NPASS Compound

Structure

NPC475358 OpenBabel07101719152D 82 90 0 0 1 0 0 0 0 0999 V2000 7.7086 3.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4216 4.4505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4216 6.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5606 7.4176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7377 -1.4403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8565 3.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8565 2.4725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4378 1.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8521 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9911 1.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7041 5.9341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7041 10.8791 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 2.5695 3.4615 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 1.7130 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1892 -1.0708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2056 -0.9674 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 5.1391 1.9780 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 11.9911 4.9451 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 16.2737 6.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8521 2.9670 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4216 3.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2781 5.9341 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7041 7.9121 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5321 -0.4729 0.0000 C 0 0 1 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 2.5695 1.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4260 2.9670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9956 1.4835 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2781 1.9780 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.9911 5.9341 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 16.2737 7.4176 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8565 1.4835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8565 1.4835 0.0000 C 0 0 2 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 8.5651 1.9780 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.1346 4.4505 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 17.1302 7.9121 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 17.1302 8.9011 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 16.2737 9.3956 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.9911 8.9011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8521 1.9780 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2781 2.9670 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1346 6.4286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7041 8.9011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.8476 9.3956 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 15.4172 8.9011 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.9911 7.9121 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7130 1.9780 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 -1.5915 -0.1673 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 17.1302 5.9341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2671 0.1889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5695 3.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 17.9867 7.4176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 17.9867 9.3956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.2737 10.3846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1346 9.3956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3265 0.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8565 -1.4835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9836 -0.1034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9956 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 12.8476 6.4286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8476 10.3846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9956 3.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5651 2.9670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2781 4.9451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8476 7.4176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7130 1.9780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2825 3.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.4172 7.9121 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 11.1346 3.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1346 7.4176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.5606 9.3956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6 30 1 0 0 0 0 8 54 1 0 0 0 0 9 68 1 0 0 0 0 10 69 1 0 0 0 0 11 70 1 0 0 0 0 12 71 1 0 0 0 0 13 16 1 0 0 0 0 13 31 2 0 0 0 0 14 15 1 0 0 0 0 14 32 1 0 0 0 0 15 53 1 0 0 0 0 16 56 1 0 0 0 0 17 18 1 0 0 0 0 17 55 1 0 0 0 0 18 57 1 0 0 0 0 19 31 1 0 0 0 0 19 32 1 0 0 0 0 20 33 1 0 0 0 0 20 39 1 0 0 0 0 21 34 1 0 0 0 0 21 40 1 0 0 0 0 22 35 1 0 0 0 0 22 41 1 0 0 0 0 23 37 1 0 0 0 0 23 38 1 0 0 0 0 24 58 1 0 0 0 0 25 1 1 6 0 0 0 25 46 1 0 0 0 0 25 72 1 0 0 0 0 26 2 1 6 0 0 0 26 47 1 0 0 0 0 26 73 1 0 0 0 0 27 3 1 6 0 0 0 27 48 1 0 0 0 0 27 74 1 0 0 0 0 28 4 1 1 0 0 0 28 49 1 0 0 0 0 28 75 1 0 0 0 0 29 5 1 6 0 0 0 29 55 1 0 0 0 0 29 59 1 0 0 0 0 30 60 2 0 0 0 0 30 76 1 0 0 0 0 31 53 1 0 0 0 0 32 77 1 6 0 0 0 33 46 1 0 0 0 0 33 68 1 1 0 0 0 34 47 1 0 0 0 0 34 69 1 6 0 0 0 35 48 1 0 0 0 0 35 70 1 6 0 0 0 36 24 1 1 0 0 0 36 42 1 0 0 0 0 36 78 1 0 0 0 0 37 53 1 6 0 0 0 37 56 1 0 0 0 0 38 54 1 6 0 0 0 38 76 1 0 0 0 0 39 72 1 0 0 0 0 39 77 1 6 0 0 0 40 73 1 0 0 0 0 40 79 1 6 0 0 0 41 74 1 0 0 0 0 41 80 1 6 0 0 0 42 43 1 0 0 0 0 42 61 1 6 0 0 0 43 44 1 0 0 0 0 43 62 1 1 0 0 0 44 51 1 0 0 0 0 44 63 1 6 0 0 0 45 50 1 0 0 0 0 45 52 1 0 0 0 0 45 64 1 6 0 0 0 46 79 1 1 0 0 0 47 80 1 1 0 0 0 48 81 1 1 0 0 0 49 50 1 0 0 0 0 49 82 1 6 0 0 0 50 71 1 6 0 0 0 51 78 1 0 0 0 0 51 82 1 1 0 0 0 52 75 1 0 0 0 0 52 81 1 1 0 0 0 53 7 1 6 0 0 0 54 55 1 1 0 0 0 55 65 1 6 0 0 0 56 57 1 1 0 0 0 56 66 1 0 0 0 0 57 54 1 6 0 0 0 57 67 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1178.61
Volume:	1131.902
LogP:	2.333
LogD:	1.608
LogS:	-3.361
# Rotatable Bonds:	18
TPSA:	337.59
# H-Bond Aceptor:	25
# H-Bond Donor:	9
# Rings:	9
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.069
Synthetic Accessibility Score:	7.297
Fsp3:	0.947
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:	-6.269
MDCK Permeability:	0.0005092148785479367
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.255
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	43.804019927978516%
Volume Distribution (VD):	-0.002
Pgp-substrate:	22.366104125976562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.132
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.071
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	0.438
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.616
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.379
AMES Toxicity:	0.158
Rat Oral Acute Toxicity:	0.623
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.108
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.319

Download Data

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

Natural Product: NPC475358

Natural Product ID:	NPC475358
*Common Name:**	[(3S,8S,9R,10R,12R,13R,14R,17S)-8,14,17-Trihydroxy-17-[(1S)-1-Hydroxyethyl]-3-[(2R,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-Hydroxy-4-Methoxy-6-Methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-10,13-Dimethyl-1,2,3,4,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-12-Yl] Acetate
IUPAC Name:	[(3S,8S,9R,10R,12R,13R,14R,17S)-8,14,17-trihydroxy-17-[(1S)-1-hydroxyethyl]-3-[(2R,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] acetate
Synonyms:
Standard InCHIKey:	ONPAIDXQYZIDII-ZCCNCLNRSA-N
Standard InCHI:	InChI=1S/C57H94O25/c1-25-46(33(68-9)20-39(72-25)77-32-14-15-53(7)31(19-32)13-16-56(66)37(53)23-38(76-30(6)60)54(8)55(65,29(5)59)17-18-57(54,56)67)79-40-21-34(69-10)47(26(2)73-40)80-41-22-35(70-11)48(27(3)74-41)81-52-45(64)50(71-12)49(28(4)75-52)82-51-44(63)43(62)42(61)36(24-58)78-51/h13,25-29,32-52,58-59,61-67H,14-24H2,1-12H3/t25-,26-,27-,28-,29+,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:	CO[C@@H]1C[C@@H](O[C@@H]([C@H]1O[C@H]1C[C@@H](OC)[C@@H]([C@H](O1)C)O[C@@H]1O[C@H](C)[C@H]([C@H]([C@H]1O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C)O[C@H]1[C@@H](OC)C[C@@H](O[C@@H]1C)O[C@H]1CC[C@]2(C(=CC[C@@]3([C@@H]2C[C@@H](OC(=O)C)[C@]2([C@]3(O)CC[C@@]2(O)[C@@H](O)C)C)O)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504242
PubChem CID:	44566883
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO33108	leptadenia hastata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623046]
NPO33108	leptadenia hastata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8786361]

☑ 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
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	98.0	%	PMID[553434]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	89.0	%	PMID[553434]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	65.0	%	PMID[553434]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	34.0	%	PMID[553434]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	30.0	%	PMID[553434]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	18.0	%	PMID[553434]

☑ 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 NPC475358 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	267
0.1-0.2	2087
0.2-0.3	6167
0.3-0.4	13203
0.4-0.5	9128
0.5-0.6	5526
0.6-0.7	3577
0.7-0.8	1582
0.8-0.85	731
0.85-0.9	373
0.9-0.95	54
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473566
0.9375	High Similarity	NPC477807
0.9286	High Similarity	NPC63609
0.9196	High Similarity	NPC477808
0.9196	High Similarity	NPC477810
0.913	High Similarity	NPC233391
0.913	High Similarity	NPC207243
0.913	High Similarity	NPC198325
0.9123	High Similarity	NPC475357
0.9115	High Similarity	NPC477031
0.9115	High Similarity	NPC146652
0.9099	High Similarity	NPC114188
0.9099	High Similarity	NPC470748
0.9099	High Similarity	NPC65167
0.9091	High Similarity	NPC102015
0.9091	High Similarity	NPC302057
0.906	High Similarity	NPC202261
0.906	High Similarity	NPC106589
0.9043	High Similarity	NPC195560
0.9043	High Similarity	NPC229962
0.9027	High Similarity	NPC32707
0.9027	High Similarity	NPC167183
0.9018	High Similarity	NPC244431
0.9018	High Similarity	NPC32361
0.9018	High Similarity	NPC210569
0.9018	High Similarity	NPC263359
0.9018	High Similarity	NPC31896
0.9008	High Similarity	NPC473805
0.9008	High Similarity	NPC473519
0.9	High Similarity	NPC295980
0.8974	High Similarity	NPC43842
0.8966	High Similarity	NPC50689
0.8938	High Similarity	NPC79900
0.8938	High Similarity	NPC144068
0.8929	High Similarity	NPC475247
0.8929	High Similarity	NPC476547
0.8929	High Similarity	NPC294129
0.8919	High Similarity	NPC125361
0.8919	High Similarity	NPC43976
0.8919	High Similarity	NPC51925
0.8919	High Similarity	NPC296761
0.8919	High Similarity	NPC154085
0.8909	High Similarity	NPC94272
0.8909	High Similarity	NPC190395
0.8898	High Similarity	NPC257207
0.8898	High Similarity	NPC295133
0.8898	High Similarity	NPC256983
0.8879	High Similarity	NPC473633
0.8879	High Similarity	NPC476085
0.886	High Similarity	NPC208832
0.885	High Similarity	NPC19888
0.8839	High Similarity	NPC477811
0.8839	High Similarity	NPC222202
0.8839	High Similarity	NPC87998
0.8839	High Similarity	NPC224314
0.8839	High Similarity	NPC23808
0.8839	High Similarity	NPC269297
0.8829	High Similarity	NPC159005
0.8829	High Similarity	NPC246124
0.8829	High Similarity	NPC472988
0.8829	High Similarity	NPC180183
0.8829	High Similarity	NPC38217
0.8829	High Similarity	NPC6931
0.8824	High Similarity	NPC248202
0.8818	High Similarity	NPC309448
0.8818	High Similarity	NPC473923
0.8818	High Similarity	NPC473476
0.8818	High Similarity	NPC242748
0.8793	High Similarity	NPC475403
0.8793	High Similarity	NPC160888
0.8783	High Similarity	NPC477030
0.8783	High Similarity	NPC477029
0.8772	High Similarity	NPC307642
0.8772	High Similarity	NPC476546
0.8761	High Similarity	NPC477032
0.8761	High Similarity	NPC13193
0.8761	High Similarity	NPC477028
0.8761	High Similarity	NPC124677
0.8761	High Similarity	NPC197231
0.875	High Similarity	NPC248746
0.875	High Similarity	NPC244086
0.875	High Similarity	NPC309278
0.875	High Similarity	NPC475550
0.875	High Similarity	NPC224098
0.875	High Similarity	NPC150372
0.875	High Similarity	NPC249265
0.875	High Similarity	NPC475333
0.875	High Similarity	NPC6806
0.875	High Similarity	NPC218571
0.875	High Similarity	NPC232054
0.875	High Similarity	NPC477027
0.875	High Similarity	NPC70204
0.875	High Similarity	NPC84956
0.875	High Similarity	NPC46190
0.875	High Similarity	NPC300557
0.875	High Similarity	NPC306131
0.875	High Similarity	NPC102016
0.875	High Similarity	NPC477809
0.875	High Similarity	NPC475670
0.875	High Similarity	NPC208383
0.875	High Similarity	NPC171073
0.875	High Similarity	NPC194207
0.875	High Similarity	NPC95051
0.875	High Similarity	NPC73243
0.875	High Similarity	NPC477026
0.875	High Similarity	NPC22779
0.875	High Similarity	NPC470433
0.8739	High Similarity	NPC208650
0.8739	High Similarity	NPC117445
0.8739	High Similarity	NPC181467
0.8739	High Similarity	NPC308262
0.8739	High Similarity	NPC473469
0.8739	High Similarity	NPC234160
0.8739	High Similarity	NPC208193
0.8739	High Similarity	NPC63368
0.8739	High Similarity	NPC14946
0.8727	High Similarity	NPC470885
0.8727	High Similarity	NPC221562
0.8727	High Similarity	NPC187400
0.8696	High Similarity	NPC11548
0.8684	High Similarity	NPC308140
0.8667	High Similarity	NPC473474
0.8661	High Similarity	NPC476541
0.8661	High Similarity	NPC476539
0.8661	High Similarity	NPC98696
0.8661	High Similarity	NPC476538
0.8661	High Similarity	NPC476540
0.8655	High Similarity	NPC74259
0.8655	High Similarity	NPC264336
0.8655	High Similarity	NPC193893
0.8655	High Similarity	NPC474423
0.8649	High Similarity	NPC473199
0.8649	High Similarity	NPC160816
0.8649	High Similarity	NPC127801
0.8649	High Similarity	NPC208477
0.8649	High Similarity	NPC208594
0.8649	High Similarity	NPC194842
0.8649	High Similarity	NPC152584
0.8649	High Similarity	NPC69737
0.8649	High Similarity	NPC474569
0.8649	High Similarity	NPC269627
0.8644	High Similarity	NPC107607
0.8621	High Similarity	NPC279638
0.8621	High Similarity	NPC212660
0.8609	High Similarity	NPC476671
0.8609	High Similarity	NPC476693
0.8584	High Similarity	NPC40440
0.8584	High Similarity	NPC42482
0.8583	High Similarity	NPC160084
0.8583	High Similarity	NPC290746
0.8583	High Similarity	NPC79250
0.8571	High Similarity	NPC120390
0.8571	High Similarity	NPC113044
0.8571	High Similarity	NPC231518
0.8571	High Similarity	NPC475219
0.8571	High Similarity	NPC14704
0.8571	High Similarity	NPC305423
0.8571	High Similarity	NPC475590
0.8571	High Similarity	NPC474908
0.8571	High Similarity	NPC475419
0.8571	High Similarity	NPC314535
0.8571	High Similarity	NPC470432
0.8571	High Similarity	NPC230507
0.8571	High Similarity	NPC283829
0.8571	High Similarity	NPC226642
0.8571	High Similarity	NPC475182
0.8571	High Similarity	NPC173555
0.8571	High Similarity	NPC161676
0.8559	High Similarity	NPC165033
0.8559	High Similarity	NPC273879
0.8559	High Similarity	NPC475521
0.8559	High Similarity	NPC291820
0.8559	High Similarity	NPC81222
0.8559	High Similarity	NPC477464
0.8547	High Similarity	NPC20979
0.8534	High Similarity	NPC473882
0.8522	High Similarity	NPC472716
0.8522	High Similarity	NPC42171
0.8522	High Similarity	NPC475312
0.8522	High Similarity	NPC112274
0.8522	High Similarity	NPC254255
0.8509	High Similarity	NPC247037
0.85	High Similarity	NPC156789
0.8496	Intermediate Similarity	NPC7213
0.8496	Intermediate Similarity	NPC220427
0.8487	Intermediate Similarity	NPC474466
0.8487	Intermediate Similarity	NPC475629
0.8487	Intermediate Similarity	NPC475556
0.8487	Intermediate Similarity	NPC475136
0.8487	Intermediate Similarity	NPC135369
0.8487	Intermediate Similarity	NPC471406
0.8487	Intermediate Similarity	NPC72260
0.8482	Intermediate Similarity	NPC181845
0.8482	Intermediate Similarity	NPC470512
0.8482	Intermediate Similarity	NPC173859
0.8475	Intermediate Similarity	NPC475899
0.8475	Intermediate Similarity	NPC218093
0.8475	Intermediate Similarity	NPC36831
0.8468	Intermediate Similarity	NPC157659
0.8468	Intermediate Similarity	NPC286969

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 NPC475358 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	2269
0.2-0.3	4199
0.3-0.4	1607
0.4-0.5	426
0.5-0.6	275
0.6-0.7	112
0.7-0.8	17
0.8-0.85	1
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD8379	Approved
0.8571	High Similarity	NPD8380	Approved
0.8571	High Similarity	NPD8296	Approved
0.8571	High Similarity	NPD8033	Approved
0.8571	High Similarity	NPD8335	Approved
0.8571	High Similarity	NPD8378	Approved
0.8487	Intermediate Similarity	NPD8294	Approved
0.8487	Intermediate Similarity	NPD8377	Approved
0.8403	Intermediate Similarity	NPD7516	Approved
0.8319	Intermediate Similarity	NPD7328	Approved
0.8319	Intermediate Similarity	NPD7327	Approved
0.7983	Intermediate Similarity	NPD8133	Approved
0.7967	Intermediate Similarity	NPD7503	Approved
0.7647	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6412	Phase 2
0.7578	Intermediate Similarity	NPD7507	Approved
0.7538	Intermediate Similarity	NPD7319	Approved
0.7422	Intermediate Similarity	NPD8328	Phase 3
0.736	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8171	Discontinued
0.7328	Intermediate Similarity	NPD7736	Approved
0.7313	Intermediate Similarity	NPD8450	Suspended
0.7252	Intermediate Similarity	NPD8293	Discontinued
0.7239	Intermediate Similarity	NPD8449	Approved
0.7132	Intermediate Similarity	NPD8515	Approved
0.7132	Intermediate Similarity	NPD8516	Approved
0.7132	Intermediate Similarity	NPD8517	Approved
0.7077	Intermediate Similarity	NPD6370	Approved
0.704	Intermediate Similarity	NPD8297	Approved
0.704	Intermediate Similarity	NPD6882	Approved
0.7025	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8513	Phase 3
0.6992	Remote Similarity	NPD6686	Approved
0.697	Remote Similarity	NPD7492	Approved
0.6953	Remote Similarity	NPD6009	Approved
0.6923	Remote Similarity	NPD6059	Approved
0.6923	Remote Similarity	NPD6319	Approved
0.6923	Remote Similarity	NPD6054	Approved
0.6917	Remote Similarity	NPD6616	Approved
0.6866	Remote Similarity	NPD7078	Approved
0.685	Remote Similarity	NPD4632	Approved
0.6829	Remote Similarity	NPD6675	Approved
0.6829	Remote Similarity	NPD5739	Approved
0.6829	Remote Similarity	NPD7128	Approved
0.6829	Remote Similarity	NPD6402	Approved
0.6828	Remote Similarity	NPD7625	Phase 1
0.6825	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6373	Approved
0.68	Remote Similarity	NPD6372	Approved
0.6754	Remote Similarity	NPD7524	Approved
0.675	Remote Similarity	NPD7638	Approved
0.6742	Remote Similarity	NPD6015	Approved
0.6742	Remote Similarity	NPD6016	Approved
0.672	Remote Similarity	NPD6899	Approved
0.672	Remote Similarity	NPD7320	Approved
0.672	Remote Similarity	NPD6881	Approved
0.6694	Remote Similarity	NPD7640	Approved
0.6694	Remote Similarity	NPD7639	Approved
0.6693	Remote Similarity	NPD6649	Approved
0.6693	Remote Similarity	NPD6650	Approved
0.6693	Remote Similarity	NPD8130	Phase 1
0.6692	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD6067	Discontinued
0.664	Remote Similarity	NPD5701	Approved
0.664	Remote Similarity	NPD5697	Approved
0.6614	Remote Similarity	NPD6883	Approved
0.6614	Remote Similarity	NPD7290	Approved
0.6614	Remote Similarity	NPD7102	Approved
0.661	Remote Similarity	NPD6399	Phase 3
0.6577	Remote Similarity	NPD7525	Registered
0.6565	Remote Similarity	NPD7115	Discovery
0.6562	Remote Similarity	NPD6847	Approved
0.6562	Remote Similarity	NPD6869	Approved
0.6562	Remote Similarity	NPD6617	Approved
0.656	Remote Similarity	NPD6008	Approved
0.6535	Remote Similarity	NPD6012	Approved
0.6535	Remote Similarity	NPD6013	Approved
0.6535	Remote Similarity	NPD6014	Approved
0.6529	Remote Similarity	NPD6083	Phase 2
0.6529	Remote Similarity	NPD6084	Phase 2
0.6519	Remote Similarity	NPD7604	Phase 2
0.6504	Remote Similarity	NPD5344	Discontinued
0.6493	Remote Similarity	NPD5983	Phase 2
0.6491	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6011	Approved
0.6449	Remote Similarity	NPD6033	Approved
0.6434	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6336	Discontinued
0.6417	Remote Similarity	NPD7748	Approved
0.6404	Remote Similarity	NPD6695	Phase 3
0.6393	Remote Similarity	NPD4755	Approved
0.6393	Remote Similarity	NPD7902	Approved
0.6387	Remote Similarity	NPD8035	Phase 2
0.6387	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD4634	Approved
0.6356	Remote Similarity	NPD6051	Approved
0.6339	Remote Similarity	NPD7645	Phase 2
0.6333	Remote Similarity	NPD4202	Approved
0.6325	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7750	Discontinued
0.629	Remote Similarity	NPD5286	Approved
0.629	Remote Similarity	NPD5285	Approved
0.629	Remote Similarity	NPD4696	Approved
0.629	Remote Similarity	NPD4700	Approved
0.6283	Remote Similarity	NPD6928	Phase 2
0.6273	Remote Similarity	NPD6942	Approved
0.6273	Remote Similarity	NPD7339	Approved
0.626	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD6274	Approved
0.624	Remote Similarity	NPD4159	Approved
0.623	Remote Similarity	NPD5695	Phase 3
0.6222	Remote Similarity	NPD7101	Approved
0.6222	Remote Similarity	NPD7100	Approved
0.621	Remote Similarity	NPD5696	Approved
0.621	Remote Similarity	NPD4225	Approved
0.6207	Remote Similarity	NPD4786	Approved
0.619	Remote Similarity	NPD5211	Phase 2
0.619	Remote Similarity	NPD5225	Approved
0.619	Remote Similarity	NPD4633	Approved
0.619	Remote Similarity	NPD5226	Approved
0.619	Remote Similarity	NPD7632	Discontinued
0.619	Remote Similarity	NPD5224	Approved
0.6172	Remote Similarity	NPD4767	Approved
0.6172	Remote Similarity	NPD4768	Approved
0.6167	Remote Similarity	NPD3168	Discontinued
0.616	Remote Similarity	NPD6648	Approved
0.6154	Remote Similarity	NPD8338	Approved
0.6154	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7900	Approved
0.6148	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6335	Approved
0.6143	Remote Similarity	NPD8074	Phase 3
0.6142	Remote Similarity	NPD5175	Approved
0.6142	Remote Similarity	NPD5174	Approved
0.614	Remote Similarity	NPD6931	Approved
0.614	Remote Similarity	NPD6930	Phase 2
0.6134	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD6909	Approved
0.6131	Remote Similarity	NPD6908	Approved
0.6111	Remote Similarity	NPD5223	Approved
0.6102	Remote Similarity	NPD7146	Approved
0.6102	Remote Similarity	NPD7521	Approved
0.6102	Remote Similarity	NPD6409	Approved
0.6102	Remote Similarity	NPD6684	Approved
0.6102	Remote Similarity	NPD7334	Approved
0.6102	Remote Similarity	NPD5330	Approved
0.6098	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD5141	Approved
0.6083	Remote Similarity	NPD5328	Approved
0.6083	Remote Similarity	NPD4753	Phase 2
0.608	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD4730	Approved
0.6077	Remote Similarity	NPD4729	Approved
0.6074	Remote Similarity	NPD6317	Approved
0.6071	Remote Similarity	NPD6933	Approved
0.6053	Remote Similarity	NPD6929	Approved
0.6036	Remote Similarity	NPD4784	Approved
0.6036	Remote Similarity	NPD4785	Approved
0.6034	Remote Similarity	NPD3667	Approved
0.6029	Remote Similarity	NPD6313	Approved
0.6029	Remote Similarity	NPD6314	Approved
0.6018	Remote Similarity	NPD6932	Approved
0.6016	Remote Similarity	NPD4754	Approved
0.6014	Remote Similarity	NPD6921	Approved
0.6014	Remote Similarity	NPD5956	Approved
0.6	Remote Similarity	NPD4748	Discontinued
0.6	Remote Similarity	NPD6903	Approved
0.6	Remote Similarity	NPD4243	Approved
0.5986	Remote Similarity	NPD8336	Approved
0.5986	Remote Similarity	NPD8337	Approved
0.5985	Remote Similarity	NPD5251	Approved
0.5985	Remote Similarity	NPD5247	Approved
0.5985	Remote Similarity	NPD5249	Phase 3
0.5985	Remote Similarity	NPD5248	Approved
0.5985	Remote Similarity	NPD5250	Approved
0.5984	Remote Similarity	NPD6079	Approved
0.5984	Remote Similarity	NPD7087	Discontinued
0.5983	Remote Similarity	NPD3669	Approved
0.5983	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD3618	Phase 1
0.5966	Remote Similarity	NPD6098	Approved
0.5954	Remote Similarity	NPD5128	Approved
0.595	Remote Similarity	NPD6904	Approved
0.595	Remote Similarity	NPD6080	Approved
0.595	Remote Similarity	NPD6673	Approved
0.5932	Remote Similarity	NPD3133	Approved
0.5932	Remote Similarity	NPD3665	Phase 1
0.5932	Remote Similarity	NPD3666	Approved
0.5913	Remote Similarity	NPD6683	Phase 2
0.5913	Remote Similarity	NPD4195	Approved
0.5909	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6926	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