NPASS Compound

Structure

NPC470622 OpenBabel07101719512D 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 3.5074 3.8848 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 -0.2260 4.0043 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 0 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 -1.2188 4.1237 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 -2.2117 4.2431 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 6 0 0 0 22 31 1 0 0 0 0 22 70 1 0 0 0 0 23 18 1 6 0 0 0 23 32 1 0 0 0 0 23 71 1 0 0 0 0 24 19 1 1 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 6 0 0 0 26 47 1 0 0 0 0 26 49 1 1 0 0 0 27 49 1 1 0 0 0 27 50 1 0 0 0 0 28 52 1 1 0 0 0 28 53 1 0 0 0 0 29 52 1 0 0 0 0 29 56 2 0 0 0 0 30 47 1 0 0 0 0 30 74 1 1 0 0 0 31 35 1 0 0 0 0 31 57 1 1 0 0 0 32 36 1 0 0 0 0 32 58 1 1 0 0 0 33 37 1 0 0 0 0 33 59 1 6 0 0 0 34 40 1 0 0 0 0 34 60 1 6 0 0 0 35 38 1 0 0 0 0 35 61 1 6 0 0 0 36 39 1 0 0 0 0 36 62 1 6 0 0 0 37 41 1 0 0 0 0 37 63 1 1 0 0 0 38 42 1 0 0 0 0 38 64 1 6 0 0 0 39 43 1 0 0 0 0 39 65 1 1 0 0 0 40 44 1 0 0 0 0 40 75 1 1 0 0 0 41 45 1 0 0 0 0 41 76 1 6 0 0 0 42 70 1 0 0 0 0 42 76 1 1 0 0 0 43 71 1 0 0 0 0 43 75 1 6 0 0 0 44 68 1 0 0 0 0 44 74 1 6 0 0 0 45 72 1 0 0 0 0 45 73 1 1 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 1 0 0 0 49 5 1 1 0 0 0 50 51 1 6 0 0 0 51 53 1 1 0 0 0 52 15 1 6 0 0 0 53 13 1 6 0 0 0 53 69 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1088.54
Volume:	1036.581
LogP:	0.796
LogD:	1.066
LogS:	-3.215
# Rotatable Bonds:	11
TPSA:	359.97
# H-Bond Aceptor:	23
# H-Bond Donor:	12
# Rings:	10
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.106
Synthetic Accessibility Score:	5.519
Fsp3:	0.962
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:	-6.419
MDCK Permeability:	7.026465027593076e-05
Pgp-inhibitor:	0.156
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.044
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.219
Plasma Protein Binding (PPB):	55.634334564208984%
Volume Distribution (VD):	0.146
Pgp-substrate:	16.646936416625977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.207
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	0.366
Half-life (T1/2):	0.834

ADMET: Toxicity

hERG Blockers:	0.151
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.007
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.114
Skin Sensitization:	0.029
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.844

Download Data

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

Natural Product: NPC470622

Natural Product ID:	NPC470622
*Common Name:**	KODLNBVLJHOXPV-IUZVLJPCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KODLNBVLJHOXPV-IUZVLJPCSA-N
Standard InCHI:	InChI=1S/C53H84O23/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/h22-28,30-45,54-55,57-65H,8-21H2,1-7H3,(H,66,67)/t22-,23+,24+,25-,26-,27+,28+,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:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](OC[C@@H]([C@@H]2O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC[C@]34[C@@]2(C)CC(=O)[C@@]2([C@H]4C[C@](C)(CC2)C(=O)O)CO3)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2088614
PubChem CID:	70682797
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]
NPO3803	Ardisia japonica	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]
NPO3803	Ardisia japonica	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
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100000000.0	nM	PMID[514567]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000000.0	nM	PMID[514567]
NPT27	Others	Unspecified	""	IC50	>	100000000.0	nM	PMID[514567]

☑ 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 NPC470622 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	540
0.1-0.2	3772
0.2-0.3	8428
0.3-0.4	12553
0.4-0.5	7772
0.5-0.6	4702
0.6-0.7	2692
0.7-0.8	1671
0.8-0.85	435
0.85-0.9	88
0.9-0.95	30
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC157571
0.9612	High Similarity	NPC66513
0.9608	High Similarity	NPC207693
0.9604	High Similarity	NPC184805
0.9604	High Similarity	NPC273189
0.9515	High Similarity	NPC22709
0.9515	High Similarity	NPC87393
0.951	High Similarity	NPC126753
0.951	High Similarity	NPC471430
0.9505	High Similarity	NPC267637
0.9307	High Similarity	NPC80640
0.9252	High Similarity	NPC477465
0.9238	High Similarity	NPC471431
0.9231	High Similarity	NPC469826
0.9151	High Similarity	NPC469824
0.9135	High Similarity	NPC138219
0.9135	High Similarity	NPC475630
0.9135	High Similarity	NPC475234
0.9135	High Similarity	NPC40716
0.9109	High Similarity	NPC80417
0.9048	High Similarity	NPC473688
0.9048	High Similarity	NPC231566
0.9048	High Similarity	NPC262567
0.9048	High Similarity	NPC471626
0.9038	High Similarity	NPC119628
0.9038	High Similarity	NPC158051
0.9038	High Similarity	NPC158367
0.8962	High Similarity	NPC469825
0.8942	High Similarity	NPC469827
0.8909	High Similarity	NPC179429
0.8824	High Similarity	NPC471375
0.8824	High Similarity	NPC471374
0.8824	High Similarity	NPC209798
0.8785	High Similarity	NPC236753
0.8785	High Similarity	NPC228190
0.8738	High Similarity	NPC471428
0.8738	High Similarity	NPC51579
0.8738	High Similarity	NPC471427
0.8738	High Similarity	NPC471426
0.8692	High Similarity	NPC92890
0.8692	High Similarity	NPC202898
0.8692	High Similarity	NPC475319
0.8611	High Similarity	NPC220836
0.8611	High Similarity	NPC233433
0.8611	High Similarity	NPC92297
0.8611	High Similarity	NPC273002
0.8611	High Similarity	NPC94086
0.8611	High Similarity	NPC473817
0.8598	High Similarity	NPC203974
0.8505	High Similarity	NPC215408
0.8435	Intermediate Similarity	NPC470478
0.8431	Intermediate Similarity	NPC471373
0.8431	Intermediate Similarity	NPC253611
0.8431	Intermediate Similarity	NPC148593
0.8431	Intermediate Similarity	NPC77717
0.8431	Intermediate Similarity	NPC267238
0.8421	Intermediate Similarity	NPC207738
0.8396	Intermediate Similarity	NPC310031
0.8396	Intermediate Similarity	NPC80191
0.8393	Intermediate Similarity	NPC79193
0.8378	Intermediate Similarity	NPC477492
0.8378	Intermediate Similarity	NPC477489
0.8365	Intermediate Similarity	NPC472273
0.835	Intermediate Similarity	NPC205129
0.835	Intermediate Similarity	NPC106701
0.835	Intermediate Similarity	NPC471425
0.835	Intermediate Similarity	NPC471424
0.835	Intermediate Similarity	NPC471429
0.835	Intermediate Similarity	NPC189575
0.8348	Intermediate Similarity	NPC473645
0.8348	Intermediate Similarity	NPC267694
0.8348	Intermediate Similarity	NPC144644
0.8348	Intermediate Similarity	NPC142151
0.8348	Intermediate Similarity	NPC37860
0.8348	Intermediate Similarity	NPC110385
0.8348	Intermediate Similarity	NPC153673
0.8333	Intermediate Similarity	NPC105800
0.8333	Intermediate Similarity	NPC232237
0.8333	Intermediate Similarity	NPC171741
0.8333	Intermediate Similarity	NPC224003
0.8333	Intermediate Similarity	NPC323231
0.8333	Intermediate Similarity	NPC470623
0.8333	Intermediate Similarity	NPC18724
0.8318	Intermediate Similarity	NPC34562
0.8318	Intermediate Similarity	NPC107385
0.8305	Intermediate Similarity	NPC469947
0.8305	Intermediate Similarity	NPC470218
0.8305	Intermediate Similarity	NPC181066
0.8304	Intermediate Similarity	NPC146563
0.8302	Intermediate Similarity	NPC477172
0.8291	Intermediate Similarity	NPC235405
0.8291	Intermediate Similarity	NPC281148
0.8291	Intermediate Similarity	NPC30735
0.8288	Intermediate Similarity	NPC473062
0.8286	Intermediate Similarity	NPC472144
0.8276	Intermediate Similarity	NPC68767
0.8276	Intermediate Similarity	NPC275225
0.8276	Intermediate Similarity	NPC293031
0.8276	Intermediate Similarity	NPC51099
0.8269	Intermediate Similarity	NPC475765
0.8269	Intermediate Similarity	NPC475785
0.8261	Intermediate Similarity	NPC51564
0.8261	Intermediate Similarity	NPC135849
0.8261	Intermediate Similarity	NPC25663
0.8246	Intermediate Similarity	NPC473824
0.8246	Intermediate Similarity	NPC475119
0.8241	Intermediate Similarity	NPC470167
0.8224	Intermediate Similarity	NPC470172
0.8224	Intermediate Similarity	NPC471254
0.822	Intermediate Similarity	NPC470477
0.8208	Intermediate Similarity	NPC20028
0.8205	Intermediate Similarity	NPC475591
0.8205	Intermediate Similarity	NPC40775
0.8205	Intermediate Similarity	NPC236870
0.8205	Intermediate Similarity	NPC187290
0.8205	Intermediate Similarity	NPC162574
0.8205	Intermediate Similarity	NPC235438
0.8205	Intermediate Similarity	NPC4749
0.8205	Intermediate Similarity	NPC10607
0.8205	Intermediate Similarity	NPC249848
0.8205	Intermediate Similarity	NPC80986
0.8205	Intermediate Similarity	NPC21691
0.8205	Intermediate Similarity	NPC107966
0.819	Intermediate Similarity	NPC476991
0.819	Intermediate Similarity	NPC472145
0.8174	Intermediate Similarity	NPC475899
0.8158	Intermediate Similarity	NPC75287
0.8158	Intermediate Similarity	NPC137414
0.8158	Intermediate Similarity	NPC305267
0.8158	Intermediate Similarity	NPC288205
0.8158	Intermediate Similarity	NPC51465
0.8158	Intermediate Similarity	NPC469820
0.8158	Intermediate Similarity	NPC469823
0.8158	Intermediate Similarity	NPC26626
0.8158	Intermediate Similarity	NPC291903
0.8158	Intermediate Similarity	NPC37134
0.8158	Intermediate Similarity	NPC476992
0.8151	Intermediate Similarity	NPC273962
0.8151	Intermediate Similarity	NPC285091
0.8148	Intermediate Similarity	NPC473406
0.8148	Intermediate Similarity	NPC471253
0.8137	Intermediate Similarity	NPC185529
0.8137	Intermediate Similarity	NPC472146
0.8137	Intermediate Similarity	NPC18536
0.8137	Intermediate Similarity	NPC50443
0.8136	Intermediate Similarity	NPC302543
0.8136	Intermediate Similarity	NPC283417
0.8136	Intermediate Similarity	NPC257211
0.8136	Intermediate Similarity	NPC200049
0.8136	Intermediate Similarity	NPC258617
0.8125	Intermediate Similarity	NPC240734
0.8125	Intermediate Similarity	NPC91838
0.8125	Intermediate Similarity	NPC11035
0.8125	Intermediate Similarity	NPC1876
0.8125	Intermediate Similarity	NPC275668
0.8125	Intermediate Similarity	NPC204392
0.812	Intermediate Similarity	NPC223301
0.812	Intermediate Similarity	NPC301449
0.812	Intermediate Similarity	NPC31838
0.812	Intermediate Similarity	NPC86222
0.812	Intermediate Similarity	NPC114484
0.812	Intermediate Similarity	NPC11242
0.812	Intermediate Similarity	NPC171544
0.812	Intermediate Similarity	NPC62725
0.812	Intermediate Similarity	NPC302887
0.812	Intermediate Similarity	NPC159309
0.812	Intermediate Similarity	NPC297263
0.812	Intermediate Similarity	NPC104372
0.812	Intermediate Similarity	NPC187618
0.812	Intermediate Similarity	NPC64715
0.812	Intermediate Similarity	NPC222580
0.812	Intermediate Similarity	NPC22956
0.8103	Intermediate Similarity	NPC477464
0.8103	Intermediate Similarity	NPC471577
0.8095	Intermediate Similarity	NPC237071
0.8095	Intermediate Similarity	NPC203434
0.8095	Intermediate Similarity	NPC235109
0.8095	Intermediate Similarity	NPC238796
0.8095	Intermediate Similarity	NPC163685
0.8087	Intermediate Similarity	NPC300419
0.8087	Intermediate Similarity	NPC220160
0.8087	Intermediate Similarity	NPC123522
0.8087	Intermediate Similarity	NPC8524
0.8087	Intermediate Similarity	NPC475514
0.8087	Intermediate Similarity	NPC68175
0.8087	Intermediate Similarity	NPC104137
0.8087	Intermediate Similarity	NPC102505
0.8087	Intermediate Similarity	NPC475209
0.8087	Intermediate Similarity	NPC471580
0.8087	Intermediate Similarity	NPC286457
0.8087	Intermediate Similarity	NPC85154
0.8087	Intermediate Similarity	NPC69811
0.8087	Intermediate Similarity	NPC191827
0.8087	Intermediate Similarity	NPC473452
0.8087	Intermediate Similarity	NPC33012
0.8087	Intermediate Similarity	NPC309223
0.8087	Intermediate Similarity	NPC470876
0.807	Intermediate Similarity	NPC164389
0.807	Intermediate Similarity	NPC54395
0.807	Intermediate Similarity	NPC475486

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 NPC470622 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	573
0.1-0.2	3784
0.2-0.3	3167
0.3-0.4	920
0.4-0.5	375
0.5-0.6	222
0.6-0.7	86
0.7-0.8	19
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8411	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD8328	Phase 3
0.7826	Intermediate Similarity	NPD8133	Approved
0.7632	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD8171	Discontinued
0.7236	Intermediate Similarity	NPD8515	Approved
0.7236	Intermediate Similarity	NPD8516	Approved
0.7236	Intermediate Similarity	NPD8517	Approved
0.7097	Intermediate Similarity	NPD8513	Phase 3
0.7094	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7736	Approved
0.6977	Remote Similarity	NPD7319	Approved
0.6952	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3669	Approved
0.6923	Remote Similarity	NPD1780	Approved
0.6923	Remote Similarity	NPD1779	Approved
0.6875	Remote Similarity	NPD7507	Approved
0.6822	Remote Similarity	NPD8293	Discontinued
0.681	Remote Similarity	NPD8138	Approved
0.681	Remote Similarity	NPD8084	Approved
0.681	Remote Similarity	NPD8085	Approved
0.681	Remote Similarity	NPD8083	Approved
0.681	Remote Similarity	NPD8139	Approved
0.681	Remote Similarity	NPD8086	Approved
0.681	Remote Similarity	NPD8082	Approved
0.678	Remote Similarity	NPD8393	Approved
0.6752	Remote Similarity	NPD8276	Approved
0.6752	Remote Similarity	NPD8275	Approved
0.6746	Remote Similarity	NPD8377	Approved
0.6746	Remote Similarity	NPD8294	Approved
0.6731	Remote Similarity	NPD7329	Approved
0.6695	Remote Similarity	NPD8081	Approved
0.6694	Remote Similarity	NPD6940	Discontinued
0.6693	Remote Similarity	NPD8380	Approved
0.6693	Remote Similarity	NPD8379	Approved
0.6693	Remote Similarity	NPD8296	Approved
0.6693	Remote Similarity	NPD8335	Approved
0.6693	Remote Similarity	NPD8378	Approved
0.6641	Remote Similarity	NPD6370	Approved
0.6635	Remote Similarity	NPD6697	Approved
0.6635	Remote Similarity	NPD6115	Approved
0.6635	Remote Similarity	NPD6118	Approved
0.6635	Remote Similarity	NPD6114	Approved
0.6583	Remote Similarity	NPD6412	Phase 2
0.6562	Remote Similarity	NPD6921	Approved
0.6562	Remote Similarity	NPD8033	Approved
0.6538	Remote Similarity	NPD6116	Phase 1
0.6538	Remote Similarity	NPD7492	Approved
0.6529	Remote Similarity	NPD6686	Approved
0.6505	Remote Similarity	NPD3703	Phase 2
0.6489	Remote Similarity	NPD6616	Approved
0.6484	Remote Similarity	NPD6059	Approved
0.6484	Remote Similarity	NPD6054	Approved
0.646	Remote Similarity	NPD8034	Phase 2
0.646	Remote Similarity	NPD8035	Phase 2
0.6442	Remote Similarity	NPD6117	Approved
0.6441	Remote Similarity	NPD1700	Approved
0.6439	Remote Similarity	NPD7078	Approved
0.6417	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6319	Approved
0.6355	Remote Similarity	NPD6928	Phase 2
0.6328	Remote Similarity	NPD7327	Approved
0.6328	Remote Similarity	NPD7328	Approved
0.6325	Remote Similarity	NPD7902	Approved
0.6311	Remote Similarity	NPD8140	Approved
0.6311	Remote Similarity	NPD8307	Discontinued
0.6308	Remote Similarity	NPD6016	Approved
0.6308	Remote Similarity	NPD6015	Approved
0.6279	Remote Similarity	NPD7516	Approved
0.626	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1810	Approved
0.625	Remote Similarity	NPD1811	Approved
0.621	Remote Similarity	NPD8305	Approved
0.621	Remote Similarity	NPD8306	Approved
0.6207	Remote Similarity	NPD7748	Approved
0.6194	Remote Similarity	NPD8074	Phase 3
0.619	Remote Similarity	NPD8297	Approved
0.619	Remote Similarity	NPD6882	Approved
0.616	Remote Similarity	NPD8087	Discontinued
0.6124	Remote Similarity	NPD6009	Approved
0.608	Remote Similarity	NPD6373	Approved
0.608	Remote Similarity	NPD6372	Approved
0.608	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD7900	Approved
0.6061	Remote Similarity	NPD7503	Approved
0.6058	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD3702	Approved
0.6034	Remote Similarity	NPD7515	Phase 2
0.6032	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD6033	Approved
0.6019	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD3181	Approved
0.5985	Remote Similarity	NPD8345	Approved
0.5985	Remote Similarity	NPD8346	Approved
0.5985	Remote Similarity	NPD8347	Approved
0.5984	Remote Similarity	NPD8301	Approved
0.5984	Remote Similarity	NPD8300	Approved
0.5984	Remote Similarity	NPD6650	Approved
0.5984	Remote Similarity	NPD6649	Approved
0.5968	Remote Similarity	NPD6402	Approved
0.5968	Remote Similarity	NPD6675	Approved
0.5968	Remote Similarity	NPD7128	Approved
0.5968	Remote Similarity	NPD5739	Approved
0.5962	Remote Similarity	NPD2687	Approved
0.5962	Remote Similarity	NPD2686	Approved
0.5962	Remote Similarity	NPD2254	Approved
0.5962	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.594	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5777	Approved
0.5896	Remote Similarity	NPD8080	Discontinued
0.5873	Remote Similarity	NPD6899	Approved
0.5873	Remote Similarity	NPD7320	Approved
0.5873	Remote Similarity	NPD6881	Approved
0.5872	Remote Similarity	NPD4802	Phase 2
0.5872	Remote Similarity	NPD4238	Approved
0.5865	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD8130	Phase 1
0.5852	Remote Similarity	NPD6067	Discontinued
0.584	Remote Similarity	NPD6008	Approved
0.5825	Remote Similarity	NPD898	Approved
0.5825	Remote Similarity	NPD896	Approved
0.5825	Remote Similarity	NPD897	Approved
0.581	Remote Similarity	NPD4245	Approved
0.581	Remote Similarity	NPD4244	Approved
0.5794	Remote Similarity	NPD5701	Approved
0.5794	Remote Similarity	NPD5697	Approved
0.5794	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD6883	Approved
0.5781	Remote Similarity	NPD7290	Approved
0.5781	Remote Similarity	NPD4634	Approved
0.5781	Remote Similarity	NPD7102	Approved
0.5769	Remote Similarity	NPD5360	Phase 3
0.5769	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6081	Approved
0.575	Remote Similarity	NPD7991	Discontinued
0.5738	Remote Similarity	NPD4225	Approved
0.5738	Remote Similarity	NPD7638	Approved
0.5736	Remote Similarity	NPD6847	Approved
0.5736	Remote Similarity	NPD6869	Approved
0.5736	Remote Similarity	NPD6617	Approved
0.5735	Remote Similarity	NPD7604	Phase 2
0.5728	Remote Similarity	NPD4224	Phase 2
0.5725	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD8392	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5714	Remote Similarity	NPD8391	Approved
0.5714	Remote Similarity	NPD3698	Phase 2
0.5714	Remote Similarity	NPD8390	Approved
0.5704	Remote Similarity	NPD8269	Approved
0.5704	Remote Similarity	NPD8267	Approved
0.5704	Remote Similarity	NPD5983	Phase 2
0.5704	Remote Similarity	NPD8268	Approved
0.5704	Remote Similarity	NPD8266	Approved
0.5703	Remote Similarity	NPD6013	Approved
0.5703	Remote Similarity	NPD6012	Approved
0.5703	Remote Similarity	NPD6014	Approved
0.5693	Remote Similarity	NPD8299	Approved
0.5693	Remote Similarity	NPD8342	Approved
0.5693	Remote Similarity	NPD8341	Approved
0.5693	Remote Similarity	NPD8340	Approved
0.5691	Remote Similarity	NPD7640	Approved
0.5691	Remote Similarity	NPD8418	Phase 2
0.5691	Remote Similarity	NPD7639	Approved
0.5686	Remote Similarity	NPD7909	Approved
0.566	Remote Similarity	NPD4789	Approved
0.5652	Remote Similarity	NPD8451	Approved
0.5652	Remote Similarity	NPD6336	Discontinued
0.563	Remote Similarity	NPD6411	Approved
0.5625	Remote Similarity	NPD6011	Approved
0.5615	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7140	Approved
0.56	Remote Similarity	NPD7632	Discontinued
0.56	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7139	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