NPASS Compound

Structure

NPC173329 OpenBabel07101718302D 45 46 0 0 1 0 0 0 0 0999 V2000 0.3902 -1.9616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0890 -1.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9685 4.5567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6841 -1.9002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4835 2.2894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9515 -0.3852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6457 0.0165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1731 3.2363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5330 2.6796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0920 4.5716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0117 -1.3028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2024 1.6566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4890 4.1080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4890 4.1080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5651 3.7253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1200 3.0182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4129 -0.5367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4890 -0.9194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5567 1.6401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1420 -1.3022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4129 3.7253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4890 -0.9194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5027 2.0943 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1200 0.1704 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6988 0.3379 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4946 2.2894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8544 1.7326 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8580 3.0182 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5651 -0.5367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5037 1.3187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5027 1.0943 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8352 1.5375 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9469 -0.3214 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4754 2.0943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8580 0.1704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1951 0.9808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4835 0.8992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1567 0.5906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0266 -0.3852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1759 0.7857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0266 3.5737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0096 -1.3682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2555 1.9780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4754 1.0943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 10 41 1 0 0 0 0 11 42 1 0 0 0 0 12 43 1 0 0 0 0 13 14 1 0 0 0 0 13 15 2 0 0 0 0 14 21 2 0 0 0 0 15 28 1 0 0 0 0 16 21 1 0 0 0 0 16 23 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 18 29 2 0 0 0 0 19 30 1 0 0 0 0 19 36 1 0 0 0 0 23 5 1 1 0 0 0 23 31 1 0 0 0 0 24 6 1 1 0 0 0 24 31 1 0 0 0 0 25 7 1 6 0 0 0 25 30 1 0 0 0 0 25 33 1 0 0 0 0 26 8 1 1 0 0 0 26 32 1 0 0 0 0 27 9 1 6 0 0 0 27 32 1 0 0 0 0 27 36 1 0 0 0 0 28 34 1 0 0 0 0 28 41 1 6 0 0 0 29 35 1 0 0 0 0 29 42 1 0 0 0 0 30 43 1 1 0 0 0 31 37 1 1 0 0 0 32 38 1 6 0 0 0 33 20 1 1 0 0 0 33 45 1 0 0 0 0 34 26 1 1 0 0 0 34 44 1 0 0 0 0 35 39 2 0 0 0 0 35 44 1 0 0 0 0 36 40 1 6 0 0 0 36 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	636.42
Volume:	680.029
LogP:	4.284
LogD:	3.947
LogS:	-5.001
# Rotatable Bonds:	8
TPSA:	123.91
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.303
Synthetic Accessibility Score:	6.054
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
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:	-4.696
MDCK Permeability:	2.1988325897837058e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.883
Human Intestinal Absorption (HIA):	0.353
20% Bioavailability (F20%):	0.508
30% Bioavailability (F30%):	0.621

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	92.65744018554688%
Volume Distribution (VD):	2.407
Pgp-substrate:	5.857372283935547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.388
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.274
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.692

ADMET: Excretion

Clearance (CL):	8.426
Half-life (T1/2):	0.177

ADMET: Toxicity

hERG Blockers:	0.492
Human Hepatotoxicity (H-HT):	0.787
Drug-inuced Liver Injury (DILI):	0.69
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.835
Carcinogencity:	0.062
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.803

Download Data

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

Natural Product: NPC173329

Natural Product ID:	NPC173329
*Common Name:**	Bafilomycin G
IUPAC Name:	(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-8-hydroxy-16-[(2S,3R,4S)-3-hydroxy-4-[(2R,4R,5S,6R)-2-hydroxy-4-methoxy-5-methyl-6-propan-2-yloxan-2-yl]pentan-2-yl]-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one
Synonyms:	Bafilomycin G
Standard InCHIKey:	SFLNWFBBCTZPBV-DCOOOOFJSA-N
Standard InCHI:	InChI=1S/C36H60O9/c1-20(2)33-25(7)30(43-12)19-36(40,45-33)27(9)32(38)26(8)34-28(41-10)15-13-14-21(3)16-23(5)31(37)24(6)17-22(4)18-29(42-11)35(39)44-34/h13-15,17-18,20,23-28,30-34,37-38,40H,16,19H2,1-12H3/b15-13+,21-14+,22-17+,29-18-/t23-,24+,25-,26-,27-,28-,30+,31-,32+,33+,34+,36+/m0/s1
SMILES:	CC(C)[C@@H]1[C@@H](C)[C@@H](C[C@@]([C@@H](C)[C@@H]([C@H](C)[C@@H]2[C@H](/C=C/C=C(C)/C[C@H](C)[C@@H]([C@H](C)/C=C(C)/C=C(/C(=O)O2)OC)O)OC)O)(O)O1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL293078
PubChem CID:	11093435
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33082	streptomyces spp.	Species	Streptomycetaceae	Bacteria	n.a.	isolated from marine habitats	n.a.	PMID[20028134]
NPO40536	Streptomyces albolongus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26933756]

☑ 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	4
Others	3

Activity Type	# Activity
Cell Line	5
Individual Protein	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6625	Individual Protein	Vacuolar ATP synthase subunit S1	Homo sapiens	Potency ratio	=	1.3	n.a.	PMID[551393]
NPT83	Cell Line	MCF7	Homo sapiens	FC	=	3.0	n.a.	PMID[551394]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	69200.0	nM	PMID[551395]
NPT492	Cell Line	Caco-2	Homo sapiens	IC50	>	100000.0	nM	PMID[551395]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	100000.0	nM	PMID[551395]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	8670.0	nM	PMID[551395]
NPT22388	SINGLE PROTEIN	Vacuolar H(+)-ATPase	Bos taurus	Potency ratio	=	1.2	n.a.	PMID[551393]

☑ 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 NPC173329 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	194
0.1-0.2	1160
0.2-0.3	3925
0.3-0.4	6938
0.4-0.5	16388
0.5-0.6	9661
0.6-0.7	3895
0.7-0.8	494
0.8-0.85	32
0.85-0.9	4
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC288350
0.89	High Similarity	NPC133625
0.8646	High Similarity	NPC120299
0.8557	High Similarity	NPC475653
0.8542	High Similarity	NPC255410
0.8454	Intermediate Similarity	NPC475332
0.8438	Intermediate Similarity	NPC300710
0.8427	Intermediate Similarity	NPC184208
0.8427	Intermediate Similarity	NPC8538
0.8421	Intermediate Similarity	NPC238090
0.8421	Intermediate Similarity	NPC472195
0.8421	Intermediate Similarity	NPC472196
0.84	Intermediate Similarity	NPC197736
0.837	Intermediate Similarity	NPC311163
0.8367	Intermediate Similarity	NPC203627
0.8333	Intermediate Similarity	NPC256368
0.8333	Intermediate Similarity	NPC159698
0.83	Intermediate Similarity	NPC473596
0.828	Intermediate Similarity	NPC316138
0.828	Intermediate Similarity	NPC199382
0.828	Intermediate Similarity	NPC313658
0.8261	Intermediate Similarity	NPC471494
0.8222	Intermediate Similarity	NPC315731
0.8211	Intermediate Similarity	NPC177668
0.82	Intermediate Similarity	NPC154132
0.82	Intermediate Similarity	NPC2313
0.82	Intermediate Similarity	NPC475157
0.82	Intermediate Similarity	NPC475655
0.82	Intermediate Similarity	NPC57586
0.82	Intermediate Similarity	NPC471637
0.8125	Intermediate Similarity	NPC476084
0.8125	Intermediate Similarity	NPC114172
0.8125	Intermediate Similarity	NPC476075
0.8125	Intermediate Similarity	NPC471324
0.8125	Intermediate Similarity	NPC206679
0.8105	Intermediate Similarity	NPC133450
0.8058	Intermediate Similarity	NPC315070
0.8041	Intermediate Similarity	NPC189651
0.8041	Intermediate Similarity	NPC475098
0.8041	Intermediate Similarity	NPC109406
0.8041	Intermediate Similarity	NPC159092
0.8021	Intermediate Similarity	NPC3952
0.8	Intermediate Similarity	NPC161855
0.8	Intermediate Similarity	NPC139712
0.7979	Intermediate Similarity	NPC208473
0.7961	Intermediate Similarity	NPC472748
0.7957	Intermediate Similarity	NPC266718
0.7905	Intermediate Similarity	NPC473807
0.79	Intermediate Similarity	NPC471490
0.7885	Intermediate Similarity	NPC472751
0.7885	Intermediate Similarity	NPC472749
0.7865	Intermediate Similarity	NPC469880
0.7864	Intermediate Similarity	NPC472747
0.7864	Intermediate Similarity	NPC472750
0.7857	Intermediate Similarity	NPC320552
0.7843	Intermediate Similarity	NPC169365
0.7843	Intermediate Similarity	NPC197447
0.7835	Intermediate Similarity	NPC327253
0.7835	Intermediate Similarity	NPC471569
0.7822	Intermediate Similarity	NPC65700
0.78	Intermediate Similarity	NPC473291
0.7789	Intermediate Similarity	NPC186332
0.7789	Intermediate Similarity	NPC47220
0.7789	Intermediate Similarity	NPC61527
0.7766	Intermediate Similarity	NPC473308
0.7742	Intermediate Similarity	NPC251026
0.7736	Intermediate Similarity	NPC193765
0.7723	Intermediate Similarity	NPC2666
0.7717	Intermediate Similarity	NPC470147
0.7717	Intermediate Similarity	NPC133226
0.77	Intermediate Similarity	NPC471492
0.7685	Intermediate Similarity	NPC17791
0.767	Intermediate Similarity	NPC219038
0.766	Intermediate Similarity	NPC142111
0.766	Intermediate Similarity	NPC473315
0.766	Intermediate Similarity	NPC44261
0.7653	Intermediate Similarity	NPC202886
0.7642	Intermediate Similarity	NPC109376
0.7634	Intermediate Similarity	NPC112868
0.7634	Intermediate Similarity	NPC474894
0.7634	Intermediate Similarity	NPC469469
0.7624	Intermediate Similarity	NPC473333
0.7624	Intermediate Similarity	NPC472995
0.7615	Intermediate Similarity	NPC317460
0.7615	Intermediate Similarity	NPC328074
0.7615	Intermediate Similarity	NPC321272
0.7615	Intermediate Similarity	NPC470025
0.7609	Intermediate Similarity	NPC180725
0.7609	Intermediate Similarity	NPC470148
0.7609	Intermediate Similarity	NPC470149
0.76	Intermediate Similarity	NPC472198
0.76	Intermediate Similarity	NPC469491
0.7596	Intermediate Similarity	NPC303653
0.7596	Intermediate Similarity	NPC140591
0.7596	Intermediate Similarity	NPC291500
0.7596	Intermediate Similarity	NPC471599
0.7596	Intermediate Similarity	NPC189609
0.7596	Intermediate Similarity	NPC201191
0.7596	Intermediate Similarity	NPC197835
0.7593	Intermediate Similarity	NPC316708
0.7582	Intermediate Similarity	NPC477203
0.7582	Intermediate Similarity	NPC474026
0.7579	Intermediate Similarity	NPC78673
0.7579	Intermediate Similarity	NPC160517
0.7579	Intermediate Similarity	NPC186155
0.7576	Intermediate Similarity	NPC472197
0.7576	Intermediate Similarity	NPC477749
0.7576	Intermediate Similarity	NPC175842
0.7576	Intermediate Similarity	NPC32494
0.7576	Intermediate Similarity	NPC472199
0.7573	Intermediate Similarity	NPC475053
0.7573	Intermediate Similarity	NPC244878
0.757	Intermediate Similarity	NPC224660
0.757	Intermediate Similarity	NPC470024
0.7556	Intermediate Similarity	NPC327041
0.7556	Intermediate Similarity	NPC285840
0.7553	Intermediate Similarity	NPC477385
0.7553	Intermediate Similarity	NPC477390
0.7551	Intermediate Similarity	NPC477748
0.7549	Intermediate Similarity	NPC40812
0.7547	Intermediate Similarity	NPC476738
0.7547	Intermediate Similarity	NPC265502
0.7547	Intermediate Similarity	NPC82251
0.7547	Intermediate Similarity	NPC476740
0.7547	Intermediate Similarity	NPC469960
0.7547	Intermediate Similarity	NPC29389
0.7547	Intermediate Similarity	NPC93026
0.7547	Intermediate Similarity	NPC172867
0.7545	Intermediate Similarity	NPC470027
0.7545	Intermediate Similarity	NPC101400
0.7545	Intermediate Similarity	NPC101965
0.7528	Intermediate Similarity	NPC329914
0.7526	Intermediate Similarity	NPC475186
0.7526	Intermediate Similarity	NPC118077
0.7525	Intermediate Similarity	NPC170204
0.7525	Intermediate Similarity	NPC272050
0.7524	Intermediate Similarity	NPC309398
0.7524	Intermediate Similarity	NPC473816
0.7524	Intermediate Similarity	NPC475367
0.7524	Intermediate Similarity	NPC474581
0.7523	Intermediate Similarity	NPC470026
0.75	Intermediate Similarity	NPC478036
0.75	Intermediate Similarity	NPC320089
0.75	Intermediate Similarity	NPC471223
0.75	Intermediate Similarity	NPC242233
0.75	Intermediate Similarity	NPC20673
0.75	Intermediate Similarity	NPC61201
0.75	Intermediate Similarity	NPC38154
0.75	Intermediate Similarity	NPC248775
0.75	Intermediate Similarity	NPC198992
0.75	Intermediate Similarity	NPC67081
0.75	Intermediate Similarity	NPC59646
0.75	Intermediate Similarity	NPC476049
0.75	Intermediate Similarity	NPC478037
0.7477	Intermediate Similarity	NPC469959
0.7477	Intermediate Similarity	NPC108682
0.7477	Intermediate Similarity	NPC472263
0.7477	Intermediate Similarity	NPC469957
0.7476	Intermediate Similarity	NPC255592
0.7476	Intermediate Similarity	NPC261377
0.7476	Intermediate Similarity	NPC308567
0.7476	Intermediate Similarity	NPC151093
0.7475	Intermediate Similarity	NPC473311
0.7473	Intermediate Similarity	NPC477202
0.7455	Intermediate Similarity	NPC313921
0.7455	Intermediate Similarity	NPC98038
0.7451	Intermediate Similarity	NPC472997
0.7451	Intermediate Similarity	NPC472996
0.7449	Intermediate Similarity	NPC260343
0.7449	Intermediate Similarity	NPC60765
0.7449	Intermediate Similarity	NPC470137
0.7444	Intermediate Similarity	NPC107654
0.7431	Intermediate Similarity	NPC89408
0.7431	Intermediate Similarity	NPC472508
0.7429	Intermediate Similarity	NPC472754
0.7426	Intermediate Similarity	NPC71589
0.7426	Intermediate Similarity	NPC470521
0.7419	Intermediate Similarity	NPC1180
0.7419	Intermediate Similarity	NPC471537
0.7407	Intermediate Similarity	NPC472507
0.74	Intermediate Similarity	NPC470373
0.74	Intermediate Similarity	NPC470379
0.74	Intermediate Similarity	NPC158061
0.7396	Intermediate Similarity	NPC475035
0.7391	Intermediate Similarity	NPC315394
0.7391	Intermediate Similarity	NPC233071
0.7391	Intermediate Similarity	NPC475711
0.7387	Intermediate Similarity	NPC287075
0.7383	Intermediate Similarity	NPC239961
0.7383	Intermediate Similarity	NPC218158
0.7374	Intermediate Similarity	NPC285588
0.7368	Intermediate Similarity	NPC10080
0.7368	Intermediate Similarity	NPC123908
0.7368	Intermediate Similarity	NPC219656
0.7364	Intermediate Similarity	NPC126897
0.7364	Intermediate Similarity	NPC297945
0.7358	Intermediate Similarity	NPC472755
0.7353	Intermediate Similarity	NPC36954
0.7353	Intermediate Similarity	NPC469583
0.7353	Intermediate Similarity	NPC471141

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 NPC173329 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1382
0.2-0.3	3502
0.3-0.4	2553
0.4-0.5	1160
0.5-0.6	306
0.6-0.7	65
0.7-0.8	6
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8602	High Similarity	NPD7838	Discovery
0.8367	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD6698	Approved
0.7835	Intermediate Similarity	NPD46	Approved
0.7404	Intermediate Similarity	NPD6648	Approved
0.74	Intermediate Similarity	NPD7983	Approved
0.7364	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5344	Discontinued
0.7248	Intermediate Similarity	NPD6686	Approved
0.7241	Intermediate Similarity	NPD7503	Approved
0.7156	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7839	Suspended
0.6833	Remote Similarity	NPD7830	Approved
0.6833	Remote Similarity	NPD7829	Approved
0.6719	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6604	Remote Similarity	NPD5282	Discontinued
0.66	Remote Similarity	NPD6110	Phase 1
0.66	Remote Similarity	NPD7154	Phase 3
0.6583	Remote Similarity	NPD8377	Approved
0.6583	Remote Similarity	NPD8294	Approved
0.6569	Remote Similarity	NPD4249	Approved
0.6555	Remote Similarity	NPD7641	Discontinued
0.6555	Remote Similarity	NPD7327	Approved
0.6555	Remote Similarity	NPD7328	Approved
0.6529	Remote Similarity	NPD8335	Approved
0.6529	Remote Similarity	NPD8378	Approved
0.6529	Remote Similarity	NPD8444	Approved
0.6529	Remote Similarity	NPD8380	Approved
0.6529	Remote Similarity	NPD8379	Approved
0.6529	Remote Similarity	NPD8296	Approved
0.6522	Remote Similarity	NPD6371	Approved
0.6514	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD7516	Approved
0.6495	Remote Similarity	NPD4756	Discovery
0.6471	Remote Similarity	NPD7505	Discontinued
0.6457	Remote Similarity	NPD7260	Phase 2
0.6452	Remote Similarity	NPD8451	Approved
0.6446	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7637	Suspended
0.641	Remote Similarity	NPD6053	Discontinued
0.64	Remote Similarity	NPD8074	Phase 3
0.64	Remote Similarity	NPD8448	Approved
0.6381	Remote Similarity	NPD6101	Approved
0.6381	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7638	Approved
0.6341	Remote Similarity	NPD8080	Discontinued
0.6333	Remote Similarity	NPD7500	Approved
0.633	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8273	Phase 1
0.6306	Remote Similarity	NPD7639	Approved
0.6306	Remote Similarity	NPD7640	Approved
0.63	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7642	Approved
0.629	Remote Similarity	NPD8328	Phase 3
0.6271	Remote Similarity	NPD8297	Approved
0.6262	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD8390	Approved
0.625	Remote Similarity	NPD8392	Approved
0.625	Remote Similarity	NPD8391	Approved
0.624	Remote Similarity	NPD8299	Approved
0.624	Remote Similarity	NPD8342	Approved
0.624	Remote Similarity	NPD8341	Approved
0.624	Remote Similarity	NPD8340	Approved
0.6239	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7524	Approved
0.619	Remote Similarity	NPD7507	Approved
0.6186	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5785	Approved
0.6154	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4822	Approved
0.6139	Remote Similarity	NPD4820	Approved
0.6139	Remote Similarity	NPD4819	Approved
0.6139	Remote Similarity	NPD4821	Approved
0.6134	Remote Similarity	NPD6882	Approved
0.6129	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD8039	Approved
0.6121	Remote Similarity	NPD6412	Phase 2
0.6117	Remote Similarity	NPD6695	Phase 3
0.6111	Remote Similarity	NPD7492	Approved
0.6102	Remote Similarity	NPD2067	Discontinued
0.61	Remote Similarity	NPD4268	Approved
0.61	Remote Similarity	NPD4271	Approved
0.6094	Remote Similarity	NPD7736	Approved
0.6066	Remote Similarity	NPD6009	Approved
0.6066	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6616	Approved
0.6061	Remote Similarity	NPD8415	Approved
0.6048	Remote Similarity	NPD6054	Approved
0.6048	Remote Similarity	NPD6319	Approved
0.6047	Remote Similarity	NPD7319	Approved
0.6038	Remote Similarity	NPD7750	Discontinued
0.6034	Remote Similarity	NPD4211	Phase 1
0.6031	Remote Similarity	NPD6845	Suspended
0.6019	Remote Similarity	NPD5209	Approved
0.6016	Remote Similarity	NPD7078	Approved
0.6015	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5363	Approved
0.598	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5362	Discontinued
0.5952	Remote Similarity	NPD6370	Approved
0.595	Remote Similarity	NPD8133	Approved
0.5942	Remote Similarity	NPD7266	Discontinued
0.5935	Remote Similarity	NPD7115	Discovery
0.5935	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6899	Approved
0.5932	Remote Similarity	NPD6881	Approved
0.5926	Remote Similarity	NPD1695	Approved
0.5917	Remote Similarity	NPD6649	Approved
0.5917	Remote Similarity	NPD6650	Approved
0.5917	Remote Similarity	NPD8130	Phase 1
0.5914	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD8293	Discontinued
0.5882	Remote Similarity	NPD6929	Approved
0.5882	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD6016	Approved
0.5873	Remote Similarity	NPD6015	Approved
0.5872	Remote Similarity	NPD3168	Discontinued
0.5872	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD969	Suspended
0.5865	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6435	Approved
0.5862	Remote Similarity	NPD1407	Approved
0.5847	Remote Similarity	NPD5697	Approved
0.5841	Remote Similarity	NPD6084	Phase 2
0.5841	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD7290	Approved
0.5833	Remote Similarity	NPD7102	Approved
0.5833	Remote Similarity	NPD6883	Approved
0.5833	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD5988	Approved
0.5825	Remote Similarity	NPD6931	Approved
0.5825	Remote Similarity	NPD7514	Phase 3
0.5825	Remote Similarity	NPD6930	Phase 2
0.5825	Remote Similarity	NPD7332	Phase 2
0.582	Remote Similarity	NPD4632	Approved
0.581	Remote Similarity	NPD5331	Approved
0.581	Remote Similarity	NPD5332	Approved
0.58	Remote Similarity	NPD8264	Approved
0.5794	Remote Similarity	NPD6059	Approved
0.5785	Remote Similarity	NPD6847	Approved
0.5785	Remote Similarity	NPD6617	Approved
0.5785	Remote Similarity	NPD6869	Approved
0.5784	Remote Similarity	NPD7145	Approved
0.5781	Remote Similarity	NPD7604	Phase 2
0.5776	Remote Similarity	NPD7632	Discontinued
0.5769	Remote Similarity	NPD4790	Discontinued
0.5769	Remote Similarity	NPD6902	Approved
0.5763	Remote Similarity	NPD5739	Approved
0.5763	Remote Similarity	NPD7128	Approved
0.5763	Remote Similarity	NPD6402	Approved
0.5763	Remote Similarity	NPD6675	Approved
0.575	Remote Similarity	NPD6014	Approved
0.575	Remote Similarity	NPD6372	Approved
0.575	Remote Similarity	NPD6012	Approved
0.575	Remote Similarity	NPD6373	Approved
0.575	Remote Similarity	NPD6013	Approved
0.5748	Remote Similarity	NPD5983	Phase 2
0.5729	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6647	Phase 2
0.5714	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6685	Approved
0.5714	Remote Similarity	NPD4269	Approved
0.5714	Remote Similarity	NPD4270	Approved
0.5703	Remote Similarity	NPD5126	Approved
0.5703	Remote Similarity	NPD7623	Phase 3
0.5703	Remote Similarity	NPD5125	Phase 3
0.5703	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6421	Discontinued
0.5701	Remote Similarity	NPD1694	Approved
0.5692	Remote Similarity	NPD6336	Discontinued
0.5686	Remote Similarity	NPD5776	Phase 2
0.5686	Remote Similarity	NPD6932	Approved
0.5686	Remote Similarity	NPD6925	Approved
0.5683	Remote Similarity	NPD8384	Approved
0.5676	Remote Similarity	NPD7087	Discontinued
0.5673	Remote Similarity	NPD5368	Approved
0.5667	Remote Similarity	NPD7320	Approved
0.5667	Remote Similarity	NPD6011	Approved
0.5664	Remote Similarity	NPD5695	Phase 3
0.5649	Remote Similarity	NPD7746	Phase 1
0.5649	Remote Similarity	NPD7747	Phase 1
0.5648	Remote Similarity	NPD5786	Approved
0.5636	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6640	Phase 3

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