NPASS Compound

Structure

NPC80986 OpenBabel07101718312D 82 90 0 0 1 0 0 0 0 0999 V2000 4.2825 3.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0640 4.3180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0750 4.3180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0640 -2.3400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0750 -2.3400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7130 0.9890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8565 -1.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8565 -0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4260 2.9670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4260 1.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8565 1.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8565 -1.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4260 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5695 0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4260 2.9670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7130 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4260 1.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5695 0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2825 1.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7130 2.9670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4216 1.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5695 -2.4725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9956 -1.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8565 1.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7130 1.9780 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4216 0.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4260 -2.9670 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9956 -0.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7130 -0.9890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8565 0.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4260 -0.9890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2781 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4260 -3.9560 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8521 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2781 -0.9890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2825 -4.4505 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8521 0.9890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4216 -1.4835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1391 -3.9560 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9956 1.4835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8521 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8521 -0.9890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9956 0.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9956 -1.4835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9956 1.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5651 -0.9890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1391 -2.9670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1391 0.9890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1391 -0.9890 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4260 0.9890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5695 3.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5695 -1.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7130 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8565 0.4945 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 -2.5695 1.4835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2781 1.9780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7130 -2.9670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8521 -1.9780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1346 0.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5695 -4.4505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7086 -0.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1346 -1.4835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2825 -5.4396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7086 1.4835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4216 -2.4725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9956 -4.4505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9956 2.4725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7086 0.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8521 1.9780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4260 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 1.9780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5651 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2825 -2.4725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1391 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2825 -1.4835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7086 -1.4835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9956 -2.4725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2825 1.4835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 53 1 0 0 0 0 3 53 1 0 0 0 0 4 54 1 0 0 0 0 5 54 1 0 0 0 0 7 56 1 0 0 0 0 9 10 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 26 2 0 0 0 0 12 32 1 0 0 0 0 13 16 1 0 0 0 0 13 31 1 0 0 0 0 14 15 1 0 0 0 0 14 33 1 0 0 0 0 15 55 1 0 0 0 0 16 57 1 0 0 0 0 17 19 1 0 0 0 0 17 53 1 0 0 0 0 18 20 1 0 0 0 0 18 56 1 0 0 0 0 19 58 1 0 0 0 0 20 58 1 0 0 0 0 21 74 1 0 0 0 0 22 27 1 0 0 0 0 22 53 1 0 0 0 0 23 59 1 0 0 0 0 24 60 1 0 0 0 0 25 61 1 0 0 0 0 26 27 1 0 0 0 0 26 56 1 0 0 0 0 27 58 1 1 0 0 0 28 23 1 6 0 0 0 28 34 1 0 0 0 0 28 75 1 0 0 0 0 29 24 1 1 0 0 0 29 35 1 0 0 0 0 29 76 1 0 0 0 0 30 25 1 6 0 0 0 30 36 1 0 0 0 0 30 77 1 0 0 0 0 31 54 1 0 0 0 0 31 55 1 6 0 0 0 32 55 1 6 0 0 0 32 57 1 0 0 0 0 33 54 1 0 0 0 0 33 78 1 6 0 0 0 34 37 1 0 0 0 0 34 62 1 6 0 0 0 35 38 1 0 0 0 0 35 63 1 6 0 0 0 36 39 1 0 0 0 0 36 64 1 1 0 0 0 37 40 1 0 0 0 0 37 65 1 6 0 0 0 38 41 1 0 0 0 0 38 66 1 1 0 0 0 39 42 1 0 0 0 0 39 67 1 6 0 0 0 40 48 1 0 0 0 0 40 68 1 1 0 0 0 41 49 1 0 0 0 0 41 69 1 6 0 0 0 42 50 1 0 0 0 0 42 70 1 1 0 0 0 43 44 1 0 0 0 0 43 45 1 0 0 0 0 43 71 1 1 0 0 0 44 46 1 0 0 0 0 44 79 1 6 0 0 0 45 47 1 6 0 0 0 45 80 1 0 0 0 0 46 51 1 0 0 0 0 46 81 1 1 0 0 0 47 72 2 0 0 0 0 47 74 1 0 0 0 0 48 75 1 0 0 0 0 48 79 1 6 0 0 0 49 76 1 0 0 0 0 49 81 1 1 0 0 0 50 77 1 0 0 0 0 50 82 1 6 0 0 0 51 78 1 6 0 0 0 51 80 1 0 0 0 0 52 73 2 0 0 0 0 52 82 1 0 0 0 0 55 6 1 6 0 0 0 56 57 1 6 0 0 0 57 8 1 6 0 0 0 58 52 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1174.61
Volume:	1137.772
LogP:	2.907
LogD:	2.808
LogS:	-3.247
# Rotatable Bonds:	17
TPSA:	380.2
# H-Bond Aceptor:	24
# H-Bond Donor:	13
# Rings:	9
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.042
Synthetic Accessibility Score:	6.931
Fsp3:	0.931
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:	-6.104
MDCK Permeability:	0.00020509721070993692
Pgp-inhibitor:	0.973
Pgp-substrate:	0.438
Human Intestinal Absorption (HIA):	0.987
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	79.04131317138672%
Volume Distribution (VD):	0.075
Pgp-substrate:	11.588891983032227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.15
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	0.314
Half-life (T1/2):	0.561

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.019
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.067

Download Data

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

Natural Product: NPC80986

Natural Product ID:	NPC80986
*Common Name:**	{28-O-Beta-D-Glucopyranosyloleanolic Acid 3-O-Beta-D-Glucopyranosyl(1->2)-[Beta-D-Galactopyranosyl(1->3)]-Beta-D-Glucuronopyranoside-6-O-N-Butyl Ester}
IUPAC Name:	butyl (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate
Synonyms:
Standard InCHIKey:	MSZGEPBXRLRWRI-LYSUEEDTSA-N
Standard InCHI:	InChI=1S/C58H94O24/c1-9-10-21-74-47(72)45-43(71)44(79-48-40(68)37(65)34(62)28(23-59)75-48)46(81-49-41(69)38(66)35(63)29(24-60)76-49)51(80-45)78-33-14-15-55(6)31(54(33,4)5)13-16-57(8)32(55)12-11-26-27-22-53(2,3)17-19-58(27,20-18-56(26,57)7)52(73)82-50-42(70)39(67)36(64)30(25-61)77-50/h11,27-46,48-51,59-71H,9-10,12-25H2,1-8H3/t27-,28+,29+,30+,31-,32+,33-,34-,35+,36+,37-,38-,39-,40+,41+,42+,43-,44-,45-,46+,48-,49-,50-,51+,55-,56+,57+,58-/m0/s1
SMILES:	CCCCOC(=O)[C@@H]1[C@H]([C@@H]([C@H]([C@H](O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3CC=C3[C@@H]5CC(C)(C)CC[C@@]5(CC[C@@]43C)C(=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)C2(C)C)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498944
PubChem CID:	16099398
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
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	9

Activity Type	# Activity
Cell Line	4
Organism	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[541851]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[541851]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.06	mg	PMID[541851]
NPT2	Others	Unspecified		Activity	=	10.6	%	PMID[541851]
NPT2	Others	Unspecified		Activity	=	43.2	%	PMID[541851]
NPT2	Others	Unspecified		Activity	=	71.6	%	PMID[541851]
NPT2	Others	Unspecified		IC50	=	480.0	molar ratio	PMID[541851]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[541851]

☑ 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 NPC80986 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	286
0.1-0.2	1994
0.2-0.3	5428
0.3-0.4	10455
0.4-0.5	11085
0.5-0.6	6855
0.6-0.7	3698
0.7-0.8	1941
0.8-0.85	359
0.85-0.9	122
0.9-0.95	347
0.95-1	127

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC236870
1.0	High Similarity	NPC10607
1.0	High Similarity	NPC21691
1.0	High Similarity	NPC187290
1.0	High Similarity	NPC4749
1.0	High Similarity	NPC475591
0.9912	High Similarity	NPC200049
0.9912	High Similarity	NPC258617
0.9912	High Similarity	NPC302543
0.9912	High Similarity	NPC257211
0.9912	High Similarity	NPC283417
0.9911	High Similarity	NPC64715
0.9911	High Similarity	NPC22956
0.9911	High Similarity	NPC159309
0.9911	High Similarity	NPC171544
0.9911	High Similarity	NPC31838
0.9911	High Similarity	NPC104372
0.9911	High Similarity	NPC223301
0.9911	High Similarity	NPC114484
0.9911	High Similarity	NPC11242
0.9911	High Similarity	NPC302887
0.9911	High Similarity	NPC187618
0.9911	High Similarity	NPC62725
0.9911	High Similarity	NPC86222
0.9911	High Similarity	NPC297263
0.9911	High Similarity	NPC301449
0.9911	High Similarity	NPC222580
0.9825	High Similarity	NPC160452
0.9825	High Similarity	NPC33068
0.9823	High Similarity	NPC213952
0.9823	High Similarity	NPC131469
0.9823	High Similarity	NPC162574
0.9823	High Similarity	NPC313110
0.9821	High Similarity	NPC118440
0.9821	High Similarity	NPC236657
0.9739	High Similarity	NPC470218
0.9739	High Similarity	NPC181066
0.9739	High Similarity	NPC469947
0.9739	High Similarity	NPC284449
0.9739	High Similarity	NPC475368
0.9737	High Similarity	NPC281148
0.9737	High Similarity	NPC2370
0.9737	High Similarity	NPC30735
0.9737	High Similarity	NPC235405
0.9737	High Similarity	NPC44716
0.9732	High Similarity	NPC469945
0.9732	High Similarity	NPC114441
0.9732	High Similarity	NPC192791
0.9732	High Similarity	NPC473884
0.9732	High Similarity	NPC180550
0.9732	High Similarity	NPC475171
0.9732	High Similarity	NPC309780
0.9732	High Similarity	NPC472949
0.9732	High Similarity	NPC214484
0.9732	High Similarity	NPC157868
0.9732	High Similarity	NPC35405
0.9732	High Similarity	NPC11551
0.9732	High Similarity	NPC6377
0.9732	High Similarity	NPC208381
0.9732	High Similarity	NPC39211
0.9652	High Similarity	NPC247315
0.9652	High Similarity	NPC470477
0.9652	High Similarity	NPC471963
0.9652	High Similarity	NPC23275
0.9652	High Similarity	NPC471962
0.9649	High Similarity	NPC249848
0.9649	High Similarity	NPC40775
0.9649	High Similarity	NPC235438
0.9649	High Similarity	NPC107966
0.9643	High Similarity	NPC286347
0.9573	High Similarity	NPC470475
0.9565	High Similarity	NPC202666
0.9565	High Similarity	NPC262199
0.9565	High Similarity	NPC471961
0.9565	High Similarity	NPC14617
0.9565	High Similarity	NPC471964
0.9561	High Similarity	NPC242840
0.9561	High Similarity	NPC31193
0.9561	High Similarity	NPC75417
0.9554	High Similarity	NPC475119
0.9554	High Similarity	NPC473824
0.9554	High Similarity	NPC224121
0.9478	High Similarity	NPC471965
0.9474	High Similarity	NPC294112
0.9469	High Similarity	NPC109588
0.9464	High Similarity	NPC51465
0.9464	High Similarity	NPC305267
0.9464	High Similarity	NPC476992
0.9464	High Similarity	NPC26626
0.9464	High Similarity	NPC75287
0.9464	High Similarity	NPC291903
0.9464	High Similarity	NPC288205
0.9464	High Similarity	NPC37134
0.9407	High Similarity	NPC470476
0.9402	High Similarity	NPC285091
0.9397	High Similarity	NPC478066
0.9386	High Similarity	NPC25663
0.9386	High Similarity	NPC207738
0.9386	High Similarity	NPC51564
0.9386	High Similarity	NPC135849
0.9381	High Similarity	NPC475209
0.9381	High Similarity	NPC102505
0.9381	High Similarity	NPC220160
0.9381	High Similarity	NPC286457
0.9381	High Similarity	NPC475514
0.9381	High Similarity	NPC191827
0.9381	High Similarity	NPC300419
0.9381	High Similarity	NPC123522
0.9381	High Similarity	NPC85154
0.9381	High Similarity	NPC104137
0.9381	High Similarity	NPC33012
0.9381	High Similarity	NPC473452
0.9381	High Similarity	NPC8524
0.9381	High Similarity	NPC309223
0.9381	High Similarity	NPC69811
0.9381	High Similarity	NPC470876
0.9375	High Similarity	NPC164389
0.9375	High Similarity	NPC475486
0.9333	High Similarity	NPC476776
0.9328	High Similarity	NPC47995
0.9328	High Similarity	NPC265841
0.931	High Similarity	NPC275343
0.9304	High Similarity	NPC476991
0.9298	High Similarity	NPC237191
0.9298	High Similarity	NPC232237
0.9298	High Similarity	NPC105800
0.9298	High Similarity	NPC473459
0.9292	High Similarity	NPC161674
0.9292	High Similarity	NPC471384
0.9286	High Similarity	NPC309714
0.9286	High Similarity	NPC251263
0.9286	High Similarity	NPC295823
0.9286	High Similarity	NPC114304
0.9286	High Similarity	NPC323341
0.9286	High Similarity	NPC151543
0.9286	High Similarity	NPC46665
0.9286	High Similarity	NPC133818
0.9286	High Similarity	NPC241909
0.9286	High Similarity	NPC475467
0.9286	High Similarity	NPC192600
0.9286	High Similarity	NPC155410
0.9286	High Similarity	NPC166422
0.9286	High Similarity	NPC219180
0.9286	High Similarity	NPC174720
0.9286	High Similarity	NPC473826
0.9286	High Similarity	NPC114287
0.9286	High Similarity	NPC475287
0.9256	High Similarity	NPC476779
0.925	High Similarity	NPC271610
0.925	High Similarity	NPC476774
0.925	High Similarity	NPC476775
0.925	High Similarity	NPC476780
0.9224	High Similarity	NPC470478
0.9217	High Similarity	NPC471577
0.9217	High Similarity	NPC473386
0.9211	High Similarity	NPC110633
0.9211	High Similarity	NPC323359
0.9211	High Similarity	NPC68175
0.9211	High Similarity	NPC148417
0.9211	High Similarity	NPC136768
0.9211	High Similarity	NPC471580
0.9204	High Similarity	NPC60557
0.9204	High Similarity	NPC475140
0.9204	High Similarity	NPC309907
0.9204	High Similarity	NPC43550
0.9204	High Similarity	NPC65105
0.9204	High Similarity	NPC4328
0.9204	High Similarity	NPC471550
0.9204	High Similarity	NPC294453
0.9204	High Similarity	NPC71065
0.9204	High Similarity	NPC293330
0.9204	High Similarity	NPC67857
0.9204	High Similarity	NPC224381
0.9204	High Similarity	NPC202828
0.9204	High Similarity	NPC161717
0.9204	High Similarity	NPC227551
0.9204	High Similarity	NPC76972
0.9204	High Similarity	NPC70809
0.9204	High Similarity	NPC475160
0.9204	High Similarity	NPC471385
0.9204	High Similarity	NPC236638
0.9204	High Similarity	NPC119592
0.9204	High Similarity	NPC250247
0.9204	High Similarity	NPC41061
0.9204	High Similarity	NPC305981
0.9204	High Similarity	NPC469782
0.9204	High Similarity	NPC79643
0.9204	High Similarity	NPC298034
0.9204	High Similarity	NPC57484
0.9204	High Similarity	NPC473714
0.9204	High Similarity	NPC261506
0.9204	High Similarity	NPC204414
0.9204	High Similarity	NPC123199
0.9204	High Similarity	NPC476068
0.9204	High Similarity	NPC54636
0.9204	High Similarity	NPC100639
0.9196	High Similarity	NPC139044
0.9196	High Similarity	NPC104071
0.9196	High Similarity	NPC324875
0.9196	High Similarity	NPC109079

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 NPC80986 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	2289
0.2-0.3	3839
0.3-0.4	1762
0.4-0.5	569
0.5-0.6	254
0.6-0.7	126
0.7-0.8	38
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9565	High Similarity	NPD8328	Phase 3
0.9381	High Similarity	NPD8295	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD7736	Approved
0.8	Intermediate Similarity	NPD8133	Approved
0.7984	Intermediate Similarity	NPD8517	Approved
0.7984	Intermediate Similarity	NPD8516	Approved
0.7984	Intermediate Similarity	NPD8515	Approved
0.784	Intermediate Similarity	NPD8513	Phase 3
0.7812	Intermediate Similarity	NPD8293	Discontinued
0.7692	Intermediate Similarity	NPD7319	Approved
0.7638	Intermediate Similarity	NPD6370	Approved
0.7597	Intermediate Similarity	NPD7507	Approved
0.7519	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD6412	Phase 2
0.748	Intermediate Similarity	NPD6054	Approved
0.748	Intermediate Similarity	NPD6319	Approved
0.748	Intermediate Similarity	NPD8294	Approved
0.748	Intermediate Similarity	NPD6059	Approved
0.748	Intermediate Similarity	NPD8377	Approved
0.7462	Intermediate Similarity	NPD6616	Approved
0.7438	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6686	Approved
0.7422	Intermediate Similarity	NPD8296	Approved
0.7422	Intermediate Similarity	NPD8378	Approved
0.7422	Intermediate Similarity	NPD8379	Approved
0.7422	Intermediate Similarity	NPD8380	Approved
0.7422	Intermediate Similarity	NPD8335	Approved
0.7414	Intermediate Similarity	NPD7902	Approved
0.7405	Intermediate Similarity	NPD7078	Approved
0.7339	Intermediate Similarity	NPD6882	Approved
0.7339	Intermediate Similarity	NPD8297	Approved
0.7304	Intermediate Similarity	NPD7748	Approved
0.7287	Intermediate Similarity	NPD8033	Approved
0.7287	Intermediate Similarity	NPD6015	Approved
0.7287	Intermediate Similarity	NPD6016	Approved
0.7258	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6009	Approved
0.7236	Intermediate Similarity	NPD6372	Approved
0.7236	Intermediate Similarity	NPD6373	Approved
0.7231	Intermediate Similarity	NPD5988	Approved
0.719	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7900	Approved
0.7131	Intermediate Similarity	NPD5739	Approved
0.7131	Intermediate Similarity	NPD6402	Approved
0.7131	Intermediate Similarity	NPD7128	Approved
0.7131	Intermediate Similarity	NPD6675	Approved
0.713	Intermediate Similarity	NPD7515	Phase 2
0.712	Intermediate Similarity	NPD6649	Approved
0.712	Intermediate Similarity	NPD6650	Approved
0.7054	Intermediate Similarity	NPD7328	Approved
0.7054	Intermediate Similarity	NPD7327	Approved
0.7016	Intermediate Similarity	NPD7320	Approved
0.7016	Intermediate Similarity	NPD6899	Approved
0.7016	Intermediate Similarity	NPD6881	Approved
0.7008	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD7516	Approved
0.6984	Remote Similarity	NPD8130	Phase 1
0.6963	Remote Similarity	NPD6033	Approved
0.6935	Remote Similarity	NPD5701	Approved
0.6935	Remote Similarity	NPD5697	Approved
0.6905	Remote Similarity	NPD6883	Approved
0.6905	Remote Similarity	NPD7290	Approved
0.6905	Remote Similarity	NPD7102	Approved
0.6894	Remote Similarity	NPD7503	Approved
0.6894	Remote Similarity	NPD6921	Approved
0.6889	Remote Similarity	NPD8074	Phase 3
0.685	Remote Similarity	NPD6617	Approved
0.685	Remote Similarity	NPD6847	Approved
0.685	Remote Similarity	NPD6869	Approved
0.6838	Remote Similarity	NPD8035	Phase 2
0.6838	Remote Similarity	NPD8034	Phase 2
0.6838	Remote Similarity	NPD6411	Approved
0.6825	Remote Similarity	NPD6012	Approved
0.6825	Remote Similarity	NPD6013	Approved
0.6825	Remote Similarity	NPD6014	Approved
0.6791	Remote Similarity	NPD7604	Phase 2
0.6772	Remote Similarity	NPD4634	Approved
0.6767	Remote Similarity	NPD5983	Phase 2
0.6746	Remote Similarity	NPD6011	Approved
0.6719	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7115	Discovery
0.6691	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6639	Remote Similarity	NPD7638	Approved
0.6639	Remote Similarity	NPD6399	Phase 3
0.6585	Remote Similarity	NPD7639	Approved
0.6585	Remote Similarity	NPD7640	Approved
0.6562	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6084	Phase 2
0.6557	Remote Similarity	NPD4755	Approved
0.6557	Remote Similarity	NPD6083	Phase 2
0.6555	Remote Similarity	NPD7983	Approved
0.6544	Remote Similarity	NPD6067	Discontinued
0.6519	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7329	Approved
0.6518	Remote Similarity	NPD7645	Phase 2
0.6515	Remote Similarity	NPD6274	Approved
0.6512	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD5779	Approved
0.65	Remote Similarity	NPD8171	Discontinued
0.65	Remote Similarity	NPD5778	Approved
0.6493	Remote Similarity	NPD7101	Approved
0.6493	Remote Similarity	NPD7100	Approved
0.6475	Remote Similarity	NPD4697	Phase 3
0.6471	Remote Similarity	NPD8080	Discontinued
0.6466	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6008	Approved
0.6452	Remote Similarity	NPD5286	Approved
0.6452	Remote Similarity	NPD4700	Approved
0.6452	Remote Similarity	NPD4696	Approved
0.6452	Remote Similarity	NPD5285	Approved
0.6418	Remote Similarity	NPD6335	Approved
0.6403	Remote Similarity	NPD8448	Approved
0.6397	Remote Similarity	NPD6909	Approved
0.6397	Remote Similarity	NPD6908	Approved
0.6391	Remote Similarity	NPD6868	Approved
0.6389	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5328	Approved
0.6383	Remote Similarity	NPD8392	Approved
0.6383	Remote Similarity	NPD8390	Approved
0.6383	Remote Similarity	NPD8391	Approved
0.6377	Remote Similarity	NPD8341	Approved
0.6377	Remote Similarity	NPD8340	Approved
0.6377	Remote Similarity	NPD8299	Approved
0.6377	Remote Similarity	NPD8342	Approved
0.6371	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD8450	Suspended
0.6356	Remote Similarity	NPD3573	Approved
0.6349	Remote Similarity	NPD5224	Approved
0.6349	Remote Similarity	NPD5211	Phase 2
0.6349	Remote Similarity	NPD5225	Approved
0.6349	Remote Similarity	NPD5226	Approved
0.6349	Remote Similarity	NPD4633	Approved
0.6343	Remote Similarity	NPD6317	Approved
0.6343	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5222	Approved
0.6341	Remote Similarity	NPD5221	Approved
0.6331	Remote Similarity	NPD8451	Approved
0.6328	Remote Similarity	NPD4768	Approved
0.6328	Remote Similarity	NPD4767	Approved
0.6319	Remote Similarity	NPD8415	Approved
0.6303	Remote Similarity	NPD5737	Approved
0.6303	Remote Similarity	NPD6672	Approved
0.6299	Remote Similarity	NPD5175	Approved
0.6299	Remote Similarity	NPD5174	Approved
0.6296	Remote Similarity	NPD6314	Approved
0.6296	Remote Similarity	NPD6313	Approved
0.6294	Remote Similarity	NPD8449	Approved
0.629	Remote Similarity	NPD5173	Approved
0.6281	Remote Similarity	NPD6079	Approved
0.6279	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD3618	Phase 1
0.627	Remote Similarity	NPD5223	Approved
0.6268	Remote Similarity	NPD5956	Approved
0.626	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD8337	Approved
0.6241	Remote Similarity	NPD8336	Approved
0.6233	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD4729	Approved
0.6231	Remote Similarity	NPD4730	Approved
0.621	Remote Similarity	NPD7839	Suspended
0.6205	Remote Similarity	NPD7799	Discontinued
0.6198	Remote Similarity	NPD46	Approved
0.6198	Remote Similarity	NPD6698	Approved
0.6187	Remote Similarity	NPD7830	Approved
0.6187	Remote Similarity	NPD7829	Approved
0.6172	Remote Similarity	NPD4754	Approved
0.6167	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD8444	Approved
0.6159	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3669	Approved
0.6154	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5248	Approved
0.6136	Remote Similarity	NPD5247	Approved
0.6136	Remote Similarity	NPD5250	Approved
0.6136	Remote Similarity	NPD5249	Phase 3
0.6136	Remote Similarity	NPD5251	Approved
0.6121	Remote Similarity	NPD1780	Approved
0.6121	Remote Similarity	NPD1779	Approved
0.6111	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7260	Phase 2
0.6107	Remote Similarity	NPD5128	Approved
0.6102	Remote Similarity	NPD4786	Approved
0.6094	Remote Similarity	NPD7632	Discontinued
0.6081	Remote Similarity	NPD6333	Approved
0.6081	Remote Similarity	NPD6334	Approved
0.6069	Remote Similarity	NPD8338	Approved
0.6068	Remote Similarity	NPD3667	Approved
0.6058	Remote Similarity	NPD7641	Discontinued
0.6048	Remote Similarity	NPD5282	Discontinued
0.6029	Remote Similarity	NPD6940	Discontinued
0.6	Remote Similarity	NPD5330	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