NPASS Compound

Structure

CID126753 OpenBabel06191715482D 76 85 0 0 1 0 0 0 0 0999 V2000 9.6932 -6.1587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5074 -3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5074 -3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2188 -4.1237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3838 -0.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2705 -2.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0504 -0.7523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -3.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.8584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6310 -1.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0074 -1.5785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1365 -2.6587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1365 -0.4984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7453 -2.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8647 -1.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0256 -2.6044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0501 -2.0275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 1.8413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4252 -1.1587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0951 -2.6587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8271 -5.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3630 1.3413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5592 -1.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0951 -1.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3838 -2.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7601 -1.5785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1450 -1.6115 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7521 -1.8673 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6310 -2.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9611 -6.1587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4970 1.8413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5592 -2.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2291 -1.1587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0951 -5.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6310 1.3413 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6932 -3.1587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0951 -4.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6310 0.3413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3630 -1.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8271 -2.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9611 -4.1587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4970 -0.1587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3630 -2.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8271 -1.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2260 -4.0043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0074 -3.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8258 -3.2042 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3838 -1.9386 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1365 -1.9386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5129 -1.5785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0646 -1.2185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5129 -0.8584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2291 2.8413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2912 -1.6587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3756 -2.6491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9611 -7.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4970 2.8413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4252 -3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -0.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -6.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7650 1.8413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6932 -4.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -4.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7650 -0.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6190 -4.9239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7669 -3.8849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -3.1587 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 8.8271 -4.6587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3630 0.3413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6932 -1.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9611 -1.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4970 -3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4970 -1.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9611 -3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 47 1 0 0 0 0 3 47 1 0 0 0 0 6 50 1 0 0 0 0 7 51 1 0 0 0 0 8 12 1 0 0 0 0 8 26 1 0 0 0 0 9 13 1 0 0 0 0 9 27 1 0 0 0 0 10 11 1 0 0 0 0 10 30 1 0 0 0 0 11 49 1 0 0 0 0 12 50 1 0 0 0 0 14 15 1 0 0 0 0 14 48 1 0 0 0 0 16 28 1 0 0 0 0 16 48 1 0 0 0 0 17 29 1 0 0 0 0 17 51 1 0 0 0 0 18 54 1 0 0 0 0 19 55 1 0 0 0 0 20 25 1 0 0 0 0 20 68 1 0 0 0 0 21 52 1 0 0 0 0 21 69 1 0 0 0 0 22 1 1 1 0 0 0 22 31 1 0 0 0 0 22 70 1 0 0 0 0 23 18 1 1 0 0 0 23 32 1 0 0 0 0 23 71 1 0 0 0 0 24 19 1 6 0 0 0 24 33 1 0 0 0 0 24 72 1 0 0 0 0 25 34 1 0 0 0 0 25 73 1 1 0 0 0 26 47 1 0 0 0 0 26 49 1 6 0 0 0 27 49 1 6 0 0 0 27 50 1 0 0 0 0 28 52 1 6 0 0 0 28 53 1 0 0 0 0 29 52 1 1 0 0 0 29 56 1 0 0 0 0 30 47 1 0 0 0 0 30 74 1 6 0 0 0 31 35 1 0 0 0 0 31 57 1 6 0 0 0 32 36 1 0 0 0 0 32 58 1 6 0 0 0 33 37 1 0 0 0 0 33 59 1 1 0 0 0 34 40 1 0 0 0 0 34 60 1 1 0 0 0 35 38 1 0 0 0 0 35 61 1 1 0 0 0 36 39 1 0 0 0 0 36 62 1 1 0 0 0 37 41 1 0 0 0 0 37 63 1 6 0 0 0 38 42 1 0 0 0 0 38 64 1 1 0 0 0 39 43 1 0 0 0 0 39 65 1 6 0 0 0 40 44 1 0 0 0 0 40 75 1 6 0 0 0 41 45 1 0 0 0 0 41 76 1 1 0 0 0 42 70 1 0 0 0 0 42 76 1 6 0 0 0 43 71 1 0 0 0 0 43 75 1 1 0 0 0 44 68 1 0 0 0 0 44 74 1 1 0 0 0 45 72 1 0 0 0 0 45 73 1 6 0 0 0 46 48 1 0 0 0 0 46 66 2 0 0 0 0 46 67 1 0 0 0 0 48 4 1 6 0 0 0 49 5 1 6 0 0 0 50 51 1 1 0 0 0 51 53 1 6 0 0 0 52 15 1 1 0 0 0 53 13 1 1 0 0 0 53 69 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1090.56
Volume:	1039.218
LogP:	0.451
LogD:	1.161
LogS:	-3.285
# Rotatable Bonds:	11
TPSA:	363.13
# H-Bond Aceptor:	23
# H-Bond Donor:	13
# Rings:	10
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.103
Synthetic Accessibility Score:	5.012
Fsp3:	0.981
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.518
MDCK Permeability:	8.473557682009414e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	53.428001403808594%
Volume Distribution (VD):	0.065
Pgp-substrate:	14.961295127868652%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.926
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.13
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.232
Half-life (T1/2):	0.812

ADMET: Toxicity

hERG Blockers:	0.252
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.004
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.725
Skin Sensitization:	0.089
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC126753

Natural Product ID:	NPC126753
*Common Name:**	Ardisiamamilloside F
IUPAC Name:	n.a.
Synonyms:	Ardisiamamilloside F
Standard InCHIKey:	GBIVVEOMDGPTFX-KORAFSQNSA-N
Standard InCHI:	InChI=1S/C53H86O23/c1-22-31(57)35(61)38(64)42(70-22)76-41-37(63)33(59)24(19-55)72-45(41)73-25-20-68-44(40(34(25)60)75-43-39(65)36(62)32(58)23(18-54)71-43)74-30-10-11-49(5)26(47(30,2)3)8-12-50(6)27(49)9-13-53-28-16-48(4,46(66)67)14-15-52(28,21-69-53)29(56)17-51(50,53)7/h22-45,54-65H,8-21H2,1-7H3,(H,66,67)/t22-,23+,24+,25-,26-,27+,28+,29+,30-,31-,32+,33+,34-,35+,36-,37-,38+,39+,40+,41+,42-,43-,44-,45-,48-,49-,50+,51-,52+,53-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1O[C@H]1CO[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC[C@]24[C@@H]5C[C@](C)(CC[C@]5(CO4)[C@@H](C[C@@]32C)O)C(=O)O)C1(C)C)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL267882
PubChem CID:	44419566
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	whole plants	Sendai, Miyagi Prefecture, Japan	2000-Sep	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17397219]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22940450]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26639	Ardisia crenata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26639	Ardisia crenata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26639	Ardisia crenata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26639	Ardisia crenata	Species	Primulaceae	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	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[547713]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[547713]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[547713]

☑ 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 NPC126753 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	512
0.1-0.2	3739
0.2-0.3	9048
0.3-0.4	12736
0.4-0.5	7194
0.5-0.6	4568
0.6-0.7	2672
0.7-0.8	1649
0.8-0.85	435
0.85-0.9	104
0.9-0.95	22
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9703	High Similarity	NPC471431
0.96	High Similarity	NPC475234
0.96	High Similarity	NPC475630
0.96	High Similarity	NPC40716
0.96	High Similarity	NPC138219
0.9515	High Similarity	NPC157571
0.951	High Similarity	NPC470622
0.9505	High Similarity	NPC262567
0.9505	High Similarity	NPC471626
0.9505	High Similarity	NPC231566
0.9505	High Similarity	NPC207693
0.9505	High Similarity	NPC473688
0.95	High Similarity	NPC158051
0.95	High Similarity	NPC158367
0.95	High Similarity	NPC119628
0.9412	High Similarity	NPC22709
0.9286	High Similarity	NPC471375
0.9286	High Similarity	NPC471374
0.9286	High Similarity	NPC209798
0.9192	High Similarity	NPC51579
0.9192	High Similarity	NPC471427
0.9192	High Similarity	NPC471428
0.9192	High Similarity	NPC471426
0.9151	High Similarity	NPC477465
0.9135	High Similarity	NPC66513
0.9126	High Similarity	NPC469826
0.9118	High Similarity	NPC184805
0.9118	High Similarity	NPC273189
0.9038	High Similarity	NPC87393
0.9029	High Similarity	NPC471430
0.902	High Similarity	NPC267637
0.8878	High Similarity	NPC148593
0.8878	High Similarity	NPC77717
0.8878	High Similarity	NPC253611
0.8878	High Similarity	NPC267238
0.8878	High Similarity	NPC471373
0.8868	High Similarity	NPC469824
0.8857	High Similarity	NPC228190
0.8857	High Similarity	NPC236753
0.8835	High Similarity	NPC469827
0.8824	High Similarity	NPC80640
0.8788	High Similarity	NPC471424
0.8788	High Similarity	NPC205129
0.8788	High Similarity	NPC189575
0.8788	High Similarity	NPC471425
0.8788	High Similarity	NPC106701
0.8788	High Similarity	NPC471429
0.8776	High Similarity	NPC224003
0.8776	High Similarity	NPC470623
0.8776	High Similarity	NPC18724
0.8776	High Similarity	NPC323231
0.8776	High Similarity	NPC171741
0.8679	High Similarity	NPC469825
0.8667	High Similarity	NPC203974
0.8636	High Similarity	NPC179429
0.8627	High Similarity	NPC80417
0.8614	High Similarity	NPC472273
0.8585	High Similarity	NPC92890
0.8585	High Similarity	NPC202898
0.8585	High Similarity	NPC475319
0.8505	High Similarity	NPC92297
0.8505	High Similarity	NPC233433
0.8505	High Similarity	NPC220836
0.8505	High Similarity	NPC273002
0.8505	High Similarity	NPC473817
0.8505	High Similarity	NPC94086
0.844	Intermediate Similarity	NPC477489
0.844	Intermediate Similarity	NPC477492
0.8396	Intermediate Similarity	NPC215408
0.8393	Intermediate Similarity	NPC475899
0.8384	Intermediate Similarity	NPC50443
0.8384	Intermediate Similarity	NPC18536
0.8365	Intermediate Similarity	NPC477172
0.835	Intermediate Similarity	NPC472144
0.8349	Intermediate Similarity	NPC275668
0.8349	Intermediate Similarity	NPC1876
0.8349	Intermediate Similarity	NPC91838
0.8349	Intermediate Similarity	NPC240734
0.8349	Intermediate Similarity	NPC204392
0.8333	Intermediate Similarity	NPC203434
0.8333	Intermediate Similarity	NPC475765
0.8333	Intermediate Similarity	NPC475785
0.8333	Intermediate Similarity	NPC237071
0.8333	Intermediate Similarity	NPC238796
0.8319	Intermediate Similarity	NPC477464
0.8288	Intermediate Similarity	NPC469821
0.8286	Intermediate Similarity	NPC80191
0.8286	Intermediate Similarity	NPC310031
0.8252	Intermediate Similarity	NPC470591
0.8252	Intermediate Similarity	NPC472145
0.8246	Intermediate Similarity	NPC142151
0.8246	Intermediate Similarity	NPC110385
0.8246	Intermediate Similarity	NPC144644
0.8246	Intermediate Similarity	NPC37860
0.8246	Intermediate Similarity	NPC267694
0.8246	Intermediate Similarity	NPC153673
0.8235	Intermediate Similarity	NPC94582
0.8235	Intermediate Similarity	NPC57964
0.8208	Intermediate Similarity	NPC34562
0.82	Intermediate Similarity	NPC472146
0.82	Intermediate Similarity	NPC185529
0.8198	Intermediate Similarity	NPC174720
0.8198	Intermediate Similarity	NPC155410
0.8198	Intermediate Similarity	NPC133818
0.8198	Intermediate Similarity	NPC151543
0.8198	Intermediate Similarity	NPC475467
0.8198	Intermediate Similarity	NPC241909
0.8198	Intermediate Similarity	NPC166422
0.8198	Intermediate Similarity	NPC473826
0.8198	Intermediate Similarity	NPC295823
0.8198	Intermediate Similarity	NPC114287
0.8198	Intermediate Similarity	NPC46665
0.8198	Intermediate Similarity	NPC475287
0.8198	Intermediate Similarity	NPC309714
0.8198	Intermediate Similarity	NPC192600
0.8198	Intermediate Similarity	NPC323341
0.8198	Intermediate Similarity	NPC251263
0.8198	Intermediate Similarity	NPC114304
0.8198	Intermediate Similarity	NPC146563
0.8198	Intermediate Similarity	NPC219180
0.819	Intermediate Similarity	NPC475574
0.8174	Intermediate Similarity	NPC470478
0.8174	Intermediate Similarity	NPC51099
0.8174	Intermediate Similarity	NPC275225
0.8174	Intermediate Similarity	NPC293031
0.8174	Intermediate Similarity	NPC477463
0.8174	Intermediate Similarity	NPC68767
0.8165	Intermediate Similarity	NPC51947
0.8165	Intermediate Similarity	NPC473844
0.8163	Intermediate Similarity	NPC471411
0.8163	Intermediate Similarity	NPC471410
0.8158	Intermediate Similarity	NPC207738
0.8158	Intermediate Similarity	NPC135849
0.8158	Intermediate Similarity	NPC51564
0.8158	Intermediate Similarity	NPC25663
0.8155	Intermediate Similarity	NPC235109
0.8142	Intermediate Similarity	NPC68175
0.8137	Intermediate Similarity	NPC305418
0.8125	Intermediate Similarity	NPC236638
0.8125	Intermediate Similarity	NPC294453
0.8125	Intermediate Similarity	NPC70809
0.8125	Intermediate Similarity	NPC79193
0.8125	Intermediate Similarity	NPC100639
0.8125	Intermediate Similarity	NPC250247
0.8125	Intermediate Similarity	NPC293330
0.8125	Intermediate Similarity	NPC476068
0.8125	Intermediate Similarity	NPC309907
0.8125	Intermediate Similarity	NPC67857
0.8125	Intermediate Similarity	NPC65105
0.8125	Intermediate Similarity	NPC79643
0.8125	Intermediate Similarity	NPC298034
0.8125	Intermediate Similarity	NPC41061
0.8125	Intermediate Similarity	NPC469782
0.8125	Intermediate Similarity	NPC471550
0.8125	Intermediate Similarity	NPC475140
0.8125	Intermediate Similarity	NPC473714
0.8125	Intermediate Similarity	NPC224381
0.8125	Intermediate Similarity	NPC54636
0.8125	Intermediate Similarity	NPC119592
0.8125	Intermediate Similarity	NPC202828
0.8125	Intermediate Similarity	NPC76972
0.8125	Intermediate Similarity	NPC123199
0.8125	Intermediate Similarity	NPC161717
0.8125	Intermediate Similarity	NPC204414
0.8125	Intermediate Similarity	NPC475160
0.8125	Intermediate Similarity	NPC4328
0.8125	Intermediate Similarity	NPC57484
0.8125	Intermediate Similarity	NPC71065
0.8125	Intermediate Similarity	NPC261506
0.8125	Intermediate Similarity	NPC227551
0.8125	Intermediate Similarity	NPC43550
0.8125	Intermediate Similarity	NPC60557
0.8125	Intermediate Similarity	NPC305981
0.8125	Intermediate Similarity	NPC471385
0.8119	Intermediate Similarity	NPC475878
0.8108	Intermediate Similarity	NPC292677
0.8108	Intermediate Similarity	NPC257468
0.8108	Intermediate Similarity	NPC475516
0.8108	Intermediate Similarity	NPC139044
0.8108	Intermediate Similarity	NPC104071
0.8108	Intermediate Similarity	NPC324875
0.8108	Intermediate Similarity	NPC104400
0.8108	Intermediate Similarity	NPC475504
0.8108	Intermediate Similarity	NPC79718
0.8108	Intermediate Similarity	NPC102439
0.8108	Intermediate Similarity	NPC469946
0.8108	Intermediate Similarity	NPC109079
0.8108	Intermediate Similarity	NPC471383
0.8108	Intermediate Similarity	NPC10320
0.8108	Intermediate Similarity	NPC276093
0.8108	Intermediate Similarity	NPC473373
0.8108	Intermediate Similarity	NPC101744
0.8095	Intermediate Similarity	NPC20028
0.8087	Intermediate Similarity	NPC473645
0.8087	Intermediate Similarity	NPC476991
0.8077	Intermediate Similarity	NPC210157
0.8073	Intermediate Similarity	NPC472079
0.8073	Intermediate Similarity	NPC88744
0.807	Intermediate Similarity	NPC36831
0.807	Intermediate Similarity	NPC276758

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 NPC126753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	552
0.1-0.2	3769
0.2-0.3	3247
0.3-0.4	875
0.4-0.5	386
0.5-0.6	212
0.6-0.7	85
0.7-0.8	22
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
0.8476	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD8133	Approved
0.7826	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8171	Discontinued
0.7583	Intermediate Similarity	NPD8328	Phase 3
0.7522	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7507	Approved
0.6992	Remote Similarity	NPD8515	Approved
0.6992	Remote Similarity	NPD8516	Approved
0.6992	Remote Similarity	NPD8517	Approved
0.699	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3669	Approved
0.6961	Remote Similarity	NPD1780	Approved
0.6961	Remote Similarity	NPD1779	Approved
0.6911	Remote Similarity	NPD8377	Approved
0.6911	Remote Similarity	NPD8294	Approved
0.6875	Remote Similarity	NPD7319	Approved
0.686	Remote Similarity	NPD6940	Discontinued
0.6855	Remote Similarity	NPD8378	Approved
0.6855	Remote Similarity	NPD8335	Approved
0.6855	Remote Similarity	NPD8380	Approved
0.6855	Remote Similarity	NPD8379	Approved
0.6855	Remote Similarity	NPD8513	Phase 3
0.6855	Remote Similarity	NPD8296	Approved
0.6838	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6697	Approved
0.6832	Remote Similarity	NPD6118	Approved
0.6832	Remote Similarity	NPD6115	Approved
0.6832	Remote Similarity	NPD6114	Approved
0.6797	Remote Similarity	NPD7736	Approved
0.6733	Remote Similarity	NPD6116	Phase 1
0.672	Remote Similarity	NPD8033	Approved
0.6695	Remote Similarity	NPD6686	Approved
0.6634	Remote Similarity	NPD6117	Approved
0.6613	Remote Similarity	NPD7328	Approved
0.6613	Remote Similarity	NPD7327	Approved
0.661	Remote Similarity	NPD6412	Phase 2
0.6589	Remote Similarity	NPD8293	Discontinued
0.656	Remote Similarity	NPD7516	Approved
0.6538	Remote Similarity	NPD6928	Phase 2
0.6535	Remote Similarity	NPD3703	Phase 2
0.6486	Remote Similarity	NPD8034	Phase 2
0.6486	Remote Similarity	NPD8035	Phase 2
0.6442	Remote Similarity	NPD7329	Approved
0.6436	Remote Similarity	NPD1811	Approved
0.6436	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1810	Approved
0.641	Remote Similarity	NPD8085	Approved
0.641	Remote Similarity	NPD8082	Approved
0.641	Remote Similarity	NPD8083	Approved
0.641	Remote Similarity	NPD8138	Approved
0.641	Remote Similarity	NPD8084	Approved
0.641	Remote Similarity	NPD8139	Approved
0.641	Remote Similarity	NPD8086	Approved
0.6406	Remote Similarity	NPD6370	Approved
0.6393	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD8393	Approved
0.6364	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD8276	Approved
0.6356	Remote Similarity	NPD8275	Approved
0.6328	Remote Similarity	NPD6921	Approved
0.6325	Remote Similarity	NPD1700	Approved
0.6308	Remote Similarity	NPD7492	Approved
0.6303	Remote Similarity	NPD8081	Approved
0.63	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD6059	Approved
0.6239	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD7748	Approved
0.6214	Remote Similarity	NPD3702	Approved
0.6212	Remote Similarity	NPD7078	Approved
0.621	Remote Similarity	NPD6882	Approved
0.621	Remote Similarity	NPD8297	Approved
0.6207	Remote Similarity	NPD7902	Approved
0.6202	Remote Similarity	NPD7503	Approved
0.6198	Remote Similarity	NPD8307	Discontinued
0.6198	Remote Similarity	NPD8140	Approved
0.6179	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6009	Approved
0.6139	Remote Similarity	NPD2687	Approved
0.6139	Remote Similarity	NPD2686	Approved
0.6139	Remote Similarity	NPD2254	Approved
0.6124	Remote Similarity	NPD6319	Approved
0.6098	Remote Similarity	NPD8305	Approved
0.6098	Remote Similarity	NPD8306	Approved
0.6078	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD6016	Approved
0.6077	Remote Similarity	NPD6015	Approved
0.6053	Remote Similarity	NPD7515	Phase 2
0.6048	Remote Similarity	NPD8087	Discontinued
0.604	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.604	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD4632	Approved
0.6031	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD6675	Approved
0.5984	Remote Similarity	NPD7128	Approved
0.5984	Remote Similarity	NPD5739	Approved
0.5984	Remote Similarity	NPD6402	Approved
0.597	Remote Similarity	NPD8074	Phase 3
0.5968	Remote Similarity	NPD6373	Approved
0.5968	Remote Similarity	NPD6372	Approved
0.5948	Remote Similarity	NPD7900	Approved
0.5948	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5777	Approved
0.5897	Remote Similarity	NPD7991	Discontinued
0.5891	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7320	Approved
0.5887	Remote Similarity	NPD6881	Approved
0.5887	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD7638	Approved
0.5878	Remote Similarity	NPD8345	Approved
0.5878	Remote Similarity	NPD8347	Approved
0.5878	Remote Similarity	NPD8346	Approved
0.5873	Remote Similarity	NPD6650	Approved
0.5873	Remote Similarity	NPD8130	Phase 1
0.5873	Remote Similarity	NPD6649	Approved
0.5865	Remote Similarity	NPD6067	Discontinued
0.5859	Remote Similarity	NPD7909	Approved
0.5833	Remote Similarity	NPD7639	Approved
0.5833	Remote Similarity	NPD8418	Phase 2
0.5833	Remote Similarity	NPD7640	Approved
0.5825	Remote Similarity	NPD4245	Approved
0.5825	Remote Similarity	NPD4244	Approved
0.5809	Remote Similarity	NPD6033	Approved
0.5806	Remote Similarity	NPD5701	Approved
0.5806	Remote Similarity	NPD5697	Approved
0.5794	Remote Similarity	NPD6883	Approved
0.5794	Remote Similarity	NPD7290	Approved
0.5794	Remote Similarity	NPD7102	Approved
0.5784	Remote Similarity	NPD5360	Phase 3
0.5784	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6081	Approved
0.5748	Remote Similarity	NPD6617	Approved
0.5748	Remote Similarity	NPD6869	Approved
0.5748	Remote Similarity	NPD6847	Approved
0.5746	Remote Similarity	NPD7604	Phase 2
0.5743	Remote Similarity	NPD4224	Phase 2
0.5738	Remote Similarity	NPD7632	Discontinued
0.5738	Remote Similarity	NPD8301	Approved
0.5738	Remote Similarity	NPD8300	Approved
0.5728	Remote Similarity	NPD3698	Phase 2
0.5726	Remote Similarity	NPD6008	Approved
0.5714	Remote Similarity	NPD3181	Approved
0.5714	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6123	Approved
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD5983	Phase 2
0.5714	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD8450	Suspended
0.5714	Remote Similarity	NPD6013	Approved
0.57	Remote Similarity	NPD371	Approved
0.5673	Remote Similarity	NPD4789	Approved
0.5672	Remote Similarity	NPD8080	Discontinued
0.5662	Remote Similarity	NPD6336	Discontinued
0.5649	Remote Similarity	NPD7115	Discovery
0.5643	Remote Similarity	NPD8449	Approved
0.5635	Remote Similarity	NPD6011	Approved
0.5635	Remote Similarity	NPD8174	Phase 2
0.5625	Remote Similarity	NPD6401	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