remote Similarity	NPC45037
0.6716	Remote Similarity	NPC230611
0.6714	Remote Similarity	NPC281629
0.6701	Remote Similarity	NPC241794
0.6701	Remote Similarity	NPC473580
0.67	Remote Similarity	NPC315388
0.6684	Remote Similarity	NPC71256
0.6684	Remote Similarity	NPC194579
0.6684	Remote Similarity	NPC70380
0.6684	Remote Similarity	NPC16188
0.6684	Remote Similarity	NPC471733
0.6684	Remote Similarity	NPC8817
0.6683	Remote Similarity	NPC276120
0.6683	Remote Similarity	NPC254700
0.6682	Remote Similarity	NPC293347
0.6667	Remote Similarity	NPC316164
0.6667	Remote Similarity	NPC83272
0.6667	Remote Similarity	NPC329992
0.6667	Remote Similarity	NPC266741
0.6651	Remote Similarity	NPC18306
0.6651	Remote Similarity	NPC314941
0.6651	Remote Similarity	NPC123859
0.6651	Remote Similarity	NPC302715
0.6651	Remote Similarity	NPC313453
0.665	Remote Similarity	NPC473402
0.665	Remote Similarity	NPC136797
0.665	Remote Similarity	NPC475544
0.665	Remote Similarity	NPC473354
0.6649	Remote Similarity	NPC470902
0.6649	Remote Similarity	NPC159721
0.6649	Remote Similarity	NPC472610
0.6649	Remote Similarity	NPC51106
0.6649	Remote Similarity	NPC91953
0.6649	Remote Similarity	NPC191835
0.6637	Remote Similarity	NPC475609
0.6636	Remote Similarity	NPC328700
0.6636	Remote Similarity	NPC257728
0.6636	Remote Similarity	NPC2173
0.6636	Remote Similarity	NPC119818
0.6636	Remote Similarity	NPC202771
0.6632	Remote Similarity	NPC470357
0.6626	Remote Similarity	NPC473786
0.6623	Remote Similarity	NPC315914
0.6622	Remote Similarity	NPC326333
0.662	Remote Similarity	NPC469689
0.662	Remote Similarity	NPC313274
0.662	Remote Similarity	NPC471031
0.6619	Remote Similarity	NPC162694
0.6619	Remote Similarity	NPC102959
0.6618	Remote Similarity	NPC469973
0.6615	Remote Similarity	NPC256689
0.6615	Remote Similarity	NPC42540
0.6615	Remote Similarity	NPC151607
0.6615	Remote Similarity	NPC283783
0.6615	Remote Similarity	NPC123011
0.6614	Remote Similarity	NPC139634
0.6614	Remote Similarity	NPC88269
0.6614	Remote Similarity	NPC105456
0.6605	Remote Similarity	NPC50548
0.6603	Remote Similarity	NPC475566
0.66	Remote Similarity	NPC469479
0.6598	Remote Similarity	NPC471734
0.6598	Remote Similarity	NPC202198
0.6596	Remote Similarity	NPC197921
0.6591	Remote Similarity	NPC257266
0.6588	Remote Similarity	NPC60516
0.6587	Remote Similarity	NPC294951
0.6584	Remote Similarity	NPC276506
0.6584	Remote Similarity	NPC473693
0.6584	Remote Similarity	NPC474858
0.6584	Remote Similarity	NPC471568
0.6582	Remote Similarity	NPC469619
0.6582	Remote Similarity	NPC56204
0.6582	Remote Similarity	NPC469670
0.6581	Remote Similarity	NPC185031
0.658	Remote Similarity	NPC75694
0.658	Remote Similarity	NPC7817

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 NPC246303 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	481
0.2-0.3	1100
0.3-0.4	2429
0.4-0.5	2896
0.5-0.6	1794
0.6-0.7	304
0.7-0.8	8
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
0.7548	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4435	Approved
0.7313	Intermediate Similarity	NPD4434	Approved
0.7206	Intermediate Similarity	NPD6504	Approved
0.7206	Intermediate Similarity	NPD6505	Approved
0.7179	Intermediate Similarity	NPD4652	Approved
0.7158	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7565	Approved
0.7092	Intermediate Similarity	NPD5711	Approved
0.7092	Intermediate Similarity	NPD5710	Approved
0.7092	Intermediate Similarity	NPD2517	Approved
0.7041	Intermediate Similarity	NPD2516	Approved
0.7024	Intermediate Similarity	NPD5852	Approved
0.7024	Intermediate Similarity	NPD5851	Approved
0.7022	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8059	Phase 3
0.7014	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2098	Approved
0.6965	Remote Similarity	NPD5484	Approved
0.6965	Remote Similarity	NPD5485	Approved
0.6946	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7133	Discontinued
0.6903	Remote Similarity	NPD8491	Approved
0.6881	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8366	Approved
0.6872	Remote Similarity	NPD2097	Approved
0.6849	Remote Similarity	NPD8153	Approved
0.6849	Remote Similarity	NPD8152	Approved
0.6832	Remote Similarity	NPD6020	Phase 2
0.6818	Remote Similarity	NPD3879	Approved
0.6816	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5137	Approved
0.6798	Remote Similarity	NPD8469	Approved
0.6792	Remote Similarity	NPD7282	Approved
0.6791	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD8162	Phase 2
0.6773	Remote Similarity	NPD3878	Approved
0.6757	Remote Similarity	NPD7930	Approved
0.6749	Remote Similarity	NPD6042	Phase 2
0.6749	Remote Similarity	NPD42	Phase 2
0.6731	Remote Similarity	NPD5037	Approved
0.6731	Remote Similarity	NPD5038	Approved
0.6719	Remote Similarity	NPD6390	Discontinued
0.6719	Remote Similarity	NPD7303	Discontinued
0.6713	Remote Similarity	NPD6823	Phase 2
0.67	Remote Similarity	NPD2888	Approved
0.67	Remote Similarity	NPD2890	Approved
0.67	Remote Similarity	NPD2017	Approved
0.67	Remote Similarity	NPD2889	Approved
0.6697	Remote Similarity	NPD7801	Approved
0.6683	Remote Similarity	NPD8303	Discontinued
0.6683	Remote Similarity	NPD5036	Approved
0.6667	Remote Similarity	NPD7827	Phase 1
0.6651	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7811	Phase 3
0.6651	Remote Similarity	NPD8320	Phase 1
0.6651	Remote Similarity	NPD7810	Phase 3
0.6651	Remote Similarity	NPD8319	Approved
0.6649	Remote Similarity	NPD7978	Discontinued
0.6636	Remote Similarity	NPD5005	Approved
0.6636	Remote Similarity	NPD7585	Approved
0.6636	Remote Similarity	NPD5006	Approved
0.6632	Remote Similarity	NPD3400	Discontinued
0.6618	Remote Similarity	NPD36	Approved
0.6618	Remote Similarity	NPD4955	Approved
0.6618	Remote Similarity	NPD4954	Approved
0.6618	Remote Similarity	NPD5026	Approved
0.6618	Remote Similarity	NPD5034	Approved
0.6618	Remote Similarity	NPD5028	Approved
0.6606	Remote Similarity	NPD8151	Discontinued
0.6591	Remote Similarity	NPD7583	Approved
0.6589	Remote Similarity	NPD4361	Phase 2
0.6589	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6836	Approved
0.6587	Remote Similarity	NPD5035	Approved
0.658	Remote Similarity	NPD2532	Approved
0.658	Remote Similarity	NPD2534	Approved
0.658	Remote Similarity	NPD2533	Approved
0.658	Remote Similarity	NPD3157	Approved
0.658	Remote Similarity	NPD3158	Phase 1
0.6577	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5030	Phase 2
0.6557	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5077	Approved
0.6557	Remote Similarity	NPD5076	Approved
0.6555	Remote Similarity	NPD6851	Approved
0.6555	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6853	Approved
0.6547	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7783	Phase 2
0.6543	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7485	Phase 3
0.6535	Remote Similarity	NPD7484	Phase 3
0.6512	Remote Similarity	NPD3659	Discontinued
0.6507	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD5265	Approved
0.6492	Remote Similarity	NPD5264	Approved
0.649	Remote Similarity	NPD5029	Approved
0.649	Remote Similarity	NPD5027	Approved
0.649	Remote Similarity	NPD5031	Approved
0.6486	Remote Similarity	NPD7701	Phase 2
0.6484	Remote Similarity	NPD6863	Phase 2
0.6471	Remote Similarity	NPD7999	Approved
0.6471	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6971	Discontinued
0.6465	Remote Similarity	NPD6534	Approved
0.6465	Remote Similarity	NPD6535	Approved
0.6462	Remote Similarity	NPD6841	Approved
0.6462	Remote Similarity	NPD6842	Approved
0.6462	Remote Similarity	NPD6843	Phase 3
0.6462	Remote Similarity	NPD7613	Discontinued
0.6455	Remote Similarity	NPD7696	Phase 3
0.6455	Remote Similarity	NPD7698	Approved
0.6455	Remote Similarity	NPD7697	Approved
0.6452	Remote Similarity	NPD7699	Phase 2
0.6452	Remote Similarity	NPD7700	Phase 2
0.6452	Remote Similarity	NPD4420	Approved
0.645	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3455	Phase 2
0.6443	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7584	Approved
0.644	Remote Similarity	NPD2437	Approved
0.644	Remote Similarity	NPD2436	Approved
0.6436	Remote Similarity	NPD5709	Phase 3
0.6435	Remote Similarity	NPD6796	Discontinued
0.6432	Remote Similarity	NPD7861	Discontinued
0.6429	Remote Similarity	NPD7523	Phase 3
0.6429	Remote Similarity	NPD7131	Phase 3
0.6425	Remote Similarity	NPD7870	Phase 2
0.6425	Remote Similarity	NPD7871	Phase 2
0.6422	Remote Similarity	NPD7608	Discontinued
0.6417	Remote Similarity	NPD5323	Approved
0.6411	Remote Similarity	NPD5039	Approved
0.6404	Remote Similarity	NPD4666	Phase 3
0.6402	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7283	Approved
0.6396	Remote Similarity	NPD8161	Suspended
0.6394	Remote Similarity	NPD4956	Approved
0.6393	Remote Similarity	NPD6779	Approved
0.6393	Remote Similarity	NPD6777	Approved
0.6393	Remote Similarity	NPD6780	Approved
0.6393	Remote Similarity	NPD6778	Approved
0.6393	Remote Similarity	NPD6781	Approved
0.6393	Remote Similarity	NPD6782	Approved
0.6393	Remote Similarity	NPD6776	Approved
0.6389	Remote Similarity	NPD4360	Phase 2
0.6389	Remote Similarity	NPD4363	Phase 3
0.6382	Remote Similarity	NPD2513	Approved
0.6381	Remote Similarity	NPD5032	Approved
0.6377	Remote Similarity	NPD7177	Discontinued
0.6372	Remote Similarity	NPD5968	Phase 3
0.6368	Remote Similarity	NPD5353	Approved
0.6364	Remote Similarity	NPD6297	Approved
0.6359	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6894	Phase 1
0.6356	Remote Similarity	NPD7874	Approved
0.6356	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD1986	Approved
0.635	Remote Similarity	NPD2515	Approved
0.635	Remote Similarity	NPD3007	Approved
0.6349	Remote Similarity	NPD8172	Phase 2
0.6349	Remote Similarity	NPD8173	Phase 2
0.6349	Remote Similarity	NPD2568	Approved
0.6346	Remote Similarity	NPD7286	Phase 2
0.6345	Remote Similarity	NPD8461	Discontinued
0.6344	Remote Similarity	NPD3136	Phase 2
0.6341	Remote Similarity	NPD7229	Phase 3
0.6338	Remote Similarity	NPD8150	Discontinued
0.6333	Remote Similarity	NPD7039	Approved
0.6333	Remote Similarity	NPD7038	Approved
0.6333	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD2891	Approved
0.633	Remote Similarity	NPD5564	Approved
0.6324	Remote Similarity	NPD6746	Phase 2
0.6321	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD2654	Approved
0.6318	Remote Similarity	NPD5772	Approved
0.6318	Remote Similarity	NPD4557	Approved
0.6318	Remote Similarity	NPD5773	Approved
0.631	Remote Similarity	NPD5299	Approved
0.6308	Remote Similarity	NPD6835	Approved
0.6308	Remote Similarity	NPD7693	Approved
0.629	Remote Similarity	NPD4125	Approved
0.6287	Remote Similarity	NPD7737	Approved
0.6287	Remote Similarity	NPD7738	Approved
0.6287	Remote Similarity	NPD7318	Phase 3
0.6286	Remote Similarity	NPD5953	Discontinued
0.6281	Remote Similarity	NPD2651	Approved
0.6281	Remote Similarity	NPD2649	Approved
0.6281	Remote Similarity	NPD2052	Approved
0.628	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.627	Remote Similarity	NPD599	Approved
0.627	Remote Similarity	NPD602	Approved
0.6269	Remote Similarity	NPD8019	Approved
0.6269	Remote Similarity	NPD5356	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