NPASS Compound

Structure

NPC475513 OpenBabel07101718312D 83 91 0 0 1 0 0 0 0 0999 V2000 -6.7792 -0.9785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0844 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1840 -3.7829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2056 -3.7829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8789 2.8044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9004 2.8044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5422 -0.4892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9318 -1.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7792 -6.8495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9318 -7.3387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7792 -5.8710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0844 -6.8495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9318 -5.3817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2370 -5.3817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8474 -1.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 -0.9785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2370 -4.4032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 1.9570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2370 0.4892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3896 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8474 1.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8474 -2.4462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7792 -2.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7788 2.5597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4740 1.9570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3896 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0844 -0.9785 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.0844 -5.8710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8474 -1.4677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9318 -2.4462 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3808 1.6658 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6266 1.4677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5422 1.4677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6948 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2370 1.4677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3896 -3.9140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0844 -2.9355 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.8701 0.8184 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2370 -2.4462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2153 0.0913 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2370 -1.4677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7792 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6266 0.4892 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9318 0.4892 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8474 0.4892 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6948 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5422 -2.4462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5422 -1.4677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2370 -1.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3214 0.4892 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0844 -0.9785 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9318 1.4677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6948 -2.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3896 1.9570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5422 0.4892 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8474 0.4892 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6948 -0.9785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6266 -2.4462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7519 2.6620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4740 2.9355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3896 0.9785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5422 -4.4032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0844 -3.9140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8432 0.7161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3896 -2.9355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4188 -0.8659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3896 -0.9785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7792 -0.9785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8474 1.4677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5422 0.4892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2370 -2.4462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9318 -1.4677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4237 1.4624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7792 1.9570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0844 1.9570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3896 -2.9355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4740 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0844 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3896 -0.9785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 29 1 0 0 0 0 3 56 1 0 0 0 0 4 56 1 0 0 0 0 5 57 1 0 0 0 0 6 57 1 0 0 0 0 8 59 1 0 0 0 0 10 29 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 30 2 0 0 0 0 15 30 1 0 0 0 0 16 19 2 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 31 2 0 0 0 0 18 37 1 0 0 0 0 19 39 1 0 0 0 0 20 23 1 0 0 0 0 20 36 1 0 0 0 0 21 22 1 0 0 0 0 21 38 1 0 0 0 0 22 58 1 0 0 0 0 23 59 1 0 0 0 0 24 32 1 0 0 0 0 24 56 1 0 0 0 0 25 62 1 0 0 0 0 26 63 1 0 0 0 0 27 64 1 0 0 0 0 28 65 1 0 0 0 0 29 52 1 0 0 0 0 31 32 1 0 0 0 0 31 60 1 0 0 0 0 32 61 1 6 0 0 0 33 25 1 6 0 0 0 33 40 1 0 0 0 0 33 76 1 0 0 0 0 34 26 1 1 0 0 0 34 41 1 0 0 0 0 34 77 1 0 0 0 0 35 27 1 6 0 0 0 35 46 1 0 0 0 0 35 78 1 0 0 0 0 36 57 1 0 0 0 0 36 58 1 1 0 0 0 37 58 1 1 0 0 0 37 59 1 0 0 0 0 38 57 1 0 0 0 0 38 79 1 1 0 0 0 39 66 2 0 0 0 0 39 80 1 0 0 0 0 40 42 1 0 0 0 0 40 67 1 1 0 0 0 41 43 1 0 0 0 0 41 68 1 6 0 0 0 42 44 1 0 0 0 0 42 69 1 6 0 0 0 43 53 1 0 0 0 0 43 70 1 1 0 0 0 44 54 1 0 0 0 0 44 71 1 1 0 0 0 45 46 1 0 0 0 0 45 47 1 0 0 0 0 45 72 1 6 0 0 0 46 81 1 1 0 0 0 47 55 1 0 0 0 0 47 82 1 1 0 0 0 48 49 1 0 0 0 0 48 60 1 6 0 0 0 48 73 1 0 0 0 0 49 61 1 6 0 0 0 49 74 1 0 0 0 0 50 51 1 0 0 0 0 50 56 1 0 0 0 0 50 80 1 1 0 0 0 51 61 1 6 0 0 0 51 83 1 0 0 0 0 52 75 2 0 0 0 0 52 83 1 0 0 0 0 53 77 1 0 0 0 0 53 81 1 6 0 0 0 54 76 1 0 0 0 0 54 82 1 6 0 0 0 55 78 1 0 0 0 0 55 79 1 6 0 0 0 58 7 1 1 0 0 0 59 60 1 6 0 0 0 60 9 1 6 0 0 0 61 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1176.61
Volume:	1161.533
LogP:	3.607
LogD:	2.833
LogS:	-3.868
# Rotatable Bonds:	18
TPSA:	350.74
# H-Bond Aceptor:	22
# H-Bond Donor:	12
# Rings:	9
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.048
Synthetic Accessibility Score:	6.987
Fsp3:	0.803
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:	-5.887
MDCK Permeability:	0.00015723257092759013
Pgp-inhibitor:	0.984
Pgp-substrate:	0.765
Human Intestinal Absorption (HIA):	0.959
20% Bioavailability (F20%):	0.304
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	84.05628204345703%
Volume Distribution (VD):	0.213
Pgp-substrate:	9.694428443908691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.156
CYP3A4-substrate:	0.065

ADMET: Excretion

Clearance (CL):	0.723
Half-life (T1/2):	0.68

ADMET: Toxicity

hERG Blockers:	0.237
Human Hepatotoxicity (H-HT):	0.117
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.415
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.782

Download Data

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

Natural Product: NPC475513

Natural Product ID:	NPC475513
*Common Name:**	Symplocososide X
IUPAC Name:	[(3R,4R,4aR,5S,6R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-5-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,6-dihydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-3-[(E)-3-phenylprop-2-enoyl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-4-yl] 2-methylbutanoate
Synonyms:	symplocososide X
Standard InCHIKey:	WCMQRJXNEXZPQG-XPXIFJCDSA-N
Standard InCHI:	InChI=1S/C61H92O22/c1-10-29(2)52(75)83-51-50(80-39(66)19-16-30-14-12-11-13-15-30)56(3,4)24-32-31-17-18-37-58(7)22-21-38(57(5,6)36(58)20-23-59(37,8)60(31,9)48(73)49(74)61(32,51)28-65)79-55-47(82-54-44(71)42(69)40(67)33(25-62)76-54)45(72)46(35(27-64)78-55)81-53-43(70)41(68)34(26-63)77-53/h11-17,19,29,32-38,40-51,53-55,62-65,67-74H,10,18,20-28H2,1-9H3/b19-16+/t29?,32-,33+,34-,35+,36-,37+,38-,40+,41-,42-,43+,44+,45-,46+,47+,48-,49+,50-,51-,53-,54-,55-,58-,59+,60-,61-/m0/s1
SMILES:	CCC(C)C(=O)OC1C(C(CC2C1(C(C(C3(C2=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)CO)OC7C(C(C(O7)CO)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)C)O)O)CO)(C)C)OC(=O)C=CC9=CC=CC=C9
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507135
PubChem CID:	44566495
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
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	n.a.	n.a.	PMID[15620235]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	Nanning City, Guangxi Province, People's Republic of China	1997-Jan	PMID[17190442]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8121	Symplocos chinensis	Species	Symplocaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	1700.0	nM	PMID[475844]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	1800.0	nM	PMID[475844]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[475844]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2100.0	nM	PMID[475844]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1600.0	nM	PMID[475844]

☑ 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 NPC475513 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	311
0.1-0.2	1077
0.2-0.3	2517
0.3-0.4	5418
0.4-0.5	10445
0.5-0.6	15120
0.6-0.7	5729
0.7-0.8	1862
0.8-0.85	148
0.85-0.9	46
0.9-0.95	22
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473755
0.9301	High Similarity	NPC69425
0.9281	High Similarity	NPC111466
0.9214	High Similarity	NPC264270
0.9214	High Similarity	NPC40085
0.9161	High Similarity	NPC329657
0.8889	High Similarity	NPC474564
0.8881	High Similarity	NPC230331
0.8851	High Similarity	NPC477470
0.8851	High Similarity	NPC477474
0.8851	High Similarity	NPC477472
0.8828	High Similarity	NPC475218
0.8828	High Similarity	NPC475447
0.8828	High Similarity	NPC476092
0.8828	High Similarity	NPC70236
0.8808	High Similarity	NPC295408
0.8808	High Similarity	NPC329960
0.8808	High Similarity	NPC150893
0.8792	High Similarity	NPC477467
0.8582	High Similarity	NPC470815
0.8571	High Similarity	NPC469448
0.8562	High Similarity	NPC320734
0.8543	High Similarity	NPC476784
0.8529	High Similarity	NPC171007
0.8529	High Similarity	NPC476971
0.8529	High Similarity	NPC190849
0.8529	High Similarity	NPC476972
0.8497	Intermediate Similarity	NPC475536
0.8497	Intermediate Similarity	NPC165234
0.8489	Intermediate Similarity	NPC476976
0.8487	Intermediate Similarity	NPC477623
0.8456	Intermediate Similarity	NPC475933
0.8456	Intermediate Similarity	NPC470158
0.8456	Intermediate Similarity	NPC476970
0.8452	Intermediate Similarity	NPC475567
0.8452	Intermediate Similarity	NPC473557
0.8452	Intermediate Similarity	NPC473468
0.8442	Intermediate Similarity	NPC475464
0.8442	Intermediate Similarity	NPC473641
0.8442	Intermediate Similarity	NPC473797
0.8442	Intermediate Similarity	NPC475437
0.8442	Intermediate Similarity	NPC475505
0.8442	Intermediate Similarity	NPC475300
0.8417	Intermediate Similarity	NPC476977
0.8408	Intermediate Similarity	NPC477469
0.8408	Intermediate Similarity	NPC477466
0.8408	Intermediate Similarity	NPC477473
0.8408	Intermediate Similarity	NPC477471
0.84	Intermediate Similarity	NPC472658
0.84	Intermediate Similarity	NPC472657
0.8397	Intermediate Similarity	NPC475175
0.8397	Intermediate Similarity	NPC475531
0.8397	Intermediate Similarity	NPC475198
0.8382	Intermediate Similarity	NPC471758
0.8382	Intermediate Similarity	NPC473083
0.8378	Intermediate Similarity	NPC92293
0.8378	Intermediate Similarity	NPC270590
0.8378	Intermediate Similarity	NPC301556
0.8378	Intermediate Similarity	NPC471101
0.8378	Intermediate Similarity	NPC266265
0.837	Intermediate Similarity	NPC12016
0.8346	Intermediate Similarity	NPC470814
0.8345	Intermediate Similarity	NPC475138
0.8344	Intermediate Similarity	NPC102465
0.8344	Intermediate Similarity	NPC34066
0.8344	Intermediate Similarity	NPC469420
0.8344	Intermediate Similarity	NPC469422
0.8344	Intermediate Similarity	NPC469398
0.8322	Intermediate Similarity	NPC475417
0.8322	Intermediate Similarity	NPC475561
0.8321	Intermediate Similarity	NPC470816
0.8321	Intermediate Similarity	NPC473110
0.8321	Intermediate Similarity	NPC473111
0.8321	Intermediate Similarity	NPC45821
0.8311	Intermediate Similarity	NPC281717
0.8309	Intermediate Similarity	NPC472373
0.8299	Intermediate Similarity	NPC29704
0.8299	Intermediate Similarity	NPC177940
0.8299	Intermediate Similarity	NPC472568
0.8299	Intermediate Similarity	NPC96903
0.8299	Intermediate Similarity	NPC469349
0.8299	Intermediate Similarity	NPC472571
0.8299	Intermediate Similarity	NPC470157
0.8299	Intermediate Similarity	NPC184817
0.8299	Intermediate Similarity	NPC200471
0.8299	Intermediate Similarity	NPC171525
0.8299	Intermediate Similarity	NPC174982
0.8299	Intermediate Similarity	NPC158663
0.8299	Intermediate Similarity	NPC471104
0.8299	Intermediate Similarity	NPC472572
0.8299	Intermediate Similarity	NPC476973
0.8299	Intermediate Similarity	NPC473088
0.8299	Intermediate Similarity	NPC472575
0.8299	Intermediate Similarity	NPC470159
0.8299	Intermediate Similarity	NPC70403
0.8267	Intermediate Similarity	NPC469415
0.8267	Intermediate Similarity	NPC478123
0.8248	Intermediate Similarity	NPC114927
0.8235	Intermediate Similarity	NPC469417
0.8235	Intermediate Similarity	NPC473871
0.8235	Intermediate Similarity	NPC473870
0.8231	Intermediate Similarity	NPC241951
0.8231	Intermediate Similarity	NPC11685
0.8231	Intermediate Similarity	NPC472569
0.8231	Intermediate Similarity	NPC475122
0.8231	Intermediate Similarity	NPC472570
0.8231	Intermediate Similarity	NPC95265
0.8231	Intermediate Similarity	NPC57628
0.8231	Intermediate Similarity	NPC470152
0.8231	Intermediate Similarity	NPC204644
0.8231	Intermediate Similarity	NPC163719
0.8231	Intermediate Similarity	NPC472573
0.8231	Intermediate Similarity	NPC188865
0.8231	Intermediate Similarity	NPC70716
0.8231	Intermediate Similarity	NPC125106
0.8231	Intermediate Similarity	NPC475759
0.8231	Intermediate Similarity	NPC476974
0.8231	Intermediate Similarity	NPC25768
0.8231	Intermediate Similarity	NPC95810
0.8227	Intermediate Similarity	NPC80599
0.8227	Intermediate Similarity	NPC475493
0.8217	Intermediate Similarity	NPC477491
0.8214	Intermediate Similarity	NPC473443
0.8212	Intermediate Similarity	NPC472548
0.8212	Intermediate Similarity	NPC477905
0.8205	Intermediate Similarity	NPC269668
0.82	Intermediate Similarity	NPC222102
0.82	Intermediate Similarity	NPC303429
0.8199	Intermediate Similarity	NPC13989
0.8195	Intermediate Similarity	NPC470914
0.8188	Intermediate Similarity	NPC473082
0.8182	Intermediate Similarity	NPC473216
0.8182	Intermediate Similarity	NPC469399
0.8182	Intermediate Similarity	NPC473399
0.8176	Intermediate Similarity	NPC472556
0.8176	Intermediate Similarity	NPC477488
0.817	Intermediate Similarity	NPC471874
0.8163	Intermediate Similarity	NPC91703
0.8163	Intermediate Similarity	NPC163087
0.8162	Intermediate Similarity	NPC70973
0.8162	Intermediate Similarity	NPC473749
0.8162	Intermediate Similarity	NPC475328
0.8162	Intermediate Similarity	NPC473889
0.8158	Intermediate Similarity	NPC77310
0.8151	Intermediate Similarity	NPC87448
0.8151	Intermediate Similarity	NPC472576
0.8151	Intermediate Similarity	NPC118080
0.8151	Intermediate Similarity	NPC16912
0.8151	Intermediate Similarity	NPC97947
0.8151	Intermediate Similarity	NPC27377
0.8151	Intermediate Similarity	NPC291599
0.8151	Intermediate Similarity	NPC41481
0.8143	Intermediate Similarity	NPC93632
0.8143	Intermediate Similarity	NPC471024
0.8143	Intermediate Similarity	NPC225103
0.8137	Intermediate Similarity	NPC469421
0.8133	Intermediate Similarity	NPC476975
0.8129	Intermediate Similarity	NPC35338
0.8129	Intermediate Similarity	NPC124878
0.8129	Intermediate Similarity	NPC10121
0.8129	Intermediate Similarity	NPC198918
0.8129	Intermediate Similarity	NPC290276
0.8129	Intermediate Similarity	NPC204214
0.8129	Intermediate Similarity	NPC10883
0.8129	Intermediate Similarity	NPC231888
0.8129	Intermediate Similarity	NPC63404
0.8129	Intermediate Similarity	NPC92283
0.8121	Intermediate Similarity	NPC474935
0.8116	Intermediate Similarity	NPC87153
0.8116	Intermediate Similarity	NPC162925
0.8105	Intermediate Similarity	NPC472549
0.8105	Intermediate Similarity	NPC5115
0.8088	Intermediate Similarity	NPC311175
0.8088	Intermediate Similarity	NPC300827
0.8088	Intermediate Similarity	NPC473439
0.8088	Intermediate Similarity	NPC37641
0.8086	Intermediate Similarity	NPC469772
0.8086	Intermediate Similarity	NPC100925
0.8086	Intermediate Similarity	NPC295941
0.8086	Intermediate Similarity	NPC469773
0.8086	Intermediate Similarity	NPC135334
0.8086	Intermediate Similarity	NPC469777
0.8086	Intermediate Similarity	NPC469778
0.8086	Intermediate Similarity	NPC469775
0.8086	Intermediate Similarity	NPC32723
0.8086	Intermediate Similarity	NPC469774
0.8086	Intermediate Similarity	NPC469776
0.8085	Intermediate Similarity	NPC472388
0.8082	Intermediate Similarity	NPC171207
0.8082	Intermediate Similarity	NPC100913
0.8082	Intermediate Similarity	NPC97667
0.8082	Intermediate Similarity	NPC472547
0.8082	Intermediate Similarity	NPC275592
0.8082	Intermediate Similarity	NPC90614
0.8079	Intermediate Similarity	NPC470245
0.8079	Intermediate Similarity	NPC473214
0.8077	Intermediate Similarity	NPC471878
0.8071	Intermediate Similarity	NPC471025
0.8063	Intermediate Similarity	NPC278272
0.8063	Intermediate Similarity	NPC120667

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 NPC475513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	702
0.2-0.3	1708
0.3-0.4	3363
0.4-0.5	2183
0.5-0.6	805
0.6-0.7	113
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7576	Intermediate Similarity	NPD7799	Discontinued
0.7551	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7266	Discontinued
0.7376	Intermediate Similarity	NPD5125	Phase 3
0.7376	Intermediate Similarity	NPD5126	Approved
0.7338	Intermediate Similarity	NPD8166	Discontinued
0.7329	Intermediate Similarity	NPD8455	Phase 2
0.731	Intermediate Similarity	NPD8313	Approved
0.731	Intermediate Similarity	NPD8312	Approved
0.7262	Intermediate Similarity	NPD7228	Approved
0.723	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7240	Approved
0.7183	Intermediate Similarity	NPD7503	Approved
0.7183	Intermediate Similarity	NPD8033	Approved
0.7168	Intermediate Similarity	NPD8407	Phase 2
0.7134	Intermediate Similarity	NPD7236	Approved
0.7113	Intermediate Similarity	NPD8294	Approved
0.7113	Intermediate Similarity	NPD8377	Approved
0.7093	Intermediate Similarity	NPD8368	Discontinued
0.7066	Intermediate Similarity	NPD8127	Discontinued
0.7063	Intermediate Similarity	NPD8380	Approved
0.7063	Intermediate Similarity	NPD8378	Approved
0.7063	Intermediate Similarity	NPD8379	Approved
0.7063	Intermediate Similarity	NPD8296	Approved
0.7063	Intermediate Similarity	NPD8335	Approved
0.7019	Intermediate Similarity	NPD7239	Suspended
0.6966	Remote Similarity	NPD8328	Phase 3
0.6962	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD37	Approved
0.6934	Remote Similarity	NPD6686	Approved
0.6932	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4966	Approved
0.6928	Remote Similarity	NPD4965	Approved
0.6928	Remote Similarity	NPD4967	Phase 2
0.6923	Remote Similarity	NPD7516	Approved
0.6901	Remote Similarity	NPD4198	Discontinued
0.6893	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7741	Discontinued
0.6871	Remote Similarity	NPD7458	Discontinued
0.6853	Remote Similarity	NPD7328	Approved
0.6853	Remote Similarity	NPD7327	Approved
0.6845	Remote Similarity	NPD6234	Discontinued
0.6839	Remote Similarity	NPD7097	Phase 1
0.6835	Remote Similarity	NPD6674	Discontinued
0.6833	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8515	Approved
0.6828	Remote Similarity	NPD8517	Approved
0.6828	Remote Similarity	NPD8516	Approved
0.6828	Remote Similarity	NPD8513	Phase 3
0.6816	Remote Similarity	NPD8435	Approved
0.6816	Remote Similarity	NPD8361	Approved
0.6816	Remote Similarity	NPD8360	Approved
0.6809	Remote Similarity	NPD6858	Approved
0.6809	Remote Similarity	NPD7094	Approved
0.6809	Remote Similarity	NPD8133	Approved
0.6798	Remote Similarity	NPD8434	Phase 2
0.6797	Remote Similarity	NPD7961	Discontinued
0.6757	Remote Similarity	NPD7507	Approved
0.6757	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD2629	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6010	Discontinued
0.6643	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD6647	Phase 2
0.6627	Remote Similarity	NPD7057	Phase 3
0.6627	Remote Similarity	NPD7058	Phase 2
0.6623	Remote Similarity	NPD7319	Approved
0.662	Remote Similarity	NPD969	Suspended
0.6619	Remote Similarity	NPD6685	Approved
0.6614	Remote Similarity	NPD8319	Approved
0.6614	Remote Similarity	NPD8320	Phase 1
0.6611	Remote Similarity	NPD8150	Discontinued
0.661	Remote Similarity	NPD7685	Pre-registration
0.6595	Remote Similarity	NPD8485	Approved
0.6579	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7199	Phase 2
0.6562	Remote Similarity	NPD8151	Discontinued
0.6561	Remote Similarity	NPD7680	Approved
0.6559	Remote Similarity	NPD7699	Phase 2
0.6559	Remote Similarity	NPD7700	Phase 2
0.6558	Remote Similarity	NPD7008	Discontinued
0.6536	Remote Similarity	NPD5736	Approved
0.6534	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6559	Discontinued
0.651	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7074	Phase 3
0.6497	Remote Similarity	NPD7472	Approved
0.6485	Remote Similarity	NPD6273	Approved
0.6481	Remote Similarity	NPD4628	Phase 3
0.648	Remote Similarity	NPD7808	Phase 3
0.6463	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7736	Approved
0.6442	Remote Similarity	NPD6190	Approved
0.6441	Remote Similarity	NPD7054	Approved
0.6429	Remote Similarity	NPD7028	Phase 2
0.6425	Remote Similarity	NPD7251	Discontinued
0.6424	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD1653	Approved
0.6403	Remote Similarity	NPD5765	Approved
0.64	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5763	Approved
0.6398	Remote Similarity	NPD6535	Approved
0.6398	Remote Similarity	NPD6534	Approved
0.6398	Remote Similarity	NPD5762	Approved
0.6395	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6912	Phase 3
0.6387	Remote Similarity	NPD7435	Discontinued
0.6383	Remote Similarity	NPD6412	Phase 2
0.638	Remote Similarity	NPD7003	Approved
0.638	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6797	Phase 2
0.6369	Remote Similarity	NPD6663	Approved
0.6369	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7610	Discontinued
0.635	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.635	Remote Similarity	NPD4225	Approved
0.635	Remote Similarity	NPD7638	Approved
0.6348	Remote Similarity	NPD5844	Phase 1
0.6329	Remote Similarity	NPD4140	Approved
0.6319	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD5048	Discontinued
0.6304	Remote Similarity	NPD7639	Approved
0.6304	Remote Similarity	NPD7640	Approved
0.6304	Remote Similarity	NPD7798	Approved
0.6302	Remote Similarity	NPD7698	Approved
0.6302	Remote Similarity	NPD7696	Phase 3
0.6302	Remote Similarity	NPD7697	Approved
0.6299	Remote Similarity	NPD3094	Phase 2
0.6296	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD3818	Discontinued
0.6292	Remote Similarity	NPD3751	Discontinued
0.6286	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD7874	Approved
0.6269	Remote Similarity	NPD7870	Phase 2
0.6269	Remote Similarity	NPD7871	Phase 2
0.6259	Remote Similarity	NPD5951	Approved
0.6257	Remote Similarity	NPD6212	Phase 3
0.6257	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD6213	Phase 3
0.6256	Remote Similarity	NPD7701	Phase 2
0.625	Remote Similarity	NPD6823	Phase 2
0.625	Remote Similarity	NPD3787	Discontinued
0.625	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2067	Discontinued
0.6243	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7095	Approved
0.6241	Remote Similarity	NPD5909	Discontinued
0.623	Remote Similarity	NPD6780	Approved
0.623	Remote Similarity	NPD6782	Approved
0.623	Remote Similarity	NPD6776	Approved
0.623	Remote Similarity	NPD6777	Approved
0.623	Remote Similarity	NPD6781	Approved
0.623	Remote Similarity	NPD6779	Approved
0.623	Remote Similarity	NPD6778	Approved
0.6225	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD7819	Suspended
0.6218	Remote Similarity	NPD7497	Discontinued
0.6216	Remote Similarity	NPD7115	Discovery
0.6207	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD3764	Approved
0.6188	Remote Similarity	NPD6355	Discontinued
0.6188	Remote Similarity	NPD5735	Approved
0.6181	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD8074	Phase 3
0.6164	Remote Similarity	NPD7714	Approved
0.6164	Remote Similarity	NPD7715	Approved
0.6162	Remote Similarity	NPD7801	Approved
0.6162	Remote Similarity	NPD7783	Phase 2
0.6162	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD3092	Approved
0.6144	Remote Similarity	NPD1091	Approved
0.614	Remote Similarity	NPD4380	Phase 2
0.6131	Remote Similarity	NPD8462	Phase 1
0.6131	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8651	Approved
0.6127	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.612	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6370	Approved
0.6114	Remote Similarity	NPD7075	Discontinued
0.6111	Remote Similarity	NPD41	Approved
0.6111	Remote Similarity	NPD5886	Approved
0.6108	Remote Similarity	NPD5058	Phase 3
0.6098	Remote Similarity	NPD6004	Phase 3
0.6098	Remote Similarity	NPD6005	Phase 3
0.6098	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6002	Phase 3
0.6095	Remote Similarity	NPD7314	Clinical (unspecified phase)

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