NPASS Compound

Structure

NPC60516 OpenBabel07101718232D 69 71 0 0 1 0 0 0 0 0999 V2000 -5.7396 0.5305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7061 -8.9539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0957 -0.8635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0262 -7.0356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5060 -1.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0095 -4.9886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4750 -0.4052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9554 -8.3357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5277 -7.6243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5813 -6.6534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0502 -5.9745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1910 -4.7353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7657 -6.6331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9064 -5.3939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7630 -6.9628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4326 -6.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6601 -8.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8320 -3.7084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8421 -1.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1530 -1.1022 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1155 -7.3766 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1446 -2.6528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2629 -5.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6937 -6.3428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4489 -6.2143 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7597 -7.8165 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9039 -3.9986 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8421 -2.4310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2642 -6.6264 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8884 -2.0379 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5264 -3.4035 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3649 -6.7584 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0248 -6.9978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4649 -3.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1855 -4.3141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7306 -7.7629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8511 -5.9162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9219 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2611 -9.4734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0752 -8.9415 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3147 -10.4443 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6065 -9.0343 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1587 -5.2862 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8239 -7.5519 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.7678 -2.4529 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8421 -2.4310 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.0375 -4.9618 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.6316 -7.3970 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -12.4092 -7.0014 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8735 -5.8685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3468 -7.6948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2484 -2.5551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.8897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2311 -4.1277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9433 -8.7118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7618 -6.2572 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8683 -0.9600 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 -0.9724 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0402 -1.5889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3686 -1.9448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0126 -3.2732 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 -3.9730 -2.1436 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6843 -2.9173 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 2.5264 -2.4310 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 6 48 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 11 13 1 0 0 0 0 11 23 2 0 0 0 0 12 14 2 0 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 16 29 1 0 0 0 0 17 43 1 0 0 0 0 18 23 1 0 0 0 0 19 65 1 0 0 0 0 20 3 1 1 0 0 0 21 4 1 6 0 0 0 22 5 1 6 0 0 0 22 31 1 0 0 0 0 22 66 1 0 0 0 0 24 50 1 0 0 0 0 25 10 1 1 0 0 0 25 33 1 0 0 0 0 25 44 1 0 0 0 0 26 15 1 1 0 0 0 26 37 1 0 0 0 0 26 45 1 0 0 0 0 27 18 1 1 0 0 0 27 34 1 0 0 0 0 27 48 1 0 0 0 0 28 19 1 1 0 0 0 28 35 1 0 0 0 0 28 67 1 0 0 0 0 29 49 1 0 0 0 0 29 51 1 6 0 0 0 30 20 1 1 0 0 0 30 39 1 0 0 0 0 30 46 1 0 0 0 0 31 36 1 0 0 0 0 31 47 1 6 0 0 0 32 21 1 1 0 0 0 32 38 1 0 0 0 0 32 49 1 0 0 0 0 33 45 2 3 0 0 0 33 52 1 0 0 0 0 34 46 2 3 0 0 0 34 53 1 0 0 0 0 35 47 2 3 0 0 0 35 54 1 0 0 0 0 36 44 2 3 0 0 0 36 55 1 0 0 0 0 37 49 1 0 0 0 0 37 56 2 0 0 0 0 38 48 1 0 0 0 0 38 57 2 0 0 0 0 39 58 2 0 0 0 0 39 66 1 0 0 0 0 40 41 2 0 0 0 0 40 42 1 0 0 0 0 40 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:	390.28
Volume:	437.082
LogP:	7.801
LogD:	4.236
LogS:	-6.351
# Rotatable Bonds:	17
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.195
Synthetic Accessibility Score:	2.142
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.952
MDCK Permeability:	2.0601464711944573e-05
Pgp-inhibitor:	0.962
Pgp-substrate:	0.177
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	99.27481842041016%
Volume Distribution (VD):	5.153
Pgp-substrate:	1.20183265209198%

ADMET: Metabolism

CYP1A2-inhibitor:	0.389
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.571
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.218
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.662
CYP2D6-substrate:	0.718
CYP3A4-inhibitor:	0.412
CYP3A4-substrate:	0.117

ADMET: Excretion

Clearance (CL):	6.505
Half-life (T1/2):	0.364

ADMET: Toxicity

hERG Blockers:	0.851
Human Hepatotoxicity (H-HT):	0.023
Drug-inuced Liver Injury (DILI):	0.134
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.086
Skin Sensitization:	0.974
Carcinogencity:	0.087
Eye Corrosion:	0.093
Eye Irritation:	0.872
Respiratory Toxicity:	0.868

Download Data

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

Natural Product: NPC60516

Natural Product ID:	NPC60516
*Common Name:**	(R)-3-((2S,5S,8S,11R,12S,15S,18S,21R)-15-(3-(Amino(Iminio)Methylamino)Propyl)-2,8-Di-Sec-Butyl-21-Hydroxy-5-(4-Hydroxybenzyl)-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)-2,8-bis[(2S)-butan-2-yl]-15-[3-(diaminomethylideneamino)propyl]-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-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:	QONBAISRUZCJFF-KMHGOLGOSA-N
Standard InCHI:	InChI=1S/C40H63N9O18S2/c1-7-20(3)30-39(58)66-22(5)31(47-35(54)28(67-69(62,63)64)19-65-68(59,60)61)36(55)44-25(10-9-17-43-40(41)42)33(52)45-26-15-16-29(51)49(37(26)56)32(21(4)8-2)38(57)48(6)27(34(53)46-30)18-23-11-13-24(50)14-12-23/h11-14,20-22,25-32,50-51H,7-10,15-19H2,1-6H3,(H,44,55)(H,45,52)(H,46,53)(H,47,54)(H4,41,42,43)(H,59,60,61)(H,62,63,64)/t20-,21-,22+,25-,26-,27-,28+,29+,30-,31-,32-/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=O)O[C@H](C)[C@@H](C(=N[C@@H](CCCNC(=N)N)C(=N[C@H]2CC[C@H](N([C@@H]([C@@H](C)CC)C(=O)N(C)[C@@H](Cc3ccc(cc3)O)C(=N1)O)C2=O)O)O)O)N=C([C@@H](COS(=O)(=O)O)OS(=O)(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078912
PubChem CID:	44254790
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11000050]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374973]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Einan Reservoir in Israel	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18163584]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18558743]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18973386]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	water bloom of the cyanobacterium Microcystis aeruginosa	n.a.	n.a.	PMID[19650639]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	bloom material	Lake Kinneret, Israel	n.a.	PMID[22280481]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Kibbutz Geva, Israel	n.a.	PMID[23153007]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Water Reservoir near Kibbutz Hafetz Haim, Israel	n.a.	PMID[23718637]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[24261937]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24642434]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24868986]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29405714]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[29847132]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9249979]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9842728]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[Title]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	2200.0	nM	PMID[507926]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[507926]

☑ 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 NPC60516 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	197
0.1-0.2	1101
0.2-0.3	5964
0.3-0.4	11897
0.4-0.5	18372
0.5-0.6	4328
0.6-0.7	511
0.7-0.8	216
0.8-0.85	75
0.85-0.9	31
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.994	High Similarity	NPC102959
0.9595	High Similarity	NPC302715
0.9353	High Similarity	NPC473404
0.918	High Similarity	NPC220060
0.8988	High Similarity	NPC63040
0.8984	High Similarity	NPC469445
0.8983	High Similarity	NPC240130
0.8983	High Similarity	NPC61332
0.8929	High Similarity	NPC15068
0.8882	High Similarity	NPC46009
0.8869	High Similarity	NPC210377
0.8869	High Similarity	NPC5719
0.8869	High Similarity	NPC22883
0.8869	High Similarity	NPC217804
0.8852	High Similarity	NPC469443
0.8852	High Similarity	NPC477551
0.8846	High Similarity	NPC477550
0.8846	High Similarity	NPC477552
0.8824	High Similarity	NPC469444
0.88	High Similarity	NPC476321
0.8786	High Similarity	NPC50016
0.8779	High Similarity	NPC273755
0.875	High Similarity	NPC471526
0.8691	High Similarity	NPC25539
0.8686	High Similarity	NPC45037
0.8663	High Similarity	NPC475204
0.8663	High Similarity	NPC475123
0.8631	High Similarity	NPC1390
0.8631	High Similarity	NPC62104
0.8596	High Similarity	NPC471050
0.8596	High Similarity	NPC471049
0.8596	High Similarity	NPC471048
0.8586	High Similarity	NPC277306
0.8586	High Similarity	NPC469442
0.8564	High Similarity	NPC473305
0.8564	High Similarity	NPC163961
0.8563	High Similarity	NPC306804
0.8514	High Similarity	NPC473354
0.8448	Intermediate Similarity	NPC274198
0.8448	Intermediate Similarity	NPC198254
0.8439	Intermediate Similarity	NPC107938
0.8439	Intermediate Similarity	NPC294516
0.8415	Intermediate Similarity	NPC473378
0.8415	Intermediate Similarity	NPC473407
0.84	Intermediate Similarity	NPC230611
0.8378	Intermediate Similarity	NPC477632
0.8378	Intermediate Similarity	NPC477638
0.8377	Intermediate Similarity	NPC194699
0.8377	Intermediate Similarity	NPC219350
0.8371	Intermediate Similarity	NPC194671
0.8371	Intermediate Similarity	NPC269750
0.8352	Intermediate Similarity	NPC137627
0.8352	Intermediate Similarity	NPC94862
0.8343	Intermediate Similarity	NPC40234
0.8343	Intermediate Similarity	NPC276506
0.8305	Intermediate Similarity	NPC26108
0.8305	Intermediate Similarity	NPC279871
0.8305	Intermediate Similarity	NPC471165
0.8305	Intermediate Similarity	NPC473402
0.8287	Intermediate Similarity	NPC294951
0.8286	Intermediate Similarity	NPC280022
0.827	Intermediate Similarity	NPC477631
0.8261	Intermediate Similarity	NPC477636
0.8258	Intermediate Similarity	NPC196243
0.8202	Intermediate Similarity	NPC159767
0.8202	Intermediate Similarity	NPC476227
0.8202	Intermediate Similarity	NPC155506
0.8158	Intermediate Similarity	NPC473450
0.815	Intermediate Similarity	NPC471527
0.8146	Intermediate Similarity	NPC248670
0.8122	Intermediate Similarity	NPC153554
0.8114	Intermediate Similarity	NPC63931
0.8079	Intermediate Similarity	NPC129486
0.8066	Intermediate Similarity	NPC119652
0.8066	Intermediate Similarity	NPC97526
0.8046	Intermediate Similarity	NPC469243
0.8045	Intermediate Similarity	NPC475532
0.8042	Intermediate Similarity	NPC477639
0.8032	Intermediate Similarity	NPC65714
0.8023	Intermediate Similarity	NPC473580
0.8	Intermediate Similarity	NPC17698
0.8	Intermediate Similarity	NPC165285
0.7947	Intermediate Similarity	NPC473371
0.7943	Intermediate Similarity	NPC475544
0.7926	Intermediate Similarity	NPC248822
0.791	Intermediate Similarity	NPC223207
0.7907	Intermediate Similarity	NPC473341
0.7906	Intermediate Similarity	NPC471592
0.788	Intermediate Similarity	NPC477637
0.7865	Intermediate Similarity	NPC471771
0.7865	Intermediate Similarity	NPC323662
0.7865	Intermediate Similarity	NPC304074
0.7865	Intermediate Similarity	NPC290755
0.7826	Intermediate Similarity	NPC475409
0.7826	Intermediate Similarity	NPC475564
0.7826	Intermediate Similarity	NPC170302
0.779	Intermediate Similarity	NPC89831
0.7778	Intermediate Similarity	NPC478005
0.7765	Intermediate Similarity	NPC61004
0.776	Intermediate Similarity	NPC329295
0.7753	Intermediate Similarity	NPC471052
0.7753	Intermediate Similarity	NPC471051
0.7753	Intermediate Similarity	NPC471053
0.7749	Intermediate Similarity	NPC328763
0.7717	Intermediate Similarity	NPC473546
0.7708	Intermediate Similarity	NPC80514
0.7701	Intermediate Similarity	NPC262166
0.7692	Intermediate Similarity	NPC328494
0.7679	Intermediate Similarity	NPC163392
0.7679	Intermediate Similarity	NPC48202
0.7679	Intermediate Similarity	NPC239762
0.7672	Intermediate Similarity	NPC96275
0.7661	Intermediate Similarity	NPC81026
0.7624	Intermediate Similarity	NPC209463
0.7621	Intermediate Similarity	NPC478007
0.7614	Intermediate Similarity	NPC476268
0.7609	Intermediate Similarity	NPC158277
0.7602	Intermediate Similarity	NPC266741
0.7592	Intermediate Similarity	NPC51047
0.7588	Intermediate Similarity	NPC91953
0.7588	Intermediate Similarity	NPC168861
0.7566	Intermediate Similarity	NPC299806
0.7557	Intermediate Similarity	NPC39431
0.7548	Intermediate Similarity	NPC478008
0.7543	Intermediate Similarity	NPC300443
0.7542	Intermediate Similarity	NPC114806
0.7541	Intermediate Similarity	NPC471568
0.7541	Intermediate Similarity	NPC196091
0.7541	Intermediate Similarity	NPC473693
0.7529	Intermediate Similarity	NPC197921
0.7528	Intermediate Similarity	NPC323336
0.7528	Intermediate Similarity	NPC326349
0.7527	Intermediate Similarity	NPC302597
0.7514	Intermediate Similarity	NPC244509
0.7514	Intermediate Similarity	NPC472923
0.75	Intermediate Similarity	NPC56685
0.7486	Intermediate Similarity	NPC24617
0.7486	Intermediate Similarity	NPC244336
0.7486	Intermediate Similarity	NPC186617
0.7486	Intermediate Similarity	NPC66490
0.7485	Intermediate Similarity	NPC469360
0.7471	Intermediate Similarity	NPC214988
0.7456	Intermediate Similarity	NPC6570
0.7448	Intermediate Similarity	NPC246591
0.7429	Intermediate Similarity	NPC2501
0.7401	Intermediate Similarity	NPC5194
0.7401	Intermediate Similarity	NPC261934
0.7401	Intermediate Similarity	NPC122590
0.7386	Intermediate Similarity	NPC7817
0.7386	Intermediate Similarity	NPC473491
0.7386	Intermediate Similarity	NPC475168
0.7385	Intermediate Similarity	NPC314083
0.7371	Intermediate Similarity	NPC470728
0.7337	Intermediate Similarity	NPC328649
0.7333	Intermediate Similarity	NPC197743
0.7333	Intermediate Similarity	NPC297145
0.7314	Intermediate Similarity	NPC311658
0.7314	Intermediate Similarity	NPC16188
0.7303	Intermediate Similarity	NPC202198
0.7302	Intermediate Similarity	NPC475421
0.7263	Intermediate Similarity	NPC470902
0.7251	Intermediate Similarity	NPC127741
0.7247	Intermediate Similarity	NPC233702
0.7246	Intermediate Similarity	NPC326027
0.7241	Intermediate Similarity	NPC52748
0.7235	Intermediate Similarity	NPC267237
0.7233	Intermediate Similarity	NPC326333
0.7225	Intermediate Similarity	NPC476989
0.7213	Intermediate Similarity	NPC241794
0.7202	Intermediate Similarity	NPC315542
0.7188	Intermediate Similarity	NPC470112
0.7188	Intermediate Similarity	NPC167763
0.7188	Intermediate Similarity	NPC470903
0.7184	Intermediate Similarity	NPC295795
0.7143	Intermediate Similarity	NPC324850
0.7143	Intermediate Similarity	NPC64140
0.7143	Intermediate Similarity	NPC477462
0.7143	Intermediate Similarity	NPC174122
0.7127	Intermediate Similarity	NPC476741
0.712	Intermediate Similarity	NPC73655
0.7119	Intermediate Similarity	NPC135121
0.7118	Intermediate Similarity	NPC326966
0.7113	Intermediate Similarity	NPC138083
0.7107	Intermediate Similarity	NPC477526
0.7102	Intermediate Similarity	NPC315266
0.7102	Intermediate Similarity	NPC477217
0.7102	Intermediate Similarity	NPC201244
0.7097	Intermediate Similarity	NPC254700
0.7092	Intermediate Similarity	NPC234069
0.7079	Intermediate Similarity	NPC471820
0.7079	Intermediate Similarity	NPC471821
0.7072	Intermediate Similarity	NPC476742
0.7059	Intermediate Similarity	NPC473502
0.7059	Intermediate Similarity	NPC141957
0.7056	Intermediate Similarity	NPC476744
0.7053	Intermediate Similarity	NPC136797
0.7052	Intermediate Similarity	NPC64205
0.7052	Intermediate Similarity	NPC68865
0.7041	Intermediate Similarity	NPC4910
0.7011	Intermediate Similarity	NPC132636

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 NPC60516 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	124
0.1-0.2	384
0.2-0.3	747
0.3-0.4	2068
0.4-0.5	3610
0.5-0.6	1937
0.6-0.7	264
0.7-0.8	15
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8382	Intermediate Similarity	NPD8303	Discontinued
0.7886	Intermediate Similarity	NPD8019	Approved
0.7784	Intermediate Similarity	NPD7495	Discontinued
0.7701	Intermediate Similarity	NPD7523	Phase 3
0.7528	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD8076	Discontinued
0.7384	Intermediate Similarity	NPD7978	Discontinued
0.7262	Intermediate Similarity	NPD3136	Phase 2
0.7247	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7484	Phase 3
0.7204	Intermediate Similarity	NPD7485	Phase 3
0.7202	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7608	Discontinued
0.7095	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7617	Discontinued
0.7053	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6681	Discovery
0.7011	Intermediate Similarity	NPD6901	Phase 3
0.6961	Remote Similarity	NPD7303	Discontinued
0.6954	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD8031	Discontinued
0.6939	Remote Similarity	NPD6853	Approved
0.6939	Remote Similarity	NPD6851	Approved
0.6895	Remote Similarity	NPD4652	Approved
0.6872	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD2098	Approved
0.6857	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7131	Phase 3
0.6813	Remote Similarity	NPD6419	Discontinued
0.6798	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6796	Discontinued
0.6772	Remote Similarity	NPD5218	Approved
0.6772	Remote Similarity	NPD5219	Approved
0.6771	Remote Similarity	NPD5137	Approved
0.6763	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD8162	Phase 2
0.6758	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2097	Approved
0.6754	Remote Similarity	NPD2888	Approved
0.6754	Remote Similarity	NPD2017	Approved
0.6754	Remote Similarity	NPD2890	Approved
0.6754	Remote Similarity	NPD2889	Approved
0.6742	Remote Similarity	NPD7450	Phase 2
0.6735	Remote Similarity	NPD6297	Approved
0.6699	Remote Similarity	NPD7811	Phase 3
0.6699	Remote Similarity	NPD7810	Phase 3
0.6684	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5356	Approved
0.6649	Remote Similarity	NPD5355	Approved
0.6648	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1330	Phase 2
0.66	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD6088	Approved
0.6573	Remote Similarity	NPD8173	Phase 2
0.6573	Remote Similarity	NPD6073	Approved
0.6573	Remote Similarity	NPD8172	Phase 2
0.6571	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3125	Approved
0.6557	Remote Similarity	NPD8323	Discontinued
0.6555	Remote Similarity	NPD6255	Approved
0.6555	Remote Similarity	NPD6254	Approved
0.6555	Remote Similarity	NPD6256	Approved
0.6554	Remote Similarity	NPD5296	Approved
0.6552	Remote Similarity	NPD4177	Approved
0.6552	Remote Similarity	NPD4175	Approved
0.6547	Remote Similarity	NPD8292	Phase 2
0.6542	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3536	Discontinued
0.6538	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD555	Phase 2
0.6508	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6253	Approved
0.6502	Remote Similarity	NPD4157	Discontinued
0.65	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5745	Approved
0.648	Remote Similarity	NPD5725	Approved
0.6477	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD3659	Discontinued
0.6464	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD2240	Approved
0.6464	Remote Similarity	NPD2239	Approved
0.6455	Remote Similarity	NPD8417	Discontinued
0.6453	Remote Similarity	NPD2561	Approved
0.6453	Remote Similarity	NPD2562	Approved
0.645	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD6863	Phase 2
0.6444	Remote Similarity	NPD3552	Approved
0.6444	Remote Similarity	NPD3555	Approved
0.6444	Remote Similarity	NPD6852	Discontinued
0.6444	Remote Similarity	NPD3553	Approved
0.6444	Remote Similarity	NPD3554	Approved
0.6436	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7613	Discontinued
0.6417	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5747	Discontinued
0.6404	Remote Similarity	NPD259	Phase 1
0.64	Remote Similarity	NPD4086	Phase 1
0.64	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5314	Approved
0.6389	Remote Similarity	NPD823	Approved
0.6389	Remote Similarity	NPD817	Approved
0.6389	Remote Similarity	NPD2568	Approved
0.6384	Remote Similarity	NPD5746	Approved
0.6369	Remote Similarity	NPD4153	Approved
0.6369	Remote Similarity	NPD6346	Approved
0.6354	Remote Similarity	NPD6294	Approved
0.6354	Remote Similarity	NPD7972	Discontinued
0.6354	Remote Similarity	NPD6295	Approved
0.6353	Remote Similarity	NPD2217	Approved
0.6353	Remote Similarity	NPD2218	Phase 2
0.6348	Remote Similarity	NPD601	Approved
0.6348	Remote Similarity	NPD597	Approved
0.6348	Remote Similarity	NPD598	Approved
0.6341	Remote Similarity	NPD8025	Phase 2
0.6333	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6390	Discontinued
0.6327	Remote Similarity	NPD6107	Approved
0.6324	Remote Similarity	NPD6676	Phase 2
0.6322	Remote Similarity	NPD4677	Discontinued
0.6322	Remote Similarity	NPD4659	Approved
0.6321	Remote Similarity	NPD5967	Approved
0.6319	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3455	Phase 2
0.6313	Remote Similarity	NPD1136	Approved
0.6313	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD1130	Approved
0.6313	Remote Similarity	NPD1423	Approved
0.6313	Remote Similarity	NPD6407	Approved
0.6313	Remote Similarity	NPD6405	Approved
0.6313	Remote Similarity	NPD1132	Approved
0.6307	Remote Similarity	NPD7451	Discontinued
0.6301	Remote Similarity	NPD6188	Approved
0.6301	Remote Similarity	NPD6189	Approved
0.6298	Remote Similarity	NPD3054	Approved
0.6298	Remote Similarity	NPD3052	Approved
0.6294	Remote Similarity	NPD317	Approved
0.6294	Remote Similarity	NPD16	Approved
0.6294	Remote Similarity	NPD856	Approved
0.6294	Remote Similarity	NPD318	Approved
0.6289	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7282	Approved
0.6284	Remote Similarity	NPD9570	Approved
0.6283	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD6623	Phase 3
0.6278	Remote Similarity	NPD3062	Approved
0.6278	Remote Similarity	NPD825	Approved
0.6278	Remote Similarity	NPD826	Approved
0.6278	Remote Similarity	NPD3061	Approved
0.6278	Remote Similarity	NPD3059	Approved
0.6277	Remote Similarity	NPD3985	Discontinued
0.627	Remote Similarity	NPD5264	Approved
0.627	Remote Similarity	NPD5265	Approved
0.6269	Remote Similarity	NPD4557	Approved
0.6264	Remote Similarity	NPD3073	Approved
0.6264	Remote Similarity	NPD2584	Suspended
0.6264	Remote Similarity	NPD3072	Approved
0.6264	Remote Similarity	NPD3071	Approved
0.6257	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD6187	Approved
0.6256	Remote Similarity	NPD3879	Approved
0.6256	Remote Similarity	NPD8070	Approved
0.625	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6677	Suspended
0.6244	Remote Similarity	NPD6967	Phase 2
0.6237	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3400	Discontinued
0.6237	Remote Similarity	NPD6646	Discontinued
0.6236	Remote Similarity	NPD5263	Approved
0.6235	Remote Similarity	NPD9568	Approved
0.6232	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD5614	Approved
0.6223	Remote Similarity	NPD5613	Approved
0.6222	Remote Similarity	NPD8356	Approved
0.6222	Remote Similarity	NPD2245	Discovery
0.6219	Remote Similarity	NPD6042	Phase 2
0.6219	Remote Similarity	NPD42	Phase 2
0.6218	Remote Similarity	NPD4227	Discontinued
0.6215	Remote Similarity	NPD4151	Approved
0.621	Remote Similarity	NPD3878	Approved
0.6207	Remote Similarity	NPD4761	Approved
0.6207	Remote Similarity	NPD4762	Approved
0.6207	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD2891	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