NPASS Compound

Structure

NPC220060 OpenBabel07101718282D 69 71 0 0 1 0 0 0 0 0999 V2000 5.1661 -10.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9423 -2.2462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1168 -3.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7026 -9.7639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6139 -2.0732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7116 -7.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1252 -10.3545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9144 -6.5246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4462 -5.7105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4641 -5.5672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0470 -7.5693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1227 -4.8518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8917 -7.4454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0566 -6.4710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2249 -4.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1980 -6.7854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4586 -0.8421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1810 -3.1889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7434 -9.6039 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8004 -3.0276 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5152 -5.3545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8836 -3.7110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4172 -5.7640 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6172 -8.3070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2491 -6.5728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8324 -3.9237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9724 -1.6843 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5152 -8.0286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4840 -3.8670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8897 -3.3686 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4024 -8.6932 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5241 -6.7306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3027 -5.6018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4586 -2.5264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1390 -3.9867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4849 -8.7461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2446 -8.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7005 -3.2911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5594 -7.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5933 -2.7830 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.9985 -6.3639 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0912 -8.0456 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5884 -7.2851 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6298 -4.8152 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9391 -7.6100 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.0381 -4.6661 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4035 -2.5264 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.8832 -7.4737 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4481 -8.8796 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 12.4910 -3.2082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4218 -7.6769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5884 -6.9952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2692 -5.4948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9724 -3.3686 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4057 -3.3481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1946 -9.6742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8628 -8.9576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1396 -2.4234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9724 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3283 -2.0402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9724 -3.3686 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3559 -3.0126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9724 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7724 -3.0008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.4862 -2.5264 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 48 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 10 12 2 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 43 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 17 65 1 0 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 20 30 1 0 0 0 0 20 66 1 0 0 0 0 22 26 2 0 0 0 0 22 40 1 0 0 0 0 23 9 1 6 0 0 0 23 32 1 0 0 0 0 23 44 1 0 0 0 0 24 11 1 6 0 0 0 24 36 1 0 0 0 0 24 45 1 0 0 0 0 25 16 1 6 0 0 0 25 33 1 0 0 0 0 25 48 1 0 0 0 0 26 50 1 0 0 0 0 27 17 1 6 0 0 0 27 34 1 0 0 0 0 27 67 1 0 0 0 0 28 49 1 0 0 0 0 28 51 1 1 0 0 0 29 18 1 6 0 0 0 29 38 1 0 0 0 0 29 46 1 0 0 0 0 30 35 1 0 0 0 0 30 47 1 1 0 0 0 31 19 1 6 0 0 0 31 37 1 0 0 0 0 31 49 1 0 0 0 0 32 45 2 3 0 0 0 32 52 1 0 0 0 0 33 46 2 3 0 0 0 33 53 1 0 0 0 0 34 47 2 3 0 0 0 34 54 1 0 0 0 0 35 44 2 3 0 0 0 35 55 1 0 0 0 0 36 49 1 0 0 0 0 36 56 2 0 0 0 0 37 48 1 0 0 0 0 37 57 2 0 0 0 0 38 58 2 0 0 0 0 38 66 1 0 0 0 0 39 41 2 0 0 0 0 39 42 1 0 0 0 0 39 43 1 0 0 0 0 59 68 1 0 0 0 0 60 68 2 0 0 0 0 61 68 2 0 0 0 0 62 69 1 0 0 0 0 63 69 2 0 0 0 0 64 69 2 0 0 0 0 65 68 1 0 0 0 0 67 69 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1041.32
Volume:	937.854
LogP:	-1.565
LogD:	-0.489
LogS:	-0.052
# Rotatable Bonds:	18
TPSA:	412.88
# H-Bond Aceptor:	27
# H-Bond Donor:	12
# Rings:	3
# Heavy Atoms:	30

MedChem Properties

QED Drug-Likeness Score:	0.027
Synthetic Accessibility Score:	7.107
Fsp3:	0.641
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.654
MDCK Permeability:	1.682771289779339e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	63.467323303222656%
Volume Distribution (VD):	0.347
Pgp-substrate:	21.06403350830078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.024
CYP2C9-inhibitor:	0.099
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	1.852
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.439
Drug-inuced Liver Injury (DILI):	0.857
AMES Toxicity:	0.16
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.377
Carcinogencity:	0.727
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC220060

Natural Product ID:	NPC220060
*Common Name:**	(R)-3-((2S,5S,8S,11R,12S,15S,18S,21R)-15-(3-(Amino(Iminio)Methylamino)Propyl)-2-Sec-Butyl-5-(3-Chloro-4-Hydroxybenzyl)-21-Hydroxy-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-Ylamino)-3-Oxopropane-1,2-Diyl Disulfate
IUPAC Name:	[(2R)-1-[[(2S,5S,8S,11R,12S,15S,18S,21R)-2-[(2S)-butan-2-yl]-5-[(3-chloro-4-hydroxyphenyl)methyl]-15-[3-(diaminomethylideneamino)propyl]-21-hydroxy-4,11-dimethyl-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]-1-oxo-3-sulfooxypropan-2-yl] hydrogen sulfate
Synonyms:
Standard InCHIKey:	CDNBDTGIQPIOQU-JJSZTCTISA-N
Standard InCHI:	InChI=1S/C39H60ClN9O18S2/c1-7-19(4)31-37(57)48(6)25(16-21-10-12-26(50)22(40)15-21)33(53)46-29(18(2)3)38(58)66-20(5)30(47-34(54)27(67-69(62,63)64)17-65-68(59,60)61)35(55)44-23(9-8-14-43-39(41)42)32(52)45-24-11-13-28(51)49(31)36(24)56/h10,12,15,18-20,23-25,27-31,50-51H,7-9,11,13-14,16-17H2,1-6H3,(H,44,55)(H,45,52)(H,46,53)(H,47,54)(H4,41,42,43)(H,59,60,61)(H,62,63,64)/t19-,20+,23-,24-,25-,27+,28+,29-,30-,31-/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=O)N(C)[C@@H](Cc2ccc(c(c2)Cl)O)C(=N[C@@H](C(C)C)C(=O)O[C@H](C)[C@@H](C(=N[C@@H](CCCNC(=N)N)C(=N[C@H]2CC[C@H](N1C2=O)O)O)O)N=C([C@@H](COS(=O)(=O)O)OS(=O)(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078913
PubChem CID:	44254976
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	=	1200.0	nM	PMID[452921]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[452921]

☑ 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 NPC220060 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	234
0.1-0.2	1434
0.2-0.3	9312
0.3-0.4	10818
0.4-0.5	18484
0.5-0.6	1883
0.6-0.7	345
0.7-0.8	152
0.8-0.85	20
0.85-0.9	4
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9786	High Similarity	NPC469445
0.9672	High Similarity	NPC469443
0.9626	High Similarity	NPC469444
0.9476	High Similarity	NPC25539
0.9372	High Similarity	NPC277306
0.9372	High Similarity	NPC469442
0.918	High Similarity	NPC60516
0.9162	High Similarity	NPC219350
0.9162	High Similarity	NPC194699
0.9126	High Similarity	NPC102959
0.883	High Similarity	NPC302715
0.8737	High Similarity	NPC473371
0.8595	High Similarity	NPC473404
0.8377	Intermediate Similarity	NPC51047
0.8281	Intermediate Similarity	NPC240130
0.8281	Intermediate Similarity	NPC61332
0.8251	Intermediate Similarity	NPC63040
0.8197	Intermediate Similarity	NPC15068
0.8182	Intermediate Similarity	NPC477551
0.8173	Intermediate Similarity	NPC477550
0.8173	Intermediate Similarity	NPC477552
0.8162	Intermediate Similarity	NPC46009
0.8144	Intermediate Similarity	NPC470728
0.8142	Intermediate Similarity	NPC22883
0.8142	Intermediate Similarity	NPC5719
0.8142	Intermediate Similarity	NPC217804
0.8142	Intermediate Similarity	NPC210377
0.8105	Intermediate Similarity	NPC476321
0.8085	Intermediate Similarity	NPC50016
0.8075	Intermediate Similarity	NPC273755
0.8063	Intermediate Similarity	NPC471526
0.8	Intermediate Similarity	NPC45037
0.7968	Intermediate Similarity	NPC475123
0.7968	Intermediate Similarity	NPC475204
0.7927	Intermediate Similarity	NPC471048
0.7927	Intermediate Similarity	NPC471050
0.7927	Intermediate Similarity	NPC471049
0.7923	Intermediate Similarity	NPC1390
0.7923	Intermediate Similarity	NPC62104
0.7913	Intermediate Similarity	NPC295795
0.7908	Intermediate Similarity	NPC473305
0.7908	Intermediate Similarity	NPC163961
0.7884	Intermediate Similarity	NPC306804
0.7842	Intermediate Similarity	NPC473354
0.7778	Intermediate Similarity	NPC473378
0.7778	Intermediate Similarity	NPC198254
0.7778	Intermediate Similarity	NPC274198
0.7778	Intermediate Similarity	NPC473407
0.7766	Intermediate Similarity	NPC107938
0.7766	Intermediate Similarity	NPC294516
0.775	Intermediate Similarity	NPC477632
0.775	Intermediate Similarity	NPC477638
0.7737	Intermediate Similarity	NPC230611
0.7723	Intermediate Similarity	NPC323662
0.772	Intermediate Similarity	NPC269750
0.772	Intermediate Similarity	NPC194671
0.7716	Intermediate Similarity	NPC94862
0.7696	Intermediate Similarity	NPC137627
0.7684	Intermediate Similarity	NPC276506
0.7684	Intermediate Similarity	NPC40234
0.767	Intermediate Similarity	NPC81845
0.7656	Intermediate Similarity	NPC26108
0.7656	Intermediate Similarity	NPC279871
0.7656	Intermediate Similarity	NPC473402
0.7656	Intermediate Similarity	NPC471165
0.7653	Intermediate Similarity	NPC294951
0.765	Intermediate Similarity	NPC477631
0.7638	Intermediate Similarity	NPC477636
0.7632	Intermediate Similarity	NPC280022
0.7617	Intermediate Similarity	NPC196243
0.7612	Intermediate Similarity	NPC328763
0.7565	Intermediate Similarity	NPC155506
0.7565	Intermediate Similarity	NPC159767
0.7565	Intermediate Similarity	NPC476227
0.7561	Intermediate Similarity	NPC473450
0.7513	Intermediate Similarity	NPC248670
0.75	Intermediate Similarity	NPC471527
0.75	Intermediate Similarity	NPC153554
0.7487	Intermediate Similarity	NPC209463
0.7474	Intermediate Similarity	NPC63931
0.7451	Intermediate Similarity	NPC477639
0.7449	Intermediate Similarity	NPC119652
0.7449	Intermediate Similarity	NPC97526
0.7448	Intermediate Similarity	NPC129486
0.7438	Intermediate Similarity	NPC65714
0.7423	Intermediate Similarity	NPC475532
0.7407	Intermediate Similarity	NPC469243
0.7385	Intermediate Similarity	NPC17698
0.7385	Intermediate Similarity	NPC165285
0.738	Intermediate Similarity	NPC473580
0.734	Intermediate Similarity	NPC248822
0.733	Intermediate Similarity	NPC471592
0.7316	Intermediate Similarity	NPC475544
0.7292	Intermediate Similarity	NPC223207
0.7286	Intermediate Similarity	NPC477637
0.7273	Intermediate Similarity	NPC473341
0.7254	Intermediate Similarity	NPC471771
0.7254	Intermediate Similarity	NPC290755
0.7254	Intermediate Similarity	NPC304074
0.7236	Intermediate Similarity	NPC170302
0.7236	Intermediate Similarity	NPC475564
0.7236	Intermediate Similarity	NPC475409
0.723	Intermediate Similarity	NPC478005
0.7198	Intermediate Similarity	NPC329295
0.7194	Intermediate Similarity	NPC89831
0.7165	Intermediate Similarity	NPC61004
0.715	Intermediate Similarity	NPC80514
0.715	Intermediate Similarity	NPC471051
0.715	Intermediate Similarity	NPC471053
0.715	Intermediate Similarity	NPC471052
0.7143	Intermediate Similarity	NPC326027
0.7136	Intermediate Similarity	NPC473546
0.713	Intermediate Similarity	NPC326333
0.7108	Intermediate Similarity	NPC96275
0.7107	Intermediate Similarity	NPC328494
0.7104	Intermediate Similarity	NPC478007
0.709	Intermediate Similarity	NPC262166
0.7049	Intermediate Similarity	NPC163392
0.7049	Intermediate Similarity	NPC48202
0.7049	Intermediate Similarity	NPC239762
0.7043	Intermediate Similarity	NPC81026
0.704	Intermediate Similarity	NPC478008
0.7035	Intermediate Similarity	NPC158277
0.7016	Intermediate Similarity	NPC476268
0.701	Intermediate Similarity	NPC299806
0.6989	Remote Similarity	NPC266741
0.6973	Remote Similarity	NPC168861
0.6973	Remote Similarity	NPC91953
0.697	Remote Similarity	NPC471568
0.697	Remote Similarity	NPC196091
0.697	Remote Similarity	NPC473693
0.6963	Remote Similarity	NPC39431
0.6959	Remote Similarity	NPC114806
0.6954	Remote Similarity	NPC302597
0.695	Remote Similarity	NPC227778
0.6947	Remote Similarity	NPC300443
0.6943	Remote Similarity	NPC326349
0.6943	Remote Similarity	NPC323336
0.6939	Remote Similarity	NPC472923
0.6927	Remote Similarity	NPC244509
0.6919	Remote Similarity	NPC186617
0.6919	Remote Similarity	NPC66490
0.6919	Remote Similarity	NPC197921
0.6911	Remote Similarity	NPC56685
0.6908	Remote Similarity	NPC246591
0.6907	Remote Similarity	NPC244336
0.6907	Remote Similarity	NPC24617
0.6882	Remote Similarity	NPC469360
0.6865	Remote Similarity	NPC214988
0.6857	Remote Similarity	NPC314083
0.6848	Remote Similarity	NPC6570
0.6842	Remote Similarity	NPC2501
0.6823	Remote Similarity	NPC261934
0.6823	Remote Similarity	NPC5194
0.6823	Remote Similarity	NPC122590
0.6806	Remote Similarity	NPC7817
0.6806	Remote Similarity	NPC473491
0.6806	Remote Similarity	NPC475168
0.68	Remote Similarity	NPC269383
0.68	Remote Similarity	NPC151030
0.6784	Remote Similarity	NPC328649
0.6769	Remote Similarity	NPC197743
0.6769	Remote Similarity	NPC297145
0.6765	Remote Similarity	NPC475421
0.6737	Remote Similarity	NPC311658
0.6737	Remote Similarity	NPC16188
0.6736	Remote Similarity	NPC202198
0.6732	Remote Similarity	NPC263507
0.6732	Remote Similarity	NPC271958
0.6732	Remote Similarity	NPC134413
0.6732	Remote Similarity	NPC45112
0.6701	Remote Similarity	NPC470902
0.6684	Remote Similarity	NPC233702
0.6683	Remote Similarity	NPC315542
0.6667	Remote Similarity	NPC52748
0.6667	Remote Similarity	NPC470112
0.6667	Remote Similarity	NPC167763
0.6667	Remote Similarity	NPC470903
0.6667	Remote Similarity	NPC241794
0.6667	Remote Similarity	NPC127741
0.665	Remote Similarity	NPC49315
0.6649	Remote Similarity	NPC476989
0.6649	Remote Similarity	NPC267237
0.6635	Remote Similarity	NPC64140
0.6635	Remote Similarity	NPC174122
0.6618	Remote Similarity	NPC477462
0.6604	Remote Similarity	NPC477526
0.6603	Remote Similarity	NPC138083
0.6599	Remote Similarity	NPC324850
0.6588	Remote Similarity	NPC234069
0.6587	Remote Similarity	NPC86678
0.6583	Remote Similarity	NPC73655
0.6582	Remote Similarity	NPC476741
0.6567	Remote Similarity	NPC254700
0.6562	Remote Similarity	NPC135121
0.6545	Remote Similarity	NPC315266
0.6545	Remote Similarity	NPC477217
0.6545	Remote Similarity	NPC201244
0.6541	Remote Similarity	NPC326966
0.6541	Remote Similarity	NPC48909

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 NPC220060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	130
0.1-0.2	478
0.2-0.3	951
0.3-0.4	2273
0.4-0.5	3863
0.5-0.6	1372
0.6-0.7	80
0.7-0.8	3
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
0.7713	Intermediate Similarity	NPD8303	Discontinued
0.7263	Intermediate Similarity	NPD8019	Approved
0.7173	Intermediate Similarity	NPD7495	Discontinued
0.709	Intermediate Similarity	NPD7523	Phase 3
0.6943	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD8076	Discontinued
0.6791	Remote Similarity	NPD7978	Discontinued
0.6771	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7485	Phase 3
0.6667	Remote Similarity	NPD3136	Phase 2
0.6667	Remote Similarity	NPD7484	Phase 3
0.6634	Remote Similarity	NPD7608	Discontinued
0.6616	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD6312	Discontinued
0.6566	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7617	Discontinued
0.6546	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4731	Phase 3
0.6507	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD6681	Discovery
0.6462	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6901	Phase 3
0.6445	Remote Similarity	NPD6853	Approved
0.6445	Remote Similarity	NPD6851	Approved
0.6443	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD8031	Discontinued
0.6429	Remote Similarity	NPD7303	Discontinued
0.6392	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.639	Remote Similarity	NPD4652	Approved
0.638	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD2098	Approved
0.634	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD6796	Discontinued
0.6321	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3933	Discontinued
0.6316	Remote Similarity	NPD5096	Phase 3
0.6316	Remote Similarity	NPD5095	Phase 3
0.6316	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7131	Phase 3
0.6308	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD8162	Phase 2
0.6294	Remote Similarity	NPD6419	Discontinued
0.628	Remote Similarity	NPD5137	Approved
0.6276	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5218	Approved
0.6275	Remote Similarity	NPD5219	Approved
0.6269	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD2017	Approved
0.6262	Remote Similarity	NPD2889	Approved
0.6262	Remote Similarity	NPD2888	Approved
0.6262	Remote Similarity	NPD2890	Approved
0.6256	Remote Similarity	NPD2097	Approved
0.6256	Remote Similarity	NPD6297	Approved
0.625	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7810	Phase 3
0.6244	Remote Similarity	NPD7811	Phase 3
0.6244	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7450	Phase 2
0.6195	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD5356	Approved
0.6158	Remote Similarity	NPD5355	Approved
0.6158	Remote Similarity	NPD829	Discontinued
0.6154	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6905	Phase 2
0.6147	Remote Similarity	NPD6058	Phase 2
0.614	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8292	Phase 2
0.6133	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6256	Approved
0.6116	Remote Similarity	NPD6255	Approved
0.6116	Remote Similarity	NPD6254	Approved
0.6114	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD1330	Phase 2
0.6091	Remote Similarity	NPD1968	Approved
0.6091	Remote Similarity	NPD1967	Approved
0.6089	Remote Similarity	NPD6057	Approved
0.6089	Remote Similarity	NPD6056	Approved
0.608	Remote Similarity	NPD6088	Approved
0.6071	Remote Similarity	NPD6253	Approved
0.6062	Remote Similarity	NPD8173	Phase 2
0.6062	Remote Similarity	NPD8172	Phase 2
0.6062	Remote Similarity	NPD6073	Approved
0.6061	Remote Similarity	NPD8323	Discontinued
0.6055	Remote Similarity	NPD4157	Discontinued
0.605	Remote Similarity	NPD3536	Discontinued
0.6047	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD3125	Approved
0.6042	Remote Similarity	NPD5296	Approved
0.6041	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD3659	Discontinued
0.6032	Remote Similarity	NPD4177	Approved
0.6032	Remote Similarity	NPD4175	Approved
0.6029	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6863	Phase 2
0.601	Remote Similarity	NPD555	Phase 2
0.6	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4086	Phase 1
0.6	Remote Similarity	NPD3602	Clinical (unspecified phase)
0.599	Remote Similarity	NPD5745	Approved
0.598	Remote Similarity	NPD8417	Discontinued
0.5979	Remote Similarity	NPD5725	Approved
0.5969	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD2240	Approved
0.5969	Remote Similarity	NPD2239	Approved
0.5961	Remote Similarity	NPD1972	Approved
0.5961	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD1973	Approved
0.596	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD6852	Discontinued
0.5949	Remote Similarity	NPD3553	Approved
0.5949	Remote Similarity	NPD3552	Approved
0.5949	Remote Similarity	NPD3554	Approved
0.5949	Remote Similarity	NPD3555	Approved
0.5941	Remote Similarity	NPD7613	Discontinued
0.5941	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD2562	Approved
0.5936	Remote Similarity	NPD2561	Approved
0.5915	Remote Similarity	NPD3366	Approved
0.5909	Remote Similarity	NPD8025	Phase 2
0.5907	Remote Similarity	NPD259	Phase 1
0.5907	Remote Similarity	NPD5747	Discontinued
0.5907	Remote Similarity	NPD7574	Phase 2
0.5897	Remote Similarity	NPD6189	Approved
0.5897	Remote Similarity	NPD6188	Approved
0.5897	Remote Similarity	NPD2568	Approved
0.5897	Remote Similarity	NPD5314	Approved
0.5897	Remote Similarity	NPD823	Approved
0.5897	Remote Similarity	NPD817	Approved
0.5895	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD7972	Discontinued
0.5888	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD5746	Approved
0.5877	Remote Similarity	NPD6107	Approved
0.5876	Remote Similarity	NPD4153	Approved
0.5876	Remote Similarity	NPD6346	Approved
0.5874	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD3098	Discontinued
0.5867	Remote Similarity	NPD7282	Approved
0.5867	Remote Similarity	NPD6294	Approved
0.5867	Remote Similarity	NPD6295	Approved
0.5865	Remote Similarity	NPD5967	Approved
0.5862	Remote Similarity	NPD6390	Discontinued
0.5859	Remote Similarity	NPD4914	Approved
0.5859	Remote Similarity	NPD5542	Phase 2
0.5858	Remote Similarity	NPD7805	Phase 3
0.5855	Remote Similarity	NPD597	Approved
0.5855	Remote Similarity	NPD598	Approved
0.5855	Remote Similarity	NPD6187	Approved
0.5855	Remote Similarity	NPD3879	Approved
0.5855	Remote Similarity	NPD601	Approved
0.5854	Remote Similarity	NPD3455	Phase 2
0.585	Remote Similarity	NPD6676	Phase 2
0.5838	Remote Similarity	NPD2218	Phase 2
0.5838	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD2217	Approved
0.5837	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.5837	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8356	Approved
0.583	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD7129	Suspended
0.5825	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD1136	Approved
0.5825	Remote Similarity	NPD6407	Approved
0.5825	Remote Similarity	NPD1130	Approved
0.5825	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD1423	Approved
0.5825	Remote Similarity	NPD6405	Approved
0.5825	Remote Similarity	NPD1132	Approved
0.582	Remote Similarity	NPD4659	Approved
0.582	Remote Similarity	NPD4677	Discontinued
0.5818	Remote Similarity	NPD6967	Phase 2
0.5817	Remote Similarity	NPD4557	Approved
0.5817	Remote Similarity	NPD4485	Approved
0.5816	Remote Similarity	NPD3052	Approved
0.5816	Remote Similarity	NPD3054	Approved
0.5813	Remote Similarity	NPD3985	Discontinued
0.5812	Remote Similarity	NPD3878	Approved
0.5812	Remote Similarity	NPD7451	Discontinued
0.5811	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.581	Remote Similarity	NPD8070	Approved
0.5808	Remote Similarity	NPD6511	Phase 1
0.5808	Remote Similarity	NPD4386	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