NPASS Compound

Structure

NPC50016 OpenBabel07101718232D 70 73 0 0 1 0 0 0 0 0999 V2000 -1.0287 -4.2366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7898 -5.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1991 -0.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2707 0.6943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7551 2.1716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4531 3.3469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9283 -1.1594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9859 2.9415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9236 6.0646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7108 5.1150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8524 6.3551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4268 4.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5684 5.6960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3742 0.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2170 -1.3976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2170 0.5487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0598 -0.9110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5720 -1.7267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4480 -0.8814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7117 -4.3295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6081 0.9717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7875 3.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5314 -1.3976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0031 -3.8305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8434 -4.7689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3593 0.3531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1883 2.4105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0268 -0.9728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3555 4.7464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3742 -0.9110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0598 0.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3102 -2.1568 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7654 -3.3578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0031 -2.8573 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5747 2.4786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6968 0.6305 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6886 -0.9110 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8459 -4.3171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0316 -0.2574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8668 1.7129 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3680 -1.8842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7326 -3.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1603 -2.3707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6030 2.5322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8459 -1.3976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9867 -2.6354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7496 -1.2885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2102 1.4733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2905 0.9288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8459 -5.2902 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6127 -2.8354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8459 -2.3707 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8158 -3.1450 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6666 2.2674 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3175 -2.8573 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.4763 2.1124 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.8833 -0.3246 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.9025 0.5487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6886 0.0622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6886 -3.8305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6796 0.6499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9974 -4.1872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1603 -1.3976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4959 3.4995 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0031 -0.9110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3476 -3.3692 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6784 -1.5790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9614 2.0920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5778 1.3682 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 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 8 56 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 29 2 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 30 2 0 0 0 0 15 17 2 0 0 0 0 15 30 1 0 0 0 0 16 31 2 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 19 39 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 23 37 1 0 0 0 0 24 38 1 0 0 0 0 28 7 1 6 0 0 0 28 41 1 0 0 0 0 28 70 1 0 0 0 0 31 58 1 0 0 0 0 32 18 1 1 0 0 0 32 47 1 0 0 0 0 32 51 1 0 0 0 0 33 20 1 1 0 0 0 33 42 1 0 0 0 0 33 53 1 0 0 0 0 34 24 1 1 0 0 0 34 43 1 0 0 0 0 34 52 1 0 0 0 0 35 22 1 1 0 0 0 35 44 1 0 0 0 0 35 56 1 0 0 0 0 36 21 1 1 0 0 0 36 48 1 0 0 0 0 36 57 1 0 0 0 0 37 45 1 0 0 0 0 37 59 1 6 0 0 0 38 50 2 0 0 0 0 38 60 1 0 0 0 0 39 57 1 0 0 0 0 39 61 1 6 0 0 0 40 27 1 1 0 0 0 40 49 1 0 0 0 0 40 54 1 0 0 0 0 41 46 1 0 0 0 0 41 55 1 6 0 0 0 42 51 2 3 0 0 0 42 62 1 0 0 0 0 43 55 2 3 0 0 0 43 63 1 0 0 0 0 44 54 2 3 0 0 0 44 64 1 0 0 0 0 45 52 2 3 0 0 0 45 65 1 0 0 0 0 46 53 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:	978.51
Volume:	984.534
LogP:	1.214
LogD:	0.858
LogS:	-2.29
# Rotatable Bonds:	16
TPSA:	323.18
# H-Bond Aceptor:	21
# H-Bond Donor:	10
# Rings:	4
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.069
Synthetic Accessibility Score:	7.11
Fsp3:	0.571
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:	-6.796
MDCK Permeability:	4.908965274807997e-05
Pgp-inhibitor:	0.088
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.274
20% Bioavailability (F20%):	0.478
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	53.158790588378906%
Volume Distribution (VD):	0.571
Pgp-substrate:	35.02817916870117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.039
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.723
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	2.386
Half-life (T1/2):	0.532

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.995
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.372
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.151
Carcinogencity:	0.121
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC50016

Natural Product ID:	NPC50016
*Common Name:**	(S)-N1-((2S,5S,8S,11R,12S,15S,18S,21R)-5-Benzyl-21-Hydroxy-2,15-Diisobutyl-8-Isopropyl-4,11-Dimethyl-3,6,9,13,16,22-Hexaoxo-10-Oxa-1,4,7,14,17-Pentaazabicyclo[16.3.1]Docosan-12-Yl)-2-((R)-2-Hydroxy-3-(4-Hydroxyphenyl)Propanamido)Succinamide
IUPAC Name:	(2S)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-21-hydroxy-4,11-dimethyl-2,15-bis(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]-2-[[(2R)-2-hydroxy-3-(4-hydroxyphenyl)propanoyl]amino]butanediamide
Synonyms:
Standard InCHIKey:	IRVJVPYNSVRRCE-VQLNKVTQSA-N
Standard InCHI:	InChI=1S/C49H70N8O13/c1-25(2)20-33-42(62)51-32-18-19-39(61)57(47(32)67)36(21-26(3)4)48(68)56(8)35(22-29-12-10-9-11-13-29)44(64)54-40(27(5)6)49(69)70-28(7)41(46(66)53-33)55-43(63)34(24-38(50)60)52-45(65)37(59)23-30-14-16-31(58)17-15-30/h9-17,25-28,32-37,39-41,58-59,61H,18-24H2,1-8H3,(H2,50,60)(H,51,62)(H,52,65)(H,53,66)(H,54,64)(H,55,63)/t28-,32+,33+,34+,35+,36+,37-,39-,40+,41+/m1/s1
SMILES:	CC(C[C@@H]1N=C(O)[C@@H](N=C([C@@H](N=C([C@@H](Cc2ccc(cc2)O)O)O)CC(=N)O)O)[C@@H](C)OC(=O)[C@@H](N=C([C@@H](N(C(=O)[C@@H](N2C(=O)[C@@H](N=C1O)CC[C@H]2O)CC(C)C)C)Cc1ccccc1)O)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385897
PubChem CID:	71726413
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.	n.a.	n.a.	PMID[12141855]
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[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	=	17600.0	nM	PMID[513997]
NPT2	Others	Unspecified		IC50	=	4300.0	nM	PMID[513997]

☑ 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 NPC50016 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	190
0.1-0.2	988
0.2-0.3	4061
0.3-0.4	13020
0.4-0.5	11917
0.5-0.6	11071
0.6-0.7	1021
0.7-0.8	328
0.8-0.85	44
0.85-0.9	30
0.9-0.95	23
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC273755
0.9627	High Similarity	NPC45037
0.95	High Similarity	NPC306804
0.9497	High Similarity	NPC40234
0.9441	High Similarity	NPC473354
0.9375	High Similarity	NPC475123
0.9375	High Similarity	NPC475204
0.9371	High Similarity	NPC294516
0.9371	High Similarity	NPC107938
0.9321	High Similarity	NPC471165
0.9317	High Similarity	NPC230611
0.9268	High Similarity	NPC269750
0.9268	High Similarity	NPC194671
0.9259	High Similarity	NPC248670
0.9259	High Similarity	NPC137627
0.9255	High Similarity	NPC46009
0.9202	High Similarity	NPC279871
0.9202	High Similarity	NPC473402
0.9202	High Similarity	NPC476227
0.9162	High Similarity	NPC294951
0.9157	High Similarity	NPC476321
0.9102	High Similarity	NPC471526
0.9085	High Similarity	NPC159767
0.9085	High Similarity	NPC26108
0.9085	High Similarity	NPC155506
0.9006	High Similarity	NPC240130
0.9006	High Similarity	NPC61332
0.896	High Similarity	NPC302715
0.8935	High Similarity	NPC471049
0.8935	High Similarity	NPC471050
0.8935	High Similarity	NPC471048
0.8895	High Similarity	NPC473305
0.8895	High Similarity	NPC163961
0.8851	High Similarity	NPC65714
0.8837	High Similarity	NPC102959
0.8817	High Similarity	NPC473404
0.8786	High Similarity	NPC60516
0.875	High Similarity	NPC473371
0.8736	High Similarity	NPC473378
0.8736	High Similarity	NPC473407
0.8735	High Similarity	NPC89831
0.8701	High Similarity	NPC471592
0.8659	High Similarity	NPC63931
0.8631	High Similarity	NPC158277
0.8494	Intermediate Similarity	NPC61004
0.8453	Intermediate Similarity	NPC477551
0.8444	Intermediate Similarity	NPC477550
0.8444	Intermediate Similarity	NPC477552
0.8364	Intermediate Similarity	NPC471527
0.8352	Intermediate Similarity	NPC469443
0.8344	Intermediate Similarity	NPC476268
0.8333	Intermediate Similarity	NPC473341
0.8303	Intermediate Similarity	NPC244336
0.8294	Intermediate Similarity	NPC328494
0.8249	Intermediate Similarity	NPC94862
0.8225	Intermediate Similarity	NPC302597
0.8221	Intermediate Similarity	NPC262166
0.8217	Intermediate Similarity	NPC163392
0.8217	Intermediate Similarity	NPC239762
0.8212	Intermediate Similarity	NPC248822
0.821	Intermediate Similarity	NPC473491
0.8187	Intermediate Similarity	NPC81026
0.8171	Intermediate Similarity	NPC477637
0.8155	Intermediate Similarity	NPC471053
0.8155	Intermediate Similarity	NPC471052
0.8155	Intermediate Similarity	NPC471051
0.8142	Intermediate Similarity	NPC323662
0.8129	Intermediate Similarity	NPC471568
0.8129	Intermediate Similarity	NPC198254
0.8129	Intermediate Similarity	NPC473693
0.8129	Intermediate Similarity	NPC274198
0.8125	Intermediate Similarity	NPC266741
0.8121	Intermediate Similarity	NPC244509
0.8118	Intermediate Similarity	NPC328649
0.8113	Intermediate Similarity	NPC91953
0.811	Intermediate Similarity	NPC56685
0.811	Intermediate Similarity	NPC122590
0.8095	Intermediate Similarity	NPC241794
0.8085	Intermediate Similarity	NPC220060
0.8084	Intermediate Similarity	NPC1390
0.8084	Intermediate Similarity	NPC62104
0.807	Intermediate Similarity	NPC186617
0.8061	Intermediate Similarity	NPC39431
0.805	Intermediate Similarity	NPC197921
0.8049	Intermediate Similarity	NPC233702
0.8046	Intermediate Similarity	NPC196243
0.8042	Intermediate Similarity	NPC469444
0.8036	Intermediate Similarity	NPC469243
0.8025	Intermediate Similarity	NPC16188
0.8023	Intermediate Similarity	NPC196091
0.8023	Intermediate Similarity	NPC276506
0.8022	Intermediate Similarity	NPC328763
0.8012	Intermediate Similarity	NPC209463
0.8	Intermediate Similarity	NPC223207
0.8	Intermediate Similarity	NPC472923
0.8	Intermediate Similarity	NPC202198
0.8	Intermediate Similarity	NPC469360
0.7978	Intermediate Similarity	NPC477632
0.7978	Intermediate Similarity	NPC477638
0.7975	Intermediate Similarity	NPC127741
0.7975	Intermediate Similarity	NPC6570
0.7965	Intermediate Similarity	NPC280022
0.7955	Intermediate Similarity	NPC97526
0.7955	Intermediate Similarity	NPC119652
0.7953	Intermediate Similarity	NPC471771
0.7953	Intermediate Similarity	NPC304074
0.7953	Intermediate Similarity	NPC290755
0.7937	Intermediate Similarity	NPC476989
0.7929	Intermediate Similarity	NPC475544
0.7927	Intermediate Similarity	NPC2501
0.7917	Intermediate Similarity	NPC469445
0.7917	Intermediate Similarity	NPC197743
0.7917	Intermediate Similarity	NPC297145
0.7895	Intermediate Similarity	NPC22883
0.7895	Intermediate Similarity	NPC5719
0.7895	Intermediate Similarity	NPC194699
0.7895	Intermediate Similarity	NPC210377
0.7895	Intermediate Similarity	NPC219350
0.7895	Intermediate Similarity	NPC217804
0.7892	Intermediate Similarity	NPC5194
0.7892	Intermediate Similarity	NPC261934
0.7886	Intermediate Similarity	NPC136797
0.7886	Intermediate Similarity	NPC477462
0.7861	Intermediate Similarity	NPC473450
0.7857	Intermediate Similarity	NPC64140
0.7857	Intermediate Similarity	NPC174122
0.7853	Intermediate Similarity	NPC475421
0.7849	Intermediate Similarity	NPC254700
0.7833	Intermediate Similarity	NPC315542
0.7833	Intermediate Similarity	NPC138083
0.7833	Intermediate Similarity	NPC299806
0.7826	Intermediate Similarity	NPC314083
0.7811	Intermediate Similarity	NPC326349
0.7811	Intermediate Similarity	NPC323336
0.7803	Intermediate Similarity	NPC63040
0.7803	Intermediate Similarity	NPC141957
0.7802	Intermediate Similarity	NPC234069
0.7798	Intermediate Similarity	NPC473580
0.7766	Intermediate Similarity	NPC242728
0.7746	Intermediate Similarity	NPC15068
0.7732	Intermediate Similarity	NPC469442
0.7732	Intermediate Similarity	NPC277306
0.773	Intermediate Similarity	NPC52748
0.7727	Intermediate Similarity	NPC475532
0.7722	Intermediate Similarity	NPC167763
0.7722	Intermediate Similarity	NPC470112
0.7722	Intermediate Similarity	NPC470903
0.7709	Intermediate Similarity	NPC475409
0.7709	Intermediate Similarity	NPC153554
0.7709	Intermediate Similarity	NPC475564
0.7709	Intermediate Similarity	NPC170302
0.7692	Intermediate Similarity	NPC276120
0.7684	Intermediate Similarity	NPC17698
0.7684	Intermediate Similarity	NPC165285
0.7676	Intermediate Similarity	NPC477631
0.7668	Intermediate Similarity	NPC478005
0.7663	Intermediate Similarity	NPC477636
0.7661	Intermediate Similarity	NPC287757
0.7661	Intermediate Similarity	NPC319320
0.766	Intermediate Similarity	NPC50548
0.7653	Intermediate Similarity	NPC25539
0.7653	Intermediate Similarity	NPC326027
0.7641	Intermediate Similarity	NPC326333
0.764	Intermediate Similarity	NPC64205
0.7619	Intermediate Similarity	NPC476744
0.7611	Intermediate Similarity	NPC32064
0.761	Intermediate Similarity	NPC326966
0.761	Intermediate Similarity	NPC257390
0.7606	Intermediate Similarity	NPC144314
0.7602	Intermediate Similarity	NPC56635
0.76	Intermediate Similarity	NPC473502
0.7598	Intermediate Similarity	NPC473546
0.759	Intermediate Similarity	NPC135121
0.7576	Intermediate Similarity	NPC201244
0.7576	Intermediate Similarity	NPC477217
0.7561	Intermediate Similarity	NPC176226
0.756	Intermediate Similarity	NPC475168
0.756	Intermediate Similarity	NPC476743
0.756	Intermediate Similarity	NPC7817
0.7557	Intermediate Similarity	NPC129486
0.7553	Intermediate Similarity	NPC149962
0.7553	Intermediate Similarity	NPC477639
0.7546	Intermediate Similarity	NPC476259
0.7545	Intermediate Similarity	NPC471820
0.7545	Intermediate Similarity	NPC471821
0.7531	Intermediate Similarity	NPC68865
0.753	Intermediate Similarity	NPC262077
0.753	Intermediate Similarity	NPC314358
0.7526	Intermediate Similarity	NPC123859
0.7512	Intermediate Similarity	NPC478007
0.75	Intermediate Similarity	NPC168113
0.7486	Intermediate Similarity	NPC164608
0.7485	Intermediate Similarity	NPC476741
0.747	Intermediate Similarity	NPC313867
0.747	Intermediate Similarity	NPC316008
0.747	Intermediate Similarity	NPC209509
0.747	Intermediate Similarity	NPC315266
0.746	Intermediate Similarity	NPC329295
0.7455	Intermediate Similarity	NPC161069
0.7455	Intermediate Similarity	NPC197682

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 NPC50016 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	120
0.1-0.2	374
0.2-0.3	782
0.3-0.4	1878
0.4-0.5	3043
0.5-0.6	2339
0.6-0.7	591
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8242	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7608	Discontinued
0.7849	Intermediate Similarity	NPD8303	Discontinued
0.7778	Intermediate Similarity	NPD7978	Discontinued
0.7661	Intermediate Similarity	NPD8019	Approved
0.7557	Intermediate Similarity	NPD7485	Phase 3
0.7557	Intermediate Similarity	NPD7484	Phase 3
0.7547	Intermediate Similarity	NPD3136	Phase 2
0.7471	Intermediate Similarity	NPD7131	Phase 3
0.7457	Intermediate Similarity	NPD7495	Discontinued
0.7446	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7811	Phase 3
0.7435	Intermediate Similarity	NPD7810	Phase 3
0.7386	Intermediate Similarity	NPD8031	Discontinued
0.7381	Intermediate Similarity	NPD8323	Discontinued
0.7368	Intermediate Similarity	NPD7523	Phase 3
0.7351	Intermediate Similarity	NPD6851	Approved
0.7351	Intermediate Similarity	NPD6853	Approved
0.7346	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7303	Discontinued
0.7289	Intermediate Similarity	NPD7450	Phase 2
0.7278	Intermediate Similarity	NPD5137	Approved
0.7241	Intermediate Similarity	NPD8417	Discontinued
0.7222	Intermediate Similarity	NPD4652	Approved
0.7209	Intermediate Similarity	NPD7613	Discontinued
0.7202	Intermediate Similarity	NPD6681	Discovery
0.7195	Intermediate Similarity	NPD6346	Approved
0.7135	Intermediate Similarity	NPD6297	Approved
0.7126	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8172	Phase 2
0.7108	Intermediate Similarity	NPD8173	Phase 2
0.7095	Intermediate Similarity	NPD2098	Approved
0.709	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4659	Approved
0.7059	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8076	Discontinued
0.7019	Intermediate Similarity	NPD3125	Approved
0.7018	Intermediate Similarity	NPD6676	Phase 2
0.6983	Remote Similarity	NPD2097	Approved
0.6978	Remote Similarity	NPD2890	Approved
0.6978	Remote Similarity	NPD2889	Approved
0.6978	Remote Similarity	NPD2888	Approved
0.6978	Remote Similarity	NPD2017	Approved
0.6975	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4103	Phase 2
0.697	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1330	Phase 2
0.6928	Remote Similarity	NPD5745	Approved
0.6919	Remote Similarity	NPD3400	Discontinued
0.6897	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6852	Discontinued
0.686	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3536	Discontinued
0.6836	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD8315	Phase 1
0.6833	Remote Similarity	NPD7972	Discontinued
0.6829	Remote Similarity	NPD7451	Discontinued
0.6818	Remote Similarity	NPD7565	Approved
0.6813	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5218	Approved
0.6813	Remote Similarity	NPD5219	Approved
0.6807	Remote Similarity	NPD5746	Approved
0.6805	Remote Similarity	NPD6073	Approved
0.6805	Remote Similarity	NPD5314	Approved
0.6805	Remote Similarity	NPD2568	Approved
0.6802	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2562	Approved
0.679	Remote Similarity	NPD2561	Approved
0.6786	Remote Similarity	NPD8265	Approved
0.6777	Remote Similarity	NPD8356	Approved
0.6776	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6295	Approved
0.6765	Remote Similarity	NPD3553	Approved
0.6765	Remote Similarity	NPD3554	Approved
0.6765	Remote Similarity	NPD3555	Approved
0.6765	Remote Similarity	NPD3552	Approved
0.6765	Remote Similarity	NPD6294	Approved
0.6761	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7617	Discontinued
0.6747	Remote Similarity	NPD4617	Approved
0.6747	Remote Similarity	NPD4620	Approved
0.6747	Remote Similarity	NPD5203	Approved
0.6747	Remote Similarity	NPD5201	Approved
0.6747	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD555	Phase 2
0.6743	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5773	Approved
0.674	Remote Similarity	NPD5772	Approved
0.6739	Remote Similarity	NPD2904	Discontinued
0.6738	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD8430	Approved
0.6725	Remote Similarity	NPD1753	Discontinued
0.6724	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8162	Phase 2
0.6708	Remote Similarity	NPD5723	Approved
0.6707	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD3455	Phase 2
0.6703	Remote Similarity	NPD6107	Approved
0.67	Remote Similarity	NPD8161	Suspended
0.6687	Remote Similarity	NPD4175	Approved
0.6687	Remote Similarity	NPD2218	Phase 2
0.6687	Remote Similarity	NPD2217	Approved
0.6687	Remote Similarity	NPD4177	Approved
0.6687	Remote Similarity	NPD2584	Suspended
0.6686	Remote Similarity	NPD8416	Discontinued
0.6686	Remote Similarity	NPD5120	Approved
0.6686	Remote Similarity	NPD3062	Approved
0.6686	Remote Similarity	NPD5119	Approved
0.6686	Remote Similarity	NPD2239	Approved
0.6686	Remote Similarity	NPD2240	Approved
0.6686	Remote Similarity	NPD3061	Approved
0.6686	Remote Similarity	NPD5121	Approved
0.6686	Remote Similarity	NPD5296	Approved
0.6686	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3059	Approved
0.6685	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD42	Phase 2
0.6667	Remote Similarity	NPD6419	Discontinued
0.6667	Remote Similarity	NPD6042	Phase 2
0.6667	Remote Similarity	NPD3985	Discontinued
0.6667	Remote Similarity	NPD7281	Phase 3
0.6667	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6901	Phase 3
0.6667	Remote Similarity	NPD7280	Phase 3
0.6649	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8643	Discontinued
0.6646	Remote Similarity	NPD4677	Discontinued
0.6634	Remote Similarity	NPD7585	Approved
0.6632	Remote Similarity	NPD5557	Phase 1
0.663	Remote Similarity	NPD6072	Discontinued
0.663	Remote Similarity	NPD6677	Suspended
0.663	Remote Similarity	NPD8070	Approved
0.6629	Remote Similarity	NPD6390	Discontinued
0.6629	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6405	Approved
0.6627	Remote Similarity	NPD6407	Approved
0.6627	Remote Similarity	NPD259	Phase 1
0.6627	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD8025	Phase 2
0.6612	Remote Similarity	NPD5967	Approved
0.661	Remote Similarity	NPD6088	Approved
0.6608	Remote Similarity	NPD5725	Approved
0.6608	Remote Similarity	NPD817	Approved
0.6608	Remote Similarity	NPD823	Approved
0.6608	Remote Similarity	NPD3054	Approved
0.6608	Remote Similarity	NPD3052	Approved
0.6607	Remote Similarity	NPD4738	Phase 2
0.6597	Remote Similarity	NPD5445	Approved
0.6593	Remote Similarity	NPD5355	Approved
0.6593	Remote Similarity	NPD5356	Approved
0.6591	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.659	Remote Similarity	NPD9570	Approved
0.6588	Remote Similarity	NPD825	Approved
0.6588	Remote Similarity	NPD826	Approved
0.6588	Remote Similarity	NPD6623	Phase 3
0.6585	Remote Similarity	NPD7583	Approved
0.658	Remote Similarity	NPD5035	Approved
0.6579	Remote Similarity	NPD5313	Approved
0.6579	Remote Similarity	NPD5312	Approved
0.6576	Remote Similarity	NPD8351	Phase 2
0.6573	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD598	Approved
0.6568	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD4619	Approved
0.6568	Remote Similarity	NPD601	Approved
0.6568	Remote Similarity	NPD597	Approved
0.6568	Remote Similarity	NPD4621	Approved
0.6566	Remote Similarity	NPD2628	Approved
0.6566	Remote Similarity	NPD2160	Approved
0.6566	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2625	Approved
0.6566	Remote Similarity	NPD2627	Approved
0.6566	Remote Similarity	NPD2626	Approved
0.6566	Remote Similarity	NPD2159	Approved
0.6564	Remote Similarity	NPD5037	Approved
0.6564	Remote Similarity	NPD5038	Approved
0.6564	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5295	Discontinued
0.6554	Remote Similarity	NPD6667	Approved
0.6554	Remote Similarity	NPD6666	Approved
0.6552	Remote Similarity	NPD3656	Approved
0.6552	Remote Similarity	NPD6863	Phase 2
0.6552	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5190	Phase 2

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