NPASS Compound

Structure

CID257211 OpenBabel06191716062D 78 86 0 0 1 0 0 0 0 0999 V2000 4.1361 8.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5160 5.9501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3626 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8740 -0.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 -2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3626 -1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3854 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5390 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5390 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 -2.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7268 4.6176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3891 7.2644 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4280 5.6971 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8463 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5390 -3.4205 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9798 3.6736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8463 -1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5390 -1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8463 1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3330 7.0114 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1190 6.3882 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2887 2.9826 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9244 -1.4659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5860 6.0675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0630 6.1352 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7707 -1.9545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3448 3.2355 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0781 -1.9545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7707 -2.9318 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8949 5.3764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3159 5.1913 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3854 -2.9318 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6171 -3.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0918 4.1795 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0781 -2.9318 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9510 5.6294 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6249 4.5002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8740 -1.1082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1868 2.8652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3854 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 -1.9545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8463 -0.4886 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 -3.3854 -1.9545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6927 0.9773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5390 -4.3977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9238 3.4207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 2.4432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0241 7.7025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8661 7.3321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5417 2.0386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9244 -0.4886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5299 5.8145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7540 6.8263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6171 -1.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6537 2.5445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2317 -1.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6171 -4.3977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4634 -2.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8513 -1.1082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 -0.2619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2428 3.1182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7829 4.8706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6980 6.5733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6809 4.7532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9244 -3.4205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1479 4.4325 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2599 4.9383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2317 -3.4205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8778 3.5563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 48 1 0 0 0 0 4 48 1 0 0 0 0 6 50 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 10 25 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 12 50 1 0 0 0 0 13 14 1 0 0 0 0 13 48 1 0 0 0 0 14 53 1 0 0 0 0 15 22 1 0 0 0 0 15 48 1 0 0 0 0 16 23 1 0 0 0 0 16 49 1 0 0 0 0 17 27 1 0 0 0 0 17 51 1 0 0 0 0 18 24 1 0 0 0 0 18 71 1 0 0 0 0 19 1 1 1 0 0 0 19 28 1 0 0 0 0 19 72 1 0 0 0 0 20 2 1 1 0 0 0 20 29 1 0 0 0 0 20 73 1 0 0 0 0 21 22 1 0 0 0 0 21 51 1 0 0 0 0 22 53 1 1 0 0 0 23 40 1 0 0 0 0 23 54 1 6 0 0 0 24 30 1 0 0 0 0 24 55 1 1 0 0 0 25 49 1 6 0 0 0 25 50 1 0 0 0 0 26 49 1 6 0 0 0 26 52 1 0 0 0 0 27 53 1 1 0 0 0 27 56 1 0 0 0 0 28 32 1 0 0 0 0 28 57 1 6 0 0 0 29 33 1 0 0 0 0 29 58 1 6 0 0 0 30 35 1 0 0 0 0 30 59 1 6 0 0 0 31 34 1 0 0 0 0 31 36 1 0 0 0 0 31 60 1 6 0 0 0 32 38 1 0 0 0 0 32 61 1 1 0 0 0 33 39 1 0 0 0 0 33 62 1 1 0 0 0 34 37 1 0 0 0 0 34 63 1 1 0 0 0 35 42 1 0 0 0 0 35 64 1 1 0 0 0 36 43 1 0 0 0 0 36 65 1 1 0 0 0 37 41 1 6 0 0 0 37 74 1 0 0 0 0 38 44 1 0 0 0 0 38 75 1 1 0 0 0 39 45 1 0 0 0 0 39 76 1 1 0 0 0 40 52 1 6 0 0 0 40 77 1 0 0 0 0 41 66 2 0 0 0 0 41 67 1 0 0 0 0 42 71 1 0 0 0 0 42 75 1 6 0 0 0 43 74 1 0 0 0 0 43 77 1 6 0 0 0 44 72 1 0 0 0 0 44 76 1 6 0 0 0 45 73 1 0 0 0 0 45 78 1 6 0 0 0 46 52 1 0 0 0 0 46 68 2 0 0 0 0 46 69 1 0 0 0 0 47 70 2 0 0 0 0 47 78 1 0 0 0 0 49 5 1 6 0 0 0 50 51 1 1 0 0 0 51 7 1 1 0 0 0 52 8 1 6 0 0 0 53 47 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1118.51
Volume:	1057.445
LogP:	0.293
LogD:	0.52
LogS:	-2.669
# Rotatable Bonds:	11
TPSA:	408.27
# H-Bond Aceptor:	25
# H-Bond Donor:	14
# Rings:	9
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.062
Synthetic Accessibility Score:	7.033
Fsp3:	0.906
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:	-6.716
MDCK Permeability:	0.00031349583878181875
Pgp-inhibitor:	0.003
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.994
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.279
Plasma Protein Binding (PPB):	49.70630645751953%
Volume Distribution (VD):	0.166
Pgp-substrate:	18.206552505493164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	0.063
Half-life (T1/2):	0.731

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.697
AMES Toxicity:	0.097
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.056
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.8

Download Data

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

Natural Product: NPC257211

Natural Product ID:	NPC257211
*Common Name:**	Zanhasaponin B
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(2S,3R,4S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-4-carboxy-8a-[(2S,3R,4R,5R,6S)-3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxycarbonyl-2,8-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms:
Standard InCHIKey:	AOIMXJGQCIOVFI-LIPHUQLUSA-N
Standard InCHI:	InChI=1S/C53H82O25/c1-19-28(57)32(61)38(75-42-35(64)30(59)24(55)18-71-42)44(72-19)76-39-33(62)29(58)20(2)73-45(39)78-47(70)53-14-13-48(3,4)15-22(53)21-9-10-25-49(5)16-23(54)40(77-43-36(65)31(60)34(63)37(74-43)41(66)67)52(8,46(68)69)26(49)11-12-50(25,6)51(21,7)17-27(53)56/h9,19-20,22-40,42-45,54-65H,10-18H2,1-8H3,(H,66,67)(H,68,69)/t19-,20-,22-,23-,24+,25+,26+,27+,28-,29-,30-,31-,32+,33+,34-,35+,36+,37-,38+,39+,40-,42-,43-,44-,45-,49+,50+,51+,52-,53+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@@H]([C@H]([C@H](C)O[C@H]1OC(=O)[C@]12CCC(C)(C)C[C@H]1C1=CC[C@@H]3[C@@]4(C)C[C@@H]([C@@H]([C@](C)([C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)C(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443894
PubChem CID:	44593350
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
NPO22492	Zanha africana	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9051916]
NPO22492	Zanha africana	Species	Sapindaceae	Eukaryota	root bark	n.a.	n.a.	PMID[9392883]
NPO25719	Eria aurantiaca	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22492	Zanha africana	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23090	Eperua leucantha	Species	Fabaceae	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	1

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2586	Individual Protein	Phospholipase A2, acidic	Naja naja	IC50	=	440000.0	nM	PMID[553987]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	20.0	ug	PMID[553986]

☑ 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 NPC257211 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	287
0.1-0.2	1985
0.2-0.3	5423
0.3-0.4	10446
0.4-0.5	11143
0.5-0.6	6931
0.6-0.7	3726
0.7-0.8	1794
0.8-0.85	382
0.85-0.9	101
0.9-0.95	356
0.95-1	123

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC236870
0.9912	High Similarity	NPC33068
0.9912	High Similarity	NPC80986
0.9912	High Similarity	NPC21691
0.9912	High Similarity	NPC10607
0.9912	High Similarity	NPC187290
0.9912	High Similarity	NPC4749
0.9912	High Similarity	NPC475591
0.9912	High Similarity	NPC213952
0.9826	High Similarity	NPC284449
0.9825	High Similarity	NPC283417
0.9825	High Similarity	NPC302543
0.9825	High Similarity	NPC200049
0.9825	High Similarity	NPC258617
0.9823	High Similarity	NPC223301
0.9823	High Similarity	NPC187618
0.9823	High Similarity	NPC302887
0.9823	High Similarity	NPC64715
0.9823	High Similarity	NPC297263
0.9823	High Similarity	NPC22956
0.9823	High Similarity	NPC171544
0.9823	High Similarity	NPC104372
0.9823	High Similarity	NPC301449
0.9823	High Similarity	NPC222580
0.9823	High Similarity	NPC114484
0.9823	High Similarity	NPC11242
0.9823	High Similarity	NPC62725
0.9823	High Similarity	NPC86222
0.9823	High Similarity	NPC159309
0.9823	High Similarity	NPC31838
0.9739	High Similarity	NPC23275
0.9739	High Similarity	NPC160452
0.9737	High Similarity	NPC162574
0.9737	High Similarity	NPC313110
0.9737	High Similarity	NPC131469
0.9735	High Similarity	NPC118440
0.9735	High Similarity	NPC236657
0.9655	High Similarity	NPC475368
0.9655	High Similarity	NPC181066
0.9655	High Similarity	NPC469947
0.9655	High Similarity	NPC470218
0.9652	High Similarity	NPC30735
0.9652	High Similarity	NPC44716
0.9652	High Similarity	NPC235405
0.9652	High Similarity	NPC281148
0.9652	High Similarity	NPC2370
0.9646	High Similarity	NPC180550
0.9646	High Similarity	NPC473884
0.9646	High Similarity	NPC475171
0.9646	High Similarity	NPC472949
0.9646	High Similarity	NPC208381
0.9646	High Similarity	NPC39211
0.9646	High Similarity	NPC192791
0.9646	High Similarity	NPC469945
0.9646	High Similarity	NPC35405
0.9646	High Similarity	NPC6377
0.9646	High Similarity	NPC11551
0.9646	High Similarity	NPC309780
0.9646	High Similarity	NPC114441
0.9646	High Similarity	NPC214484
0.9646	High Similarity	NPC157868
0.9569	High Similarity	NPC471963
0.9569	High Similarity	NPC247315
0.9569	High Similarity	NPC470477
0.9569	High Similarity	NPC471962
0.9565	High Similarity	NPC249848
0.9565	High Similarity	NPC40775
0.9565	High Similarity	NPC235438
0.9565	High Similarity	NPC107966
0.9558	High Similarity	NPC286347
0.9492	High Similarity	NPC470475
0.9483	High Similarity	NPC471961
0.9483	High Similarity	NPC262199
0.9483	High Similarity	NPC478066
0.9483	High Similarity	NPC14617
0.9483	High Similarity	NPC471964
0.9483	High Similarity	NPC202666
0.9478	High Similarity	NPC31193
0.9478	High Similarity	NPC75417
0.9478	High Similarity	NPC242840
0.9469	High Similarity	NPC300419
0.9469	High Similarity	NPC473824
0.9469	High Similarity	NPC224121
0.9469	High Similarity	NPC475119
0.9417	High Similarity	NPC476776
0.9397	High Similarity	NPC471965
0.9391	High Similarity	NPC294112
0.9386	High Similarity	NPC237191
0.9386	High Similarity	NPC109588
0.9381	High Similarity	NPC37134
0.9381	High Similarity	NPC476992
0.9381	High Similarity	NPC288205
0.9381	High Similarity	NPC51465
0.9381	High Similarity	NPC75287
0.9381	High Similarity	NPC26626
0.9381	High Similarity	NPC305267
0.9381	High Similarity	NPC291903
0.9333	High Similarity	NPC476775
0.9333	High Similarity	NPC271610
0.9333	High Similarity	NPC476774
0.9333	High Similarity	NPC476780
0.9328	High Similarity	NPC470476
0.9322	High Similarity	NPC285091
0.9304	High Similarity	NPC51564
0.9304	High Similarity	NPC471577
0.9304	High Similarity	NPC207738
0.9304	High Similarity	NPC135849
0.9304	High Similarity	NPC25663
0.9298	High Similarity	NPC123522
0.9298	High Similarity	NPC85154
0.9298	High Similarity	NPC470876
0.9298	High Similarity	NPC33012
0.9298	High Similarity	NPC473452
0.9298	High Similarity	NPC8524
0.9298	High Similarity	NPC286457
0.9298	High Similarity	NPC475514
0.9298	High Similarity	NPC191827
0.9298	High Similarity	NPC309223
0.9298	High Similarity	NPC69811
0.9298	High Similarity	NPC102505
0.9298	High Similarity	NPC475209
0.9298	High Similarity	NPC104137
0.9298	High Similarity	NPC220160
0.9292	High Similarity	NPC475486
0.9292	High Similarity	NPC164389
0.9262	High Similarity	NPC476778
0.9262	High Similarity	NPC476777
0.9256	High Similarity	NPC178264
0.9256	High Similarity	NPC192765
0.9256	High Similarity	NPC30279
0.9256	High Similarity	NPC46823
0.9256	High Similarity	NPC312650
0.9256	High Similarity	NPC71391
0.9256	High Similarity	NPC473918
0.9256	High Similarity	NPC277212
0.925	High Similarity	NPC88311
0.925	High Similarity	NPC472267
0.925	High Similarity	NPC273878
0.925	High Similarity	NPC244296
0.925	High Similarity	NPC269484
0.925	High Similarity	NPC477196
0.925	High Similarity	NPC252657
0.925	High Similarity	NPC47995
0.925	High Similarity	NPC470912
0.925	High Similarity	NPC11577
0.925	High Similarity	NPC82380
0.925	High Similarity	NPC1314
0.925	High Similarity	NPC470518
0.925	High Similarity	NPC9470
0.925	High Similarity	NPC115656
0.925	High Similarity	NPC107536
0.925	High Similarity	NPC252289
0.925	High Similarity	NPC305793
0.925	High Similarity	NPC280029
0.925	High Similarity	NPC141600
0.925	High Similarity	NPC97918
0.925	High Similarity	NPC265841
0.9231	High Similarity	NPC275343
0.9224	High Similarity	NPC144644
0.9224	High Similarity	NPC473645
0.9224	High Similarity	NPC37860
0.9224	High Similarity	NPC110385
0.9224	High Similarity	NPC267694
0.9224	High Similarity	NPC476991
0.9224	High Similarity	NPC142151
0.9224	High Similarity	NPC153673
0.9217	High Similarity	NPC473459
0.9217	High Similarity	NPC232237
0.9217	High Similarity	NPC105800
0.9217	High Similarity	NPC470514
0.9217	High Similarity	NPC470513
0.9211	High Similarity	NPC161674
0.9211	High Similarity	NPC471384
0.9204	High Similarity	NPC114287
0.9204	High Similarity	NPC151543
0.9204	High Similarity	NPC155410
0.9204	High Similarity	NPC475287
0.9204	High Similarity	NPC73318
0.9204	High Similarity	NPC309714
0.9204	High Similarity	NPC133818
0.9204	High Similarity	NPC251263
0.9204	High Similarity	NPC473343
0.9204	High Similarity	NPC166422
0.9204	High Similarity	NPC323341
0.9204	High Similarity	NPC46665
0.9204	High Similarity	NPC163183
0.9204	High Similarity	NPC475467
0.9204	High Similarity	NPC238935
0.9204	High Similarity	NPC192600
0.9204	High Similarity	NPC219180
0.9204	High Similarity	NPC150400
0.9204	High Similarity	NPC473826
0.9204	High Similarity	NPC96641
0.9204	High Similarity	NPC134835
0.9204	High Similarity	NPC174720
0.9204	High Similarity	NPC241909
0.9204	High Similarity	NPC295823
0.9204	High Similarity	NPC475208
0.9204	High Similarity	NPC114304
0.9187	High Similarity	NPC279915

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 NPC257211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	2301
0.2-0.3	3844
0.3-0.4	1753
0.4-0.5	565
0.5-0.6	247
0.6-0.7	123
0.7-0.8	37
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9483	High Similarity	NPD8328	Phase 3
0.9298	High Similarity	NPD8295	Clinical (unspecified phase)
0.8362	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD7736	Approved
0.7934	Intermediate Similarity	NPD8133	Approved
0.792	Intermediate Similarity	NPD8517	Approved
0.792	Intermediate Similarity	NPD8515	Approved
0.792	Intermediate Similarity	NPD8516	Approved
0.7778	Intermediate Similarity	NPD8513	Phase 3
0.7752	Intermediate Similarity	NPD8293	Discontinued
0.7634	Intermediate Similarity	NPD7319	Approved
0.7578	Intermediate Similarity	NPD6370	Approved
0.7538	Intermediate Similarity	NPD7507	Approved
0.7521	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7492	Approved
0.7438	Intermediate Similarity	NPD6412	Phase 2
0.7422	Intermediate Similarity	NPD6319	Approved
0.7422	Intermediate Similarity	NPD6054	Approved
0.7422	Intermediate Similarity	NPD8294	Approved
0.7422	Intermediate Similarity	NPD8377	Approved
0.7422	Intermediate Similarity	NPD6059	Approved
0.7405	Intermediate Similarity	NPD6616	Approved
0.7377	Intermediate Similarity	NPD6686	Approved
0.7364	Intermediate Similarity	NPD8296	Approved
0.7364	Intermediate Similarity	NPD8380	Approved
0.7364	Intermediate Similarity	NPD8379	Approved
0.7364	Intermediate Similarity	NPD8335	Approved
0.7364	Intermediate Similarity	NPD8378	Approved
0.735	Intermediate Similarity	NPD7902	Approved
0.7348	Intermediate Similarity	NPD7078	Approved
0.728	Intermediate Similarity	NPD6882	Approved
0.728	Intermediate Similarity	NPD8297	Approved
0.7241	Intermediate Similarity	NPD7748	Approved
0.7231	Intermediate Similarity	NPD6016	Approved
0.7231	Intermediate Similarity	NPD8033	Approved
0.7231	Intermediate Similarity	NPD6015	Approved
0.72	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6009	Approved
0.7177	Intermediate Similarity	NPD6373	Approved
0.7177	Intermediate Similarity	NPD6372	Approved
0.7176	Intermediate Similarity	NPD5988	Approved
0.7131	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7900	Approved
0.7094	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7516	Approved
0.7073	Intermediate Similarity	NPD7128	Approved
0.7073	Intermediate Similarity	NPD6675	Approved
0.7073	Intermediate Similarity	NPD6402	Approved
0.7073	Intermediate Similarity	NPD5739	Approved
0.7069	Intermediate Similarity	NPD7515	Phase 2
0.7063	Intermediate Similarity	NPD6650	Approved
0.7063	Intermediate Similarity	NPD6649	Approved
0.7	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD7328	Approved
0.697	Remote Similarity	NPD6921	Approved
0.696	Remote Similarity	NPD6881	Approved
0.696	Remote Similarity	NPD7320	Approved
0.696	Remote Similarity	NPD6899	Approved
0.6953	Remote Similarity	NPD4632	Approved
0.6929	Remote Similarity	NPD8130	Phase 1
0.6912	Remote Similarity	NPD6033	Approved
0.688	Remote Similarity	NPD5697	Approved
0.688	Remote Similarity	NPD5701	Approved
0.685	Remote Similarity	NPD6883	Approved
0.685	Remote Similarity	NPD7290	Approved
0.685	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD7503	Approved
0.6838	Remote Similarity	NPD8074	Phase 3
0.6797	Remote Similarity	NPD6869	Approved
0.6797	Remote Similarity	NPD6617	Approved
0.6797	Remote Similarity	NPD6847	Approved
0.678	Remote Similarity	NPD8035	Phase 2
0.678	Remote Similarity	NPD8034	Phase 2
0.678	Remote Similarity	NPD6411	Approved
0.6772	Remote Similarity	NPD6014	Approved
0.6772	Remote Similarity	NPD6012	Approved
0.6772	Remote Similarity	NPD6013	Approved
0.6741	Remote Similarity	NPD7604	Phase 2
0.6719	Remote Similarity	NPD4634	Approved
0.6716	Remote Similarity	NPD5983	Phase 2
0.6693	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7115	Discovery
0.6642	Remote Similarity	NPD6336	Discontinued
0.6641	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6101	Approved
0.6589	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7638	Approved
0.6583	Remote Similarity	NPD6399	Phase 3
0.6532	Remote Similarity	NPD7640	Approved
0.6532	Remote Similarity	NPD7639	Approved
0.6504	Remote Similarity	NPD6083	Phase 2
0.6504	Remote Similarity	NPD6084	Phase 2
0.6504	Remote Similarity	NPD4755	Approved
0.65	Remote Similarity	NPD7983	Approved
0.6496	Remote Similarity	NPD6067	Discontinued
0.6471	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6274	Approved
0.646	Remote Similarity	NPD7329	Approved
0.646	Remote Similarity	NPD7645	Phase 2
0.6458	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4225	Approved
0.6446	Remote Similarity	NPD5778	Approved
0.6446	Remote Similarity	NPD5779	Approved
0.6446	Remote Similarity	NPD8171	Discontinued
0.6444	Remote Similarity	NPD7101	Approved
0.6444	Remote Similarity	NPD7100	Approved
0.6423	Remote Similarity	NPD4697	Phase 3
0.6423	Remote Similarity	NPD8080	Discontinued
0.641	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6008	Approved
0.64	Remote Similarity	NPD4700	Approved
0.64	Remote Similarity	NPD5286	Approved
0.64	Remote Similarity	NPD4696	Approved
0.64	Remote Similarity	NPD5285	Approved
0.6389	Remote Similarity	NPD8415	Approved
0.637	Remote Similarity	NPD6335	Approved
0.6357	Remote Similarity	NPD8448	Approved
0.6357	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.635	Remote Similarity	NPD6908	Approved
0.635	Remote Similarity	NPD6909	Approved
0.6343	Remote Similarity	NPD6868	Approved
0.6338	Remote Similarity	NPD8392	Approved
0.6338	Remote Similarity	NPD8391	Approved
0.6338	Remote Similarity	NPD8390	Approved
0.6333	Remote Similarity	NPD5328	Approved
0.6331	Remote Similarity	NPD8341	Approved
0.6331	Remote Similarity	NPD8299	Approved
0.6331	Remote Similarity	NPD8342	Approved
0.6331	Remote Similarity	NPD8340	Approved
0.632	Remote Similarity	NPD5696	Approved
0.6319	Remote Similarity	NPD8450	Suspended
0.6303	Remote Similarity	NPD3573	Approved
0.6299	Remote Similarity	NPD5224	Approved
0.6299	Remote Similarity	NPD5225	Approved
0.6299	Remote Similarity	NPD5211	Phase 2
0.6299	Remote Similarity	NPD5226	Approved
0.6299	Remote Similarity	NPD4633	Approved
0.6296	Remote Similarity	NPD6317	Approved
0.6296	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.629	Remote Similarity	NPD5221	Approved
0.629	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.629	Remote Similarity	NPD5222	Approved
0.6286	Remote Similarity	NPD8451	Approved
0.6279	Remote Similarity	NPD4768	Approved
0.6279	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD6672	Approved
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD8449	Approved
0.625	Remote Similarity	NPD6313	Approved
0.625	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD6314	Approved
0.625	Remote Similarity	NPD5175	Approved
0.624	Remote Similarity	NPD5173	Approved
0.623	Remote Similarity	NPD6079	Approved
0.6224	Remote Similarity	NPD5956	Approved
0.622	Remote Similarity	NPD5223	Approved
0.6218	Remote Similarity	NPD3618	Phase 1
0.621	Remote Similarity	NPD5695	Phase 3
0.6202	Remote Similarity	NPD5141	Approved
0.6198	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD8336	Approved
0.6197	Remote Similarity	NPD8337	Approved
0.619	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD4730	Approved
0.6183	Remote Similarity	NPD4729	Approved
0.6168	Remote Similarity	NPD7799	Discontinued
0.616	Remote Similarity	NPD7839	Suspended
0.6148	Remote Similarity	NPD46	Approved
0.6148	Remote Similarity	NPD6698	Approved
0.6143	Remote Similarity	NPD7829	Approved
0.6143	Remote Similarity	NPD7830	Approved
0.6138	Remote Similarity	NPD8338	Approved
0.6124	Remote Similarity	NPD4754	Approved
0.6116	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD8444	Approved
0.6115	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD3669	Approved
0.6102	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.609	Remote Similarity	NPD5249	Phase 3
0.609	Remote Similarity	NPD5250	Approved
0.609	Remote Similarity	NPD5251	Approved
0.609	Remote Similarity	NPD5248	Approved
0.609	Remote Similarity	NPD5247	Approved
0.6069	Remote Similarity	NPD7260	Phase 2
0.6068	Remote Similarity	NPD1779	Approved
0.6068	Remote Similarity	NPD1780	Approved
0.6063	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5128	Approved
0.605	Remote Similarity	NPD4786	Approved
0.6047	Remote Similarity	NPD7632	Discontinued
0.604	Remote Similarity	NPD6333	Approved
0.604	Remote Similarity	NPD6334	Approved
0.6039	Remote Similarity	NPD7625	Phase 1
0.6023	Remote Similarity	NPD8368	Discontinued
0.6017	Remote Similarity	NPD3667	Approved
0.6014	Remote Similarity	NPD7641	Discontinued
0.6	Remote Similarity	NPD5282	Discontinued

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