NPASS Compound

Structure

NPC295795 OpenBabel07101719142D 47 49 0 0 1 0 0 0 0 0999 V2000 -2.0237 -5.7918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0674 -6.2076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3546 -5.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4345 -3.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9345 -2.3506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9345 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4345 -1.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5688 -1.0365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9215 -0.5012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2816 -2.1954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3764 -5.2565 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5907 -1.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8778 -0.0854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2305 0.4498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9345 -4.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3035 -2.4034 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2927 -4.5134 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2087 0.6577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4345 -4.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -3.3544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2708 -4.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4345 0.2475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8560 0.1225 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.5614 1.1930 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.4345 0.2475 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9345 1.1135 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4345 -4.9487 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9345 -0.6186 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0163 -3.5623 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -3.9781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6344 -1.6602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5177 1.6088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -5.8147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6636 -4.0976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5798 -5.6723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 1 3 1 0 0 0 0 3 15 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 7 18 1 0 0 0 0 8 34 1 0 0 0 0 9 35 1 0 0 0 0 10 16 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 20 2 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 15 2 1 1 0 0 0 15 24 1 0 0 0 0 17 6 1 1 0 0 0 17 21 1 0 0 0 0 18 46 1 6 0 0 0 19 25 2 0 0 0 0 19 30 1 0 0 0 0 20 25 1 0 0 0 0 20 31 1 0 0 0 0 21 14 1 1 0 0 0 21 37 1 0 0 0 0 22 26 1 1 0 0 0 22 37 1 0 0 0 0 23 27 1 0 0 0 0 23 38 1 1 0 0 0 24 28 1 1 0 0 0 24 36 1 0 0 0 0 25 39 1 0 0 0 0 26 34 2 3 0 0 0 26 40 1 0 0 0 0 27 36 2 3 0 0 0 27 41 1 0 0 0 0 28 37 1 0 0 0 0 28 42 2 0 0 0 0 29 32 2 0 0 0 0 29 33 1 0 0 0 0 29 35 1 0 0 0 0 43 47 1 0 0 0 0 44 47 2 0 0 0 0 45 47 2 0 0 0 0 46 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	766.18
Volume:	664.112
LogP:	1.309
LogD:	0.513
LogS:	-1.67
# Rotatable Bonds:	18
TPSA:	246.97
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	3
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.058
Synthetic Accessibility Score:	4.764
Fsp3:	0.655
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:	-5.76
MDCK Permeability:	9.451133337279316e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.755
Human Intestinal Absorption (HIA):	0.889
20% Bioavailability (F20%):	0.886
30% Bioavailability (F30%):	0.847

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	94.574951171875%
Volume Distribution (VD):	0.325
Pgp-substrate:	6.139050483703613%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	3.367
Half-life (T1/2):	0.146

ADMET: Toxicity

hERG Blockers:	0.173
Human Hepatotoxicity (H-HT):	0.808
Drug-inuced Liver Injury (DILI):	0.716
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.312
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.233
Carcinogencity:	0.395
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.785

Download Data

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

Natural Product: NPC295795

Natural Product ID:	NPC295795
*Common Name:**	Rel-(2S,3As,6R,7As)-1-((2R,3S)-2-((R)-3-(3-Bromo-5-Chloro-4-Hydroxyphenyl)-2-Hydroxypropanamido)-3-Methylpentanoyl)-2-(4-Guanidinobutylcarbamoyl)Octahydro-1H-Indol-6-Yl Hydrogen Sulfate
IUPAC Name:	[(2S,3aS,6R,7aS)-1-[(2R,3S)-2-[[(2R)-3-(3-bromo-5-chloro-4-hydroxyphenyl)-2-hydroxypropanoyl]amino]-3-methylpentanoyl]-2-[4-(diaminomethylideneamino)butylcarbamoyl]-2,3,3a,4,5,6,7,7a-octahydroindol-6-yl] hydrogen sulfate
Synonyms:
Standard InCHIKey:	WGFZRUTWFMYTPD-GPSFYHMWSA-N
Standard InCHI:	InChI=1S/C29H44BrClN6O9S/c1-3-15(2)24(36-27(41)23(38)12-16-10-19(30)25(39)20(31)11-16)28(42)37-21-14-18(46-47(43,44)45)7-6-17(21)13-22(37)26(40)34-8-4-5-9-35-29(32)33/h10-11,15,17-18,21-24,38-39H,3-9,12-14H2,1-2H3,(H,34,40)(H,36,41)(H4,32,33,35)(H,43,44,45)/t15-,17-,18+,21-,22-,23+,24+/m0/s1
SMILES:	CC[C@@H]([C@H](C(=O)N1[C@H]2C[C@@H](CC[C@H]2C[C@H]1C(=NCCCCNC(=N)N)O)OS(=O)(=O)O)N=C([C@@H](Cc1cc(Cl)c(c(c1)Br)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2207402
PubChem CID:	71459739
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004830] Dipeptides

*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	>	45500.0	nM	PMID[545770]
NPT2	Others	Unspecified		IC50	=	12200.0	nM	PMID[545770]

☑ 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 NPC295795 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	289
0.1-0.2	1803
0.2-0.3	13841
0.3-0.4	16476
0.4-0.5	9006
0.5-0.6	1010
0.6-0.7	229
0.7-0.8	32
0.8-0.85	2
0.85-0.9	5
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9731	High Similarity	NPC81845
0.8942	High Similarity	NPC80514
0.883	High Similarity	NPC51047
0.8783	High Similarity	NPC470728
0.8723	High Similarity	NPC96275
0.8677	High Similarity	NPC246591
0.7913	Intermediate Similarity	NPC220060
0.7794	Intermediate Similarity	NPC469443
0.7788	Intermediate Similarity	NPC469444
0.7762	Intermediate Similarity	NPC469445
0.7696	Intermediate Similarity	NPC280022
0.7692	Intermediate Similarity	NPC119652
0.7692	Intermediate Similarity	NPC97526
0.7594	Intermediate Similarity	NPC469442
0.7594	Intermediate Similarity	NPC277306
0.7523	Intermediate Similarity	NPC25539
0.7512	Intermediate Similarity	NPC94862
0.7447	Intermediate Similarity	NPC476268
0.7406	Intermediate Similarity	NPC219350
0.7406	Intermediate Similarity	NPC194699
0.722	Intermediate Similarity	NPC102959
0.7184	Intermediate Similarity	NPC60516
0.7163	Intermediate Similarity	NPC302715
0.7095	Intermediate Similarity	NPC473371
0.7085	Intermediate Similarity	NPC89831
0.705	Intermediate Similarity	NPC475532
0.7042	Intermediate Similarity	NPC473450
0.702	Intermediate Similarity	NPC209463
0.7015	Intermediate Similarity	NPC165285
0.7015	Intermediate Similarity	NPC17698
0.7005	Intermediate Similarity	NPC63931
0.7	Intermediate Similarity	NPC65714
0.6985	Remote Similarity	NPC129486
0.6967	Remote Similarity	NPC477638
0.6967	Remote Similarity	NPC477632
0.6901	Remote Similarity	NPC471592
0.6878	Remote Similarity	NPC475564
0.6878	Remote Similarity	NPC170302
0.6878	Remote Similarity	NPC475409
0.6866	Remote Similarity	NPC274198
0.6866	Remote Similarity	NPC276506
0.6866	Remote Similarity	NPC198254
0.6847	Remote Similarity	NPC471165
0.6845	Remote Similarity	NPC473404
0.6825	Remote Similarity	NPC248822
0.6792	Remote Similarity	NPC477631
0.6788	Remote Similarity	NPC473491
0.678	Remote Similarity	NPC473546
0.6777	Remote Similarity	NPC61332
0.6777	Remote Similarity	NPC477636
0.6777	Remote Similarity	NPC240130
0.6776	Remote Similarity	NPC329295
0.6732	Remote Similarity	NPC196243
0.6717	Remote Similarity	NPC244336
0.6713	Remote Similarity	NPC477552
0.6713	Remote Similarity	NPC477550
0.6684	Remote Similarity	NPC168861
0.6683	Remote Similarity	NPC469243
0.6683	Remote Similarity	NPC475544
0.6667	Remote Similarity	NPC328494
0.6651	Remote Similarity	NPC477551
0.665	Remote Similarity	NPC244509
0.665	Remote Similarity	NPC473580
0.6635	Remote Similarity	NPC153554
0.6633	Remote Similarity	NPC56685
0.6633	Remote Similarity	NPC262166
0.6632	Remote Similarity	NPC16188
0.662	Remote Similarity	NPC477639
0.6618	Remote Similarity	NPC475204
0.6618	Remote Similarity	NPC475123
0.6602	Remote Similarity	NPC26108
0.6601	Remote Similarity	NPC328649
0.6584	Remote Similarity	NPC223207
0.6583	Remote Similarity	NPC326349
0.6583	Remote Similarity	NPC323336
0.657	Remote Similarity	NPC50016
0.6567	Remote Similarity	NPC241794
0.6553	Remote Similarity	NPC273755
0.6552	Remote Similarity	NPC61004
0.6552	Remote Similarity	NPC304074
0.6552	Remote Similarity	NPC290755
0.6552	Remote Similarity	NPC471771
0.6548	Remote Similarity	NPC202198
0.6546	Remote Similarity	NPC311658
0.6545	Remote Similarity	NPC476989
0.6528	Remote Similarity	NPC227953
0.6524	Remote Similarity	NPC476321
0.652	Remote Similarity	NPC302597
0.6518	Remote Similarity	NPC478005
0.6502	Remote Similarity	NPC217804
0.6502	Remote Similarity	NPC210377
0.6502	Remote Similarity	NPC22883
0.6502	Remote Similarity	NPC5719
0.6493	Remote Similarity	NPC471526
0.6492	Remote Similarity	NPC197045
0.6473	Remote Similarity	NPC248670
0.6456	Remote Similarity	NPC46009
0.6447	Remote Similarity	NPC20755
0.6445	Remote Similarity	NPC477637
0.6442	Remote Similarity	NPC136797
0.6439	Remote Similarity	NPC63040
0.6429	Remote Similarity	NPC45037
0.6414	Remote Similarity	NPC233702
0.6408	Remote Similarity	NPC66490
0.6406	Remote Similarity	NPC214988
0.6402	Remote Similarity	NPC77435
0.6402	Remote Similarity	NPC259071
0.6394	Remote Similarity	NPC137627
0.639	Remote Similarity	NPC15068
0.6385	Remote Similarity	NPC471049
0.6385	Remote Similarity	NPC471050
0.6385	Remote Similarity	NPC471048
0.6382	Remote Similarity	NPC5194
0.6382	Remote Similarity	NPC261934
0.6364	Remote Similarity	NPC473354
0.6351	Remote Similarity	NPC471337
0.6347	Remote Similarity	NPC202866
0.6335	Remote Similarity	NPC323662
0.6321	Remote Similarity	NPC48202
0.6316	Remote Similarity	NPC306804
0.6313	Remote Similarity	NPC163961
0.6313	Remote Similarity	NPC473305
0.6308	Remote Similarity	NPC477254
0.6305	Remote Similarity	NPC1390
0.6305	Remote Similarity	NPC62104
0.6298	Remote Similarity	NPC40234
0.6286	Remote Similarity	NPC476227
0.6284	Remote Similarity	NPC473378
0.6284	Remote Similarity	NPC473407
0.6283	Remote Similarity	NPC267237
0.6282	Remote Similarity	NPC478007
0.628	Remote Similarity	NPC107938
0.628	Remote Similarity	NPC294516
0.6273	Remote Similarity	NPC475843
0.6269	Remote Similarity	NPC242159
0.6269	Remote Similarity	NPC313694
0.6244	Remote Similarity	NPC73655
0.624	Remote Similarity	NPC33064
0.6232	Remote Similarity	NPC254700
0.6229	Remote Similarity	NPC478008
0.6227	Remote Similarity	NPC328763
0.6227	Remote Similarity	NPC471338
0.6227	Remote Similarity	NPC474678
0.6211	Remote Similarity	NPC474087
0.6209	Remote Similarity	NPC227778
0.6202	Remote Similarity	NPC141957
0.6197	Remote Similarity	NPC269750
0.6197	Remote Similarity	NPC194671
0.6195	Remote Similarity	NPC114806
0.6193	Remote Similarity	NPC315266
0.619	Remote Similarity	NPC230611
0.618	Remote Similarity	NPC471335
0.6178	Remote Similarity	NPC473724
0.6176	Remote Similarity	NPC324850
0.6176	Remote Similarity	NPC233926
0.6175	Remote Similarity	NPC8093
0.6175	Remote Similarity	NPC121571
0.6162	Remote Similarity	NPC81026
0.6157	Remote Similarity	NPC294951
0.6151	Remote Similarity	NPC214142
0.6146	Remote Similarity	NPC24617
0.6143	Remote Similarity	NPC269383
0.6143	Remote Similarity	NPC151030
0.6132	Remote Similarity	NPC158277
0.6132	Remote Similarity	NPC473402
0.6132	Remote Similarity	NPC279871
0.6132	Remote Similarity	NPC159767
0.6132	Remote Similarity	NPC155506
0.6125	Remote Similarity	NPC261251
0.6119	Remote Similarity	NPC147847
0.6111	Remote Similarity	NPC266741
0.61	Remote Similarity	NPC100547
0.6089	Remote Similarity	NPC300443
0.6087	Remote Similarity	NPC471339
0.6085	Remote Similarity	NPC49315
0.6074	Remote Similarity	NPC322135
0.6074	Remote Similarity	NPC223409
0.6074	Remote Similarity	NPC95240
0.6073	Remote Similarity	NPC174607
0.6058	Remote Similarity	NPC118559
0.6058	Remote Similarity	NPC124920
0.6058	Remote Similarity	NPC34580
0.6058	Remote Similarity	NPC304307
0.6055	Remote Similarity	NPC299806
0.6049	Remote Similarity	NPC14288
0.6039	Remote Similarity	NPC471527
0.6029	Remote Similarity	NPC472923
0.6029	Remote Similarity	NPC47672
0.6029	Remote Similarity	NPC39431
0.6027	Remote Similarity	NPC276120
0.6025	Remote Similarity	NPC54803
0.6025	Remote Similarity	NPC321592
0.6019	Remote Similarity	NPC263507
0.6019	Remote Similarity	NPC271958
0.6019	Remote Similarity	NPC45112
0.6019	Remote Similarity	NPC134413
0.6019	Remote Similarity	NPC186617
0.6017	Remote Similarity	NPC471336
0.6017	Remote Similarity	NPC470746
0.601	Remote Similarity	NPC326966

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 NPC295795 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	548
0.2-0.3	1093
0.3-0.4	2969
0.4-0.5	3787
0.5-0.6	586
0.6-0.7	11
0.7-0.8	0
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
0.7056	Intermediate Similarity	NPD8303	Discontinued
0.6751	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7495	Discontinued
0.6522	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7617	Discontinued
0.6465	Remote Similarity	NPD7523	Phase 3
0.6406	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD8019	Approved
0.6346	Remote Similarity	NPD5137	Approved
0.6169	Remote Similarity	NPD7303	Discontinued
0.6162	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD4652	Approved
0.6142	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7484	Phase 3
0.6095	Remote Similarity	NPD7485	Phase 3
0.6091	Remote Similarity	NPD8076	Discontinued
0.6089	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD2098	Approved
0.6019	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.601	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.601	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.596	Remote Similarity	NPD7450	Phase 2
0.5959	Remote Similarity	NPD3136	Phase 2
0.5941	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD6901	Phase 3
0.5939	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD3337	Discontinued
0.5933	Remote Similarity	NPD2097	Approved
0.5931	Remote Similarity	NPD7613	Discontinued
0.593	Remote Similarity	NPD7978	Discontinued
0.5928	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.592	Remote Similarity	NPD6676	Phase 2
0.5913	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4731	Phase 3
0.5848	Remote Similarity	NPD6058	Phase 2
0.5829	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7131	Phase 3
0.5818	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD829	Discontinued
0.5805	Remote Similarity	NPD6419	Discontinued
0.5802	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD9718	Approved
0.5792	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.578	Remote Similarity	NPD3933	Discontinued
0.578	Remote Similarity	NPD5095	Phase 3
0.578	Remote Similarity	NPD5096	Phase 3
0.5771	Remote Similarity	NPD6312	Discontinued
0.5767	Remote Similarity	NPD7608	Discontinued
0.5766	Remote Similarity	NPD6557	Phase 2
0.5756	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6681	Discovery
0.5736	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD8172	Phase 2
0.5729	Remote Similarity	NPD6073	Approved
0.5729	Remote Similarity	NPD8173	Phase 2
0.5726	Remote Similarity	NPD8106	Phase 2
0.5721	Remote Similarity	NPD2888	Approved
0.5721	Remote Similarity	NPD2890	Approved
0.5721	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD2017	Approved
0.5721	Remote Similarity	NPD2889	Approved
0.5721	Remote Similarity	NPD5649	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD1973	Approved
0.5721	Remote Similarity	NPD1972	Approved
0.5714	Remote Similarity	NPD5542	Phase 2
0.5714	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.57	Remote Similarity	NPD3364	Phase 3
0.5685	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.5685	Remote Similarity	NPD1330	Phase 2
0.5677	Remote Similarity	NPD2562	Approved
0.5677	Remote Similarity	NPD2561	Approved
0.5668	Remote Similarity	NPD8292	Phase 2
0.5665	Remote Similarity	NPD4386	Approved
0.5665	Remote Similarity	NPD4387	Approved
0.5663	Remote Similarity	NPD5263	Approved
0.5662	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6796	Discontinued
0.5654	Remote Similarity	NPD5218	Approved
0.5654	Remote Similarity	NPD8031	Discontinued
0.5654	Remote Similarity	NPD5219	Approved
0.5652	Remote Similarity	NPD4915	Approved
0.565	Remote Similarity	NPD5314	Approved
0.5642	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.563	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.5622	Remote Similarity	NPD3552	Approved
0.5622	Remote Similarity	NPD3553	Approved
0.5622	Remote Similarity	NPD3555	Approved
0.5622	Remote Similarity	NPD3554	Approved
0.5619	Remote Similarity	NPD6057	Approved
0.5619	Remote Similarity	NPD4157	Discontinued
0.5619	Remote Similarity	NPD6056	Approved
0.5611	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.5605	Remote Similarity	NPD5567	Approved
0.56	Remote Similarity	NPD7113	Clinical (unspecified phase)

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