NPASS Compound

Structure

NPC473404 OpenBabel07101719182D 70 72 0 0 1 0 0 0 0 0999 V2000 5.9139 4.3615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1101 -5.6126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4277 -5.7054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0858 2.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7682 1.9327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4811 -0.1022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5389 -1.6754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1982 5.0204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2698 4.7300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0571 3.7807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2592 -4.5844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3482 -4.9255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1286 3.4903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7705 -2.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6129 -0.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6129 -2.8965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4554 -1.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8255 -4.5315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 1.0110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3632 -3.8680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1306 1.6699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4193 -3.6249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1885 -4.2020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0855 -0.4645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2421 -5.1734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9002 1.4935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6973 -0.6783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7705 -1.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4554 -2.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5973 -4.3071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7747 1.3014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0089 -5.3656 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2431 -0.9509 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3206 -3.7628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9159 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2172 -3.8747 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3433 2.6192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8466 0.5222 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1365 -1.5463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1363 -4.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4904 0.6426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6246 -0.2000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2701 -2.5099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9450 -5.1009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6110 -2.8343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8798 0.4152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4905 -2.3243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7396 -1.7058 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4015 -1.9832 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3304 -3.2838 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9875 2.2507 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0837 -3.4646 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 -5.3120 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7959 0.3094 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0650 -1.2559 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5842 -1.8619 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7444 -4.5466 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.2978 -2.8965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6316 1.8822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6462 -3.0016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2717 2.9095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3724 3.2780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3731 -5.7747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4189 0.9330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2635 0.5336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2426 -2.5367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3602 -5.9807 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5745 -2.9680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6151 1.3513 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 8 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 7 56 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 13 35 1 0 0 0 0 14 16 1 0 0 0 0 14 28 2 0 0 0 0 15 17 2 0 0 0 0 15 28 1 0 0 0 0 16 29 2 0 0 0 0 17 29 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 36 1 0 0 0 0 21 37 1 0 0 0 0 22 50 1 0 0 0 0 23 25 1 0 0 0 0 24 28 1 0 0 0 0 27 6 1 6 0 0 0 27 39 1 0 0 0 0 27 70 1 0 0 0 0 29 58 1 0 0 0 0 30 12 1 1 0 0 0 30 40 1 0 0 0 0 30 52 1 0 0 0 0 31 19 1 6 0 0 0 31 41 1 0 0 0 0 31 51 1 0 0 0 0 32 18 1 1 0 0 0 32 44 1 0 0 0 0 32 53 1 0 0 0 0 33 24 1 1 0 0 0 33 42 1 0 0 0 0 33 56 1 0 0 0 0 34 23 1 1 0 0 0 34 45 1 0 0 0 0 34 57 1 0 0 0 0 35 51 2 3 0 0 0 35 59 1 0 0 0 0 36 57 1 0 0 0 0 36 60 1 6 0 0 0 37 61 2 0 0 0 0 37 62 1 0 0 0 0 38 26 1 1 0 0 0 38 46 1 0 0 0 0 38 54 1 0 0 0 0 39 43 1 0 0 0 0 39 55 1 6 0 0 0 40 53 2 3 0 0 0 40 63 1 0 0 0 0 41 55 2 3 0 0 0 41 64 1 0 0 0 0 42 54 2 3 0 0 0 42 65 1 0 0 0 0 43 52 2 3 0 0 0 43 66 1 0 0 0 0 44 57 1 0 0 0 0 44 67 2 0 0 0 0 45 56 1 0 0 0 0 45 68 2 0 0 0 0 46 69 2 0 0 0 0 46 70 1 0 0 0 0 47 48 2 0 0 0 0 47 49 1 0 0 0 0 47 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	986.54
Volume:	985.765
LogP:	0.577
LogD:	0.283
LogS:	-2.087
# Rotatable Bonds:	22
TPSA:	355.57
# H-Bond Aceptor:	23
# H-Bond Donor:	12
# Rings:	3
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.039
Synthetic Accessibility Score:	6.904
Fsp3:	0.66
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:	-7.172
MDCK Permeability:	4.8427809815621004e-05
Pgp-inhibitor:	0.073
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.975
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	49.286956787109375%
Volume Distribution (VD):	0.442
Pgp-substrate:	42.815120697021484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.026
CYP2C9-inhibitor:	0.098
CYP2C9-substrate:	0.593
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	3.035
Half-life (T1/2):	0.881

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.954
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.157
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.366
Carcinogencity:	0.101
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.533

Download Data

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

Natural Product: NPC473404

Natural Product ID:	NPC473404
*Common Name:**	Micropeptin B
IUPAC Name:	(4S)-5-[[(2S,5S,8S,11R,12S,15S,18S,21R)-15-[3-(diaminomethylideneamino)propyl]-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-2-(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-4-(hexanoylamino)-5-oxopentanoic acid
Synonyms:
Standard InCHIKey:	IJAPBAZLQXFSLT-MYAMMQBASA-N
Standard InCHI:	InChI=1S/C47H74N10O13/c1-8-9-10-13-35(59)51-31(19-21-37(61)62)41(64)55-39-27(6)70-46(69)38(26(4)5)54-42(65)33(24-28-14-16-29(58)17-15-28)56(7)45(68)34(23-25(2)3)57-36(60)20-18-32(44(57)67)53-40(63)30(52-43(39)66)12-11-22-50-47(48)49/h14-17,25-27,30-34,36,38-39,58,60H,8-13,18-24H2,1-7H3,(H,51,59)(H,52,66)(H,53,63)(H,54,65)(H,55,64)(H,61,62)(H4,48,49,50)/t27-,30+,31+,32+,33+,34+,36-,38+,39+/m1/s1
SMILES:	CCCCCC(=N[C@H](C(=N[C@H]1[C@@H](C)OC(=O)[C@@H](N=C(O)[C@H](Cc2ccc(cc2)O)N(C)C(=O)[C@@H](N2C(=O)[C@@H](N=C([C@@H](N=C1O)CCCNC(=N)N)O)CC[C@H]2O)CC(C)C)C(C)C)O)CCC(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL412954
PubChem CID:	44448129
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11000050]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374973]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Einan Reservoir in Israel	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18163584]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18558743]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18973386]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	water bloom of the cyanobacterium Microcystis aeruginosa	n.a.	n.a.	PMID[19650639]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	bloom material	Lake Kinneret, Israel	n.a.	PMID[22280481]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Kibbutz Geva, Israel	n.a.	PMID[23153007]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Water Reservoir near Kibbutz Hafetz Haim, Israel	n.a.	PMID[23718637]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[24261937]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24642434]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24868986]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29405714]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[29847132]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9249979]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9842728]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[Title]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	260.0	nM	PMID[540223]
NPT2	Others	Unspecified		IC50	=	0.25	ug.mL-1	PMID[540224]

☑ 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 NPC473404 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	192
0.1-0.2	1012
0.2-0.3	4943
0.3-0.4	12423
0.4-0.5	17071
0.5-0.6	6015
0.6-0.7	660
0.7-0.8	246
0.8-0.85	85
0.85-0.9	43
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9503	High Similarity	NPC46009
0.9408	High Similarity	NPC102959
0.9353	High Similarity	NPC60516
0.9353	High Similarity	NPC240130
0.9353	High Similarity	NPC61332
0.9191	High Similarity	NPC302715
0.9036	High Similarity	NPC306804
0.903	High Similarity	NPC475204
0.903	High Similarity	NPC475123
0.9024	High Similarity	NPC294516
0.9024	High Similarity	NPC107938
0.8989	High Similarity	NPC477551
0.8922	High Similarity	NPC273755
0.8883	High Similarity	NPC469443
0.8876	High Similarity	NPC477550
0.8876	High Similarity	NPC477552
0.8869	High Similarity	NPC473402
0.8862	High Similarity	NPC230611
0.8824	High Similarity	NPC269750
0.8824	High Similarity	NPC194671
0.8824	High Similarity	NPC45037
0.8817	High Similarity	NPC50016
0.8802	High Similarity	NPC274198
0.8802	High Similarity	NPC198254
0.8757	High Similarity	NPC155506
0.8757	High Similarity	NPC159767
0.8698	High Similarity	NPC137627
0.869	High Similarity	NPC276506
0.869	High Similarity	NPC40234
0.8659	High Similarity	NPC1390
0.8659	High Similarity	NPC62104
0.8647	High Similarity	NPC476227
0.8647	High Similarity	NPC279871
0.8603	High Similarity	NPC477638
0.8603	High Similarity	NPC477632
0.8596	High Similarity	NPC196243
0.8595	High Similarity	NPC220060
0.8571	High Similarity	NPC473450
0.8548	High Similarity	NPC469444
0.8538	High Similarity	NPC473354
0.8492	Intermediate Similarity	NPC477631
0.8466	Intermediate Similarity	NPC473341
0.8452	Intermediate Similarity	NPC5719
0.8452	Intermediate Similarity	NPC210377
0.8452	Intermediate Similarity	NPC217804
0.8452	Intermediate Similarity	NPC22883
0.843	Intermediate Similarity	NPC471165
0.8413	Intermediate Similarity	NPC469445
0.8412	Intermediate Similarity	NPC129486
0.8396	Intermediate Similarity	NPC219350
0.8396	Intermediate Similarity	NPC194699
0.8383	Intermediate Similarity	NPC469243
0.838	Intermediate Similarity	NPC477636
0.8372	Intermediate Similarity	NPC475532
0.8371	Intermediate Similarity	NPC94862
0.8364	Intermediate Similarity	NPC473580
0.8353	Intermediate Similarity	NPC63040
0.8343	Intermediate Similarity	NPC153554
0.8324	Intermediate Similarity	NPC17698
0.8324	Intermediate Similarity	NPC26108
0.8324	Intermediate Similarity	NPC165285
0.8305	Intermediate Similarity	NPC294951
0.8304	Intermediate Similarity	NPC280022
0.8295	Intermediate Similarity	NPC476321
0.8294	Intermediate Similarity	NPC15068
0.8274	Intermediate Similarity	NPC475544
0.8251	Intermediate Similarity	NPC477639
0.8249	Intermediate Similarity	NPC471526
0.8235	Intermediate Similarity	NPC223207
0.8232	Intermediate Similarity	NPC248822
0.822	Intermediate Similarity	NPC277306
0.822	Intermediate Similarity	NPC469442
0.8187	Intermediate Similarity	NPC61004
0.8187	Intermediate Similarity	NPC471771
0.8187	Intermediate Similarity	NPC290755
0.8187	Intermediate Similarity	NPC304074
0.8161	Intermediate Similarity	NPC248670
0.8135	Intermediate Similarity	NPC25539
0.8129	Intermediate Similarity	NPC63931
0.8101	Intermediate Similarity	NPC471050
0.8101	Intermediate Similarity	NPC471049
0.8101	Intermediate Similarity	NPC471048
0.809	Intermediate Similarity	NPC477637
0.8079	Intermediate Similarity	NPC97526
0.8079	Intermediate Similarity	NPC119652
0.8077	Intermediate Similarity	NPC163961
0.8077	Intermediate Similarity	NPC473305
0.8043	Intermediate Similarity	NPC328763
0.8025	Intermediate Similarity	NPC91953
0.8024	Intermediate Similarity	NPC262166
0.8012	Intermediate Similarity	NPC163392
0.8012	Intermediate Similarity	NPC239762
0.8012	Intermediate Similarity	NPC48202
0.7988	Intermediate Similarity	NPC81026
0.7964	Intermediate Similarity	NPC300443
0.7963	Intermediate Similarity	NPC197921
0.7956	Intermediate Similarity	NPC299806
0.7953	Intermediate Similarity	NPC114806
0.7946	Intermediate Similarity	NPC65714
0.7935	Intermediate Similarity	NPC473378
0.7935	Intermediate Similarity	NPC473407
0.7933	Intermediate Similarity	NPC475409
0.7933	Intermediate Similarity	NPC170302
0.7933	Intermediate Similarity	NPC475564
0.7929	Intermediate Similarity	NPC244509
0.7927	Intermediate Similarity	NPC266741
0.7914	Intermediate Similarity	NPC469360
0.791	Intermediate Similarity	NPC158277
0.7895	Intermediate Similarity	NPC24617
0.7895	Intermediate Similarity	NPC244336
0.7872	Intermediate Similarity	NPC323662
0.787	Intermediate Similarity	NPC39431
0.7861	Intermediate Similarity	NPC473371
0.7829	Intermediate Similarity	NPC302597
0.7821	Intermediate Similarity	NPC473546
0.7819	Intermediate Similarity	NPC471592
0.7816	Intermediate Similarity	NPC472923
0.7811	Intermediate Similarity	NPC56685
0.7797	Intermediate Similarity	NPC328494
0.7797	Intermediate Similarity	NPC89831
0.7791	Intermediate Similarity	NPC214988
0.7784	Intermediate Similarity	NPC66490
0.7784	Intermediate Similarity	NPC478005
0.7766	Intermediate Similarity	NPC329295
0.7754	Intermediate Similarity	NPC314083
0.7746	Intermediate Similarity	NPC471527
0.7733	Intermediate Similarity	NPC323336
0.7733	Intermediate Similarity	NPC326349
0.7727	Intermediate Similarity	NPC328649
0.7706	Intermediate Similarity	NPC5194
0.7706	Intermediate Similarity	NPC261934
0.7692	Intermediate Similarity	NPC473491
0.768	Intermediate Similarity	NPC475421
0.7676	Intermediate Similarity	NPC96275
0.7627	Intermediate Similarity	NPC209463
0.7624	Intermediate Similarity	NPC478007
0.7619	Intermediate Similarity	NPC311658
0.7619	Intermediate Similarity	NPC16188
0.7616	Intermediate Similarity	NPC476268
0.7602	Intermediate Similarity	NPC202198
0.7594	Intermediate Similarity	NPC51047
0.759	Intermediate Similarity	NPC168861
0.7588	Intermediate Similarity	NPC7817
0.7588	Intermediate Similarity	NPC475168
0.7584	Intermediate Similarity	NPC186617
0.7558	Intermediate Similarity	NPC470902
0.7554	Intermediate Similarity	NPC470903
0.7554	Intermediate Similarity	NPC470112
0.7554	Intermediate Similarity	NPC167763
0.7549	Intermediate Similarity	NPC478008
0.7546	Intermediate Similarity	NPC267237
0.7544	Intermediate Similarity	NPC233702
0.7542	Intermediate Similarity	NPC473693
0.7542	Intermediate Similarity	NPC471568
0.7542	Intermediate Similarity	NPC196091
0.753	Intermediate Similarity	NPC476989
0.7529	Intermediate Similarity	NPC2501
0.75	Intermediate Similarity	NPC122590
0.75	Intermediate Similarity	NPC241794
0.7455	Intermediate Similarity	NPC6570
0.7447	Intermediate Similarity	NPC246591
0.7429	Intermediate Similarity	NPC324850
0.7423	Intermediate Similarity	NPC326966
0.738	Intermediate Similarity	NPC315542
0.7374	Intermediate Similarity	NPC254700
0.7368	Intermediate Similarity	NPC470728
0.7368	Intermediate Similarity	NPC477526
0.736	Intermediate Similarity	NPC471051
0.736	Intermediate Similarity	NPC471052
0.736	Intermediate Similarity	NPC471053
0.7344	Intermediate Similarity	NPC80514
0.7337	Intermediate Similarity	NPC52748
0.7333	Intermediate Similarity	NPC141957
0.7333	Intermediate Similarity	NPC473502
0.7322	Intermediate Similarity	NPC136797
0.7316	Intermediate Similarity	NPC174122
0.7316	Intermediate Similarity	NPC64140
0.7313	Intermediate Similarity	NPC326333
0.7305	Intermediate Similarity	NPC132636
0.7288	Intermediate Similarity	NPC287757
0.7288	Intermediate Similarity	NPC319320
0.7287	Intermediate Similarity	NPC235194
0.7267	Intermediate Similarity	NPC471820
0.7267	Intermediate Similarity	NPC471821
0.7263	Intermediate Similarity	NPC234069
0.7254	Intermediate Similarity	NPC59827
0.7254	Intermediate Similarity	NPC184933
0.7251	Intermediate Similarity	NPC314358
0.7246	Intermediate Similarity	NPC127741
0.7241	Intermediate Similarity	NPC326027
0.7239	Intermediate Similarity	NPC469666
0.7235	Intermediate Similarity	NPC476978
0.7235	Intermediate Similarity	NPC326241
0.7232	Intermediate Similarity	NPC197743
0.7232	Intermediate Similarity	NPC297145
0.7211	Intermediate Similarity	NPC4910
0.7207	Intermediate Similarity	NPC73655
0.7202	Intermediate Similarity	NPC242159
0.7202	Intermediate Similarity	NPC313694
0.7196	Intermediate Similarity	NPC138083

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 NPC473404 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	119
0.1-0.2	365
0.2-0.3	709
0.3-0.4	1844
0.4-0.5	3450
0.5-0.6	2237
0.6-0.7	401
0.7-0.8	22
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8735	High Similarity	NPD8303	Discontinued
0.8214	Intermediate Similarity	NPD8019	Approved
0.8107	Intermediate Similarity	NPD7495	Discontinued
0.8024	Intermediate Similarity	NPD7523	Phase 3
0.7836	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8076	Discontinued
0.759	Intermediate Similarity	NPD7978	Discontinued
0.7578	Intermediate Similarity	NPD3136	Phase 2
0.7544	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7484	Phase 3
0.7486	Intermediate Similarity	NPD7485	Phase 3
0.7457	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6681	Discovery
0.7322	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7617	Discontinued
0.7305	Intermediate Similarity	NPD6901	Phase 3
0.7287	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7608	Discontinued
0.7222	Intermediate Similarity	NPD8031	Discontinued
0.7151	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7303	Discontinued
0.7143	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6851	Approved
0.7105	Intermediate Similarity	NPD6853	Approved
0.7102	Intermediate Similarity	NPD7131	Phase 3
0.7076	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4652	Approved
0.7033	Intermediate Similarity	NPD2098	Approved
0.7031	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7811	Phase 3
0.702	Intermediate Similarity	NPD7810	Phase 3
0.7018	Intermediate Similarity	NPD7450	Phase 2
0.7006	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1330	Phase 2
0.7	Intermediate Similarity	NPD8162	Phase 2
0.7	Intermediate Similarity	NPD8163	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3125	Approved
0.6944	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8172	Phase 2
0.6941	Remote Similarity	NPD8173	Phase 2
0.694	Remote Similarity	NPD5219	Approved
0.694	Remote Similarity	NPD5218	Approved
0.6936	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5137	Approved
0.6923	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2097	Approved
0.6919	Remote Similarity	NPD2889	Approved
0.6919	Remote Similarity	NPD2017	Approved
0.6919	Remote Similarity	NPD2888	Approved
0.6919	Remote Similarity	NPD2890	Approved
0.6895	Remote Similarity	NPD6297	Approved
0.6893	Remote Similarity	NPD6419	Discontinued
0.6848	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6073	Approved
0.6837	Remote Similarity	NPD8292	Phase 2
0.6836	Remote Similarity	NPD6088	Approved
0.6836	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2562	Approved
0.6829	Remote Similarity	NPD2561	Approved
0.6826	Remote Similarity	NPD4175	Approved
0.6826	Remote Similarity	NPD4177	Approved
0.6824	Remote Similarity	NPD5296	Approved
0.6818	Remote Similarity	NPD8323	Discontinued
0.6805	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3552	Approved
0.6802	Remote Similarity	NPD3554	Approved
0.6802	Remote Similarity	NPD3555	Approved
0.6802	Remote Similarity	NPD3553	Approved
0.68	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5745	Approved
0.6753	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5725	Approved
0.6744	Remote Similarity	NPD2568	Approved
0.6735	Remote Similarity	NPD4157	Discontinued
0.6721	Remote Similarity	NPD5355	Approved
0.6721	Remote Similarity	NPD5356	Approved
0.6705	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD3536	Discontinued
0.6703	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4659	Approved
0.6682	Remote Similarity	NPD6796	Discontinued
0.6667	Remote Similarity	NPD5747	Discontinued
0.6667	Remote Similarity	NPD6405	Approved
0.6667	Remote Similarity	NPD6407	Approved
0.6667	Remote Similarity	NPD7613	Discontinued
0.6667	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD317	Approved
0.6667	Remote Similarity	NPD16	Approved
0.6667	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD318	Approved
0.6667	Remote Similarity	NPD856	Approved
0.665	Remote Similarity	NPD8025	Phase 2
0.6649	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3052	Approved
0.6647	Remote Similarity	NPD5746	Approved
0.6647	Remote Similarity	NPD3054	Approved
0.6634	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6346	Approved
0.6628	Remote Similarity	NPD4153	Approved
0.6618	Remote Similarity	NPD6255	Approved
0.6618	Remote Similarity	NPD6256	Approved
0.6618	Remote Similarity	NPD6254	Approved
0.6609	Remote Similarity	NPD6294	Approved
0.6609	Remote Similarity	NPD6295	Approved
0.6609	Remote Similarity	NPD6852	Discontinued
0.659	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.659	Remote Similarity	NPD555	Phase 2
0.6587	Remote Similarity	NPD4677	Discontinued
0.6585	Remote Similarity	NPD6863	Phase 2
0.6576	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3400	Discontinued
0.6571	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6253	Approved
0.6568	Remote Similarity	NPD7451	Discontinued
0.6562	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5967	Approved
0.6552	Remote Similarity	NPD817	Approved
0.6552	Remote Similarity	NPD5314	Approved
0.6552	Remote Similarity	NPD823	Approved
0.6545	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3659	Discontinued
0.6534	Remote Similarity	NPD2240	Approved
0.6534	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD2239	Approved
0.6532	Remote Similarity	NPD6623	Phase 3
0.6528	Remote Similarity	NPD6042	Phase 2
0.6528	Remote Similarity	NPD42	Phase 2
0.6527	Remote Similarity	NPD3071	Approved
0.6527	Remote Similarity	NPD3073	Approved
0.6527	Remote Similarity	NPD2584	Suspended
0.6527	Remote Similarity	NPD3072	Approved
0.6522	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3157	Approved
0.6519	Remote Similarity	NPD3158	Phase 1
0.6512	Remote Similarity	NPD601	Approved
0.6512	Remote Similarity	NPD598	Approved
0.6512	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD597	Approved
0.6509	Remote Similarity	NPD1131	Approved
0.6509	Remote Similarity	NPD1129	Approved
0.6509	Remote Similarity	NPD1133	Approved
0.6509	Remote Similarity	NPD1134	Approved
0.6509	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4103	Phase 2
0.6509	Remote Similarity	NPD1135	Approved
0.6505	Remote Similarity	NPD7972	Discontinued
0.6503	Remote Similarity	NPD9568	Approved
0.6502	Remote Similarity	NPD7282	Approved
0.6495	Remote Similarity	NPD5557	Phase 1
0.6491	Remote Similarity	NPD5263	Approved
0.6484	Remote Similarity	NPD6390	Discontinued
0.6484	Remote Similarity	NPD2186	Approved
0.648	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3909	Discontinued
0.6474	Remote Similarity	NPD2245	Discovery
0.6474	Remote Similarity	NPD6107	Approved
0.6474	Remote Similarity	NPD1136	Approved
0.6474	Remote Similarity	NPD1132	Approved
0.6474	Remote Similarity	NPD1130	Approved
0.6474	Remote Similarity	NPD259	Phase 1
0.6471	Remote Similarity	NPD602	Approved
0.6471	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD599	Approved
0.6471	Remote Similarity	NPD4151	Approved
0.6468	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4762	Approved
0.6467	Remote Similarity	NPD4761	Approved
0.6467	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6967	Phase 2
0.6461	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4086	Phase 1
0.6452	Remote Similarity	NPD4227	Discontinued
0.6446	Remote Similarity	NPD7342	Discontinued
0.6445	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD9570	Approved
0.6437	Remote Similarity	NPD3062	Approved
0.6437	Remote Similarity	NPD3059	Approved
0.6437	Remote Similarity	NPD3061	Approved
0.6432	Remote Similarity	NPD8417	Discontinued
0.6425	Remote Similarity	NPD2459	Approved
0.6425	Remote Similarity	NPD2458	Approved
0.6425	Remote Similarity	NPD2460	Phase 3
0.6424	Remote Similarity	NPD316	Approved
0.6417	Remote Similarity	NPD5773	Approved
0.6417	Remote Similarity	NPD5772	Approved
0.6414	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6557	Phase 2
0.6413	Remote Similarity	NPD8315	Phase 1

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