NPASS Compound

Structure

NPC84128 OpenBabel07101718242D 73 72 0 0 1 0 0 0 0 0999 V2000 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 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 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 1 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 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.2583 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3923 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 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 0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 6.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 29 1 0 0 0 0 7 29 1 0 0 0 0 8 30 1 0 0 0 0 9 30 1 0 0 0 0 15 36 1 0 0 0 0 16 58 1 0 0 0 0 17 59 1 0 0 0 0 18 60 1 0 0 0 0 19 61 1 0 0 0 0 20 62 1 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 27 1 0 0 0 0 27 39 1 0 0 0 0 28 29 1 0 0 0 0 31 10 1 1 0 0 0 31 40 1 0 0 0 0 32 11 1 1 0 0 0 32 41 1 0 0 0 0 33 12 1 6 0 0 0 33 43 1 0 0 0 0 34 13 1 6 0 0 0 34 44 1 0 0 0 0 35 14 1 6 0 0 0 35 45 1 0 0 0 0 36 55 2 3 0 0 0 36 63 1 0 0 0 0 37 26 1 6 0 0 0 37 46 1 0 0 0 0 37 55 1 0 0 0 0 38 28 1 1 0 0 0 38 47 1 0 0 0 0 38 58 1 0 0 0 0 39 54 2 0 0 0 0 39 64 1 0 0 0 0 40 48 1 6 0 0 0 40 56 1 0 0 0 0 41 49 1 1 0 0 0 41 57 1 0 0 0 0 42 30 1 6 0 0 0 42 50 1 0 0 0 0 42 59 1 0 0 0 0 43 51 1 6 0 0 0 43 60 1 0 0 0 0 44 52 1 6 0 0 0 44 61 1 0 0 0 0 45 53 1 6 0 0 0 45 62 1 0 0 0 0 46 56 2 3 0 0 0 46 65 1 0 0 0 0 47 57 2 3 0 0 0 47 66 1 0 0 0 0 48 58 1 0 0 0 0 48 67 2 0 0 0 0 49 59 1 0 0 0 0 49 68 2 0 0 0 0 50 60 1 0 0 0 0 50 69 2 0 0 0 0 51 61 1 0 0 0 0 51 70 2 0 0 0 0 52 62 1 0 0 0 0 52 71 2 0 0 0 0 53 72 2 0 0 0 0 53 73 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1035.73
Volume:	1094.542
LogP:	3.544
LogD:	2.602
LogS:	-4.323
# Rotatable Bonds:	40
TPSA:	269.24
# H-Bond Aceptor:	20
# H-Bond Donor:	6
# Rings:	0
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.065
Synthetic Accessibility Score:	5.783
Fsp3:	0.811
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:	-5.385
MDCK Permeability:	9.329065505880862e-06
Pgp-inhibitor:	0.999
Pgp-substrate:	0.803
Human Intestinal Absorption (HIA):	0.918
20% Bioavailability (F20%):	0.359
30% Bioavailability (F30%):	0.18

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	85.90055084228516%
Volume Distribution (VD):	0.605
Pgp-substrate:	2.216092824935913%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.377
CYP3A4-substrate:	0.392

ADMET: Excretion

Clearance (CL):	6.506
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.102
Carcinogencity:	0.01
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.007

Download Data

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

Natural Product: NPC84128

Natural Product ID:	NPC84128
*Common Name:**	Ac-(R)-Gln-(2S,3S)-Ile-(S)-N-Me-Leu-(2S,3S)-Ile-(S)-N-Me-Val-(2S,3S)-N-Me-Ile-(2S,3S)-N-Me-Ile-(2S,3S)-N-Me-Ile-Oh
IUPAC Name:	(2S,3S)-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2R)-2-acetamido-5-amino-5-oxopentanoyl]amino]-3-methylpentanoyl]-methylamino]-4-methylpentanoyl]amino]-3-methylpentanoyl]-methylamino]-3-methylbutanoyl]-methylamino]-3-methylpentanoyl]-methylamino]-3-methylpentanoyl]-methylamino]-3-methylpentanoic acid
Synonyms:
Standard InCHIKey:	YEHYELQIMQIGQU-VMIGUSPASA-N
Standard InCHI:	InChI=1S/C53H97N9O11/c1-21-31(10)40(56-46(65)37(55-36(15)63)26-27-39(54)64)48(67)58(16)38(28-29(6)7)47(66)57-41(32(11)22-2)49(68)59(17)42(30(8)9)50(69)60(18)43(33(12)23-3)51(70)61(19)44(34(13)24-4)52(71)62(20)45(53(72)73)35(14)25-5/h29-35,37-38,40-45H,21-28H2,1-20H3,(H2,54,64)(H,55,63)(H,56,65)(H,57,66)(H,72,73)/t31-,32-,33-,34-,35-,37+,38-,40-,41-,42-,43-,44-,45-/m0/s1
SMILES:	CC[C@@H]([C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@@H]([C@H](CC)C)C(=O)O)C)[C@H](CC)C)C)[C@H](CC)C)C)C(C)C)C)N=C([C@@H](N(C(=O)[C@H]([C@H](CC)C)N=C([C@H](N=C(O)C)CCC(=N)O)O)C)CC(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505901
PubChem CID:	11665244
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

*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	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[12444684]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[16441074]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Australian	n.a.	PMID[18288804]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[19199645]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Mangrove Rhizophora apiculata	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[25689430]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[26928174]

☑ 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
MIC	2
Others	2

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	Activity	=	4.0	n.a.	PMID[508335]
NPT137	Cell Line	L1210	Mus musculus	Activity	=	16.0	n.a.	PMID[508336]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	25.0	ug.mL-1	PMID[508335]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	50.0	ug.mL-1	PMID[508336]

☑ 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 NPC84128 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	233
0.1-0.2	18015
0.2-0.3	20037
0.3-0.4	2941
0.4-0.5	953
0.5-0.6	301
0.6-0.7	178
0.7-0.8	35
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC53858
0.8095	Intermediate Similarity	NPC472351
0.7738	Intermediate Similarity	NPC23984
0.7619	Intermediate Similarity	NPC476156
0.7619	Intermediate Similarity	NPC476117
0.7619	Intermediate Similarity	NPC476243
0.7619	Intermediate Similarity	NPC476137
0.7529	Intermediate Similarity	NPC476302
0.75	Intermediate Similarity	NPC31756
0.7391	Intermediate Similarity	NPC471098
0.7391	Intermediate Similarity	NPC62263
0.7391	Intermediate Similarity	NPC173763
0.7356	Intermediate Similarity	NPC235078
0.7292	Intermediate Similarity	NPC220234
0.7283	Intermediate Similarity	NPC474576
0.7283	Intermediate Similarity	NPC477538
0.7234	Intermediate Similarity	NPC280066
0.7229	Intermediate Similarity	NPC327272
0.72	Intermediate Similarity	NPC241394
0.7174	Intermediate Similarity	NPC475801
0.7174	Intermediate Similarity	NPC474593
0.7143	Intermediate Similarity	NPC473495
0.7128	Intermediate Similarity	NPC301010
0.7125	Intermediate Similarity	NPC306696
0.7111	Intermediate Similarity	NPC477539
0.7108	Intermediate Similarity	NPC209156
0.7108	Intermediate Similarity	NPC161774
0.7108	Intermediate Similarity	NPC256312
0.7108	Intermediate Similarity	NPC266888
0.71	Intermediate Similarity	NPC128303
0.7093	Intermediate Similarity	NPC312315
0.7083	Intermediate Similarity	NPC473597
0.7071	Intermediate Similarity	NPC5864
0.7071	Intermediate Similarity	NPC301148
0.7071	Intermediate Similarity	NPC124554
0.7059	Intermediate Similarity	NPC59867
0.7037	Intermediate Similarity	NPC472579
0.6939	Remote Similarity	NPC475440
0.6932	Remote Similarity	NPC475542
0.6931	Remote Similarity	NPC124549
0.6914	Remote Similarity	NPC250953
0.6883	Remote Similarity	NPC327170
0.6883	Remote Similarity	NPC329564
0.6881	Remote Similarity	NPC477237
0.6867	Remote Similarity	NPC196007
0.6867	Remote Similarity	NPC76297
0.6867	Remote Similarity	NPC214532
0.6854	Remote Similarity	NPC246005
0.6854	Remote Similarity	NPC284456
0.6854	Remote Similarity	NPC6902
0.6854	Remote Similarity	NPC184473
0.6832	Remote Similarity	NPC198344
0.6765	Remote Similarity	NPC323720
0.6757	Remote Similarity	NPC477238
0.6753	Remote Similarity	NPC317143
0.6753	Remote Similarity	NPC321468
0.6753	Remote Similarity	NPC327748
0.6753	Remote Similarity	NPC316826
0.6735	Remote Similarity	NPC47076
0.6735	Remote Similarity	NPC134504
0.6731	Remote Similarity	NPC67009
0.6731	Remote Similarity	NPC171734
0.6711	Remote Similarity	NPC318260
0.6711	Remote Similarity	NPC317147
0.6706	Remote Similarity	NPC263281
0.6706	Remote Similarity	NPC178919
0.6699	Remote Similarity	NPC475637
0.6627	Remote Similarity	NPC322274
0.6591	Remote Similarity	NPC477145
0.6591	Remote Similarity	NPC473741
0.6577	Remote Similarity	NPC469899
0.6574	Remote Similarity	NPC63191
0.6574	Remote Similarity	NPC471202
0.6569	Remote Similarity	NPC475149
0.6569	Remote Similarity	NPC471097
0.6556	Remote Similarity	NPC470783
0.6543	Remote Similarity	NPC262615
0.6538	Remote Similarity	NPC321536
0.6526	Remote Similarity	NPC275715
0.65	Remote Similarity	NPC105297
0.6465	Remote Similarity	NPC117829
0.6463	Remote Similarity	NPC287693
0.6458	Remote Similarity	NPC477729
0.6447	Remote Similarity	NPC322573
0.6429	Remote Similarity	NPC38172
0.6429	Remote Similarity	NPC126779
0.6373	Remote Similarity	NPC13175
0.6373	Remote Similarity	NPC475791
0.6364	Remote Similarity	NPC472536
0.6364	Remote Similarity	NPC103391
0.6354	Remote Similarity	NPC155230
0.6353	Remote Similarity	NPC478256
0.6341	Remote Similarity	NPC128559
0.6329	Remote Similarity	NPC292299
0.6329	Remote Similarity	NPC34838
0.6327	Remote Similarity	NPC315237
0.6322	Remote Similarity	NPC138435
0.6322	Remote Similarity	NPC320221
0.631	Remote Similarity	NPC470110
0.6306	Remote Similarity	NPC296043
0.6275	Remote Similarity	NPC475188
0.6275	Remote Similarity	NPC475758
0.6267	Remote Similarity	NPC322946
0.6265	Remote Similarity	NPC128005
0.6265	Remote Similarity	NPC84182
0.625	Remote Similarity	NPC329216
0.625	Remote Similarity	NPC143722
0.625	Remote Similarity	NPC263207
0.6235	Remote Similarity	NPC29598
0.6235	Remote Similarity	NPC212866
0.6228	Remote Similarity	NPC470652
0.6222	Remote Similarity	NPC37681
0.6222	Remote Similarity	NPC191774
0.6207	Remote Similarity	NPC141325
0.6203	Remote Similarity	NPC472578
0.619	Remote Similarity	NPC470109
0.618	Remote Similarity	NPC476130
0.618	Remote Similarity	NPC476324
0.6174	Remote Similarity	NPC160688
0.617	Remote Similarity	NPC95478
0.617	Remote Similarity	NPC155670
0.617	Remote Similarity	NPC145748
0.6154	Remote Similarity	NPC38463
0.6154	Remote Similarity	NPC470654
0.6154	Remote Similarity	NPC478017
0.6154	Remote Similarity	NPC470650
0.6154	Remote Similarity	NPC315131
0.6154	Remote Similarity	NPC315535
0.6154	Remote Similarity	NPC470653
0.6154	Remote Similarity	NPC325985
0.6125	Remote Similarity	NPC320598
0.6125	Remote Similarity	NPC254541
0.6118	Remote Similarity	NPC10716
0.6111	Remote Similarity	NPC207820
0.6105	Remote Similarity	NPC227051
0.6104	Remote Similarity	NPC316889
0.6104	Remote Similarity	NPC321118
0.6098	Remote Similarity	NPC327252
0.6091	Remote Similarity	NPC476875
0.6071	Remote Similarity	NPC470108
0.6067	Remote Similarity	NPC86064
0.6044	Remote Similarity	NPC316242
0.6038	Remote Similarity	NPC476877
0.6034	Remote Similarity	NPC315188
0.6033	Remote Similarity	NPC313657
0.6023	Remote Similarity	NPC315897
0.6022	Remote Similarity	NPC314466
0.602	Remote Similarity	NPC322966
0.6	Remote Similarity	NPC80350
0.6	Remote Similarity	NPC189301
0.6	Remote Similarity	NPC176164
0.598	Remote Similarity	NPC469739
0.5976	Remote Similarity	NPC314510
0.5955	Remote Similarity	NPC43219
0.5955	Remote Similarity	NPC476248
0.5952	Remote Similarity	NPC174304
0.5952	Remote Similarity	NPC325597
0.5932	Remote Similarity	NPC50520
0.593	Remote Similarity	NPC319046
0.5926	Remote Similarity	NPC476876
0.5909	Remote Similarity	NPC328457
0.5904	Remote Similarity	NPC243964
0.59	Remote Similarity	NPC476019
0.5875	Remote Similarity	NPC278209
0.5868	Remote Similarity	NPC470655
0.5868	Remote Similarity	NPC470651
0.5862	Remote Similarity	NPC193280
0.5862	Remote Similarity	NPC314273
0.5833	Remote Similarity	NPC57420
0.5833	Remote Similarity	NPC289691
0.5833	Remote Similarity	NPC315744
0.5833	Remote Similarity	NPC205176
0.5818	Remote Similarity	NPC296143
0.5795	Remote Similarity	NPC476285
0.5795	Remote Similarity	NPC476291
0.5789	Remote Similarity	NPC328378
0.5778	Remote Similarity	NPC126186
0.5769	Remote Similarity	NPC197087
0.5769	Remote Similarity	NPC144780
0.5769	Remote Similarity	NPC190184
0.5769	Remote Similarity	NPC189178
0.5769	Remote Similarity	NPC263065
0.5761	Remote Similarity	NPC472594
0.573	Remote Similarity	NPC470781
0.5682	Remote Similarity	NPC15864
0.5667	Remote Similarity	NPC55274
0.5663	Remote Similarity	NPC177191
0.5652	Remote Similarity	NPC470782
0.5641	Remote Similarity	NPC239357
0.5641	Remote Similarity	NPC471131
0.5606	Remote Similarity	NPC77905
0.5603	Remote Similarity	NPC288109

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 NPC84128 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	77
0.1-0.2	2147
0.2-0.3	5100
0.3-0.4	1262
0.4-0.5	420
0.5-0.6	101
0.6-0.7	35
0.7-0.8	6
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.878	High Similarity	NPD7759	Phase 2
0.878	High Similarity	NPD7760	Phase 2
0.7935	Intermediate Similarity	NPD8038	Phase 2
0.7647	Intermediate Similarity	NPD1125	Discovery
0.7529	Intermediate Similarity	NPD7763	Phase 2
0.7529	Intermediate Similarity	NPD7762	Phase 2
0.7442	Intermediate Similarity	NPD2683	Discontinued
0.734	Intermediate Similarity	NPD7841	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4825	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4261	Phase 1
0.7037	Intermediate Similarity	NPD620	Approved
0.7021	Intermediate Similarity	NPD6699	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6120	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6122	Discontinued
0.6739	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5792	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3176	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2682	Approved
0.6559	Remote Similarity	NPD5791	Phase 2
0.6543	Remote Similarity	NPD6437	Approved
0.6543	Remote Similarity	NPD6438	Approved
0.6517	Remote Similarity	NPD4815	Discontinued
0.6429	Remote Similarity	NPD4242	Approved
0.6421	Remote Similarity	NPD3177	Phase 3
0.6413	Remote Similarity	NPD7643	Phase 1
0.641	Remote Similarity	NPD9433	Approved
0.64	Remote Similarity	NPD1784	Approved
0.6386	Remote Similarity	NPD1429	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD612	Discontinued
0.6344	Remote Similarity	NPD9577	Approved
0.6337	Remote Similarity	NPD3713	Approved
0.6337	Remote Similarity	NPD3714	Approved
0.6337	Remote Similarity	NPD3715	Approved
0.631	Remote Similarity	NPD322	Phase 1
0.631	Remote Similarity	NPD4241	Registered
0.6267	Remote Similarity	NPD9441	Phase 2
0.6237	Remote Similarity	NPD4829	Discontinued
0.6235	Remote Similarity	NPD7840	Approved
0.6222	Remote Similarity	NPD4278	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD1147	Phase 2
0.6173	Remote Similarity	NPD574	Approved
0.6168	Remote Similarity	NPD6937	Approved
0.6163	Remote Similarity	NPD2220	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD8298	Phase 2
0.6098	Remote Similarity	NPD575	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD9425	Approved
0.6047	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD1825	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2264	Approved
0.6	Remote Similarity	NPD2263	Discontinued
0.6	Remote Similarity	NPD2265	Approved
0.6	Remote Similarity	NPD886	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD9649	Approved
0.5952	Remote Similarity	NPD348	Approved
0.5949	Remote Similarity	NPD1456	Approved
0.593	Remote Similarity	NPD337	Discontinued
0.5909	Remote Similarity	NPD2262	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5359	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD4276	Approved
0.5823	Remote Similarity	NPD4277	Approved
0.5795	Remote Similarity	NPD1439	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD366	Approved
0.5769	Remote Similarity	NPD8785	Approved
0.5769	Remote Similarity	NPD9205	Approved
0.5769	Remote Similarity	NPD9204	Approved
0.575	Remote Similarity	NPD4281	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD9451	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD2147	Approved
0.5684	Remote Similarity	NPD3628	Phase 3
0.5679	Remote Similarity	NPD583	Approved
0.5679	Remote Similarity	NPD843	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD584	Approved
0.5679	Remote Similarity	NPD581	Approved
0.5667	Remote Similarity	NPD265	Phase 3
0.5667	Remote Similarity	NPD266	Phase 3
0.5604	Remote Similarity	NPD9217	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