NPASS Compound

Structure

CID110602 OpenBabel06191715462D 77 82 0 0 1 0 0 0 0 0999 V2000 -9.9780 2.1225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3491 4.3001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5751 6.0173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3913 3.3401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6636 4.7019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1756 1.5138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0542 1.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6208 -4.3545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7756 -6.3430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2381 -3.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0121 -5.1479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1582 -5.4191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7841 -6.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4404 -2.0049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0068 -1.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3570 -0.8812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2467 -3.3001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0206 -5.0173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5495 -4.6258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1753 -5.6802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4435 -1.9264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5763 -0.2782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5799 -1.5106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6465 4.9629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6651 2.3486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9986 0.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0377 5.7563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4584 1.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9493 4.9629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6465 -3.9629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9493 -3.9629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2608 -1.3486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0280 0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9578 5.0935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2608 2.3486 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6379 -4.0935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5580 -4.7563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0542 -0.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0130 -1.0239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5794 -0.1997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2638 4.0391 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2588 1.9659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3320 4.0391 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2638 -3.0391 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3320 -3.0391 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3369 -0.9659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2588 -0.9659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3369 1.9659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2979 4.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4659 3.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1298 -2.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2979 -3.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5958 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 -1.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8369 2.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9706 0.5936 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1298 3.5391 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 2.8320 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2979 4.2979 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2979 -3.2979 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8369 -1.8320 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4659 -2.5391 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.5958 1.0000 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 -4.4284 5.2893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8572 4.3324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7386 -3.3324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1674 -4.2893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5872 -0.1305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0345 -2.4407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6303 3.4407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9914 1.1305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4375 6.4191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5128 3.1140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0463 5.6258 0.0000 S 0 0 3 0 0 0 0 0 0 0 0 0 2.3823 2.1225 0.0000 S 0 0 3 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 34 1 0 0 0 0 3 34 1 0 0 0 0 5 76 1 0 0 0 0 6 77 1 0 0 0 0 7 35 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 16 26 1 0 0 0 0 17 36 2 0 0 0 0 18 36 1 0 0 0 0 19 37 2 0 0 0 0 20 37 1 0 0 0 0 21 39 2 0 0 0 0 22 40 2 0 0 0 0 24 27 1 0 0 0 0 25 28 1 0 0 0 0 26 65 1 0 0 0 0 27 76 1 0 0 0 0 28 77 1 0 0 0 0 29 34 1 0 0 0 0 30 36 1 0 0 0 0 31 37 1 0 0 0 0 32 38 1 0 0 0 0 33 38 2 0 0 0 0 33 57 1 0 0 0 0 35 4 1 6 0 0 0 38 39 1 0 0 0 0 39 40 1 0 0 0 0 40 57 1 0 0 0 0 41 24 1 1 0 0 0 41 49 1 0 0 0 0 41 58 1 0 0 0 0 42 25 1 1 0 0 0 42 56 1 0 0 0 0 42 59 1 0 0 0 0 43 29 1 1 0 0 0 43 50 1 0 0 0 0 43 60 1 0 0 0 0 44 30 1 1 0 0 0 44 51 1 0 0 0 0 44 61 1 0 0 0 0 45 31 1 1 0 0 0 45 52 1 0 0 0 0 45 63 1 0 0 0 0 46 32 1 1 0 0 0 46 53 1 0 0 0 0 46 62 1 0 0 0 0 47 23 1 1 0 0 0 47 54 1 0 0 0 0 47 65 1 0 0 0 0 48 35 1 1 0 0 0 48 55 1 0 0 0 0 48 64 1 0 0 0 0 49 60 2 3 0 0 0 49 66 1 0 0 0 0 50 59 2 3 0 0 0 50 67 1 0 0 0 0 51 62 2 3 0 0 0 51 68 1 0 0 0 0 52 61 2 3 0 0 0 52 69 1 0 0 0 0 53 64 2 3 0 0 0 53 70 1 0 0 0 0 54 63 2 3 0 0 0 54 71 1 0 0 0 0 55 58 2 3 0 0 0 55 72 1 0 0 0 0 56 65 1 0 0 0 0 56 73 2 0 0 0 0 74 76 2 0 0 0 0 75 77 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1097.51
Volume:	1102.228
LogP:	3.088
LogD:	1.21
LogS:	-3.585
# Rotatable Bonds:	16
TPSA:	296.39
# H-Bond Aceptor:	19
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.071
Synthetic Accessibility Score:	6.9
Fsp3:	0.5
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:	-4.811
MDCK Permeability:	3.3875465305754915e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.302
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	59.794410705566406%
Volume Distribution (VD):	0.703
Pgp-substrate:	18.468692779541016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.867
CYP2D6-inhibitor:	0.076
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.162
CYP3A4-substrate:	0.01

ADMET: Excretion

Clearance (CL):	0.94
Half-life (T1/2):	0.865

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.111
Rat Oral Acute Toxicity:	0.965
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.158
Carcinogencity:	0.397
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC110602

Natural Product ID:	NPC110602
*Common Name:**	Cyclolinopeptide G
IUPAC Name:	(3S,6S,9S,12S,15S,18S,21S,24S)-18,21-dibenzyl-12-[(2S)-butan-2-yl]-15-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-3,9-bis(2-methylsulfinylethyl)-1,4,7,10,13,16,19,22-octazabicyclo[22.3.0]heptacosane-2,5,8,11,14,17,20,23-octone
Synonyms:
Standard InCHIKey:	MGTCVHJATWUGDT-JVXUKOSASA-N
Standard InCHI:	InChI=1S/C56H75N9O10S2/c1-7-35(4)48-55(72)58-41(24-27-76(5)74)49(66)60-43(29-34(2)3)50(67)59-42(25-28-77(6)75)56(73)65-26-16-23-47(65)54(71)63-45(31-37-19-12-9-13-20-37)52(69)61-44(30-36-17-10-8-11-18-36)51(68)62-46(53(70)64-48)32-38-33-57-40-22-15-14-21-39(38)40/h8-15,17-22,33-35,41-48,57H,7,16,23-32H2,1-6H3,(H,58,72)(H,59,67)(H,60,66)(H,61,69)(H,62,68)(H,63,71)(H,64,70)/t35-,41-,42-,43-,44-,45-,46-,47-,48-,76?,77?/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=N[C@@H](CCS(=O)C)C(=N[C@@H](CC(C)C)C(=N[C@@H](CCS(=O)C)C(=O)N2CCC[C@H]2C(=N[C@@H](Cc2ccccc2)C(=N[C@@H](Cc2ccccc2)C(=N[C@@H](Cc2c[nH]c3ccccc23)C(=N1)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3787164
PubChem CID:	10724885
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:0004831] Oligopeptides

*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
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/ejlt.201100207]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.5219/332]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24417583]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[26923696]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	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	1

Activity Type	# Activity
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21723	CELL-LINE	Bone marrow cell	n.a.	IC50	=	4040.0	nM	PMID[522753]

☑ 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 NPC110602 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	402
0.1-0.2	2878
0.2-0.3	22003
0.3-0.4	10684
0.4-0.5	2483
0.5-0.6	2582
0.6-0.7	1269
0.7-0.8	335
0.8-0.85	38
0.85-0.9	14
0.9-0.95	0
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC31385
1.0	High Similarity	NPC75726
0.8883	High Similarity	NPC213629
0.88	High Similarity	NPC75634
0.8711	High Similarity	NPC171317
0.8711	High Similarity	NPC473640
0.8673	High Similarity	NPC475506
0.8667	High Similarity	NPC100321
0.8643	High Similarity	NPC54420
0.8629	High Similarity	NPC155143
0.8579	High Similarity	NPC94752
0.8557	High Similarity	NPC162860
0.8505	High Similarity	NPC478028
0.8477	Intermediate Similarity	NPC293917
0.8439	Intermediate Similarity	NPC478157
0.8426	Intermediate Similarity	NPC478029
0.8406	Intermediate Similarity	NPC477714
0.8374	Intermediate Similarity	NPC478158
0.8374	Intermediate Similarity	NPC107077
0.8374	Intermediate Similarity	NPC223791
0.8366	Intermediate Similarity	NPC323927
0.8293	Intermediate Similarity	NPC320968
0.8269	Intermediate Similarity	NPC477715
0.8267	Intermediate Similarity	NPC473376
0.8247	Intermediate Similarity	NPC17059
0.8186	Intermediate Similarity	NPC326363
0.8178	Intermediate Similarity	NPC153400
0.8143	Intermediate Similarity	NPC281049
0.8115	Intermediate Similarity	NPC248454
0.8115	Intermediate Similarity	NPC59269
0.8112	Intermediate Similarity	NPC321708
0.8093	Intermediate Similarity	NPC228835
0.809	Intermediate Similarity	NPC294693
0.8053	Intermediate Similarity	NPC314603
0.8037	Intermediate Similarity	NPC325976
0.8032	Intermediate Similarity	NPC160105
0.8	Intermediate Similarity	NPC165495
0.7991	Intermediate Similarity	NPC63279
0.799	Intermediate Similarity	NPC193761
0.7959	Intermediate Similarity	NPC15102
0.7955	Intermediate Similarity	NPC297642
0.7952	Intermediate Similarity	NPC54744
0.7949	Intermediate Similarity	NPC163055
0.794	Intermediate Similarity	NPC473763
0.794	Intermediate Similarity	NPC117244
0.7895	Intermediate Similarity	NPC63751
0.7887	Intermediate Similarity	NPC11126
0.7846	Intermediate Similarity	NPC91179
0.7842	Intermediate Similarity	NPC49954
0.7842	Intermediate Similarity	NPC474561
0.784	Intermediate Similarity	NPC79386
0.7816	Intermediate Similarity	NPC476874
0.7783	Intermediate Similarity	NPC165743
0.7773	Intermediate Similarity	NPC69843
0.7742	Intermediate Similarity	NPC155444
0.7738	Intermediate Similarity	NPC475859
0.7738	Intermediate Similarity	NPC474877
0.7738	Intermediate Similarity	NPC475969
0.7736	Intermediate Similarity	NPC153980
0.7736	Intermediate Similarity	NPC6865
0.7732	Intermediate Similarity	NPC469938
0.7727	Intermediate Similarity	NPC56109
0.7727	Intermediate Similarity	NPC191382
0.7706	Intermediate Similarity	NPC64216
0.7704	Intermediate Similarity	NPC248041
0.7704	Intermediate Similarity	NPC283219
0.7704	Intermediate Similarity	NPC126709
0.7692	Intermediate Similarity	NPC267885
0.7692	Intermediate Similarity	NPC477175
0.7692	Intermediate Similarity	NPC477176
0.7692	Intermediate Similarity	NPC470730
0.7692	Intermediate Similarity	NPC470729
0.7689	Intermediate Similarity	NPC72956
0.7688	Intermediate Similarity	NPC99939
0.7688	Intermediate Similarity	NPC308931
0.7684	Intermediate Similarity	NPC282231
0.7673	Intermediate Similarity	NPC243716
0.7671	Intermediate Similarity	NPC19170
0.7659	Intermediate Similarity	NPC227582
0.7658	Intermediate Similarity	NPC477177
0.7657	Intermediate Similarity	NPC478013
0.7653	Intermediate Similarity	NPC145885
0.7653	Intermediate Similarity	NPC471194
0.7653	Intermediate Similarity	NPC471193
0.7653	Intermediate Similarity	NPC84827
0.7653	Intermediate Similarity	NPC14113
0.765	Intermediate Similarity	NPC235684
0.7644	Intermediate Similarity	NPC28945
0.7641	Intermediate Similarity	NPC149155
0.7641	Intermediate Similarity	NPC203468
0.7641	Intermediate Similarity	NPC110500
0.7636	Intermediate Similarity	NPC319232
0.7636	Intermediate Similarity	NPC24370
0.7633	Intermediate Similarity	NPC252338
0.7633	Intermediate Similarity	NPC470497
0.7632	Intermediate Similarity	NPC279918
0.7628	Intermediate Similarity	NPC470732
0.7628	Intermediate Similarity	NPC470731
0.7621	Intermediate Similarity	NPC470499
0.7606	Intermediate Similarity	NPC211572
0.7606	Intermediate Similarity	NPC80597
0.7606	Intermediate Similarity	NPC70922
0.7606	Intermediate Similarity	NPC212376
0.7606	Intermediate Similarity	NPC75540
0.7605	Intermediate Similarity	NPC125181
0.7605	Intermediate Similarity	NPC263117
0.7605	Intermediate Similarity	NPC242872
0.7573	Intermediate Similarity	NPC272483
0.7568	Intermediate Similarity	NPC297862
0.7553	Intermediate Similarity	NPC469765
0.7553	Intermediate Similarity	NPC469763
0.7553	Intermediate Similarity	NPC73952
0.7553	Intermediate Similarity	NPC469760
0.7553	Intermediate Similarity	NPC25008
0.7553	Intermediate Similarity	NPC259644
0.7553	Intermediate Similarity	NPC469786
0.7552	Intermediate Similarity	NPC194640
0.7547	Intermediate Similarity	NPC314957
0.7546	Intermediate Similarity	NPC471192
0.7545	Intermediate Similarity	NPC89987
0.7538	Intermediate Similarity	NPC233936
0.7531	Intermediate Similarity	NPC314056
0.7525	Intermediate Similarity	NPC213468
0.7523	Intermediate Similarity	NPC476491
0.7476	Intermediate Similarity	NPC476073
0.7474	Intermediate Similarity	NPC54988
0.7464	Intermediate Similarity	NPC106771
0.7464	Intermediate Similarity	NPC303820
0.7464	Intermediate Similarity	NPC205254
0.7464	Intermediate Similarity	NPC23420
0.746	Intermediate Similarity	NPC200214
0.7452	Intermediate Similarity	NPC131887
0.7436	Intermediate Similarity	NPC201700
0.7436	Intermediate Similarity	NPC78020
0.7435	Intermediate Similarity	NPC469762
0.7434	Intermediate Similarity	NPC323752
0.7429	Intermediate Similarity	NPC94211
0.7429	Intermediate Similarity	NPC300183
0.7429	Intermediate Similarity	NPC52909
0.7429	Intermediate Similarity	NPC475935
0.7416	Intermediate Similarity	NPC74413
0.7407	Intermediate Similarity	NPC216713
0.7397	Intermediate Similarity	NPC473310
0.7396	Intermediate Similarity	NPC92796
0.7396	Intermediate Similarity	NPC135141
0.7393	Intermediate Similarity	NPC477630
0.7393	Intermediate Similarity	NPC477635
0.7389	Intermediate Similarity	NPC474707
0.7388	Intermediate Similarity	NPC321939
0.7387	Intermediate Similarity	NPC64436
0.7382	Intermediate Similarity	NPC469785
0.7376	Intermediate Similarity	NPC472294
0.7371	Intermediate Similarity	NPC311276
0.7356	Intermediate Similarity	NPC11445
0.7354	Intermediate Similarity	NPC53947
0.735	Intermediate Similarity	NPC219336
0.7342	Intermediate Similarity	NPC253987
0.7336	Intermediate Similarity	NPC285343
0.7336	Intermediate Similarity	NPC473362
0.7336	Intermediate Similarity	NPC166492
0.7323	Intermediate Similarity	NPC161861
0.7321	Intermediate Similarity	NPC262898
0.7317	Intermediate Similarity	NPC478012
0.7317	Intermediate Similarity	NPC65215
0.7317	Intermediate Similarity	NPC173028
0.7317	Intermediate Similarity	NPC478011
0.7313	Intermediate Similarity	NPC63031
0.7313	Intermediate Similarity	NPC16659
0.7313	Intermediate Similarity	NPC300688
0.7311	Intermediate Similarity	NPC260900
0.7309	Intermediate Similarity	NPC476817
0.7308	Intermediate Similarity	NPC195239
0.7308	Intermediate Similarity	NPC157828
0.73	Intermediate Similarity	NPC15573
0.73	Intermediate Similarity	NPC217372
0.73	Intermediate Similarity	NPC183662
0.7297	Intermediate Similarity	NPC473317
0.7287	Intermediate Similarity	NPC314176
0.7286	Intermediate Similarity	NPC265576
0.7282	Intermediate Similarity	NPC95783
0.7281	Intermediate Similarity	NPC54981
0.7281	Intermediate Similarity	NPC82370
0.7277	Intermediate Similarity	NPC317701
0.7273	Intermediate Similarity	NPC179701
0.7268	Intermediate Similarity	NPC317030
0.7268	Intermediate Similarity	NPC204565
0.7265	Intermediate Similarity	NPC312942
0.7265	Intermediate Similarity	NPC327095
0.7264	Intermediate Similarity	NPC265710
0.7255	Intermediate Similarity	NPC280290
0.7254	Intermediate Similarity	NPC216643
0.725	Intermediate Similarity	NPC478006
0.7249	Intermediate Similarity	NPC471957
0.7246	Intermediate Similarity	NPC476460
0.7234	Intermediate Similarity	NPC314372
0.7232	Intermediate Similarity	NPC40455
0.7227	Intermediate Similarity	NPC314882
0.7225	Intermediate Similarity	NPC470823
0.7222	Intermediate Similarity	NPC475024
0.7222	Intermediate Similarity	NPC194411

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 NPC110602 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	525
0.2-0.3	1061
0.3-0.4	1947
0.4-0.5	2348
0.5-0.6	2312
0.6-0.7	646
0.7-0.8	90
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9021	High Similarity	NPD8272	Phase 2
0.8832	High Similarity	NPD8493	Clinical (unspecified phase)
0.8684	High Similarity	NPD8110	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD8072	Approved
0.8389	Intermediate Similarity	NPD7711	Discontinued
0.835	Intermediate Similarity	NPD8073	Approved
0.835	Intermediate Similarity	NPD7970	Approved
0.835	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.823	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD7944	Discontinued
0.8068	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD8431	Approved
0.8031	Intermediate Similarity	NPD6595	Phase 3
0.8029	Intermediate Similarity	NPD7470	Discontinued
0.7981	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7731	Approved
0.7844	Intermediate Similarity	NPD7730	Approved
0.7837	Intermediate Similarity	NPD8322	Phase 2
0.7834	Intermediate Similarity	NPD7271	Approved
0.7828	Intermediate Similarity	NPD7953	Approved
0.7828	Intermediate Similarity	NPD7791	Approved
0.7828	Intermediate Similarity	NPD7790	Approved
0.7828	Intermediate Similarity	NPD7952	Approved
0.7828	Intermediate Similarity	NPD7950	Approved
0.7828	Intermediate Similarity	NPD7789	Approved
0.7828	Intermediate Similarity	NPD7951	Approved
0.7822	Intermediate Similarity	NPD7618	Phase 3
0.7822	Intermediate Similarity	NPD7619	Phase 3
0.782	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD7957	Phase 1
0.7788	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7773	Intermediate Similarity	NPD7824	Approved
0.7757	Intermediate Similarity	NPD5818	Discontinued
0.7736	Intermediate Similarity	NPD8093	Discontinued
0.7727	Intermediate Similarity	NPD7780	Approved
0.7727	Intermediate Similarity	NPD7781	Approved
0.7677	Intermediate Similarity	NPD5106	Approved
0.7677	Intermediate Similarity	NPD5105	Approved
0.7677	Intermediate Similarity	NPD2095	Phase 2
0.7677	Intermediate Similarity	NPD2094	Phase 2
0.7677	Intermediate Similarity	NPD2092	Phase 2
0.7667	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD5426	Phase 3
0.7653	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD482	Approved
0.7638	Intermediate Similarity	NPD2096	Phase 2
0.7638	Intermediate Similarity	NPD2091	Phase 2
0.7617	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD3961	Discontinued
0.7612	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD7948	Phase 1
0.7547	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD8094	Discontinued
0.7526	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD750	Phase 2
0.7477	Intermediate Similarity	NPD7603	Discontinued
0.7474	Intermediate Similarity	NPD2642	Approved
0.7474	Intermediate Similarity	NPD2639	Approved
0.7458	Intermediate Similarity	NPD8284	Discontinued
0.7438	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD6044	Discontinued
0.7424	Intermediate Similarity	NPD4075	Phase 2
0.7419	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6217	Discontinued
0.7374	Intermediate Similarity	NPD5065	Approved
0.736	Intermediate Similarity	NPD3610	Approved
0.736	Intermediate Similarity	NPD3609	Approved
0.7347	Intermediate Similarity	NPD2641	Approved
0.7347	Intermediate Similarity	NPD2640	Approved
0.7324	Intermediate Similarity	NPD8169	Discontinued
0.7321	Intermediate Similarity	NPD6664	Approved
0.7273	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD1404	Approved
0.7268	Intermediate Similarity	NPD1403	Approved
0.7264	Intermediate Similarity	NPD4076	Approved
0.7264	Intermediate Similarity	NPD4079	Approved
0.7251	Intermediate Similarity	NPD6999	Discontinued
0.7251	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD8075	Discontinued
0.7243	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6173	Approved
0.723	Intermediate Similarity	NPD3015	Discontinued
0.7222	Intermediate Similarity	NPD7666	Phase 3
0.7222	Intermediate Similarity	NPD7665	Phase 2
0.7214	Intermediate Similarity	NPD3506	Approved
0.7214	Intermediate Similarity	NPD3505	Approved
0.7214	Intermediate Similarity	NPD2144	Approved
0.7195	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8256	Approved
0.7195	Intermediate Similarity	NPD8257	Approved
0.7192	Intermediate Similarity	NPD3038	Discontinued
0.7189	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8386	Phase 2
0.7172	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD8114	Approved
0.7163	Intermediate Similarity	NPD4903	Approved
0.7163	Intermediate Similarity	NPD8115	Approved
0.7163	Intermediate Similarity	NPD4905	Approved
0.7163	Intermediate Similarity	NPD4906	Approved
0.7156	Intermediate Similarity	NPD8261	Discontinued
0.715	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4904	Approved
0.713	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7779	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4181	Approved
0.7114	Intermediate Similarity	NPD4128	Approved
0.7103	Intermediate Similarity	NPD5017	Discontinued
0.7083	Intermediate Similarity	NPD5901	Discontinued
0.7081	Intermediate Similarity	NPD4918	Discontinued
0.708	Intermediate Similarity	NPD7716	Approved
0.708	Intermediate Similarity	NPD7717	Approved
0.7056	Intermediate Similarity	NPD8026	Phase 1
0.7056	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7001	Phase 3
0.7039	Intermediate Similarity	NPD7564	Discontinued
0.7031	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD8484	Phase 2
0.7024	Intermediate Similarity	NPD4399	Phase 2
0.7023	Intermediate Similarity	NPD7817	Phase 1
0.702	Intermediate Similarity	NPD3323	Discontinued
0.7018	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3843	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6165	Phase 2
0.6987	Remote Similarity	NPD6164	Phase 2
0.6986	Remote Similarity	NPD7981	Discontinued
0.6985	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8247	Approved
0.6983	Remote Similarity	NPD8246	Approved
0.697	Remote Similarity	NPD8317	Phase 2
0.697	Remote Similarity	NPD8316	Phase 2
0.697	Remote Similarity	NPD5315	Discontinued
0.6968	Remote Similarity	NPD786	Approved
0.6967	Remote Similarity	NPD6665	Discontinued
0.6963	Remote Similarity	NPD4397	Phase 1
0.6943	Remote Similarity	NPD8289	Discontinued
0.6931	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.691	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD2172	Phase 1
0.6898	Remote Similarity	NPD4600	Approved
0.6898	Remote Similarity	NPD4601	Approved
0.6898	Remote Similarity	NPD484	Approved
0.6895	Remote Similarity	NPD5906	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD1722	Approved
0.6893	Remote Similarity	NPD6452	Discontinued
0.689	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7026	Phase 2
0.6889	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6771	Discontinued
0.6881	Remote Similarity	NPD1325	Approved
0.6881	Remote Similarity	NPD1326	Approved
0.6878	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6178	Phase 3
0.6867	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7727	Phase 2
0.6866	Remote Similarity	NPD5636	Discontinued
0.6864	Remote Similarity	NPD7834	Approved
0.6863	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6492	Phase 2
0.686	Remote Similarity	NPD8408	Discontinued
0.6856	Remote Similarity	NPD3100	Discontinued
0.6854	Remote Similarity	NPD2717	Phase 2
0.685	Remote Similarity	NPD3583	Phase 2
0.6842	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4949	Discontinued
0.684	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8240	Discontinued
0.6838	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4640	Approved
0.6832	Remote Similarity	NPD4639	Approved
0.6832	Remote Similarity	NPD4638	Approved
0.6832	Remote Similarity	NPD5021	Discontinued
0.6828	Remote Similarity	NPD5199	Approved
0.6828	Remote Similarity	NPD5198	Approved
0.6821	Remote Similarity	NPD4462	Approved
0.6821	Remote Similarity	NPD4463	Approved
0.682	Remote Similarity	NPD5043	Discontinued
0.6818	Remote Similarity	NPD6732	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