NPASS Compound

Structure

NPC46009 OpenBabel07101718192D 70 72 0 0 1 0 0 0 0 0999 V2000 -1.1942 -6.4161 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 -2.1227 -6.7065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8384 -6.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6257 -5.0984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3414 -4.4396 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 -2.2592 4.5844 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 -1.3482 4.9255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8443 -2.8315 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 -4.8503 0.3847 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 -4.6376 1.3340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3304 3.2838 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 -4.1346 -0.2741 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 -3.6316 -1.8822 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 -5.3533 1.9928 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 -3.2061 0.0163 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 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3473 -1.2234 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 -2.9934 0.9655 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 -2.7032 -1.5918 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 -6.2817 1.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1405 2.9421 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 -2.4904 -0.6426 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 28 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 29 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 11 1 0 0 0 0 11 12 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 25 1 0 0 0 0 16 38 1 0 0 0 0 17 19 1 0 0 0 0 17 31 2 0 0 0 0 18 20 2 0 0 0 0 18 31 1 0 0 0 0 19 32 2 0 0 0 0 20 32 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 39 1 0 0 0 0 24 40 1 0 0 0 0 25 50 1 0 0 0 0 26 28 1 0 0 0 0 27 31 1 0 0 0 0 30 6 1 6 0 0 0 30 42 1 0 0 0 0 30 70 1 0 0 0 0 32 58 1 0 0 0 0 33 15 1 1 0 0 0 33 43 1 0 0 0 0 33 52 1 0 0 0 0 34 22 1 1 0 0 0 34 44 1 0 0 0 0 34 51 1 0 0 0 0 35 21 1 1 0 0 0 35 47 1 0 0 0 0 35 53 1 0 0 0 0 36 27 1 1 0 0 0 36 45 1 0 0 0 0 36 56 1 0 0 0 0 37 26 1 1 0 0 0 37 48 1 0 0 0 0 37 57 1 0 0 0 0 38 51 2 3 0 0 0 38 59 1 0 0 0 0 39 57 1 0 0 0 0 39 60 1 6 0 0 0 40 61 2 0 0 0 0 40 62 1 0 0 0 0 41 29 1 1 0 0 0 41 49 1 0 0 0 0 41 54 1 0 0 0 0 42 46 1 0 0 0 0 42 55 1 6 0 0 0 43 53 2 3 0 0 0 43 63 1 0 0 0 0 44 55 2 3 0 0 0 44 64 1 0 0 0 0 45 54 2 3 0 0 0 45 65 1 0 0 0 0 46 52 2 3 0 0 0 46 66 1 0 0 0 0 47 57 1 0 0 0 0 47 67 2 0 0 0 0 48 56 1 0 0 0 0 48 68 2 0 0 0 0 49 69 2 0 0 0 0 49 70 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	986.57
Volume:	1001.0
LogP:	1.669
LogD:	0.985
LogS:	-2.477
# Rotatable Bonds:	23
TPSA:	319.69
# H-Bond Aceptor:	21
# H-Bond Donor:	10
# Rings:	3
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.063
Synthetic Accessibility Score:	6.842
Fsp3:	0.694
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:	-6.535
MDCK Permeability:	4.2997846321668476e-05
Pgp-inhibitor:	0.673
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.966
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	50.76382064819336%
Volume Distribution (VD):	0.477
Pgp-substrate:	40.2503547668457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.105
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.125
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	3.305
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.332
Carcinogencity:	0.112
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.64

Download Data

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

Natural Product: NPC46009

Natural Product ID:	NPC46009
*Common Name:**	Micropeptin A
IUPAC Name:	(4S)-5-[[(2S,5S,8S,11R,12S,15S,18S,21R)-15-(4-aminobutyl)-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-(octanoylamino)-5-oxopentanoic acid
Synonyms:	Micropeptin A
Standard InCHIKey:	NIHAVBBFFMHNQH-VWAREKNTSA-N
Standard InCHI:	InChI=1S/C49H78N8O13/c1-8-9-10-11-12-16-38(59)51-34(22-24-40(61)62)44(64)55-42-30(6)70-49(69)41(29(4)5)54-45(65)36(27-31-17-19-32(58)20-18-31)56(7)48(68)37(26-28(2)3)57-39(60)23-21-35(47(57)67)53-43(63)33(52-46(42)66)15-13-14-25-50/h17-20,28-30,33-37,39,41-42,58,60H,8-16,21-27,50H2,1-7H3,(H,51,59)(H,52,66)(H,53,63)(H,54,65)(H,55,64)(H,61,62)/t30-,33+,34+,35+,36+,37+,39-,41+,42+/m1/s1
SMILES:	CCCCCCCC(=N[C@@H](CCC(=O)O)C(=N[C@H]1[C@@H](C)OC(=O)[C@H](C(C)C)N=C([C@H](Cc2ccc(cc2)O)N(C)C(=O)[C@H](CC(C)C)N2[C@@H](CC[C@@H](C2=O)N=C([C@H](CCCCN)N=C1O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563769
PubChem CID:	45268664
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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	=	70.0	nM	PMID[507813]
NPT2	Others	Unspecified	IC50	>	100000.0	nM	PMID[507814]
NPT2	Others	Unspecified	IC50	=	70.0	nM	PMID[507814]

☑ 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 NPC46009 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	177
0.1-0.2	939
0.2-0.3	4044
0.3-0.4	12858
0.4-0.5	13776
0.5-0.6	9564
0.6-0.7	879
0.7-0.8	319
0.8-0.85	93
0.85-0.9	28
0.9-0.95	19
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9503	High Similarity	NPC473404
0.9494	High Similarity	NPC306804
0.949	High Similarity	NPC475123
0.949	High Similarity	NPC475204
0.9487	High Similarity	NPC294516
0.9487	High Similarity	NPC107938
0.9371	High Similarity	NPC273755
0.9313	High Similarity	NPC473402
0.9308	High Similarity	NPC230611
0.9259	High Similarity	NPC45037
0.9259	High Similarity	NPC194671
0.9259	High Similarity	NPC269750
0.9255	High Similarity	NPC50016
0.9193	High Similarity	NPC155506
0.9193	High Similarity	NPC159767
0.913	High Similarity	NPC137627
0.9125	High Similarity	NPC40234
0.9074	High Similarity	NPC279871
0.9074	High Similarity	NPC476227
0.8957	High Similarity	NPC473354
0.8935	High Similarity	NPC102959
0.8903	High Similarity	NPC473341
0.8882	High Similarity	NPC60516
0.8882	High Similarity	NPC61332
0.8882	High Similarity	NPC240130
0.8841	High Similarity	NPC471165
0.8728	High Similarity	NPC302715
0.8727	High Similarity	NPC26108
0.8698	High Similarity	NPC294951
0.869	High Similarity	NPC476321
0.8639	High Similarity	NPC471526
0.8613	High Similarity	NPC248822
0.8589	High Similarity	NPC61004
0.8554	High Similarity	NPC248670
0.8539	High Similarity	NPC477551
0.8528	High Similarity	NPC63931
0.848	Intermediate Similarity	NPC471049
0.848	Intermediate Similarity	NPC471048
0.848	Intermediate Similarity	NPC471050
0.8471	Intermediate Similarity	NPC477637
0.8448	Intermediate Similarity	NPC473305
0.8448	Intermediate Similarity	NPC163961
0.8442	Intermediate Similarity	NPC91953
0.8436	Intermediate Similarity	NPC469443
0.8431	Intermediate Similarity	NPC239762
0.8431	Intermediate Similarity	NPC163392
0.8428	Intermediate Similarity	NPC262166
0.8427	Intermediate Similarity	NPC477552
0.8427	Intermediate Similarity	NPC477550
0.8409	Intermediate Similarity	NPC328763
0.8397	Intermediate Similarity	NPC81026
0.8377	Intermediate Similarity	NPC197921
0.8333	Intermediate Similarity	NPC266741
0.8333	Intermediate Similarity	NPC473450
0.8323	Intermediate Similarity	NPC274198
0.8323	Intermediate Similarity	NPC198254
0.8323	Intermediate Similarity	NPC469360
0.8323	Intermediate Similarity	NPC244509
0.8305	Intermediate Similarity	NPC65714
0.8295	Intermediate Similarity	NPC473378
0.8295	Intermediate Similarity	NPC473407
0.8284	Intermediate Similarity	NPC158277
0.8282	Intermediate Similarity	NPC244336
0.8261	Intermediate Similarity	NPC39431
0.8232	Intermediate Similarity	NPC469243
0.8222	Intermediate Similarity	NPC323662
0.8218	Intermediate Similarity	NPC299806
0.8214	Intermediate Similarity	NPC276506
0.8212	Intermediate Similarity	NPC473371
0.821	Intermediate Similarity	NPC473580
0.8204	Intermediate Similarity	NPC302597
0.8199	Intermediate Similarity	NPC56685
0.8193	Intermediate Similarity	NPC472923
0.8171	Intermediate Similarity	NPC1390
0.8171	Intermediate Similarity	NPC62104
0.8167	Intermediate Similarity	NPC471592
0.8166	Intermediate Similarity	NPC328494
0.8166	Intermediate Similarity	NPC89831
0.8162	Intermediate Similarity	NPC220060
0.8156	Intermediate Similarity	NPC477638
0.8156	Intermediate Similarity	NPC477632
0.8129	Intermediate Similarity	NPC196243
0.8121	Intermediate Similarity	NPC471527
0.8121	Intermediate Similarity	NPC475544
0.8118	Intermediate Similarity	NPC469444
0.811	Intermediate Similarity	NPC323336
0.811	Intermediate Similarity	NPC326349
0.8101	Intermediate Similarity	NPC314083
0.8095	Intermediate Similarity	NPC328649
0.8086	Intermediate Similarity	NPC5194
0.8086	Intermediate Similarity	NPC261934
0.8084	Intermediate Similarity	NPC223207
0.8075	Intermediate Similarity	NPC473491
0.8045	Intermediate Similarity	NPC477631
0.8036	Intermediate Similarity	NPC290755
0.8036	Intermediate Similarity	NPC304074
0.8036	Intermediate Similarity	NPC471771
0.8035	Intermediate Similarity	NPC475421
0.8	Intermediate Similarity	NPC16188
0.7989	Intermediate Similarity	NPC469445
0.7988	Intermediate Similarity	NPC209463
0.7988	Intermediate Similarity	NPC476268
0.7976	Intermediate Similarity	NPC22883
0.7976	Intermediate Similarity	NPC5719
0.7976	Intermediate Similarity	NPC210377
0.7976	Intermediate Similarity	NPC217804
0.7975	Intermediate Similarity	NPC202198
0.7968	Intermediate Similarity	NPC219350
0.7968	Intermediate Similarity	NPC194699
0.7963	Intermediate Similarity	NPC475168
0.7963	Intermediate Similarity	NPC7817
0.7941	Intermediate Similarity	NPC129486
0.7941	Intermediate Similarity	NPC186617
0.7933	Intermediate Similarity	NPC477636
0.7927	Intermediate Similarity	NPC470902
0.7921	Intermediate Similarity	NPC94862
0.7914	Intermediate Similarity	NPC233702
0.7911	Intermediate Similarity	NPC476989
0.7907	Intermediate Similarity	NPC475532
0.7901	Intermediate Similarity	NPC2501
0.7898	Intermediate Similarity	NPC167763
0.7898	Intermediate Similarity	NPC470903
0.7898	Intermediate Similarity	NPC470112
0.7895	Intermediate Similarity	NPC473693
0.7895	Intermediate Similarity	NPC471568
0.7895	Intermediate Similarity	NPC196091
0.7886	Intermediate Similarity	NPC153554
0.7882	Intermediate Similarity	NPC63040
0.7866	Intermediate Similarity	NPC122590
0.7861	Intermediate Similarity	NPC17698
0.7861	Intermediate Similarity	NPC165285
0.7857	Intermediate Similarity	NPC241794
0.7836	Intermediate Similarity	NPC280022
0.7834	Intermediate Similarity	NPC6570
0.7824	Intermediate Similarity	NPC15068
0.7814	Intermediate Similarity	NPC477639
0.7806	Intermediate Similarity	NPC326966
0.7801	Intermediate Similarity	NPC277306
0.7801	Intermediate Similarity	NPC469442
0.772	Intermediate Similarity	NPC25539
0.7719	Intermediate Similarity	NPC254700
0.7709	Intermediate Similarity	NPC315542
0.7706	Intermediate Similarity	NPC471052
0.7706	Intermediate Similarity	NPC471053
0.7706	Intermediate Similarity	NPC471051
0.7702	Intermediate Similarity	NPC52748
0.7692	Intermediate Similarity	NPC477526
0.7674	Intermediate Similarity	NPC141957
0.7674	Intermediate Similarity	NPC473502
0.7657	Intermediate Similarity	NPC136797
0.7637	Intermediate Similarity	NPC174122
0.7637	Intermediate Similarity	NPC64140
0.7633	Intermediate Similarity	NPC319320
0.7633	Intermediate Similarity	NPC287757
0.7627	Intermediate Similarity	NPC119652
0.7627	Intermediate Similarity	NPC97526
0.7622	Intermediate Similarity	NPC471820
0.7622	Intermediate Similarity	NPC471821
0.7617	Intermediate Similarity	NPC326333
0.7613	Intermediate Similarity	NPC469666
0.761	Intermediate Similarity	NPC127741
0.7607	Intermediate Similarity	NPC314358
0.7593	Intermediate Similarity	NPC476978
0.7582	Intermediate Similarity	NPC234069
0.7574	Intermediate Similarity	NPC197743
0.7574	Intermediate Similarity	NPC297145
0.7568	Intermediate Similarity	NPC184933
0.7568	Intermediate Similarity	NPC59827
0.7562	Intermediate Similarity	NPC313694
0.7562	Intermediate Similarity	NPC242159
0.7546	Intermediate Similarity	NPC313867
0.7546	Intermediate Similarity	NPC316008
0.7538	Intermediate Similarity	NPC326027
0.753	Intermediate Similarity	NPC324081
0.7527	Intermediate Similarity	NPC4910
0.7516	Intermediate Similarity	NPC48202
0.7514	Intermediate Similarity	NPC138083
0.75	Intermediate Similarity	NPC476742
0.7486	Intermediate Similarity	NPC475409
0.7486	Intermediate Similarity	NPC475564
0.7486	Intermediate Similarity	NPC170302
0.7485	Intermediate Similarity	NPC315283
0.7485	Intermediate Similarity	NPC314388
0.7485	Intermediate Similarity	NPC114806
0.7485	Intermediate Similarity	NPC300443
0.7468	Intermediate Similarity	NPC257390
0.7461	Intermediate Similarity	NPC478005
0.746	Intermediate Similarity	NPC242728
0.7458	Intermediate Similarity	NPC477462
0.7456	Intermediate Similarity	NPC476741
0.7455	Intermediate Similarity	NPC135121
0.7452	Intermediate Similarity	NPC325651
0.7447	Intermediate Similarity	NPC477527
0.7439	Intermediate Similarity	NPC5620
0.7439	Intermediate Similarity	NPC477217
0.7439	Intermediate Similarity	NPC201244
0.7439	Intermediate Similarity	NPC315266
0.7432	Intermediate Similarity	NPC329731
0.7427	Intermediate Similarity	NPC24617
0.7425	Intermediate Similarity	NPC476743

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 NPC46009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	116
0.1-0.2	364
0.2-0.3	756
0.3-0.4	1874
0.4-0.5	3115
0.5-0.6	2260
0.6-0.7	624
0.7-0.8	39
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
0.8253	Intermediate Similarity	NPD8303	Discontinued
0.8221	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7978	Discontinued
0.7974	Intermediate Similarity	NPD3136	Phase 2
0.7738	Intermediate Similarity	NPD8019	Approved
0.7733	Intermediate Similarity	NPD7484	Phase 3
0.7733	Intermediate Similarity	NPD7485	Phase 3
0.7633	Intermediate Similarity	NPD7495	Discontinued
0.7593	Intermediate Similarity	NPD6681	Discovery
0.7586	Intermediate Similarity	NPD7608	Discontinued
0.7545	Intermediate Similarity	NPD7523	Phase 3
0.7485	Intermediate Similarity	NPD7303	Discontinued
0.7457	Intermediate Similarity	NPD8031	Discontinued
0.744	Intermediate Similarity	NPD7131	Phase 3
0.7421	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4652	Approved
0.7362	Intermediate Similarity	NPD7450	Phase 2
0.7358	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1330	Phase 2
0.7356	Intermediate Similarity	NPD2098	Approved
0.7322	Intermediate Similarity	NPD6853	Approved
0.7322	Intermediate Similarity	NPD6851	Approved
0.7316	Intermediate Similarity	NPD7810	Phase 3
0.7316	Intermediate Similarity	NPD7811	Phase 3
0.7308	Intermediate Similarity	NPD3125	Approved
0.7301	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD8172	Phase 2
0.7284	Intermediate Similarity	NPD8173	Phase 2
0.7241	Intermediate Similarity	NPD2097	Approved
0.7232	Intermediate Similarity	NPD2017	Approved
0.7232	Intermediate Similarity	NPD2889	Approved
0.7232	Intermediate Similarity	NPD2888	Approved
0.7232	Intermediate Similarity	NPD2890	Approved
0.7228	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8076	Discontinued
0.716	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5137	Approved
0.7143	Intermediate Similarity	NPD8323	Discontinued
0.7104	Intermediate Similarity	NPD6297	Approved
0.7099	Intermediate Similarity	NPD5745	Approved
0.7076	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6073	Approved
0.707	Intermediate Similarity	NPD2562	Approved
0.707	Intermediate Similarity	NPD2561	Approved
0.7063	Intermediate Similarity	NPD4177	Approved
0.7063	Intermediate Similarity	NPD4175	Approved
0.7059	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5296	Approved
0.703	Intermediate Similarity	NPD3552	Approved
0.703	Intermediate Similarity	NPD3554	Approved
0.703	Intermediate Similarity	NPD3553	Approved
0.703	Intermediate Similarity	NPD3555	Approved
0.7025	Intermediate Similarity	NPD4659	Approved
0.7024	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7613	Discontinued
0.6975	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5746	Approved
0.6973	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2568	Approved
0.697	Remote Similarity	NPD5725	Approved
0.6966	Remote Similarity	NPD5218	Approved
0.6966	Remote Similarity	NPD5219	Approved
0.6951	Remote Similarity	NPD6346	Approved
0.6935	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5355	Approved
0.6932	Remote Similarity	NPD5356	Approved
0.6919	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3536	Discontinued
0.6909	Remote Similarity	NPD555	Phase 2
0.6903	Remote Similarity	NPD16	Approved
0.6903	Remote Similarity	NPD856	Approved
0.6903	Remote Similarity	NPD317	Approved
0.6903	Remote Similarity	NPD318	Approved
0.6895	Remote Similarity	NPD7617	Discontinued
0.6894	Remote Similarity	NPD7451	Discontinued
0.6894	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5747	Discontinued
0.689	Remote Similarity	NPD6405	Approved
0.689	Remote Similarity	NPD6407	Approved
0.6885	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3400	Discontinued
0.6872	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3054	Approved
0.6867	Remote Similarity	NPD3052	Approved
0.686	Remote Similarity	NPD6088	Approved
0.6855	Remote Similarity	NPD2584	Suspended
0.6839	Remote Similarity	NPD9568	Approved
0.6832	Remote Similarity	NPD4103	Phase 2
0.6832	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6294	Approved
0.6826	Remote Similarity	NPD6295	Approved
0.6826	Remote Similarity	NPD6852	Discontinued
0.6826	Remote Similarity	NPD6901	Phase 3
0.6813	Remote Similarity	NPD4677	Discontinued
0.6798	Remote Similarity	NPD7972	Discontinued
0.6792	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD259	Phase 1
0.6782	Remote Similarity	NPD6390	Discontinued
0.678	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD823	Approved
0.6766	Remote Similarity	NPD5314	Approved
0.6766	Remote Similarity	NPD817	Approved
0.6765	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6107	Approved
0.675	Remote Similarity	NPD3071	Approved
0.675	Remote Similarity	NPD3073	Approved
0.675	Remote Similarity	NPD3072	Approved
0.6747	Remote Similarity	NPD6623	Phase 3
0.6746	Remote Similarity	NPD2240	Approved
0.6746	Remote Similarity	NPD9570	Approved
0.6746	Remote Similarity	NPD2239	Approved
0.6739	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1129	Approved
0.6728	Remote Similarity	NPD1134	Approved
0.6728	Remote Similarity	NPD1133	Approved
0.6728	Remote Similarity	NPD1135	Approved
0.6728	Remote Similarity	NPD1131	Approved
0.6728	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD598	Approved
0.6727	Remote Similarity	NPD601	Approved
0.6727	Remote Similarity	NPD597	Approved
0.6727	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3158	Phase 1
0.6724	Remote Similarity	NPD3157	Approved
0.6724	Remote Similarity	NPD6419	Discontinued
0.6723	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8417	Discontinued
0.672	Remote Similarity	NPD6042	Phase 2
0.672	Remote Similarity	NPD42	Phase 2
0.6707	Remote Similarity	NPD5263	Approved
0.6707	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8315	Phase 1
0.6704	Remote Similarity	NPD5772	Approved
0.6704	Remote Similarity	NPD5773	Approved
0.6687	Remote Similarity	NPD1130	Approved
0.6687	Remote Similarity	NPD1132	Approved
0.6687	Remote Similarity	NPD602	Approved
0.6687	Remote Similarity	NPD1136	Approved
0.6687	Remote Similarity	NPD4761	Approved
0.6687	Remote Similarity	NPD4762	Approved
0.6687	Remote Similarity	NPD4151	Approved
0.6687	Remote Similarity	NPD599	Approved
0.6687	Remote Similarity	NPD2245	Discovery
0.6686	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1967	Approved
0.6686	Remote Similarity	NPD1968	Approved
0.6686	Remote Similarity	NPD4731	Phase 3
0.6686	Remote Similarity	NPD6676	Phase 2
0.6686	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3455	Phase 2
0.6667	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4227	Discontinued
0.6648	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1725	Approved
0.6647	Remote Similarity	NPD3059	Approved
0.6647	Remote Similarity	NPD826	Approved
0.6647	Remote Similarity	NPD3061	Approved
0.6647	Remote Similarity	NPD3062	Approved
0.6647	Remote Similarity	NPD825	Approved
0.6647	Remote Similarity	NPD8416	Discontinued
0.6647	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2217	Approved
0.6646	Remote Similarity	NPD2218	Phase 2
0.6646	Remote Similarity	NPD316	Approved
0.6634	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD2891	Approved
0.6628	Remote Similarity	NPD2460	Phase 3
0.6628	Remote Similarity	NPD2459	Approved
0.6628	Remote Similarity	NPD2458	Approved
0.6611	Remote Similarity	NPD4557	Approved
0.6611	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3687	Approved
0.661	Remote Similarity	NPD3686	Approved
0.6609	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6667	Approved
0.6609	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6666	Approved
0.6608	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4676	Approved
0.6606	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6863	Phase 2
0.66	Remote Similarity	NPD8162	Phase 2
0.66	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5557	Phase 1
0.6588	Remote Similarity	NPD8356	Approved
0.6588	Remote Similarity	NPD1753	Discontinued
0.6587	Remote Similarity	NPD1423	Approved
0.6585	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD858	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