NPASS Compound

Structure

NPC202261 OpenBabel07101719142D 87 97 0 0 1 0 0 0 0 0999 V2000 2.4023 2.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0038 3.8987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7504 5.6329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8589 4.1197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7504 6.6227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8671 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0361 -0.3059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1789 -2.7804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3217 -2.2855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1789 0.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3217 0.6839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8932 -2.7804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7504 -1.2957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5231 -1.1066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6973 2.5560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 2.2370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1792 3.6533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4648 0.6839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9226 8.5484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8166 8.1458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6015 2.1534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1073 2.9144 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8932 5.1380 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8908 3.9139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8932 7.1176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0361 -2.2855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7504 -2.2855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3217 -1.2957 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1789 -0.8008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4645 -0.8008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9414 1.2957 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1792 4.6431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4648 1.6737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9414 -0.3059 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8932 -0.8008 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5231 0.4949 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0115 2.5118 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3220 5.1380 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1150 1.5274 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4648 4.6431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3142 0.9456 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1789 4.1482 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7050 1.1690 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0361 5.6329 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6076 2.1686 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1789 5.1380 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7504 1.6737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9042 0.5872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5209 7.2045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4648 3.6533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4100 1.3482 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0361 3.6533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7504 0.6839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3217 6.6227 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4645 0.1890 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0361 -1.2957 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8268 8.1458 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9898 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8191 9.5328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2285 4.6495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8932 8.1074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6076 -2.7804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0364 5.1380 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3220 2.1686 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8123 3.0936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3220 6.1278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0192 1.1248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6076 5.1380 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4177 -0.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3217 3.6533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0077 -0.3972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5796 6.8986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7233 9.1302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5849 2.9726 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3220 3.1584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6076 0.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1224 7.2045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1035 1.9742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3065 2.3326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8932 4.1482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0361 6.6227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8932 0.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6092 0.7664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6076 3.1584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3217 5.6329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0361 2.6635 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 2 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 8 9 1 0 0 0 0 8 26 2 0 0 0 0 10 11 1 0 0 0 0 10 29 1 0 0 0 0 11 55 1 0 0 0 0 12 26 1 0 0 0 0 12 27 1 0 0 0 0 13 27 1 0 0 0 0 13 35 1 0 0 0 0 14 30 1 0 0 0 0 15 21 1 0 0 0 0 15 78 1 0 0 0 0 16 31 1 0 0 0 0 16 74 1 0 0 0 0 17 32 1 0 0 0 0 17 75 1 0 0 0 0 18 33 1 0 0 0 0 18 76 1 0 0 0 0 19 57 1 0 0 0 0 19 59 1 0 0 0 0 20 57 1 0 0 0 0 20 77 1 0 0 0 0 21 43 1 0 0 0 0 22 2 1 6 0 0 0 22 37 1 0 0 0 0 22 79 1 0 0 0 0 23 3 1 1 0 0 0 23 44 1 0 0 0 0 23 80 1 0 0 0 0 24 60 2 0 0 0 0 24 74 1 0 0 0 0 25 61 2 0 0 0 0 25 81 1 0 0 0 0 26 56 1 0 0 0 0 27 62 1 1 0 0 0 28 9 1 6 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 29 56 1 1 0 0 0 30 55 1 1 0 0 0 31 36 1 0 0 0 0 31 58 1 6 0 0 0 32 38 1 0 0 0 0 32 63 1 1 0 0 0 33 45 1 0 0 0 0 33 64 1 6 0 0 0 34 14 1 1 0 0 0 34 36 1 0 0 0 0 34 87 1 0 0 0 0 35 56 1 1 0 0 0 35 82 1 0 0 0 0 36 55 1 1 0 0 0 37 39 1 0 0 0 0 37 65 1 1 0 0 0 38 40 1 0 0 0 0 38 66 1 6 0 0 0 39 41 1 0 0 0 0 39 67 1 6 0 0 0 40 50 1 0 0 0 0 40 68 1 1 0 0 0 41 51 1 0 0 0 0 41 69 1 1 0 0 0 42 46 1 0 0 0 0 42 52 1 0 0 0 0 42 70 1 1 0 0 0 43 48 1 0 0 0 0 43 83 1 6 0 0 0 44 46 1 0 0 0 0 44 81 1 6 0 0 0 45 47 1 0 0 0 0 45 84 1 6 0 0 0 46 85 1 1 0 0 0 47 53 1 0 0 0 0 47 86 1 1 0 0 0 48 58 1 6 0 0 0 48 71 1 0 0 0 0 49 54 1 0 0 0 0 49 57 1 1 0 0 0 49 72 1 0 0 0 0 50 75 1 0 0 0 0 50 84 1 6 0 0 0 51 79 1 0 0 0 0 51 83 1 6 0 0 0 52 80 1 0 0 0 0 52 86 1 6 0 0 0 53 76 1 0 0 0 0 53 82 1 6 0 0 0 54 77 1 0 0 0 0 54 85 1 6 0 0 0 55 6 1 1 0 0 0 56 7 1 1 0 0 0 57 73 1 1 0 0 0 58 78 1 6 0 0 0 58 87 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1248.54
Volume:	1161.973
LogP:	0.388
LogD:	0.509
LogS:	-3.483
# Rotatable Bonds:	16
TPSA:	426.35
# H-Bond Aceptor:	29
# H-Bond Donor:	13
# Rings:	11
# Heavy Atoms:	29

MedChem Properties

QED Drug-Likeness Score:	0.058
Synthetic Accessibility Score:	5.705
Fsp3:	0.897
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:	-6.459
MDCK Permeability:	0.000355464726453647
Pgp-inhibitor:	0.001
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.177
Plasma Protein Binding (PPB):	27.965354919433594%
Volume Distribution (VD):	0.017
Pgp-substrate:	36.71813201904297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	-0.272
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.531
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.841
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.157
Maximum Recommended Daily Dose:	0.197
Skin Sensitization:	0.497
Carcinogencity:	0.236
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC202261

Natural Product ID:	NPC202261
*Common Name:**	GWKXWFUKJVEVIT-OCZWOLEMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GWKXWFUKJVEVIT-OCZWOLEMSA-N
Standard InCHI:	InChI=1S/C58H88O29/c1-21-15-78-58(48(71)43(21)83-51-41(69)39(67)37(65)22(2)79-51)31(16-74-24(4)60)36-34(87-58)14-30-28-9-8-26-12-27(62)13-35(56(26,7)29(28)10-11-55(30,36)6)82-53-47(45(33(64)18-76-53)84-50-40(68)38(66)32(63)17-75-50)86-52-42(70)46(44(23(3)80-52)81-25(5)61)85-54-49(72)57(73,19-59)20-77-54/h8,22-23,27-54,59,62-73H,1,9-20H2,2-7H3/t22-,23+,27-,28-,29+,30+,31+,32-,33+,34+,35-,36+,37-,38+,39+,40-,41-,42-,43+,44+,45+,46+,47-,48+,49+,50+,51+,52+,53+,54+,55+,56+,57-,58+/m1/s1
SMILES:	C=C1CO[C@]2([C@@H](COC(=O)C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@H](C[C@H]([C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)OC(=O)C)O[C@H]3[C@@H]([C@@](CO)(CO3)O)O)O)O)O2)[C@H]([C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504992
PubChem CID:	10975315
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

*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
NPO6205	Helleborus orientalis	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12608856]

☑ 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
NPT924	Cell Line	HSC-2	Homo sapiens	IC50	>	200.0	ug.mL-1	PMID[507812]

☑ 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 NPC202261 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	299
0.1-0.2	2099
0.2-0.3	6149
0.3-0.4	13598
0.4-0.5	8812
0.5-0.6	6276
0.6-0.7	3202
0.7-0.8	1661
0.8-0.85	383
0.85-0.9	182
0.9-0.95	23
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC106589
0.9912	High Similarity	NPC43842
0.9825	High Similarity	NPC295133
0.9825	High Similarity	NPC257207
0.9735	High Similarity	NPC207243
0.9735	High Similarity	NPC233391
0.9735	High Similarity	NPC198325
0.9646	High Similarity	NPC195560
0.9646	High Similarity	NPC229962
0.9561	High Similarity	NPC50689
0.9474	High Similarity	NPC473633
0.9474	High Similarity	NPC476085
0.9469	High Similarity	NPC477807
0.9386	High Similarity	NPC160888
0.9386	High Similarity	NPC475403
0.9381	High Similarity	NPC477029
0.9381	High Similarity	NPC63609
0.9381	High Similarity	NPC477030
0.9292	High Similarity	NPC11548
0.9292	High Similarity	NPC477808
0.9211	High Similarity	NPC477031
0.9115	High Similarity	NPC112274
0.9115	High Similarity	NPC42171
0.906	High Similarity	NPC475358
0.906	High Similarity	NPC473566
0.9052	High Similarity	NPC10366
0.9052	High Similarity	NPC475357
0.9035	High Similarity	NPC51154
0.9027	High Similarity	NPC13190
0.9027	High Similarity	NPC475247
0.9027	High Similarity	NPC294129
0.8992	High Similarity	NPC208193
0.8992	High Similarity	NPC117445
0.8992	High Similarity	NPC308262
0.8966	High Similarity	NPC476690
0.8966	High Similarity	NPC100048
0.8966	High Similarity	NPC20979
0.8957	High Similarity	NPC477810
0.8947	High Similarity	NPC254255
0.8938	High Similarity	NPC222202
0.8938	High Similarity	NPC477811
0.8938	High Similarity	NPC269297
0.8938	High Similarity	NPC87998
0.8938	High Similarity	NPC224314
0.8938	High Similarity	NPC23808
0.8938	High Similarity	NPC247037
0.8908	High Similarity	NPC74259
0.8908	High Similarity	NPC474423
0.8879	High Similarity	NPC148965
0.8879	High Similarity	NPC146652
0.887	High Similarity	NPC469348
0.887	High Similarity	NPC469347
0.887	High Similarity	NPC476693
0.886	High Similarity	NPC477032
0.886	High Similarity	NPC124677
0.886	High Similarity	NPC13193
0.886	High Similarity	NPC470748
0.886	High Similarity	NPC477028
0.885	High Similarity	NPC300557
0.885	High Similarity	NPC95051
0.885	High Similarity	NPC470433
0.885	High Similarity	NPC306131
0.885	High Similarity	NPC232054
0.885	High Similarity	NPC224098
0.885	High Similarity	NPC477809
0.885	High Similarity	NPC22779
0.885	High Similarity	NPC208383
0.885	High Similarity	NPC46190
0.885	High Similarity	NPC309278
0.885	High Similarity	NPC477027
0.885	High Similarity	NPC73243
0.885	High Similarity	NPC475670
0.885	High Similarity	NPC477026
0.885	High Similarity	NPC475333
0.885	High Similarity	NPC218571
0.885	High Similarity	NPC70204
0.885	High Similarity	NPC248746
0.885	High Similarity	NPC249265
0.885	High Similarity	NPC475550
0.885	High Similarity	NPC84956
0.885	High Similarity	NPC244086
0.885	High Similarity	NPC150372
0.885	High Similarity	NPC6806
0.885	High Similarity	NPC102016
0.885	High Similarity	NPC171073
0.885	High Similarity	NPC194207
0.8824	High Similarity	NPC120390
0.8824	High Similarity	NPC475590
0.8824	High Similarity	NPC314535
0.8824	High Similarity	NPC475419
0.8824	High Similarity	NPC474908
0.8824	High Similarity	NPC173555
0.8793	High Similarity	NPC167183
0.8793	High Similarity	NPC32707
0.8783	High Similarity	NPC263359
0.8783	High Similarity	NPC31896
0.8783	High Similarity	NPC32361
0.8783	High Similarity	NPC210569
0.8783	High Similarity	NPC244431
0.8761	High Similarity	NPC476539
0.8761	High Similarity	NPC295980
0.8761	High Similarity	NPC476541
0.8761	High Similarity	NPC98696
0.8761	High Similarity	NPC476538
0.8761	High Similarity	NPC476540
0.875	High Similarity	NPC193893
0.875	High Similarity	NPC264336
0.8739	High Similarity	NPC475556
0.8739	High Similarity	NPC107607
0.8739	High Similarity	NPC72260
0.8739	High Similarity	NPC475629
0.8729	High Similarity	NPC218093
0.8707	High Similarity	NPC144068
0.8707	High Similarity	NPC79900
0.8696	High Similarity	NPC114188
0.8696	High Similarity	NPC197231
0.8696	High Similarity	NPC476547
0.8684	High Similarity	NPC302057
0.8684	High Similarity	NPC40440
0.8684	High Similarity	NPC42482
0.8678	High Similarity	NPC256983
0.8673	High Similarity	NPC161676
0.8673	High Similarity	NPC305423
0.8673	High Similarity	NPC113044
0.8673	High Similarity	NPC226642
0.8673	High Similarity	NPC94272
0.8673	High Similarity	NPC470432
0.8673	High Similarity	NPC14704
0.8673	High Similarity	NPC283829
0.8673	High Similarity	NPC230507
0.8667	High Similarity	NPC231518
0.8667	High Similarity	NPC475219
0.8655	High Similarity	NPC55532
0.8655	High Similarity	NPC469756
0.8655	High Similarity	NPC291820
0.8655	High Similarity	NPC292467
0.8655	High Similarity	NPC236973
0.8655	High Similarity	NPC30483
0.8655	High Similarity	NPC81222
0.8655	High Similarity	NPC470897
0.8655	High Similarity	NPC32177
0.8644	High Similarity	NPC203862
0.8621	High Similarity	NPC19888
0.8621	High Similarity	NPC308140
0.8609	High Similarity	NPC141433
0.8584	High Similarity	NPC473476
0.8584	High Similarity	NPC309448
0.8584	High Similarity	NPC181845
0.8584	High Similarity	NPC473923
0.8583	High Similarity	NPC135369
0.8583	High Similarity	NPC474466
0.8583	High Similarity	NPC475136
0.8571	High Similarity	NPC476692
0.8571	High Similarity	NPC476691
0.8559	High Similarity	NPC212660
0.8559	High Similarity	NPC207637
0.8547	High Similarity	NPC476671
0.8534	High Similarity	NPC65167
0.8522	High Similarity	NPC14630
0.8522	High Similarity	NPC157530
0.8522	High Similarity	NPC250089
0.8512	High Similarity	NPC40749
0.8509	High Similarity	NPC190395
0.85	High Similarity	NPC329905
0.85	High Similarity	NPC44899
0.85	High Similarity	NPC5883
0.85	High Similarity	NPC304260
0.85	High Similarity	NPC29639
0.8487	Intermediate Similarity	NPC471355
0.8487	Intermediate Similarity	NPC471353
0.8487	Intermediate Similarity	NPC77319
0.8487	Intermediate Similarity	NPC474418
0.8487	Intermediate Similarity	NPC27507
0.8487	Intermediate Similarity	NPC93883
0.8487	Intermediate Similarity	NPC34390
0.8487	Intermediate Similarity	NPC157376
0.8487	Intermediate Similarity	NPC99728
0.8487	Intermediate Similarity	NPC50305
0.8487	Intermediate Similarity	NPC84987
0.8487	Intermediate Similarity	NPC473852
0.8487	Intermediate Similarity	NPC142066
0.8487	Intermediate Similarity	NPC309034
0.8487	Intermediate Similarity	NPC243196
0.8487	Intermediate Similarity	NPC158344
0.8487	Intermediate Similarity	NPC471354
0.8487	Intermediate Similarity	NPC471351
0.8487	Intermediate Similarity	NPC244402
0.8487	Intermediate Similarity	NPC196429
0.8487	Intermediate Similarity	NPC87250
0.8475	Intermediate Similarity	NPC208832
0.8455	Intermediate Similarity	NPC473474
0.8448	Intermediate Similarity	NPC470867
0.8448	Intermediate Similarity	NPC170974
0.8448	Intermediate Similarity	NPC103627
0.8448	Intermediate Similarity	NPC191439
0.8443	Intermediate Similarity	NPC15918
0.8443	Intermediate Similarity	NPC94072
0.8443	Intermediate Similarity	NPC305771
0.8443	Intermediate Similarity	NPC169816
0.8435	Intermediate Similarity	NPC220427

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 NPC202261 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	2237
0.2-0.3	4230
0.3-0.4	1631
0.4-0.5	431
0.5-0.6	271
0.6-0.7	66
0.7-0.8	17
0.8-0.85	4
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD8379	Approved
0.8824	High Similarity	NPD8296	Approved
0.8824	High Similarity	NPD8378	Approved
0.8824	High Similarity	NPD8335	Approved
0.8824	High Similarity	NPD8380	Approved
0.8739	High Similarity	NPD8294	Approved
0.8739	High Similarity	NPD8377	Approved
0.8667	High Similarity	NPD8033	Approved
0.8417	Intermediate Similarity	NPD7327	Approved
0.8417	Intermediate Similarity	NPD7328	Approved
0.8347	Intermediate Similarity	NPD7516	Approved
0.8083	Intermediate Similarity	NPD8133	Approved
0.8065	Intermediate Similarity	NPD7503	Approved
0.7812	Intermediate Similarity	NPD7507	Approved
0.7769	Intermediate Similarity	NPD7319	Approved
0.7438	Intermediate Similarity	NPD6412	Phase 2
0.7407	Intermediate Similarity	NPD8450	Suspended
0.7364	Intermediate Similarity	NPD8515	Approved
0.7364	Intermediate Similarity	NPD8516	Approved
0.7364	Intermediate Similarity	NPD8517	Approved
0.7333	Intermediate Similarity	NPD8449	Approved
0.7304	Intermediate Similarity	NPD8171	Discontinued
0.7293	Intermediate Similarity	NPD7736	Approved
0.7236	Intermediate Similarity	NPD6686	Approved
0.7231	Intermediate Similarity	NPD8513	Phase 3
0.7218	Intermediate Similarity	NPD8293	Discontinued
0.72	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD8328	Phase 3
0.7054	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6370	Approved
0.7034	Intermediate Similarity	NPD7625	Phase 1
0.6992	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7078	Approved
0.694	Remote Similarity	NPD7492	Approved
0.6894	Remote Similarity	NPD6059	Approved
0.6894	Remote Similarity	NPD6054	Approved
0.6889	Remote Similarity	NPD6616	Approved
0.686	Remote Similarity	NPD7638	Approved
0.6803	Remote Similarity	NPD7640	Approved
0.6803	Remote Similarity	NPD7639	Approved
0.6744	Remote Similarity	NPD8297	Approved
0.6744	Remote Similarity	NPD6882	Approved
0.6716	Remote Similarity	NPD6016	Approved
0.6716	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6642	Remote Similarity	NPD6319	Approved
0.6618	Remote Similarity	NPD6067	Discontinued
0.661	Remote Similarity	NPD6051	Approved
0.6581	Remote Similarity	NPD7524	Approved
0.6565	Remote Similarity	NPD4632	Approved
0.6562	Remote Similarity	NPD7320	Approved
0.6535	Remote Similarity	NPD6402	Approved
0.6535	Remote Similarity	NPD6008	Approved
0.6535	Remote Similarity	NPD7128	Approved
0.6535	Remote Similarity	NPD5739	Approved
0.6535	Remote Similarity	NPD6675	Approved
0.6512	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6372	Approved
0.6512	Remote Similarity	NPD6373	Approved
0.6489	Remote Similarity	NPD6053	Discontinued
0.6466	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4225	Approved
0.6446	Remote Similarity	NPD6399	Phase 3
0.6434	Remote Similarity	NPD6881	Approved
0.6434	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD6033	Approved
0.6412	Remote Similarity	NPD8130	Phase 1
0.6412	Remote Similarity	NPD6649	Approved
0.6412	Remote Similarity	NPD6650	Approved
0.6379	Remote Similarity	NPD6695	Phase 3
0.6371	Remote Similarity	NPD6084	Phase 2
0.6371	Remote Similarity	NPD6083	Phase 2
0.6357	Remote Similarity	NPD5697	Approved
0.6357	Remote Similarity	NPD8074	Phase 3
0.6357	Remote Similarity	NPD5701	Approved
0.6349	Remote Similarity	NPD5344	Discontinued
0.6336	Remote Similarity	NPD7290	Approved
0.6336	Remote Similarity	NPD6883	Approved
0.6336	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7102	Approved
0.632	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7750	Discontinued
0.6299	Remote Similarity	NPD7632	Discontinued
0.6288	Remote Similarity	NPD6847	Approved
0.6288	Remote Similarity	NPD6617	Approved
0.6288	Remote Similarity	NPD6869	Approved
0.6261	Remote Similarity	NPD7525	Registered
0.6261	Remote Similarity	NPD6928	Phase 2
0.626	Remote Similarity	NPD6012	Approved
0.626	Remote Similarity	NPD6014	Approved
0.626	Remote Similarity	NPD6013	Approved
0.6259	Remote Similarity	NPD7604	Phase 2
0.6232	Remote Similarity	NPD5983	Phase 2
0.6231	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7637	Suspended
0.622	Remote Similarity	NPD4159	Approved
0.6195	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6011	Approved
0.617	Remote Similarity	NPD6336	Discontinued
0.6165	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7748	Approved
0.6121	Remote Similarity	NPD6930	Phase 2
0.6121	Remote Similarity	NPD6931	Approved
0.6111	Remote Similarity	NPD5956	Approved
0.6111	Remote Similarity	NPD7902	Approved
0.6111	Remote Similarity	NPD4755	Approved
0.6107	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7339	Approved
0.6106	Remote Similarity	NPD6942	Approved
0.6098	Remote Similarity	NPD8035	Phase 2
0.6098	Remote Similarity	NPD8034	Phase 2
0.609	Remote Similarity	NPD4634	Approved
0.608	Remote Similarity	NPD5695	Phase 3
0.608	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7799	Discontinued
0.6063	Remote Similarity	NPD5696	Approved
0.605	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.605	Remote Similarity	NPD4786	Approved
0.6048	Remote Similarity	NPD4202	Approved
0.6047	Remote Similarity	NPD5211	Phase 2
0.6034	Remote Similarity	NPD6929	Approved
0.6034	Remote Similarity	NPD7645	Phase 2
0.6016	Remote Similarity	NPD7838	Discovery
0.6016	Remote Similarity	NPD6648	Approved
0.6016	Remote Similarity	NPD5285	Approved
0.6016	Remote Similarity	NPD4700	Approved
0.6016	Remote Similarity	NPD46	Approved
0.6016	Remote Similarity	NPD4696	Approved
0.6016	Remote Similarity	NPD5286	Approved
0.6016	Remote Similarity	NPD6698	Approved
0.5985	Remote Similarity	NPD6274	Approved
0.5984	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6903	Approved
0.5972	Remote Similarity	NPD8336	Approved
0.5972	Remote Similarity	NPD8337	Approved
0.5971	Remote Similarity	NPD7100	Approved
0.5971	Remote Similarity	NPD7101	Approved
0.597	Remote Similarity	NPD6371	Approved
0.5968	Remote Similarity	NPD5693	Phase 1
0.5968	Remote Similarity	NPD7087	Discontinued
0.5968	Remote Similarity	NPD7515	Phase 2
0.5954	Remote Similarity	NPD5141	Approved
0.595	Remote Similarity	NPD7334	Approved
0.595	Remote Similarity	NPD5330	Approved
0.595	Remote Similarity	NPD6684	Approved
0.595	Remote Similarity	NPD6409	Approved
0.595	Remote Similarity	NPD7146	Approved
0.595	Remote Similarity	NPD7521	Approved
0.5935	Remote Similarity	NPD4753	Phase 2
0.5923	Remote Similarity	NPD5226	Approved
0.5923	Remote Similarity	NPD5224	Approved
0.5923	Remote Similarity	NPD5225	Approved
0.5923	Remote Similarity	NPD4633	Approved
0.5913	Remote Similarity	NPD6933	Approved
0.5909	Remote Similarity	NPD4767	Approved
0.5909	Remote Similarity	NPD4768	Approved
0.5902	Remote Similarity	NPD4251	Approved
0.5902	Remote Similarity	NPD4250	Approved
0.5899	Remote Similarity	NPD6335	Approved
0.5887	Remote Similarity	NPD6921	Approved
0.5887	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD6909	Approved
0.5887	Remote Similarity	NPD6908	Approved
0.5882	Remote Similarity	NPD3667	Approved
0.5878	Remote Similarity	NPD5175	Approved
0.5878	Remote Similarity	NPD5174	Approved
0.5877	Remote Similarity	NPD4784	Approved
0.5877	Remote Similarity	NPD4785	Approved
0.5873	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7900	Approved
0.5868	Remote Similarity	NPD6893	Approved
0.5868	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5776	Phase 2
0.5862	Remote Similarity	NPD6925	Approved
0.5862	Remote Similarity	NPD6932	Approved
0.5847	Remote Similarity	NPD7514	Phase 3
0.5846	Remote Similarity	NPD5223	Approved
0.5841	Remote Similarity	NPD4243	Approved
0.5827	Remote Similarity	NPD6317	Approved
0.5821	Remote Similarity	NPD4730	Approved
0.5821	Remote Similarity	NPD4729	Approved
0.582	Remote Similarity	NPD4249	Approved
0.582	Remote Similarity	NPD6098	Approved
0.5812	Remote Similarity	NPD7145	Approved
0.5811	Remote Similarity	NPD8338	Approved
0.5806	Remote Similarity	NPD6673	Approved
0.5806	Remote Similarity	NPD5328	Approved
0.5806	Remote Similarity	NPD6904	Approved
0.5806	Remote Similarity	NPD6080	Approved
0.5793	Remote Similarity	NPD8448	Approved
0.5786	Remote Similarity	NPD6313	Approved
0.5786	Remote Similarity	NPD6314	Approved
0.5785	Remote Similarity	NPD3665	Phase 1
0.5785	Remote Similarity	NPD3666	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