NPASS Compound

Structure

CID308140 OpenBabel06191716112D 82 91 0 0 1 0 0 0 0 0999 V2000 0.5375 9.5469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9224 4.9614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2325 0.8859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9442 3.2130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5375 7.8149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8093 1.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4026 2.3994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0375 6.9489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0460 -0.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1742 1.7995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6392 -0.0276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5810 2.7130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6283 -0.2367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4081 4.3310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5375 13.0110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0375 8.6809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0375 8.6809 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9442 5.1693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2215 0.6768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0405 -1.0457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4081 2.5039 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8203 1.6949 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0013 3.4175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5375 6.0828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6649 5.0002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0375 12.1450 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2011 4.5002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0375 12.1450 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5375 11.2790 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0375 10.4130 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0375 10.4130 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2270 0.7814 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0068 3.5220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0375 13.8771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5375 13.0110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4625 11.2790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5375 9.5469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5375 9.5469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4570 5.9783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5375 11.2790 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 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 8 11 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 26 2 0 0 0 0 11 31 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 15 1 0 0 0 0 13 29 1 0 0 0 0 14 56 1 0 0 0 0 15 57 1 0 0 0 0 16 26 1 0 0 0 0 16 27 1 0 0 0 0 17 30 1 0 0 0 0 18 58 1 0 0 0 0 19 59 1 0 0 0 0 20 21 1 0 0 0 0 20 72 1 0 0 0 0 21 1 1 1 0 0 0 22 31 2 0 0 0 0 22 35 1 0 0 0 0 23 3 1 6 0 0 0 23 36 1 0 0 0 0 23 73 1 0 0 0 0 24 4 1 1 0 0 0 24 37 1 0 0 0 0 24 74 1 0 0 0 0 25 5 1 1 0 0 0 25 48 1 0 0 0 0 25 75 1 0 0 0 0 26 56 1 0 0 0 0 27 76 1 6 0 0 0 28 10 1 1 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 29 56 1 6 0 0 0 30 57 1 6 0 0 0 31 77 1 0 0 0 0 32 17 1 6 0 0 0 32 35 1 0 0 0 0 32 77 1 0 0 0 0 33 18 1 1 0 0 0 33 38 1 0 0 0 0 33 78 1 0 0 0 0 34 19 1 1 0 0 0 34 49 1 0 0 0 0 34 79 1 0 0 0 0 35 57 1 6 0 0 0 36 39 1 0 0 0 0 36 60 1 1 0 0 0 37 40 1 0 0 0 0 37 61 1 6 0 0 0 38 41 1 0 0 0 0 38 62 1 6 0 0 0 39 44 1 0 0 0 0 39 63 1 6 0 0 0 40 45 1 0 0 0 0 40 64 1 1 0 0 0 41 43 1 0 0 0 0 41 65 1 1 0 0 0 42 46 1 0 0 0 0 42 48 1 0 0 0 0 42 66 1 1 0 0 0 43 51 1 0 0 0 0 43 67 1 6 0 0 0 44 52 1 0 0 0 0 44 68 1 6 0 0 0 45 53 1 0 0 0 0 45 69 1 1 0 0 0 46 54 1 0 0 0 0 46 70 1 1 0 0 0 47 49 1 0 0 0 0 47 50 1 0 0 0 0 47 71 1 1 0 0 0 48 80 1 6 0 0 0 49 81 1 6 0 0 0 50 55 1 0 0 0 0 50 82 1 6 0 0 0 51 72 1 1 0 0 0 51 78 1 0 0 0 0 52 73 1 0 0 0 0 52 80 1 1 0 0 0 53 74 1 0 0 0 0 53 82 1 6 0 0 0 54 75 1 0 0 0 0 54 81 1 6 0 0 0 55 76 1 1 0 0 0 55 79 1 0 0 0 0 56 6 1 6 0 0 0 57 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1176.59
Volume:	1123.346
LogP:	2.036
LogD:	1.88
LogS:	-3.27
# Rotatable Bonds:	16
TPSA:	384.75
# H-Bond Aceptor:	25
# H-Bond Donor:	14
# Rings:	10
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.073
Synthetic Accessibility Score:	7.172
Fsp3:	0.93
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:	-6.217
MDCK Permeability:	0.0007699545240029693
Pgp-inhibitor:	0.034
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	62.62084197998047%
Volume Distribution (VD):	-0.236
Pgp-substrate:	12.542611122131348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	-0.109
Half-life (T1/2):	0.685

ADMET: Toxicity

hERG Blockers:	0.797
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.358
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.937
Carcinogencity:	0.193
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC308140

Natural Product ID:	NPC308140
*Common Name:**	MOSQNTRCEDPVHL-MZUJVJCZSA-N
IUPAC Name:	n.a.
Synonyms:	Pseudoproto-Pb
Standard InCHIKey:	MOSQNTRCEDPVHL-MZUJVJCZSA-N
Standard InCHI:	InChI=1S/C57H92O25/c1-21(20-72-51-43(67)41(65)38(62)33(18-58)78-51)8-11-31-22(2)35-32(77-31)17-30-28-10-9-26-16-27(12-14-56(26,6)29(28)13-15-57(30,35)7)76-55-50(82-53-45(69)40(64)37(61)24(4)74-53)47(71)49(34(19-59)79-55)81-54-46(70)42(66)48(25(5)75-54)80-52-44(68)39(63)36(60)23(3)73-52/h9,21,23-25,27-30,32-55,58-71H,8,10-20H2,1-7H3/t21-,23+,24+,25+,27+,28-,29+,30+,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+/m1/s1
SMILES:	C[C@H](CCC1=C(C)[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@H](CC[C@]5(C)[C@H]4CC[C@]23C)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)O)O)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)O1)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071191
PubChem CID:	70688903
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
NPO27472	Daiswa polyphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27472	Daiswa polyphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27472	Daiswa polyphylla	Species	Melanthiaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	6520.0	nM	PMID[575634]

☑ 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 NPC308140 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	290
0.1-0.2	2070
0.2-0.3	6515
0.3-0.4	14041
0.4-0.5	9111
0.5-0.6	5662
0.6-0.7	2847
0.7-0.8	1341
0.8-0.85	488
0.85-0.9	209
0.9-0.95	117
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.981	High Similarity	NPC208832
0.9714	High Similarity	NPC476546
0.9615	High Similarity	NPC222202
0.9615	High Similarity	NPC224314
0.9615	High Similarity	NPC23808
0.9615	High Similarity	NPC87998
0.9615	High Similarity	NPC269297
0.9615	High Similarity	NPC477811
0.9524	High Similarity	NPC13193
0.9519	High Similarity	NPC102016
0.9519	High Similarity	NPC194207
0.9519	High Similarity	NPC224098
0.9519	High Similarity	NPC475550
0.9519	High Similarity	NPC95051
0.9519	High Similarity	NPC300557
0.9519	High Similarity	NPC249265
0.9519	High Similarity	NPC248746
0.9519	High Similarity	NPC46190
0.9519	High Similarity	NPC309278
0.9519	High Similarity	NPC475333
0.9519	High Similarity	NPC208383
0.9519	High Similarity	NPC22779
0.9519	High Similarity	NPC73243
0.9519	High Similarity	NPC232054
0.9519	High Similarity	NPC6806
0.9519	High Similarity	NPC171073
0.9519	High Similarity	NPC218571
0.9519	High Similarity	NPC84956
0.9519	High Similarity	NPC244086
0.9519	High Similarity	NPC470433
0.9519	High Similarity	NPC477809
0.9519	High Similarity	NPC150372
0.9515	High Similarity	NPC94272
0.9434	High Similarity	NPC32361
0.9434	High Similarity	NPC210569
0.9434	High Similarity	NPC244431
0.9434	High Similarity	NPC31896
0.9434	High Similarity	NPC263359
0.9423	High Similarity	NPC98696
0.9358	High Similarity	NPC475357
0.9352	High Similarity	NPC148965
0.9346	High Similarity	NPC79900
0.934	High Similarity	NPC92710
0.934	High Similarity	NPC294129
0.934	High Similarity	NPC477028
0.934	High Similarity	NPC475247
0.934	High Similarity	NPC477032
0.934	High Similarity	NPC124677
0.934	High Similarity	NPC476547
0.9327	High Similarity	NPC470432
0.9327	High Similarity	NPC305423
0.9327	High Similarity	NPC230507
0.9327	High Similarity	NPC283829
0.9327	High Similarity	NPC161676
0.9327	High Similarity	NPC14704
0.9327	High Similarity	NPC113044
0.9259	High Similarity	NPC477810
0.9259	High Similarity	NPC167183
0.9259	High Similarity	NPC32707
0.9259	High Similarity	NPC477808
0.9252	High Similarity	NPC42171
0.9245	High Similarity	NPC247037
0.9238	High Similarity	NPC128123
0.9231	High Similarity	NPC181845
0.9174	High Similarity	NPC477030
0.9174	High Similarity	NPC477029
0.9151	High Similarity	NPC477026
0.9151	High Similarity	NPC42482
0.9151	High Similarity	NPC70204
0.9151	High Similarity	NPC306131
0.9151	High Similarity	NPC477027
0.9151	High Similarity	NPC475670
0.9151	High Similarity	NPC40440
0.9151	High Similarity	NPC302057
0.9091	High Similarity	NPC477807
0.9083	High Similarity	NPC11548
0.9074	High Similarity	NPC254255
0.9065	High Similarity	NPC141433
0.9057	High Similarity	NPC476540
0.9057	High Similarity	NPC476541
0.9057	High Similarity	NPC476538
0.9057	High Similarity	NPC476539
0.9048	High Similarity	NPC242748
0.9048	High Similarity	NPC473923
0.9048	High Similarity	NPC309448
0.9048	High Similarity	NPC474569
0.9048	High Similarity	NPC473476
0.9	High Similarity	NPC477031
0.9	High Similarity	NPC63609
0.8991	High Similarity	NPC307642
0.8981	High Similarity	NPC197231
0.8981	High Similarity	NPC470748
0.8962	High Similarity	NPC190395
0.8947	High Similarity	NPC476542
0.8942	High Similarity	NPC272015
0.8899	High Similarity	NPC112274
0.8899	High Similarity	NPC19888
0.8879	High Similarity	NPC295980
0.8879	High Similarity	NPC159005
0.8879	High Similarity	NPC6931
0.885	High Similarity	NPC198325
0.885	High Similarity	NPC207243
0.885	High Similarity	NPC233391
0.8818	High Similarity	NPC51154
0.8818	High Similarity	NPC469348
0.8818	High Similarity	NPC469347
0.8818	High Similarity	NPC476693
0.8818	High Similarity	NPC476671
0.8807	High Similarity	NPC13190
0.8785	High Similarity	NPC63368
0.8785	High Similarity	NPC14946
0.8785	High Similarity	NPC208650
0.8785	High Similarity	NPC473469
0.8785	High Similarity	NPC226642
0.8774	High Similarity	NPC470885
0.8774	High Similarity	NPC221562
0.8774	High Similarity	NPC187400
0.8761	High Similarity	NPC195560
0.8761	High Similarity	NPC229962
0.875	High Similarity	NPC282669
0.875	High Similarity	NPC20979
0.8738	High Similarity	NPC473890
0.8738	High Similarity	NPC243728
0.8704	High Similarity	NPC246124
0.8704	High Similarity	NPC180183
0.8704	High Similarity	NPC220427
0.8704	High Similarity	NPC7213
0.8696	High Similarity	NPC169816
0.8696	High Similarity	NPC15918
0.8696	High Similarity	NPC94072
0.8696	High Similarity	NPC305771
0.8692	High Similarity	NPC152584
0.8692	High Similarity	NPC269627
0.8692	High Similarity	NPC26798
0.8692	High Similarity	NPC160816
0.8692	High Similarity	NPC208477
0.8692	High Similarity	NPC194842
0.8692	High Similarity	NPC127801
0.8692	High Similarity	NPC208594
0.8692	High Similarity	NPC69737
0.8684	High Similarity	NPC50689
0.8684	High Similarity	NPC473566
0.8684	High Similarity	NPC475358
0.8654	High Similarity	NPC158088
0.8636	High Similarity	NPC114188
0.8624	High Similarity	NPC476835
0.8621	High Similarity	NPC202261
0.8621	High Similarity	NPC106589
0.8621	High Similarity	NPC256983
0.8611	High Similarity	NPC181467
0.8609	High Similarity	NPC476543
0.8609	High Similarity	NPC249553
0.8609	High Similarity	NPC182900
0.8609	High Similarity	NPC476544
0.8609	High Similarity	NPC476545
0.8596	High Similarity	NPC473633
0.8596	High Similarity	NPC476085
0.8585	High Similarity	NPC312553
0.8585	High Similarity	NPC159036
0.8585	High Similarity	NPC288694
0.8545	High Similarity	NPC470867
0.8534	High Similarity	NPC43842
0.8534	High Similarity	NPC475431
0.8532	High Similarity	NPC49032
0.8532	High Similarity	NPC125324
0.8532	High Similarity	NPC51172
0.8519	High Similarity	NPC470512
0.8519	High Similarity	NPC173859
0.8509	High Similarity	NPC160888
0.8509	High Similarity	NPC476692
0.8509	High Similarity	NPC475403
0.8509	High Similarity	NPC476691
0.8509	High Similarity	NPC10366
0.8505	High Similarity	NPC155010
0.8505	High Similarity	NPC16573
0.8505	High Similarity	NPC131479
0.8505	High Similarity	NPC189852
0.8505	High Similarity	NPC157659
0.8505	High Similarity	NPC16520
0.8505	High Similarity	NPC473020
0.8505	High Similarity	NPC211879
0.8505	High Similarity	NPC114874
0.8505	High Similarity	NPC31907
0.8505	High Similarity	NPC472252
0.8505	High Similarity	NPC286969
0.8505	High Similarity	NPC245280
0.8505	High Similarity	NPC8039
0.8505	High Similarity	NPC123796
0.8505	High Similarity	NPC120123
0.8496	Intermediate Similarity	NPC146652
0.8496	Intermediate Similarity	NPC279638
0.8491	Intermediate Similarity	NPC470434
0.8491	Intermediate Similarity	NPC267510
0.8482	Intermediate Similarity	NPC144068
0.8462	Intermediate Similarity	NPC295133
0.8462	Intermediate Similarity	NPC257207
0.8462	Intermediate Similarity	NPC207617
0.8455	Intermediate Similarity	NPC14630
0.8455	Intermediate Similarity	NPC250089
0.8455	Intermediate Similarity	NPC151134

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 NPC308140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	2195
0.2-0.3	4309
0.3-0.4	1615
0.4-0.5	434
0.5-0.6	266
0.6-0.7	76
0.7-0.8	11
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8205	Intermediate Similarity	NPD8377	Approved
0.8205	Intermediate Similarity	NPD8294	Approved
0.8136	Intermediate Similarity	NPD8379	Approved
0.8136	Intermediate Similarity	NPD8033	Approved
0.8136	Intermediate Similarity	NPD8296	Approved
0.8136	Intermediate Similarity	NPD8335	Approved
0.8136	Intermediate Similarity	NPD8380	Approved
0.8136	Intermediate Similarity	NPD8378	Approved
0.7857	Intermediate Similarity	NPD8450	Suspended
0.783	Intermediate Similarity	NPD8171	Discontinued
0.7788	Intermediate Similarity	NPD6412	Phase 2
0.7778	Intermediate Similarity	NPD8449	Approved
0.7731	Intermediate Similarity	NPD7328	Approved
0.7731	Intermediate Similarity	NPD7327	Approved
0.7686	Intermediate Similarity	NPD7503	Approved
0.7667	Intermediate Similarity	NPD7516	Approved
0.7542	Intermediate Similarity	NPD8133	Approved
0.7302	Intermediate Similarity	NPD7507	Approved
0.7155	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD7319	Approved
0.7059	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD8328	Phase 3
0.6975	Remote Similarity	NPD6686	Approved
0.6935	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6370	Approved
0.6923	Remote Similarity	NPD7736	Approved
0.6846	Remote Similarity	NPD8293	Discontinued
0.6796	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6059	Approved
0.6772	Remote Similarity	NPD6054	Approved
0.6727	Remote Similarity	NPD7524	Approved
0.6699	Remote Similarity	NPD7339	Approved
0.6699	Remote Similarity	NPD6942	Approved
0.6698	Remote Similarity	NPD6928	Phase 2
0.6615	Remote Similarity	NPD6067	Discontinued
0.6606	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8516	Approved
0.6589	Remote Similarity	NPD8515	Approved
0.6589	Remote Similarity	NPD6015	Approved
0.6589	Remote Similarity	NPD8517	Approved
0.6589	Remote Similarity	NPD6016	Approved
0.6577	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7492	Approved
0.6542	Remote Similarity	NPD7525	Registered
0.6538	Remote Similarity	NPD5988	Approved
0.6532	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6616	Approved
0.6514	Remote Similarity	NPD6695	Phase 3
0.648	Remote Similarity	NPD8297	Approved
0.648	Remote Similarity	NPD6882	Approved
0.6466	Remote Similarity	NPD7078	Approved
0.6462	Remote Similarity	NPD8513	Phase 3
0.6458	Remote Similarity	NPD7625	Phase 1
0.6449	Remote Similarity	NPD7645	Phase 2
0.6435	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD7750	Discontinued
0.6406	Remote Similarity	NPD6009	Approved
0.6385	Remote Similarity	NPD6319	Approved
0.6321	Remote Similarity	NPD6933	Approved
0.6306	Remote Similarity	NPD4786	Approved
0.6303	Remote Similarity	NPD7638	Approved
0.6299	Remote Similarity	NPD4632	Approved
0.6296	Remote Similarity	NPD6929	Approved
0.6296	Remote Similarity	NPD6033	Approved
0.629	Remote Similarity	NPD7320	Approved
0.6286	Remote Similarity	NPD4785	Approved
0.6286	Remote Similarity	NPD4784	Approved
0.626	Remote Similarity	NPD6402	Approved
0.626	Remote Similarity	NPD6675	Approved
0.626	Remote Similarity	NPD5739	Approved
0.626	Remote Similarity	NPD7128	Approved
0.625	Remote Similarity	NPD4243	Approved
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7639	Approved
0.624	Remote Similarity	NPD6373	Approved
0.624	Remote Similarity	NPD6372	Approved
0.6239	Remote Similarity	NPD6931	Approved
0.6239	Remote Similarity	NPD6930	Phase 2
0.622	Remote Similarity	NPD6053	Discontinued
0.6218	Remote Similarity	NPD6083	Phase 2
0.6218	Remote Similarity	NPD6084	Phase 2
0.616	Remote Similarity	NPD6881	Approved
0.616	Remote Similarity	NPD6899	Approved
0.6142	Remote Similarity	NPD6650	Approved
0.6142	Remote Similarity	NPD8130	Phase 1
0.6142	Remote Similarity	NPD6649	Approved
0.6132	Remote Similarity	NPD6924	Approved
0.6132	Remote Similarity	NPD6926	Approved
0.6129	Remote Similarity	NPD6008	Approved
0.6126	Remote Similarity	NPD3667	Approved
0.6111	Remote Similarity	NPD6932	Approved
0.6111	Remote Similarity	NPD5776	Phase 2
0.6111	Remote Similarity	NPD6925	Approved
0.6091	Remote Similarity	NPD4748	Discontinued
0.6087	Remote Similarity	NPD5956	Approved
0.6083	Remote Similarity	NPD4755	Approved
0.608	Remote Similarity	NPD5697	Approved
0.608	Remote Similarity	NPD5701	Approved
0.6068	Remote Similarity	NPD7087	Discontinued
0.6066	Remote Similarity	NPD4159	Approved
0.6063	Remote Similarity	NPD4634	Approved
0.6063	Remote Similarity	NPD6883	Approved
0.6063	Remote Similarity	NPD7290	Approved
0.6063	Remote Similarity	NPD7102	Approved
0.6055	Remote Similarity	NPD7145	Approved
0.605	Remote Similarity	NPD7991	Discontinued
0.6034	Remote Similarity	NPD4753	Phase 2
0.6034	Remote Similarity	NPD6051	Approved
0.6031	Remote Similarity	NPD7115	Discovery
0.6018	Remote Similarity	NPD3666	Approved
0.6018	Remote Similarity	NPD3665	Phase 1
0.6018	Remote Similarity	NPD3133	Approved
0.6017	Remote Similarity	NPD4202	Approved
0.6016	Remote Similarity	NPD6617	Approved
0.6016	Remote Similarity	NPD6869	Approved
0.6016	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD6683	Phase 2
0.5984	Remote Similarity	NPD5286	Approved
0.5984	Remote Similarity	NPD6014	Approved
0.5984	Remote Similarity	NPD5285	Approved
0.5984	Remote Similarity	NPD6012	Approved
0.5984	Remote Similarity	NPD4700	Approved
0.5984	Remote Similarity	NPD6013	Approved
0.5984	Remote Similarity	NPD4696	Approved
0.597	Remote Similarity	NPD5983	Phase 2
0.5966	Remote Similarity	NPD7748	Approved
0.5965	Remote Similarity	NPD6893	Approved
0.595	Remote Similarity	NPD7902	Approved
0.5948	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6903	Approved
0.5946	Remote Similarity	NPD7514	Phase 3
0.5943	Remote Similarity	NPD7152	Approved
0.5943	Remote Similarity	NPD7150	Approved
0.5943	Remote Similarity	NPD7151	Approved
0.5942	Remote Similarity	NPD8337	Approved
0.5942	Remote Similarity	NPD8336	Approved
0.5932	Remote Similarity	NPD8034	Phase 2
0.5932	Remote Similarity	NPD8035	Phase 2
0.5932	Remote Similarity	NPD7637	Suspended
0.5926	Remote Similarity	NPD4190	Phase 3
0.5926	Remote Similarity	NPD5275	Approved
0.5917	Remote Similarity	NPD5695	Phase 3
0.5913	Remote Similarity	NPD6684	Approved
0.5913	Remote Similarity	NPD5330	Approved
0.5913	Remote Similarity	NPD7521	Approved
0.5913	Remote Similarity	NPD7146	Approved
0.5913	Remote Similarity	NPD6409	Approved
0.5913	Remote Similarity	NPD7334	Approved
0.5912	Remote Similarity	NPD6336	Discontinued
0.5906	Remote Similarity	NPD6011	Approved
0.5905	Remote Similarity	NPD6923	Approved
0.5905	Remote Similarity	NPD6922	Approved
0.5902	Remote Similarity	NPD5696	Approved
0.5897	Remote Similarity	NPD5328	Approved
0.5893	Remote Similarity	NPD6902	Approved
0.5891	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5211	Phase 2
0.5887	Remote Similarity	NPD5225	Approved
0.5887	Remote Similarity	NPD5224	Approved
0.5887	Remote Similarity	NPD5226	Approved
0.5887	Remote Similarity	NPD4633	Approved
0.5873	Remote Similarity	NPD4768	Approved
0.5873	Remote Similarity	NPD4767	Approved
0.5862	Remote Similarity	NPD4250	Approved
0.5862	Remote Similarity	NPD4251	Approved
0.5859	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4195	Approved
0.5849	Remote Similarity	NPD7143	Approved
0.5849	Remote Similarity	NPD7144	Approved
0.584	Remote Similarity	NPD5175	Approved
0.584	Remote Similarity	NPD5174	Approved
0.5806	Remote Similarity	NPD5223	Approved
0.5804	Remote Similarity	NPD7509	Discontinued
0.5804	Remote Similarity	NPD7332	Phase 2
0.5798	Remote Similarity	NPD6079	Approved
0.5798	Remote Similarity	NPD7515	Phase 2
0.5794	Remote Similarity	NPD5141	Approved
0.5789	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD4629	Approved
0.5785	Remote Similarity	NPD5210	Approved
0.5781	Remote Similarity	NPD4729	Approved
0.5781	Remote Similarity	NPD4730	Approved
0.5776	Remote Similarity	NPD3618	Phase 1
0.5776	Remote Similarity	NPD4249	Approved
0.5772	Remote Similarity	NPD4225	Approved
0.5772	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.576	Remote Similarity	NPD7632	Discontinued
0.5752	Remote Similarity	NPD6898	Phase 1
0.5739	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD3668	Phase 3
0.5714	Remote Similarity	NPD6274	Approved
0.5714	Remote Similarity	NPD4754	Approved
0.5714	Remote Similarity	NPD3168	Discontinued
0.5704	Remote Similarity	NPD7100	Approved
0.5704	Remote Similarity	NPD7101	Approved
0.5702	Remote Similarity	NPD4221	Approved
0.5702	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4223	Phase 3
0.5702	Remote Similarity	NPD7900	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