NPASS Compound

Structure

NPC476268 OpenBabel07101719512D 33 35 0 0 1 0 0 0 0 0999 V2000 -0.2579 3.5963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9052 3.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8689 1.2475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2290 -0.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8470 1.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2071 -0.2388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6180 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5817 0.0885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 2.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5599 0.2964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5162 0.7122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9126 0.8316 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9344 0.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -2.6456 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2653 1.3669 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.4943 0.9201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2216 1.7827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6254 -0.3273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 -0.5352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 6 1 0 0 0 0 3 14 2 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 8 1 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 15 5 1 6 0 0 0 15 19 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 6 0 0 0 18 9 1 6 0 0 0 18 24 1 0 0 0 0 18 26 1 0 0 0 0 19 12 1 6 0 0 0 19 27 1 0 0 0 0 20 22 1 1 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 30 1 6 0 0 0 22 25 2 0 0 0 0 22 31 1 0 0 0 0 23 26 2 3 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 24 33 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	461.25
Volume:	467.904
LogP:	1.392
LogD:	1.876
LogS:	-2.853
# Rotatable Bonds:	10
TPSA:	153.19
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	4.04
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.828
MDCK Permeability:	2.4910494175856e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.932
Human Intestinal Absorption (HIA):	0.177
20% Bioavailability (F20%):	0.33
30% Bioavailability (F30%):	0.889

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	55.856231689453125%
Volume Distribution (VD):	0.469
Pgp-substrate:	46.71351623535156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.053
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.265
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.331
CYP3A4-substrate:	0.534

ADMET: Excretion

Clearance (CL):	5.197
Half-life (T1/2):	0.488

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.972
Drug-inuced Liver Injury (DILI):	0.795
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.395
Maximum Recommended Daily Dose:	0.774
Skin Sensitization:	0.299
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC476268

Natural Product ID:	NPC476268
*Common Name:**	Aeruginosin Ei461
IUPAC Name:	(2S,3aR,6R,7aR)-6-hydroxy-1-[(2R)-2-[[(2S)-2-hydroxy-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxamide
Synonyms:	Aeruginosin Ei461
Standard InCHIKey:	FEBDAAYWFMTVBF-HYMUMSMOSA-N
Standard InCHI:	InChI=1S/C24H35N3O6/c1-13(2)9-18(26-23(32)21(30)10-14-3-6-16(28)7-4-14)24(33)27-19-12-17(29)8-5-15(19)11-20(27)22(25)31/h3-4,6-7,13,15,17-21,28-30H,5,8-12H2,1-2H3,(H2,25,31)(H,26,32)/t15-,17-,18-,19-,20+,21+/m1/s1
SMILES:	CC(C[C@H](C(=O)N1[C@@H]2C[C@H](O)CC[C@@H]2C[C@H]1C(=N)O)N=C([C@H](Cc1ccc(cc1)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559914
PubChem CID:	11155437
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
Others	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	15.0	%	PMID[534655]
NPT2	Others	Unspecified		Inhibition	=	15.0	%	PMID[534656]

☑ 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 NPC476268 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	172
0.1-0.2	910
0.2-0.3	3741
0.3-0.4	13200
0.4-0.5	14427
0.5-0.6	8645
0.6-0.7	1210
0.7-0.8	328
0.8-0.85	47
0.85-0.9	15
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9221	High Similarity	NPC89831
0.8846	High Similarity	NPC280022
0.8812	High Similarity	NPC97526
0.8812	High Similarity	NPC119652
0.8792	High Similarity	NPC473491
0.8774	High Similarity	NPC63931
0.8742	High Similarity	NPC471165
0.8716	High Similarity	NPC16188
0.8636	High Similarity	NPC244336
0.863	High Similarity	NPC476989
0.8562	High Similarity	NPC244509
0.8554	High Similarity	NPC96275
0.8554	High Similarity	NPC94862
0.8553	High Similarity	NPC56685
0.8553	High Similarity	NPC262166
0.85	High Similarity	NPC328494
0.8452	Intermediate Similarity	NPC51047
0.8438	Intermediate Similarity	NPC475204
0.8438	Intermediate Similarity	NPC475123
0.8431	Intermediate Similarity	NPC202198
0.8408	Intermediate Similarity	NPC241794
0.8395	Intermediate Similarity	NPC26108
0.8367	Intermediate Similarity	NPC242159
0.8367	Intermediate Similarity	NPC313694
0.8344	Intermediate Similarity	NPC50016
0.8333	Intermediate Similarity	NPC273755
0.8313	Intermediate Similarity	NPC302597
0.8284	Intermediate Similarity	NPC246591
0.825	Intermediate Similarity	NPC61004
0.8247	Intermediate Similarity	NPC233702
0.8221	Intermediate Similarity	NPC248670
0.8199	Intermediate Similarity	NPC328649
0.8199	Intermediate Similarity	NPC209463
0.8194	Intermediate Similarity	NPC261934
0.8194	Intermediate Similarity	NPC5194
0.8187	Intermediate Similarity	NPC470728
0.8171	Intermediate Similarity	NPC136797
0.8158	Intermediate Similarity	NPC81026
0.8133	Intermediate Similarity	NPC45037
0.811	Intermediate Similarity	NPC137627
0.8101	Intermediate Similarity	NPC323336
0.8101	Intermediate Similarity	NPC326349
0.8092	Intermediate Similarity	NPC266741
0.8061	Intermediate Similarity	NPC473354
0.8046	Intermediate Similarity	NPC80514
0.8025	Intermediate Similarity	NPC254700
0.8	Intermediate Similarity	NPC306804
0.7988	Intermediate Similarity	NPC40234
0.7988	Intermediate Similarity	NPC46009
0.7975	Intermediate Similarity	NPC107938
0.7975	Intermediate Similarity	NPC294516
0.7952	Intermediate Similarity	NPC476227
0.7911	Intermediate Similarity	NPC39431
0.7892	Intermediate Similarity	NPC475532
0.7866	Intermediate Similarity	NPC141957
0.7844	Intermediate Similarity	NPC165285
0.7844	Intermediate Similarity	NPC17698
0.7843	Intermediate Similarity	NPC251439
0.7831	Intermediate Similarity	NPC230611
0.7824	Intermediate Similarity	NPC477637
0.7824	Intermediate Similarity	NPC476321
0.7818	Intermediate Similarity	NPC129486
0.7811	Intermediate Similarity	NPC194671
0.7811	Intermediate Similarity	NPC269750
0.7778	Intermediate Similarity	NPC471526
0.7778	Intermediate Similarity	NPC475544
0.7778	Intermediate Similarity	NPC469243
0.775	Intermediate Similarity	NPC473580
0.7742	Intermediate Similarity	NPC315266
0.7738	Intermediate Similarity	NPC155506
0.7738	Intermediate Similarity	NPC158277
0.7738	Intermediate Similarity	NPC473402
0.7738	Intermediate Similarity	NPC159767
0.7738	Intermediate Similarity	NPC279871
0.7733	Intermediate Similarity	NPC294951
0.7724	Intermediate Similarity	NPC6975
0.7722	Intermediate Similarity	NPC324081
0.7716	Intermediate Similarity	NPC287757
0.7716	Intermediate Similarity	NPC319320
0.7697	Intermediate Similarity	NPC6570
0.7683	Intermediate Similarity	NPC289776
0.7683	Intermediate Similarity	NPC133470
0.7683	Intermediate Similarity	NPC191863
0.7667	Intermediate Similarity	NPC326966
0.7667	Intermediate Similarity	NPC257390
0.7665	Intermediate Similarity	NPC274198
0.7665	Intermediate Similarity	NPC198254
0.7665	Intermediate Similarity	NPC276506
0.7661	Intermediate Similarity	NPC475564
0.7661	Intermediate Similarity	NPC475409
0.7661	Intermediate Similarity	NPC170302
0.7657	Intermediate Similarity	NPC102959
0.7655	Intermediate Similarity	NPC252878
0.765	Intermediate Similarity	NPC81845
0.764	Intermediate Similarity	NPC477632
0.764	Intermediate Similarity	NPC477638
0.7636	Intermediate Similarity	NPC472923
0.7636	Intermediate Similarity	NPC223207
0.763	Intermediate Similarity	NPC471048
0.763	Intermediate Similarity	NPC471049
0.763	Intermediate Similarity	NPC471050
0.7616	Intermediate Similarity	NPC473404
0.7614	Intermediate Similarity	NPC60516
0.7613	Intermediate Similarity	NPC168861
0.7605	Intermediate Similarity	NPC186617
0.7603	Intermediate Similarity	NPC46427
0.759	Intermediate Similarity	NPC471771
0.759	Intermediate Similarity	NPC304074
0.759	Intermediate Similarity	NPC290755
0.7586	Intermediate Similarity	NPC202521
0.7584	Intermediate Similarity	NPC469666
0.7584	Intermediate Similarity	NPC302715
0.7582	Intermediate Similarity	NPC64205
0.756	Intermediate Similarity	NPC473693
0.756	Intermediate Similarity	NPC471568
0.756	Intermediate Similarity	NPC196091
0.7558	Intermediate Similarity	NPC39822
0.7544	Intermediate Similarity	NPC473546
0.7543	Intermediate Similarity	NPC276120
0.7517	Intermediate Similarity	NPC476990
0.7516	Intermediate Similarity	NPC122590
0.7514	Intermediate Similarity	NPC240130
0.7514	Intermediate Similarity	NPC163961
0.7514	Intermediate Similarity	NPC61332
0.7514	Intermediate Similarity	NPC473305
0.75	Intermediate Similarity	NPC287401
0.75	Intermediate Similarity	NPC91953
0.7486	Intermediate Similarity	NPC65714
0.7486	Intermediate Similarity	NPC138083
0.7485	Intermediate Similarity	NPC196243
0.7472	Intermediate Similarity	NPC473378
0.7472	Intermediate Similarity	NPC473407
0.7468	Intermediate Similarity	NPC127741
0.7457	Intermediate Similarity	NPC32064
0.7452	Intermediate Similarity	NPC52748
0.7447	Intermediate Similarity	NPC295795
0.7438	Intermediate Similarity	NPC2501
0.7436	Intermediate Similarity	NPC150712
0.7436	Intermediate Similarity	NPC197921
0.743	Intermediate Similarity	NPC477631
0.7418	Intermediate Similarity	NPC477552
0.7418	Intermediate Similarity	NPC477550
0.7417	Intermediate Similarity	NPC325651
0.7416	Intermediate Similarity	NPC477636
0.7415	Intermediate Similarity	NPC474862
0.7403	Intermediate Similarity	NPC329295
0.7403	Intermediate Similarity	NPC473371
0.7389	Intermediate Similarity	NPC469360
0.7386	Intermediate Similarity	NPC208757
0.7386	Intermediate Similarity	NPC315542
0.7372	Intermediate Similarity	NPC471201
0.7368	Intermediate Similarity	NPC130309
0.7365	Intermediate Similarity	NPC175726
0.7365	Intermediate Similarity	NPC474082
0.7363	Intermediate Similarity	NPC471592
0.7355	Intermediate Similarity	NPC471264
0.7355	Intermediate Similarity	NPC471265
0.7355	Intermediate Similarity	NPC109580
0.7337	Intermediate Similarity	NPC477551
0.7337	Intermediate Similarity	NPC473502
0.7329	Intermediate Similarity	NPC283760
0.7326	Intermediate Similarity	NPC164608
0.7326	Intermediate Similarity	NPC477462
0.732	Intermediate Similarity	NPC45191
0.7312	Intermediate Similarity	NPC311658
0.731	Intermediate Similarity	NPC470545
0.7299	Intermediate Similarity	NPC475421
0.7296	Intermediate Similarity	NPC209509
0.7296	Intermediate Similarity	NPC471680
0.7292	Intermediate Similarity	NPC317254
0.729	Intermediate Similarity	NPC151706
0.729	Intermediate Similarity	NPC9687
0.729	Intermediate Similarity	NPC476102
0.729	Intermediate Similarity	NPC475318
0.729	Intermediate Similarity	NPC49577
0.729	Intermediate Similarity	NPC90194
0.729	Intermediate Similarity	NPC474787
0.729	Intermediate Similarity	NPC118099
0.729	Intermediate Similarity	NPC76785
0.729	Intermediate Similarity	NPC474811
0.729	Intermediate Similarity	NPC475598
0.729	Intermediate Similarity	NPC293377
0.729	Intermediate Similarity	NPC474855
0.729	Intermediate Similarity	NPC79465
0.729	Intermediate Similarity	NPC260045
0.729	Intermediate Similarity	NPC273907
0.7288	Intermediate Similarity	NPC299806
0.7284	Intermediate Similarity	NPC7817
0.7284	Intermediate Similarity	NPC475168
0.7279	Intermediate Similarity	NPC200964
0.7273	Intermediate Similarity	NPC244866
0.7267	Intermediate Similarity	NPC9373
0.7261	Intermediate Similarity	NPC322526
0.7261	Intermediate Similarity	NPC214988
0.726	Intermediate Similarity	NPC470546
0.7257	Intermediate Similarity	NPC153554
0.7255	Intermediate Similarity	NPC255447
0.725	Intermediate Similarity	NPC262077
0.725	Intermediate Similarity	NPC314358
0.7243	Intermediate Similarity	NPC469443

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 NPC476268 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	382
0.2-0.3	632
0.3-0.4	1754
0.4-0.5	3274
0.5-0.6	2292
0.6-0.7	662
0.7-0.8	33
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
0.8693	High Similarity	NPD7118	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD5137	Approved
0.7914	Intermediate Similarity	NPD8303	Discontinued
0.7718	Intermediate Similarity	NPD3136	Phase 2
0.7692	Intermediate Similarity	NPD6676	Phase 2
0.7673	Intermediate Similarity	NPD7303	Discontinued
0.7636	Intermediate Similarity	NPD2098	Approved
0.7625	Intermediate Similarity	NPD7131	Phase 3
0.7562	Intermediate Similarity	NPD7613	Discontinued
0.756	Intermediate Similarity	NPD4652	Approved
0.7548	Intermediate Similarity	NPD7450	Phase 2
0.7516	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2097	Approved
0.75	Intermediate Similarity	NPD7485	Phase 3
0.75	Intermediate Similarity	NPD7484	Phase 3
0.7394	Intermediate Similarity	NPD7495	Discontinued
0.7389	Intermediate Similarity	NPD7978	Discontinued
0.7386	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD8172	Phase 2
0.7355	Intermediate Similarity	NPD8173	Phase 2
0.732	Intermediate Similarity	NPD1330	Phase 2
0.732	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7608	Discontinued
0.7248	Intermediate Similarity	NPD2562	Approved
0.7248	Intermediate Similarity	NPD2561	Approved
0.7246	Intermediate Similarity	NPD5772	Approved
0.7246	Intermediate Similarity	NPD5773	Approved
0.7225	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4659	Approved
0.7195	Intermediate Similarity	NPD7523	Phase 3
0.7193	Intermediate Similarity	NPD2888	Approved
0.7193	Intermediate Similarity	NPD2890	Approved
0.7193	Intermediate Similarity	NPD2889	Approved
0.7193	Intermediate Similarity	NPD2017	Approved
0.7179	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6073	Approved
0.7134	Intermediate Similarity	NPD5314	Approved
0.7127	Intermediate Similarity	NPD7617	Discontinued
0.7115	Intermediate Similarity	NPD6346	Approved
0.7105	Intermediate Similarity	NPD4103	Phase 2
0.7105	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7695	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3553	Approved
0.7089	Intermediate Similarity	NPD3554	Approved
0.7089	Intermediate Similarity	NPD3552	Approved
0.7089	Intermediate Similarity	NPD3555	Approved
0.7083	Intermediate Similarity	NPD8019	Approved
0.7078	Intermediate Similarity	NPD5263	Approved
0.7059	Intermediate Similarity	NPD7451	Discontinued
0.7051	Intermediate Similarity	NPD1136	Approved
0.7051	Intermediate Similarity	NPD1132	Approved
0.7051	Intermediate Similarity	NPD1130	Approved
0.7047	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3125	Approved
0.7025	Intermediate Similarity	NPD2568	Approved
0.7019	Intermediate Similarity	NPD6681	Discovery
0.7007	Intermediate Similarity	NPD3123	Discovery
0.7006	Intermediate Similarity	NPD3061	Approved
0.7006	Intermediate Similarity	NPD3062	Approved
0.7006	Intermediate Similarity	NPD3059	Approved
0.6993	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD598	Approved
0.6987	Remote Similarity	NPD601	Approved
0.6987	Remote Similarity	NPD597	Approved
0.6983	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7011	Discontinued
0.697	Remote Similarity	NPD3985	Discontinued
0.6959	Remote Similarity	NPD317	Approved
0.6959	Remote Similarity	NPD856	Approved
0.6959	Remote Similarity	NPD16	Approved
0.6959	Remote Similarity	NPD318	Approved
0.6943	Remote Similarity	NPD1423	Approved
0.6933	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD817	Approved
0.6918	Remote Similarity	NPD823	Approved
0.6913	Remote Similarity	NPD5303	Approved
0.6913	Remote Similarity	NPD5304	Approved
0.6913	Remote Similarity	NPD2218	Phase 2
0.6913	Remote Similarity	NPD2217	Approved
0.6909	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2584	Suspended
0.6906	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3626	Phase 3
0.6902	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.689	Remote Similarity	NPD8323	Discontinued
0.6887	Remote Similarity	NPD3421	Phase 3
0.6883	Remote Similarity	NPD3053	Approved
0.6883	Remote Similarity	NPD3055	Approved
0.6867	Remote Similarity	NPD2874	Phase 2
0.6867	Remote Similarity	NPD6419	Discontinued
0.6864	Remote Similarity	NPD8417	Discontinued
0.6851	Remote Similarity	NPD7281	Phase 3
0.6851	Remote Similarity	NPD7280	Phase 3
0.6842	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5481	Discontinued
0.6825	Remote Similarity	NPD7811	Phase 3
0.6825	Remote Similarity	NPD7810	Phase 3
0.6821	Remote Similarity	NPD8031	Discontinued
0.6818	Remote Similarity	NPD5310	Approved
0.6818	Remote Similarity	NPD5311	Approved
0.6815	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5725	Approved
0.6813	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6853	Approved
0.6813	Remote Similarity	NPD6851	Approved
0.6803	Remote Similarity	NPD2229	Approved
0.6803	Remote Similarity	NPD2228	Approved
0.6803	Remote Similarity	NPD2234	Approved
0.6802	Remote Similarity	NPD5967	Approved
0.68	Remote Similarity	NPD316	Approved
0.6797	Remote Similarity	NPD3072	Approved
0.6797	Remote Similarity	NPD3071	Approved
0.6797	Remote Similarity	NPD3073	Approved
0.6795	Remote Similarity	NPD4177	Approved
0.6795	Remote Similarity	NPD4175	Approved
0.6792	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8416	Discontinued
0.679	Remote Similarity	NPD2240	Approved
0.679	Remote Similarity	NPD2239	Approved
0.6778	Remote Similarity	NPD6297	Approved
0.6774	Remote Similarity	NPD2159	Approved
0.6774	Remote Similarity	NPD2625	Approved
0.6774	Remote Similarity	NPD2628	Approved
0.6774	Remote Similarity	NPD2160	Approved
0.6774	Remote Similarity	NPD2627	Approved
0.6774	Remote Similarity	NPD2626	Approved
0.6772	Remote Similarity	NPD4621	Approved
0.6772	Remote Similarity	NPD4619	Approved
0.6768	Remote Similarity	NPD4236	Phase 3
0.6768	Remote Similarity	NPD4237	Approved
0.6768	Remote Similarity	NPD3638	Discontinued
0.6766	Remote Similarity	NPD3536	Discontinued
0.6752	Remote Similarity	NPD4676	Approved
0.6752	Remote Similarity	NPD4125	Approved
0.675	Remote Similarity	NPD555	Phase 2
0.6748	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2977	Approved
0.6744	Remote Similarity	NPD2978	Approved
0.6733	Remote Similarity	NPD9616	Approved
0.6733	Remote Similarity	NPD9613	Approved
0.6733	Remote Similarity	NPD9615	Approved
0.6732	Remote Similarity	NPD4761	Approved
0.6732	Remote Similarity	NPD4762	Approved
0.6732	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD9621	Approved
0.6731	Remote Similarity	NPD9619	Approved
0.6731	Remote Similarity	NPD9620	Approved
0.673	Remote Similarity	NPD6405	Approved
0.673	Remote Similarity	NPD5745	Approved
0.673	Remote Similarity	NPD6407	Approved
0.673	Remote Similarity	NPD259	Phase 1
0.6727	Remote Similarity	NPD3400	Discontinued
0.6726	Remote Similarity	NPD7526	Approved
0.6726	Remote Similarity	NPD52	Approved
0.6726	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5218	Approved
0.6724	Remote Similarity	NPD5219	Approved
0.6708	Remote Similarity	NPD3052	Approved
0.6708	Remote Similarity	NPD3054	Approved
0.6708	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4256	Phase 2
0.6707	Remote Similarity	NPD4257	Approved
0.6707	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD9569	Approved
0.6687	Remote Similarity	NPD9570	Approved
0.6686	Remote Similarity	NPD3007	Approved
0.6686	Remote Similarity	NPD4227	Discontinued
0.6686	Remote Similarity	NPD2515	Approved
0.6667	Remote Similarity	NPD3645	Discontinued
0.6667	Remote Similarity	NPD42	Phase 2
0.6667	Remote Similarity	NPD2458	Approved
0.6667	Remote Similarity	NPD9568	Approved
0.6667	Remote Similarity	NPD1135	Approved
0.6667	Remote Similarity	NPD2460	Phase 3
0.6667	Remote Similarity	NPD6042	Phase 2
0.6667	Remote Similarity	NPD1134	Approved
0.6667	Remote Similarity	NPD2459	Approved
0.6667	Remote Similarity	NPD1129	Approved
0.6667	Remote Similarity	NPD3060	Approved
0.6667	Remote Similarity	NPD1131	Approved
0.6667	Remote Similarity	NPD1133	Approved
0.6667	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6852	Discontinued
0.6649	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7565	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