NPASS Compound

Structure

NPC475270 OpenBabel07101719522D 78 82 0 0 1 0 0 0 0 0999 V2000 4.6328 -3.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1272 4.1152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2007 -9.7791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2601 3.4690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0656 -8.1619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5974 -0.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5175 -0.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0242 -4.3181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1959 -3.9446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2923 -2.2593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4458 -4.6337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9403 3.1452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6171 -8.8833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5123 -4.9568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8543 -6.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9557 -6.6603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6009 -5.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9778 -6.8009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1349 -4.7720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3253 -5.9269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.6603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4133 -3.8241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3918 -6.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8986 -6.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4133 -2.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6993 0.5589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0067 2.8221 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0496 -8.0747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8757 0.4658 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8358 0.6987 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1687 -3.8241 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1799 -3.8574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5706 -1.3114 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6452 -5.6030 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7657 0.2358 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1349 -1.8884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1687 -2.8362 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0191 0.8828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3131 -2.3423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0856 0.5596 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7315 -4.5787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1480 -3.6829 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7475 -4.6660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4294 -1.1700 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4576 -2.8362 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8986 -0.4104 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8543 -0.4104 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9557 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8198 1.8521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4661 -7.1789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1940 1.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5804 -2.8744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4576 -3.8241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6452 -1.0573 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9778 0.1406 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1141 1.6466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0336 -1.4780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0242 -2.3423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2061 1.8528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3131 -1.3544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3390 1.2066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2990 -5.3873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1320 -3.5957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5664 1.2051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4501 -7.0917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4723 2.1286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8862 1.5290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3131 -4.3181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5964 -2.9616 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9246 -0.7281 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1793 -4.7720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5788 -0.7342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6009 -1.0573 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3310 -5.5617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2340 0.9479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9969 -1.9786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1793 -1.8884 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 11 14 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 24 34 1 0 0 0 0 25 36 1 0 0 0 0 26 67 1 0 0 0 0 27 4 1 1 0 0 0 27 49 1 0 0 0 0 28 5 1 1 0 0 0 28 50 1 0 0 0 0 29 6 1 1 0 0 0 29 30 1 0 0 0 0 29 51 1 0 0 0 0 30 7 1 6 0 0 0 30 56 1 0 0 0 0 31 8 1 1 0 0 0 31 37 1 0 0 0 0 31 68 1 0 0 0 0 32 9 1 6 0 0 0 32 43 1 0 0 0 0 32 69 1 0 0 0 0 33 10 1 1 0 0 0 33 44 1 0 0 0 0 33 70 1 0 0 0 0 34 23 1 1 0 0 0 34 71 1 0 0 0 0 35 26 1 1 0 0 0 35 38 1 0 0 0 0 35 72 1 0 0 0 0 36 57 2 0 0 0 0 36 73 1 0 0 0 0 37 39 1 0 0 0 0 37 58 1 6 0 0 0 38 40 1 0 0 0 0 38 59 1 6 0 0 0 39 45 1 0 0 0 0 39 60 1 1 0 0 0 40 46 1 0 0 0 0 40 61 1 1 0 0 0 41 42 1 0 0 0 0 41 43 1 0 0 0 0 41 62 1 6 0 0 0 42 52 1 0 0 0 0 42 63 1 1 0 0 0 43 74 1 1 0 0 0 44 47 1 0 0 0 0 44 76 1 6 0 0 0 45 53 1 0 0 0 0 45 77 1 6 0 0 0 46 54 1 0 0 0 0 46 78 1 6 0 0 0 47 48 1 0 0 0 0 47 73 1 1 0 0 0 48 55 1 0 0 0 0 48 75 1 1 0 0 0 49 64 2 0 0 0 0 49 67 1 0 0 0 0 50 65 2 0 0 0 0 50 74 1 0 0 0 0 51 66 2 0 0 0 0 51 75 1 0 0 0 0 52 69 1 0 0 0 0 52 76 1 6 0 0 0 53 68 1 1 0 0 0 53 71 1 0 0 0 0 54 72 1 1 0 0 0 54 77 1 0 0 0 0 55 70 1 1 0 0 0 55 78 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1122.62
Volume:	1108.683
LogP:	5.391
LogD:	4.049
LogS:	-4.454
# Rotatable Bonds:	19
TPSA:	320.65
# H-Bond Aceptor:	23
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.066
Synthetic Accessibility Score:	7.822
Fsp3:	0.927
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:	-5.325
MDCK Permeability:	0.00028810487128794193
Pgp-inhibitor:	1.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.492
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.327

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	89.19174194335938%
Volume Distribution (VD):	0.769
Pgp-substrate:	6.774776458740234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.837
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	1.533
Half-life (T1/2):	0.323

ADMET: Toxicity

hERG Blockers:	0.951
Human Hepatotoxicity (H-HT):	0.93
Drug-inuced Liver Injury (DILI):	0.765
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.292
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.232

Download Data

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

Natural Product: NPC475270

Natural Product ID:	NPC475270
*Common Name:**	Orizabin Xix
IUPAC Name:	n.a.
Synonyms:	Orizabin XIX
Standard InCHIKey:	ONBYPUFDFAQJFE-FGEZWTBKSA-N
Standard InCHI:	InChI=1S/C55H94O23/c1-11-14-20-23-34-24-21-18-16-15-17-19-22-25-36(57)73-47-44(76-52-42(63)41(62)43(32(9)69-52)74-50(65)28(5)13-3)33(10)70-55(48(47)75-51(66)29(6)30(7)56)78-46-40(61)38(59)35(26-67-49(64)27(4)12-2)72-54(46)77-45-39(60)37(58)31(8)68-53(45)71-34/h27-35,37-48,52-56,58-63H,11-26H2,1-10H3/t27-,28-,29-,30-,31+,32+,33-,34-,35+,37+,38+,39-,40-,41+,42+,43+,44-,45+,46+,47+,48+,52-,53-,54-,55-/m0/s1
SMILES:	CCCCC[C@H]1CCCCCCCCCC(=O)O[C@H]2[C@H]([C@H](O[C@H]3[C@H](O[C@H]4[C@H](O1)O[C@H](C)[C@H]([C@@H]4O)O)O[C@H](COC(=O)[C@H](CC)C)[C@H]([C@@H]3O)O)O[C@@H](C)[C@@H]2O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@H]1O)O)OC(=O)[C@H](CC)C)OC(=O)[C@H]([C@@H](O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502424
PubChem CID:	11018647
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*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
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	Roots	Mexican	n.a.	PMID[10479311]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	PMID[16562846]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[485183]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	512.0	ug.mL-1	PMID[485183]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	256.0	ug.mL-1	PMID[485183]

☑ 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 NPC475270 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	624
0.1-0.2	4158
0.2-0.3	11947
0.3-0.4	12424
0.4-0.5	7794
0.5-0.6	3767
0.6-0.7	1584
0.7-0.8	290
0.8-0.85	24
0.85-0.9	21
0.9-0.95	32
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477347
1.0	High Similarity	NPC475327
1.0	High Similarity	NPC476087
1.0	High Similarity	NPC238056
1.0	High Similarity	NPC173328
1.0	High Similarity	NPC475667
1.0	High Similarity	NPC269318
1.0	High Similarity	NPC297768
1.0	High Similarity	NPC186992
0.974	High Similarity	NPC60849
0.974	High Similarity	NPC477332
0.974	High Similarity	NPC472352
0.9733	High Similarity	NPC477346
0.9733	High Similarity	NPC85759
0.9733	High Similarity	NPC146992
0.9733	High Similarity	NPC294748
0.9733	High Similarity	NPC22742
0.9733	High Similarity	NPC158302
0.9733	High Similarity	NPC477344
0.9481	High Similarity	NPC472201
0.9481	High Similarity	NPC115013
0.9481	High Similarity	NPC477318
0.9481	High Similarity	NPC259294
0.9481	High Similarity	NPC119583
0.9481	High Similarity	NPC169345
0.9481	High Similarity	NPC472204
0.9481	High Similarity	NPC472205
0.9481	High Similarity	NPC472200
0.9481	High Similarity	NPC472202
0.9481	High Similarity	NPC477331
0.9481	High Similarity	NPC89843
0.9481	High Similarity	NPC290012
0.9481	High Similarity	NPC224953
0.9481	High Similarity	NPC143421
0.9481	High Similarity	NPC472203
0.9481	High Similarity	NPC27289
0.9481	High Similarity	NPC126685
0.9481	High Similarity	NPC477319
0.9481	High Similarity	NPC123204
0.9481	High Similarity	NPC307400
0.9481	High Similarity	NPC44782
0.9481	High Similarity	NPC184915
0.9481	High Similarity	NPC477317
0.9481	High Similarity	NPC183888
0.9351	High Similarity	NPC267592
0.9333	High Similarity	NPC477350
0.9211	High Similarity	NPC476781
0.9211	High Similarity	NPC476783
0.9211	High Similarity	NPC216883
0.9211	High Similarity	NPC476782
0.9091	High Similarity	NPC477326
0.9091	High Similarity	NPC477329
0.9091	High Similarity	NPC475425
0.9091	High Similarity	NPC113745
0.9091	High Similarity	NPC477323
0.9091	High Similarity	NPC477328
0.9091	High Similarity	NPC281563
0.9091	High Similarity	NPC477330
0.9091	High Similarity	NPC477320
0.9091	High Similarity	NPC146380
0.9091	High Similarity	NPC109887
0.9091	High Similarity	NPC477325
0.8933	High Similarity	NPC225748
0.8933	High Similarity	NPC206823
0.8933	High Similarity	NPC163812
0.8933	High Similarity	NPC39266
0.8933	High Similarity	NPC169085
0.8933	High Similarity	NPC9763
0.8667	High Similarity	NPC52268
0.8667	High Similarity	NPC53760
0.8533	High Similarity	NPC241265
0.8533	High Similarity	NPC211428
0.8533	High Similarity	NPC285003
0.8442	Intermediate Similarity	NPC291228
0.8442	Intermediate Similarity	NPC308096
0.8427	Intermediate Similarity	NPC475593
0.8427	Intermediate Similarity	NPC475241
0.8427	Intermediate Similarity	NPC475540
0.8427	Intermediate Similarity	NPC473765
0.8427	Intermediate Similarity	NPC473605
0.8427	Intermediate Similarity	NPC475164
0.8427	Intermediate Similarity	NPC475525
0.8427	Intermediate Similarity	NPC475375
0.8427	Intermediate Similarity	NPC476066
0.8415	Intermediate Similarity	NPC248415
0.84	Intermediate Similarity	NPC67099
0.84	Intermediate Similarity	NPC250619
0.84	Intermediate Similarity	NPC50228
0.84	Intermediate Similarity	NPC97736
0.8312	Intermediate Similarity	NPC185419
0.8312	Intermediate Similarity	NPC184550
0.8267	Intermediate Similarity	NPC206601
0.8202	Intermediate Similarity	NPC238264
0.8202	Intermediate Similarity	NPC477345
0.8202	Intermediate Similarity	NPC477348
0.814	Intermediate Similarity	NPC51662
0.8	Intermediate Similarity	NPC471761
0.8	Intermediate Similarity	NPC190418
0.8	Intermediate Similarity	NPC471760
0.8	Intermediate Similarity	NPC76881
0.8	Intermediate Similarity	NPC12040
0.7978	Intermediate Similarity	NPC477349
0.7802	Intermediate Similarity	NPC44682
0.7802	Intermediate Similarity	NPC163409
0.7733	Intermediate Similarity	NPC325773
0.7727	Intermediate Similarity	NPC314364
0.7662	Intermediate Similarity	NPC477756
0.7662	Intermediate Similarity	NPC477764
0.7662	Intermediate Similarity	NPC477752
0.7662	Intermediate Similarity	NPC477751
0.7629	Intermediate Similarity	NPC469827
0.759	Intermediate Similarity	NPC474003
0.7576	Intermediate Similarity	NPC207693
0.7564	Intermediate Similarity	NPC477754
0.7564	Intermediate Similarity	NPC477761
0.7564	Intermediate Similarity	NPC477759
0.7564	Intermediate Similarity	NPC477758
0.7564	Intermediate Similarity	NPC477760
0.75	Intermediate Similarity	NPC22709
0.7471	Intermediate Similarity	NPC473500
0.7471	Intermediate Similarity	NPC38295
0.7471	Intermediate Similarity	NPC470313
0.7471	Intermediate Similarity	NPC156089
0.7467	Intermediate Similarity	NPC477763
0.7467	Intermediate Similarity	NPC477757
0.7467	Intermediate Similarity	NPC477755
0.7467	Intermediate Similarity	NPC477762
0.7467	Intermediate Similarity	NPC477750
0.7467	Intermediate Similarity	NPC477753
0.7449	Intermediate Similarity	NPC231271
0.7449	Intermediate Similarity	NPC470519
0.7426	Intermediate Similarity	NPC470622
0.7416	Intermediate Similarity	NPC470657
0.7403	Intermediate Similarity	NPC6848
0.74	Intermediate Similarity	NPC469826
0.7374	Intermediate Similarity	NPC184805
0.7374	Intermediate Similarity	NPC273189
0.7333	Intermediate Similarity	NPC31349
0.7327	Intermediate Similarity	NPC469825
0.73	Intermediate Similarity	NPC471430
0.73	Intermediate Similarity	NPC126753
0.7282	Intermediate Similarity	NPC157571
0.7273	Intermediate Similarity	NPC267637
0.7241	Intermediate Similarity	NPC21693
0.7241	Intermediate Similarity	NPC236649
0.72	Intermediate Similarity	NPC320032
0.72	Intermediate Similarity	NPC317023
0.7184	Intermediate Similarity	NPC469824
0.7158	Intermediate Similarity	NPC215570
0.7129	Intermediate Similarity	NPC287269
0.7125	Intermediate Similarity	NPC32148
0.7087	Intermediate Similarity	NPC66513
0.7087	Intermediate Similarity	NPC471431
0.7075	Intermediate Similarity	NPC476992
0.7075	Intermediate Similarity	NPC75287
0.7075	Intermediate Similarity	NPC51465
0.7075	Intermediate Similarity	NPC288205
0.7075	Intermediate Similarity	NPC26626
0.7075	Intermediate Similarity	NPC305267
0.7071	Intermediate Similarity	NPC80640
0.7071	Intermediate Similarity	NPC310031
0.7071	Intermediate Similarity	NPC80191
0.7071	Intermediate Similarity	NPC227622
0.7067	Intermediate Similarity	NPC472025
0.7065	Intermediate Similarity	NPC470009
0.7053	Intermediate Similarity	NPC472198
0.7051	Intermediate Similarity	NPC268243
0.7048	Intermediate Similarity	NPC146563
0.7021	Intermediate Similarity	NPC472199
0.701	Intermediate Similarity	NPC472273
0.7009	Intermediate Similarity	NPC69811
0.7009	Intermediate Similarity	NPC309223
0.7009	Intermediate Similarity	NPC102505
0.7009	Intermediate Similarity	NPC104137
0.7009	Intermediate Similarity	NPC220160
0.7009	Intermediate Similarity	NPC286457
0.7009	Intermediate Similarity	NPC471580
0.7009	Intermediate Similarity	NPC33012
0.7009	Intermediate Similarity	NPC123522
0.7009	Intermediate Similarity	NPC475119
0.7009	Intermediate Similarity	NPC473452
0.7009	Intermediate Similarity	NPC8524
0.7009	Intermediate Similarity	NPC191827
0.7009	Intermediate Similarity	NPC475209
0.7009	Intermediate Similarity	NPC470876
0.7009	Intermediate Similarity	NPC85154
0.7009	Intermediate Similarity	NPC475514
0.7009	Intermediate Similarity	NPC473824
0.7	Intermediate Similarity	NPC288471
0.699	Remote Similarity	NPC228190
0.699	Remote Similarity	NPC87393
0.699	Remote Similarity	NPC236753
0.6981	Remote Similarity	NPC477465
0.6981	Remote Similarity	NPC475486
0.6981	Remote Similarity	NPC164389
0.6981	Remote Similarity	NPC54395
0.697	Remote Similarity	NPC476611
0.6961	Remote Similarity	NPC138219
0.6961	Remote Similarity	NPC475630
0.6961	Remote Similarity	NPC475234

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 NPC475270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	681
0.1-0.2	4082
0.2-0.3	2937
0.3-0.4	875
0.4-0.5	366
0.5-0.6	151
0.6-0.7	55
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8272	Intermediate Similarity	NPD7329	Approved
0.7467	Intermediate Similarity	NPD6123	Approved
0.7317	Intermediate Similarity	NPD3181	Approved
0.7125	Intermediate Similarity	NPD897	Approved
0.7125	Intermediate Similarity	NPD898	Approved
0.7125	Intermediate Similarity	NPD896	Approved
0.7071	Intermediate Similarity	NPD8086	Approved
0.7071	Intermediate Similarity	NPD8082	Approved
0.7071	Intermediate Similarity	NPD8139	Approved
0.7071	Intermediate Similarity	NPD8085	Approved
0.7071	Intermediate Similarity	NPD8083	Approved
0.7071	Intermediate Similarity	NPD8084	Approved
0.7071	Intermediate Similarity	NPD8138	Approved
0.703	Intermediate Similarity	NPD8393	Approved
0.7	Intermediate Similarity	NPD8275	Approved
0.7	Intermediate Similarity	NPD8276	Approved
0.6931	Remote Similarity	NPD8081	Approved
0.6796	Remote Similarity	NPD8140	Approved
0.6796	Remote Similarity	NPD8307	Discontinued
0.6765	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD7346	Approved
0.6667	Remote Similarity	NPD3730	Approved
0.6667	Remote Similarity	NPD8305	Approved
0.6667	Remote Similarity	NPD8306	Approved
0.6667	Remote Similarity	NPD3728	Approved
0.6607	Remote Similarity	NPD8515	Approved
0.6607	Remote Similarity	NPD8517	Approved
0.6607	Remote Similarity	NPD8516	Approved
0.6604	Remote Similarity	NPD8087	Discontinued
0.6569	Remote Similarity	NPD7139	Approved
0.6569	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7140	Approved
0.6545	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7909	Approved
0.6542	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD893	Approved
0.6533	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD891	Phase 3
0.6533	Remote Similarity	NPD888	Phase 3
0.6533	Remote Similarity	NPD892	Phase 3
0.6522	Remote Similarity	NPD3669	Approved
0.6522	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.646	Remote Similarity	NPD8513	Phase 3
0.642	Remote Similarity	NPD8961	Approved
0.64	Remote Similarity	NPD2269	Approved
0.6372	Remote Similarity	NPD8346	Approved
0.6372	Remote Similarity	NPD8347	Approved
0.6372	Remote Similarity	NPD8345	Approved
0.6348	Remote Similarity	NPD8328	Phase 3
0.6304	Remote Similarity	NPD1780	Approved
0.6304	Remote Similarity	NPD1779	Approved
0.6267	Remote Similarity	NPD905	Approved
0.6267	Remote Similarity	NPD904	Phase 3
0.6263	Remote Similarity	NPD8171	Discontinued
0.6262	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8301	Approved
0.625	Remote Similarity	NPD8300	Approved
0.6204	Remote Similarity	NPD6941	Approved
0.6162	Remote Similarity	NPD7983	Approved
0.6154	Remote Similarity	NPD4238	Approved
0.6154	Remote Similarity	NPD4802	Phase 2
0.6104	Remote Similarity	NPD887	Approved
0.6104	Remote Similarity	NPD895	Approved
0.6104	Remote Similarity	NPD889	Approved
0.6104	Remote Similarity	NPD894	Approved
0.6076	Remote Similarity	NPD2267	Suspended
0.6061	Remote Similarity	NPD6698	Approved
0.6061	Remote Similarity	NPD46	Approved
0.6034	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD8959	Approved
0.5983	Remote Similarity	NPD8080	Discontinued
0.5981	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD1447	Phase 3
0.5941	Remote Similarity	NPD1446	Phase 3
0.5932	Remote Similarity	NPD7829	Approved
0.5932	Remote Similarity	NPD7830	Approved
0.5917	Remote Similarity	NPD8448	Approved
0.5902	Remote Similarity	NPD8391	Approved
0.5902	Remote Similarity	NPD8390	Approved
0.5902	Remote Similarity	NPD8392	Approved
0.5897	Remote Similarity	NPD8444	Approved
0.5889	Remote Similarity	NPD1810	Approved
0.5889	Remote Similarity	NPD1811	Approved
0.5882	Remote Similarity	NPD8340	Approved
0.5882	Remote Similarity	NPD8341	Approved
0.5882	Remote Similarity	NPD8342	Approved
0.5882	Remote Similarity	NPD8299	Approved
0.5877	Remote Similarity	NPD6940	Discontinued
0.5875	Remote Similarity	NPD73	Approved
0.5867	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8451	Approved
0.5823	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.581	Remote Similarity	NPD2255	Approved
0.581	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD369	Approved
0.5769	Remote Similarity	NPD7839	Suspended
0.5714	Remote Similarity	NPD881	Approved
0.5691	Remote Similarity	NPD7319	Approved
0.5676	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD8074	Phase 3
0.563	Remote Similarity	NPD8269	Approved
0.563	Remote Similarity	NPD8266	Approved
0.563	Remote Similarity	NPD8268	Approved
0.563	Remote Similarity	NPD8267	Approved
0.5619	Remote Similarity	NPD6428	Approved
0.56	Remote Similarity	NPD8998	Phase 2
0.56	Remote Similarity	NPD8999	Phase 3
0.56	Remote Similarity	NPD8997	Approved
0.56	Remote Similarity	NPD8993	Phase 1
0.56	Remote Similarity	NPD9000	Phase 3

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