NPASS Compound

Structure

NPC109588 OpenBabel07101719402D 69 76 0 0 1 0 0 0 0 0999 V2000 -1.8664 4.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7096 0.9870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0578 -2.3353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8548 -1.4805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8548 -0.4935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8220 5.4117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8548 1.4805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8548 -1.4805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4191 2.9610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7096 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4191 1.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5643 0.4935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7096 2.9610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5643 0.4935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9834 -8.3896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9834 -1.4805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1287 -3.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0708 -2.3353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8548 1.4805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7096 1.9740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4191 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9834 -7.4026 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9834 -0.4935 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2739 -4.4416 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7096 -0.9870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8548 0.4935 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8382 -6.9091 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8382 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4191 -3.9481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8382 -5.9221 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8382 0.9870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4191 -2.9610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9834 -5.4286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9834 1.4805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4191 -0.9870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2739 -2.4675 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1287 -5.9221 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1287 0.9870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4762 3.8323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4191 0.9870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5643 3.4545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7096 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5643 -1.4805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8548 0.4935 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5643 1.4805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8382 -8.8831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8382 -1.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5643 -3.1901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2739 0.4935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6930 -7.4026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6930 -0.4935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5643 -4.4416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6930 -5.4286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6930 1.4805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5643 -2.4675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9834 -4.4416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9834 2.4675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2593 3.2314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4191 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6050 4.8108 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1287 -2.9610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1287 -6.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1287 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2739 -5.4286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2739 -1.4805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2739 1.4805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 46 1 0 0 0 0 6 63 1 0 0 0 0 7 8 1 0 0 0 0 7 21 2 0 0 0 0 8 28 1 0 0 0 0 9 10 1 0 0 0 0 9 27 1 0 0 0 0 10 47 1 0 0 0 0 11 13 1 0 0 0 0 11 43 1 0 0 0 0 12 14 1 0 0 0 0 12 46 1 0 0 0 0 13 48 1 0 0 0 0 14 48 1 0 0 0 0 15 22 1 0 0 0 0 15 43 1 0 0 0 0 16 23 1 0 0 0 0 16 44 1 0 0 0 0 17 49 1 0 0 0 0 18 50 1 0 0 0 0 19 26 1 0 0 0 0 19 64 1 0 0 0 0 20 45 1 0 0 0 0 20 51 1 0 0 0 0 21 22 1 0 0 0 0 21 46 1 0 0 0 0 22 48 1 1 0 0 0 23 37 1 0 0 0 0 23 52 2 0 0 0 0 24 17 1 1 0 0 0 24 29 1 0 0 0 0 24 65 1 0 0 0 0 25 18 1 6 0 0 0 25 30 1 0 0 0 0 25 66 1 0 0 0 0 26 31 1 0 0 0 0 26 67 1 1 0 0 0 27 44 1 6 0 0 0 27 45 1 0 0 0 0 28 44 1 6 0 0 0 28 47 1 0 0 0 0 29 32 1 0 0 0 0 29 53 1 6 0 0 0 30 33 1 0 0 0 0 30 54 1 1 0 0 0 31 34 1 0 0 0 0 31 55 1 6 0 0 0 32 35 1 0 0 0 0 32 56 1 1 0 0 0 33 36 1 0 0 0 0 33 57 1 6 0 0 0 34 38 1 0 0 0 0 34 58 1 1 0 0 0 35 39 1 0 0 0 0 35 59 1 6 0 0 0 36 40 1 0 0 0 0 36 60 1 1 0 0 0 37 45 1 6 0 0 0 37 68 1 0 0 0 0 38 64 1 0 0 0 0 38 68 1 6 0 0 0 39 65 1 0 0 0 0 39 67 1 1 0 0 0 40 66 1 0 0 0 0 40 69 1 6 0 0 0 41 43 1 0 0 0 0 41 61 2 0 0 0 0 41 63 1 0 0 0 0 42 62 2 0 0 0 0 42 69 1 0 0 0 0 43 1 1 1 0 0 0 44 2 1 6 0 0 0 45 3 1 6 0 0 0 46 47 1 6 0 0 0 47 5 1 6 0 0 0 48 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	986.47
Volume:	944.361
LogP:	1.016
LogD:	0.35
LogS:	-3.29
# Rotatable Bonds:	12
TPSA:	338.35
# H-Bond Aceptor:	21
# H-Bond Donor:	11
# Rings:	8
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.065
Synthetic Accessibility Score:	6.597
Fsp3:	0.896
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:	-6.083
MDCK Permeability:	8.845764386933297e-05
Pgp-inhibitor:	0.454
Pgp-substrate:	0.667
Human Intestinal Absorption (HIA):	0.962
20% Bioavailability (F20%):	0.859
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	55.117088317871094%
Volume Distribution (VD):	0.329
Pgp-substrate:	20.776994705200195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.329
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.208
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	0.662
Half-life (T1/2):	0.824

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.123
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.44
Skin Sensitization:	0.01
Carcinogencity:	0.026
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.056

Download Data

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

Natural Product: NPC109588

Natural Product ID:	NPC109588
*Common Name:**	2-O-Methyl 4A-O-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl] (2S,4Ar,6Ar,6As,6Br,8Ar,9R,10R,12Ar,14Bs)-10-[(2S,3R,4R,5R)-3,4-Dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-9-(Hydroxymethyl)-2,6A,6B,9,12A-Pentamethyl-11-Oxo-3,4,5,6,6A,7,8,8A,10,12,13,14B-Dodecahydro-1H-Picene-2,4A-Dicarboxylate
IUPAC Name:	2-O-methyl 4a-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,12aR,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-11-oxo-3,4,5,6,6a,7,8,8a,10,12,13,14b-dodecahydro-1H-picene-2,4a-dicarboxylate
Synonyms:
Standard InCHIKey:	ODARBAYTGJLCBX-WOSKTBFYSA-N
Standard InCHI:	InChI=1S/C48H74O21/c1-43(41(61)63-6)11-13-48(42(62)69-40-36(60)33(57)30(54)25(18-50)66-40)14-12-46(4)21(22(48)15-43)7-8-28-44(2)16-23(52)37(45(3,20-51)27(44)9-10-47(28,46)5)68-38-34(58)31(55)26(19-64-38)67-39-35(59)32(56)29(53)24(17-49)65-39/h7,22,24-40,49-51,53-60H,8-20H2,1-6H3/t22-,24+,25+,26+,27+,28+,29+,30+,31-,32-,33-,34+,35+,36+,37-,38-,39-,40-,43-,44-,45-,46+,47+,48-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2CO[C@H]([C@@H]([C@H]2O)O)O[C@H]2C(=O)C[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3C[C@](C)(CC2)C(=O)OC)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL402231
PubChem CID:	24770164
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene 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
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	roots	n.a.	n.a.	PMID[18177012]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[26595875]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	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
Others	5

Activity Type	# Activity
Cell Line	5
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	Activity	>	101.0	uM	PMID[514290]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	101000.0	nM	PMID[514290]
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	>	101000.0	nM	PMID[514290]
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	>	101000.0	nM	PMID[514290]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	120.0	%	PMID[514290]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	115.0	%	PMID[514290]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	98.0	%	PMID[514290]

☑ 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 NPC109588 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	273
0.1-0.2	1860
0.2-0.3	5360
0.3-0.4	11661
0.4-0.5	10307
0.5-0.6	6450
0.6-0.7	3879
0.7-0.8	1931
0.8-0.85	344
0.85-0.9	239
0.9-0.95	268
0.95-1	125

Similarity Score	Similarity Level	Natural Product ID
0.9727	High Similarity	NPC192791
0.9643	High Similarity	NPC162574
0.9554	High Similarity	NPC159309
0.9554	High Similarity	NPC22956
0.9554	High Similarity	NPC104372
0.9554	High Similarity	NPC223301
0.9554	High Similarity	NPC86222
0.9554	High Similarity	NPC297263
0.9554	High Similarity	NPC31838
0.9554	High Similarity	NPC301449
0.9554	High Similarity	NPC64715
0.9554	High Similarity	NPC11242
0.9554	High Similarity	NPC171544
0.9554	High Similarity	NPC114484
0.9554	High Similarity	NPC62725
0.9554	High Similarity	NPC222580
0.9537	High Similarity	NPC292677
0.9537	High Similarity	NPC257468
0.9537	High Similarity	NPC469946
0.9537	High Similarity	NPC475504
0.9537	High Similarity	NPC101744
0.9537	High Similarity	NPC473373
0.9537	High Similarity	NPC471383
0.9537	High Similarity	NPC109079
0.9537	High Similarity	NPC10320
0.9537	High Similarity	NPC79718
0.9537	High Similarity	NPC324875
0.9537	High Similarity	NPC139044
0.9537	High Similarity	NPC475516
0.9537	High Similarity	NPC102439
0.9537	High Similarity	NPC104400
0.9537	High Similarity	NPC104071
0.9537	High Similarity	NPC276093
0.9474	High Similarity	NPC471963
0.9474	High Similarity	NPC471962
0.9474	High Similarity	NPC247315
0.9469	High Similarity	NPC10607
0.9469	High Similarity	NPC187290
0.9469	High Similarity	NPC80986
0.9469	High Similarity	NPC21691
0.9469	High Similarity	NPC4749
0.9469	High Similarity	NPC236870
0.9469	High Similarity	NPC213952
0.9469	High Similarity	NPC475591
0.9464	High Similarity	NPC118440
0.9464	High Similarity	NPC236657
0.9455	High Similarity	NPC471384
0.9455	High Similarity	NPC291903
0.9455	High Similarity	NPC37134
0.9455	High Similarity	NPC161674
0.9455	High Similarity	NPC58448
0.9455	High Similarity	NPC160415
0.945	High Similarity	NPC73318
0.945	High Similarity	NPC295823
0.945	High Similarity	NPC114287
0.945	High Similarity	NPC155410
0.945	High Similarity	NPC114304
0.945	High Similarity	NPC258885
0.945	High Similarity	NPC163183
0.945	High Similarity	NPC219180
0.945	High Similarity	NPC192600
0.945	High Similarity	NPC251263
0.945	High Similarity	NPC174720
0.945	High Similarity	NPC96641
0.945	High Similarity	NPC473343
0.945	High Similarity	NPC124296
0.945	High Similarity	NPC241909
0.945	High Similarity	NPC475287
0.945	High Similarity	NPC46665
0.945	High Similarity	NPC475467
0.945	High Similarity	NPC150400
0.945	High Similarity	NPC133818
0.945	High Similarity	NPC309714
0.945	High Similarity	NPC151543
0.945	High Similarity	NPC323341
0.945	High Similarity	NPC473826
0.945	High Similarity	NPC134835
0.945	High Similarity	NPC166422
0.9444	High Similarity	NPC164419
0.9391	High Similarity	NPC181066
0.9391	High Similarity	NPC469947
0.9386	High Similarity	NPC2370
0.9386	High Similarity	NPC283417
0.9386	High Similarity	NPC200049
0.9386	High Similarity	NPC302543
0.9386	High Similarity	NPC471964
0.9386	High Similarity	NPC235405
0.9386	High Similarity	NPC281148
0.9386	High Similarity	NPC44716
0.9386	High Similarity	NPC14617
0.9386	High Similarity	NPC30735
0.9386	High Similarity	NPC262199
0.9386	High Similarity	NPC258617
0.9386	High Similarity	NPC257211
0.9386	High Similarity	NPC471961
0.9386	High Similarity	NPC202666
0.9381	High Similarity	NPC187618
0.9381	High Similarity	NPC302887
0.9375	High Similarity	NPC39211
0.9375	High Similarity	NPC157868
0.9375	High Similarity	NPC473884
0.9375	High Similarity	NPC469945
0.9375	High Similarity	NPC475171
0.9375	High Similarity	NPC35405
0.9375	High Similarity	NPC11551
0.9375	High Similarity	NPC114441
0.9375	High Similarity	NPC6377
0.9375	High Similarity	NPC208381
0.9375	High Similarity	NPC214484
0.9375	High Similarity	NPC472949
0.9375	High Similarity	NPC309780
0.9375	High Similarity	NPC180550
0.9369	High Similarity	NPC148417
0.9369	High Similarity	NPC300419
0.9369	High Similarity	NPC136768
0.9369	High Similarity	NPC473824
0.9369	High Similarity	NPC68175
0.9369	High Similarity	NPC110633
0.9369	High Similarity	NPC475119
0.9364	High Similarity	NPC76972
0.9364	High Similarity	NPC123199
0.9364	High Similarity	NPC71065
0.9364	High Similarity	NPC70809
0.9364	High Similarity	NPC4328
0.9364	High Similarity	NPC471385
0.9364	High Similarity	NPC309907
0.9364	High Similarity	NPC65105
0.9364	High Similarity	NPC119592
0.9364	High Similarity	NPC100639
0.9364	High Similarity	NPC475160
0.9364	High Similarity	NPC294453
0.9364	High Similarity	NPC54636
0.9364	High Similarity	NPC298034
0.9364	High Similarity	NPC202828
0.9364	High Similarity	NPC293330
0.9364	High Similarity	NPC224381
0.9364	High Similarity	NPC161717
0.9364	High Similarity	NPC227551
0.9364	High Similarity	NPC79643
0.9364	High Similarity	NPC471550
0.9364	High Similarity	NPC204414
0.9364	High Similarity	NPC41061
0.9364	High Similarity	NPC469782
0.9364	High Similarity	NPC164389
0.9364	High Similarity	NPC236638
0.9364	High Similarity	NPC305981
0.9364	High Similarity	NPC57484
0.9364	High Similarity	NPC475486
0.9364	High Similarity	NPC261506
0.9364	High Similarity	NPC476068
0.9364	High Similarity	NPC475140
0.9364	High Similarity	NPC43550
0.9364	High Similarity	NPC60557
0.9364	High Similarity	NPC473714
0.9364	High Similarity	NPC250247
0.9364	High Similarity	NPC67857
0.9358	High Similarity	NPC473383
0.9358	High Similarity	NPC128925
0.9358	High Similarity	NPC139894
0.9358	High Similarity	NPC256798
0.9352	High Similarity	NPC164194
0.9352	High Similarity	NPC59804
0.9352	High Similarity	NPC174679
0.9352	High Similarity	NPC475296
0.9352	High Similarity	NPC56713
0.9352	High Similarity	NPC270667
0.9352	High Similarity	NPC474589
0.9352	High Similarity	NPC136877
0.9352	High Similarity	NPC127056
0.9352	High Similarity	NPC29069
0.9352	High Similarity	NPC279554
0.9352	High Similarity	NPC90856
0.9304	High Similarity	NPC470477
0.9304	High Similarity	NPC160452
0.9304	High Similarity	NPC33068
0.9298	High Similarity	NPC313110
0.9298	High Similarity	NPC249848
0.9298	High Similarity	NPC131469
0.9298	High Similarity	NPC107966
0.9298	High Similarity	NPC40775
0.9298	High Similarity	NPC471965
0.9298	High Similarity	NPC235438
0.9286	High Similarity	NPC232237
0.9286	High Similarity	NPC286347
0.9286	High Similarity	NPC105800
0.9286	High Similarity	NPC36831
0.9279	High Similarity	NPC75287
0.9279	High Similarity	NPC26626
0.9279	High Similarity	NPC288205
0.9279	High Similarity	NPC305267
0.9279	High Similarity	NPC51465
0.9279	High Similarity	NPC476992
0.9273	High Similarity	NPC138334
0.9273	High Similarity	NPC47063
0.9273	High Similarity	NPC189884
0.9273	High Similarity	NPC204458
0.9266	High Similarity	NPC30397
0.9266	High Similarity	NPC297208
0.9266	High Similarity	NPC235841
0.9266	High Similarity	NPC108748

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 NPC109588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	2180
0.2-0.3	3870
0.3-0.4	1834
0.4-0.5	578
0.5-0.6	251
0.6-0.7	139
0.7-0.8	35
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9386	High Similarity	NPD8328	Phase 3
0.9027	High Similarity	NPD8295	Clinical (unspecified phase)
0.8739	High Similarity	NPD8132	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD8133	Approved
0.7913	Intermediate Similarity	NPD6412	Phase 2
0.7857	Intermediate Similarity	NPD7736	Approved
0.7838	Intermediate Similarity	NPD7902	Approved
0.7727	Intermediate Similarity	NPD7748	Approved
0.7724	Intermediate Similarity	NPD8377	Approved
0.7724	Intermediate Similarity	NPD8294	Approved
0.7692	Intermediate Similarity	NPD6686	Approved
0.7661	Intermediate Similarity	NPD8380	Approved
0.7661	Intermediate Similarity	NPD8296	Approved
0.7661	Intermediate Similarity	NPD8335	Approved
0.7661	Intermediate Similarity	NPD8379	Approved
0.7661	Intermediate Similarity	NPD8378	Approved
0.7638	Intermediate Similarity	NPD8293	Discontinued
0.7568	Intermediate Similarity	NPD7900	Approved
0.7568	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD7507	Approved
0.7545	Intermediate Similarity	NPD7515	Phase 2
0.752	Intermediate Similarity	NPD8033	Approved
0.752	Intermediate Similarity	NPD8516	Approved
0.752	Intermediate Similarity	NPD8515	Approved
0.752	Intermediate Similarity	NPD8517	Approved
0.752	Intermediate Similarity	NPD8513	Phase 3
0.746	Intermediate Similarity	NPD6370	Approved
0.7438	Intermediate Similarity	NPD6882	Approved
0.7438	Intermediate Similarity	NPD8297	Approved
0.7385	Intermediate Similarity	NPD7319	Approved
0.7355	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7492	Approved
0.7339	Intermediate Similarity	NPD6009	Approved
0.7333	Intermediate Similarity	NPD6373	Approved
0.7333	Intermediate Similarity	NPD6372	Approved
0.7302	Intermediate Similarity	NPD6319	Approved
0.7302	Intermediate Similarity	NPD6059	Approved
0.7302	Intermediate Similarity	NPD6054	Approved
0.7288	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6616	Approved
0.728	Intermediate Similarity	NPD7328	Approved
0.728	Intermediate Similarity	NPD7327	Approved
0.725	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7078	Approved
0.7227	Intermediate Similarity	NPD5739	Approved
0.7227	Intermediate Similarity	NPD6402	Approved
0.7227	Intermediate Similarity	NPD7128	Approved
0.7227	Intermediate Similarity	NPD6675	Approved
0.7222	Intermediate Similarity	NPD7516	Approved
0.7213	Intermediate Similarity	NPD6649	Approved
0.7213	Intermediate Similarity	NPD6650	Approved
0.7109	Intermediate Similarity	NPD6016	Approved
0.7109	Intermediate Similarity	NPD6015	Approved
0.7109	Intermediate Similarity	NPD7503	Approved
0.7107	Intermediate Similarity	NPD6881	Approved
0.7107	Intermediate Similarity	NPD7320	Approved
0.7107	Intermediate Similarity	NPD6899	Approved
0.7097	Intermediate Similarity	NPD4632	Approved
0.708	Intermediate Similarity	NPD8035	Phase 2
0.708	Intermediate Similarity	NPD8034	Phase 2
0.7073	Intermediate Similarity	NPD8130	Phase 1
0.7054	Intermediate Similarity	NPD5988	Approved
0.7025	Intermediate Similarity	NPD5697	Approved
0.7025	Intermediate Similarity	NPD5701	Approved
0.7018	Intermediate Similarity	NPD6399	Phase 3
0.6992	Remote Similarity	NPD6883	Approved
0.6992	Remote Similarity	NPD7102	Approved
0.6992	Remote Similarity	NPD7290	Approved
0.6935	Remote Similarity	NPD6847	Approved
0.6935	Remote Similarity	NPD6617	Approved
0.6935	Remote Similarity	NPD6869	Approved
0.6923	Remote Similarity	NPD6084	Phase 2
0.6923	Remote Similarity	NPD6083	Phase 2
0.6911	Remote Similarity	NPD6014	Approved
0.6911	Remote Similarity	NPD6013	Approved
0.6911	Remote Similarity	NPD6012	Approved
0.687	Remote Similarity	NPD7604	Phase 2
0.687	Remote Similarity	NPD6067	Discontinued
0.6864	Remote Similarity	NPD7638	Approved
0.6846	Remote Similarity	NPD5983	Phase 2
0.6829	Remote Similarity	NPD6011	Approved
0.6807	Remote Similarity	NPD7640	Approved
0.6807	Remote Similarity	NPD7639	Approved
0.68	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7115	Discovery
0.6791	Remote Similarity	NPD6033	Approved
0.6774	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6336	Discontinued
0.6759	Remote Similarity	NPD7645	Phase 2
0.6724	Remote Similarity	NPD8171	Discontinued
0.6723	Remote Similarity	NPD5696	Approved
0.672	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6921	Approved
0.6696	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6639	Remote Similarity	NPD4755	Approved
0.6637	Remote Similarity	NPD3618	Phase 1
0.661	Remote Similarity	NPD5695	Phase 3
0.6609	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD8074	Phase 3
0.6589	Remote Similarity	NPD6274	Approved
0.6587	Remote Similarity	NPD4634	Approved
0.6565	Remote Similarity	NPD7101	Approved
0.6565	Remote Similarity	NPD7100	Approved
0.6555	Remote Similarity	NPD4697	Phase 3
0.6532	Remote Similarity	NPD6008	Approved
0.6529	Remote Similarity	NPD4696	Approved
0.6529	Remote Similarity	NPD5286	Approved
0.6529	Remote Similarity	NPD5285	Approved
0.6529	Remote Similarity	NPD4700	Approved
0.6522	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6411	Approved
0.6489	Remote Similarity	NPD6335	Approved
0.648	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5328	Approved
0.6466	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD6909	Approved
0.6462	Remote Similarity	NPD6868	Approved
0.646	Remote Similarity	NPD4786	Approved
0.6446	Remote Similarity	NPD4225	Approved
0.6435	Remote Similarity	NPD3573	Approved
0.6429	Remote Similarity	NPD8450	Suspended
0.6429	Remote Similarity	NPD3667	Approved
0.6423	Remote Similarity	NPD5224	Approved
0.6423	Remote Similarity	NPD5226	Approved
0.6423	Remote Similarity	NPD5211	Phase 2
0.6423	Remote Similarity	NPD4633	Approved
0.6423	Remote Similarity	NPD5225	Approved
0.6417	Remote Similarity	NPD5222	Approved
0.6417	Remote Similarity	NPD5221	Approved
0.6417	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6317	Approved
0.641	Remote Similarity	NPD46	Approved
0.641	Remote Similarity	NPD6698	Approved
0.64	Remote Similarity	NPD4767	Approved
0.64	Remote Similarity	NPD4768	Approved
0.6372	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD3669	Approved
0.6371	Remote Similarity	NPD5175	Approved
0.6371	Remote Similarity	NPD5174	Approved
0.6364	Remote Similarity	NPD6313	Approved
0.6364	Remote Similarity	NPD6314	Approved
0.6364	Remote Similarity	NPD5173	Approved
0.6357	Remote Similarity	NPD8449	Approved
0.6356	Remote Similarity	NPD6079	Approved
0.6348	Remote Similarity	NPD7334	Approved
0.6348	Remote Similarity	NPD7146	Approved
0.6348	Remote Similarity	NPD6684	Approved
0.6348	Remote Similarity	NPD5330	Approved
0.6348	Remote Similarity	NPD6098	Approved
0.6348	Remote Similarity	NPD7521	Approved
0.6348	Remote Similarity	NPD6409	Approved
0.6343	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5223	Approved
0.6331	Remote Similarity	NPD5956	Approved
0.6325	Remote Similarity	NPD6673	Approved
0.6325	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6101	Approved
0.6325	Remote Similarity	NPD6080	Approved
0.6325	Remote Similarity	NPD6904	Approved
0.6325	Remote Similarity	NPD4753	Phase 2
0.632	Remote Similarity	NPD5141	Approved
0.6311	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4202	Approved
0.6299	Remote Similarity	NPD4730	Approved
0.6299	Remote Similarity	NPD4729	Approved
0.6296	Remote Similarity	NPD8080	Discontinued
0.629	Remote Similarity	NPD7632	Discontinued
0.624	Remote Similarity	NPD4754	Approved
0.6239	Remote Similarity	NPD6903	Approved
0.6224	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7983	Approved
0.6212	Remote Similarity	NPD6940	Discontinued
0.6202	Remote Similarity	NPD5250	Approved
0.6202	Remote Similarity	NPD5247	Approved
0.6202	Remote Similarity	NPD5251	Approved
0.6202	Remote Similarity	NPD5249	Phase 3
0.6202	Remote Similarity	NPD5248	Approved
0.6198	Remote Similarity	NPD5210	Approved
0.6198	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4629	Approved
0.6195	Remote Similarity	NPD1780	Approved
0.6195	Remote Similarity	NPD1779	Approved
0.6187	Remote Similarity	NPD8337	Approved
0.6187	Remote Similarity	NPD8336	Approved
0.6174	Remote Similarity	NPD3133	Approved
0.6174	Remote Similarity	NPD3665	Phase 1
0.6174	Remote Similarity	NPD3666	Approved
0.6172	Remote Similarity	NPD5128	Approved
0.617	Remote Similarity	NPD7260	Phase 2
0.6167	Remote Similarity	NPD5779	Approved
0.6167	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD8415	Approved
0.6133	Remote Similarity	NPD7625	Phase 1
0.6119	Remote Similarity	NPD7641	Discontinued
0.6116	Remote Similarity	NPD5282	Discontinued
0.6115	Remote Similarity	NPD8448	Approved
0.6106	Remote Similarity	NPD7525	Registered

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