NPASS Compound

Structure

NPC476096 OpenBabel07101719172D 63 66 0 0 1 0 0 0 0 0999 V2000 -3.0895 -2.2597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0361 5.7340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3341 4.7513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4925 -0.7778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2506 -0.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9544 1.5366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4831 4.2600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1747 -1.9007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0361 4.7513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3341 -3.3992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7560 -3.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1422 2.7860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2912 3.2773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1422 1.8033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9122 -3.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2292 -3.0584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4065 -2.5134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4402 2.7860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2912 1.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4390 -3.0584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1994 -2.6607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5891 1.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1599 -2.1544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7381 1.8033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2900 -1.5844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6682 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1851 4.2600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5208 -0.6314 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8916 0.5347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9827 1.6830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3679 3.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4402 1.8033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8676 -2.6607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4917 -2.1544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1851 0.3293 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2463 -1.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8871 1.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3072 -0.0871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1851 1.3120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7291 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3341 1.8033 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4831 1.3120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3645 -0.4571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1851 3.2773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5781 -1.0013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4831 0.3293 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5042 1.3030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6237 2.5978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2190 4.2600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6358 -3.2734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2043 -0.7827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8871 0.3293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0361 2.7860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0327 -0.4571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1563 -1.0885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9199 0.6811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3700 0.9147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3679 1.8033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6218 -1.5844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3341 -0.1620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0361 1.8033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3341 2.7860 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 8 1 0 0 0 0 2 9 1 0 0 0 0 3 27 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 17 1 0 0 0 0 9 27 2 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 18 32 2 0 0 0 0 19 32 1 0 0 0 0 20 33 1 0 0 0 0 21 34 1 0 0 0 0 22 24 2 0 0 0 0 22 32 1 0 0 0 0 23 25 1 0 0 0 0 23 33 1 0 0 0 0 24 37 1 0 0 0 0 25 36 1 0 0 0 0 26 54 1 0 0 0 0 27 44 1 0 0 0 0 28 4 1 6 0 0 0 28 38 1 0 0 0 0 28 55 1 0 0 0 0 29 47 2 0 0 0 0 29 56 1 0 0 0 0 30 48 2 0 0 0 0 30 57 1 0 0 0 0 31 49 2 0 0 0 0 31 58 1 0 0 0 0 33 50 2 0 0 0 0 34 17 1 6 0 0 0 34 59 1 0 0 0 0 35 26 1 1 0 0 0 35 39 1 0 0 0 0 35 60 1 0 0 0 0 36 51 2 0 0 0 0 36 54 1 0 0 0 0 37 52 2 0 0 0 0 37 61 1 0 0 0 0 38 40 1 0 0 0 0 38 56 1 6 0 0 0 39 41 1 0 0 0 0 39 61 1 6 0 0 0 40 43 1 0 0 0 0 40 57 1 6 0 0 0 41 42 1 0 0 0 0 41 62 1 1 0 0 0 42 46 1 0 0 0 0 42 58 1 6 0 0 0 43 45 1 0 0 0 0 43 63 1 1 0 0 0 44 53 2 0 0 0 0 44 62 1 0 0 0 0 45 55 1 6 0 0 0 45 59 1 0 0 0 0 46 60 1 1 0 0 0 46 63 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	886.4
Volume:	887.742
LogP:	4.638
LogD:	2.856
LogS:	-4.788
# Rotatable Bonds:	15
TPSA:	211.79
# H-Bond Aceptor:	17
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.16
Synthetic Accessibility Score:	6.674
Fsp3:	0.63
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.903
MDCK Permeability:	8.313530270243064e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.275
Human Intestinal Absorption (HIA):	0.221
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	87.6043930053711%
Volume Distribution (VD):	2.272
Pgp-substrate:	5.8717570304870605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.278
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.693
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.968
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.966
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	2.251
Half-life (T1/2):	0.597

ADMET: Toxicity

hERG Blockers:	0.419
Human Hepatotoxicity (H-HT):	0.993
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.287
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.062
Skin Sensitization:	0.947
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.065

Download Data

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

Natural Product: NPC476096

Natural Product ID:	NPC476096
*Common Name:**	NYGAQLGOMHZMDL-RTCKPQKQSA-N
IUPAC Name:	n.a.
Synonyms:	3',2'-O-Diacetylipomoeassin A
Standard InCHIKey:	NYGAQLGOMHZMDL-RTCKPQKQSA-N
Standard InCHI:	InChI=1S/C46H62O17/c1-8-17-34-21-16-11-10-15-20-33(50)23-25-36(51)54-26-35-39(61-37(52)24-22-32-18-13-12-14-19-32)41(62-44(53)27(3)9-2)42(58-31(7)49)46(60-35)63-43-40(57-30(6)48)38(56-29(5)47)28(4)55-45(43)59-34/h9,12-14,18-19,22,24,28,34-35,38-43,45-46H,8,10-11,15-17,20-21,23,25-26H2,1-7H3/b24-22+,27-9+/t28-,34+,35-,38+,39-,40+,41+,42-,43-,45+,46+/m1/s1
SMILES:	CCC[C@H]1CCCCCCC(=O)CCC(=O)OC[C@H]2O[C@@H](O[C@H]3[C@H](O1)O[C@H](C)[C@@H]([C@@H]3OC(=O)C)OC(=O)C)[C@H](OC(=O)C)[C@H]([C@@H]2OC(=O)/C=C/c1ccccc1)OC(=O)/C(=C/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525977
PubChem CID:	11216755
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002967] Hexacarboxylic acids and derivatives

*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
NPO17901	Ipomoea squamosa	Species	Convolvulaceae	Eukaryota	leaves	Suriname rainforest	n.a.	PMID[15844934]
NPO17901	Ipomoea squamosa	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	15800.0	nM	PMID[519920]

☑ 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 NPC476096 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	265
0.1-0.2	1056
0.2-0.3	2358
0.3-0.4	6717
0.4-0.5	11870
0.5-0.6	16054
0.6-0.7	3928
0.7-0.8	413
0.8-0.85	14
0.85-0.9	15
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9569	High Similarity	NPC473881
0.9483	High Similarity	NPC140561
0.9483	High Similarity	NPC141970
0.925	High Similarity	NPC231627
0.9174	High Similarity	NPC237182
0.9174	High Similarity	NPC226101
0.9	High Similarity	NPC162925
0.9	High Similarity	NPC87153
0.8926	High Similarity	NPC77651
0.8926	High Similarity	NPC28069
0.8852	High Similarity	NPC35338
0.8852	High Similarity	NPC204214
0.8852	High Similarity	NPC10121
0.8852	High Similarity	NPC198918
0.8852	High Similarity	NPC124878
0.8852	High Similarity	NPC63404
0.8852	High Similarity	NPC290276
0.8852	High Similarity	NPC92283
0.8852	High Similarity	NPC10883
0.8852	High Similarity	NPC231888
0.878	High Similarity	NPC471025
0.871	High Similarity	NPC471024
0.8548	High Similarity	NPC471026
0.8548	High Similarity	NPC147032
0.8448	Intermediate Similarity	NPC470825
0.824	Intermediate Similarity	NPC57607
0.819	Intermediate Similarity	NPC184633
0.8189	Intermediate Similarity	NPC148026
0.8151	Intermediate Similarity	NPC474641
0.811	Intermediate Similarity	NPC114096
0.8095	Intermediate Similarity	NPC244454
0.8062	Intermediate Similarity	NPC11025
0.8	Intermediate Similarity	NPC289415
0.8	Intermediate Similarity	NPC475478
0.8	Intermediate Similarity	NPC319995
0.7984	Intermediate Similarity	NPC301857
0.7956	Intermediate Similarity	NPC111466
0.7939	Intermediate Similarity	NPC471880
0.7939	Intermediate Similarity	NPC475569
0.7934	Intermediate Similarity	NPC29607
0.7907	Intermediate Similarity	NPC195224
0.7899	Intermediate Similarity	NPC264270
0.7899	Intermediate Similarity	NPC40085
0.7899	Intermediate Similarity	NPC43584
0.7891	Intermediate Similarity	NPC470818
0.7883	Intermediate Similarity	NPC284957
0.7874	Intermediate Similarity	NPC469742
0.7863	Intermediate Similarity	NPC17567
0.7829	Intermediate Similarity	NPC473423
0.782	Intermediate Similarity	NPC470143
0.782	Intermediate Similarity	NPC322503
0.7803	Intermediate Similarity	NPC475493
0.7786	Intermediate Similarity	NPC27712
0.7778	Intermediate Similarity	NPC229600
0.7759	Intermediate Similarity	NPC469527
0.7734	Intermediate Similarity	NPC138798
0.7727	Intermediate Similarity	NPC469519
0.7727	Intermediate Similarity	NPC472418
0.771	Intermediate Similarity	NPC225103
0.7687	Intermediate Similarity	NPC136608
0.7687	Intermediate Similarity	NPC38420
0.7652	Intermediate Similarity	NPC473443
0.7652	Intermediate Similarity	NPC472388
0.763	Intermediate Similarity	NPC473216
0.763	Intermediate Similarity	NPC473399
0.7603	Intermediate Similarity	NPC30563
0.7594	Intermediate Similarity	NPC472361
0.7591	Intermediate Similarity	NPC475195
0.7591	Intermediate Similarity	NPC101686
0.7591	Intermediate Similarity	NPC469364
0.7591	Intermediate Similarity	NPC65262
0.7583	Intermediate Similarity	NPC40178
0.7581	Intermediate Similarity	NPC476476
0.7574	Intermediate Similarity	NPC263829
0.7556	Intermediate Similarity	NPC473359
0.7554	Intermediate Similarity	NPC473755
0.7554	Intermediate Similarity	NPC475513
0.7538	Intermediate Similarity	NPC145287
0.7537	Intermediate Similarity	NPC472394
0.7537	Intermediate Similarity	NPC235294
0.7537	Intermediate Similarity	NPC46137
0.7537	Intermediate Similarity	NPC209851
0.7537	Intermediate Similarity	NPC80599
0.7534	Intermediate Similarity	NPC87403
0.7521	Intermediate Similarity	NPC474148
0.7521	Intermediate Similarity	NPC276061
0.7518	Intermediate Similarity	NPC471345
0.75	Intermediate Similarity	NPC106677
0.75	Intermediate Similarity	NPC47536
0.75	Intermediate Similarity	NPC169398
0.75	Intermediate Similarity	NPC329657
0.7483	Intermediate Similarity	NPC477735
0.7481	Intermediate Similarity	NPC472437
0.7481	Intermediate Similarity	NPC473082
0.7481	Intermediate Similarity	NPC159811
0.748	Intermediate Similarity	NPC470814
0.746	Intermediate Similarity	NPC469574
0.7447	Intermediate Similarity	NPC293154
0.7434	Intermediate Similarity	NPC77273
0.7432	Intermediate Similarity	NPC477736
0.7426	Intermediate Similarity	NPC471911
0.7426	Intermediate Similarity	NPC4242
0.7424	Intermediate Similarity	NPC267733
0.7424	Intermediate Similarity	NPC276047
0.7417	Intermediate Similarity	NPC474111
0.7417	Intermediate Similarity	NPC329705
0.7413	Intermediate Similarity	NPC212808
0.741	Intermediate Similarity	NPC475400
0.741	Intermediate Similarity	NPC324262
0.741	Intermediate Similarity	NPC62800
0.7407	Intermediate Similarity	NPC281798
0.7407	Intermediate Similarity	NPC138777
0.7407	Intermediate Similarity	NPC246869
0.7407	Intermediate Similarity	NPC225384
0.7405	Intermediate Similarity	NPC317163
0.7405	Intermediate Similarity	NPC473083
0.7397	Intermediate Similarity	NPC69425
0.7394	Intermediate Similarity	NPC296659
0.7394	Intermediate Similarity	NPC471028
0.7394	Intermediate Similarity	NPC202391
0.7391	Intermediate Similarity	NPC184109
0.7377	Intermediate Similarity	NPC93084
0.7377	Intermediate Similarity	NPC174099
0.7377	Intermediate Similarity	NPC251854
0.7376	Intermediate Similarity	NPC148080
0.7376	Intermediate Similarity	NPC469623
0.7368	Intermediate Similarity	NPC173150
0.7368	Intermediate Similarity	NPC471882
0.7368	Intermediate Similarity	NPC45224
0.7368	Intermediate Similarity	NPC471881
0.7368	Intermediate Similarity	NPC35288
0.7368	Intermediate Similarity	NPC288416
0.7368	Intermediate Similarity	NPC156692
0.7368	Intermediate Similarity	NPC230331
0.7368	Intermediate Similarity	NPC103533
0.7364	Intermediate Similarity	NPC473439
0.7364	Intermediate Similarity	NPC300827
0.7357	Intermediate Similarity	NPC475530
0.7357	Intermediate Similarity	NPC473799
0.7357	Intermediate Similarity	NPC77493
0.7355	Intermediate Similarity	NPC20485
0.7348	Intermediate Similarity	NPC470816
0.7347	Intermediate Similarity	NPC106818
0.7333	Intermediate Similarity	NPC305162
0.7324	Intermediate Similarity	NPC478250
0.7324	Intermediate Similarity	NPC469367
0.7317	Intermediate Similarity	NPC1082
0.7317	Intermediate Similarity	NPC305912
0.7315	Intermediate Similarity	NPC477467
0.7311	Intermediate Similarity	NPC474365
0.7311	Intermediate Similarity	NPC301943
0.7305	Intermediate Similarity	NPC80098
0.7305	Intermediate Similarity	NPC47471
0.7305	Intermediate Similarity	NPC476377
0.7305	Intermediate Similarity	NPC79908
0.7299	Intermediate Similarity	NPC114116
0.7299	Intermediate Similarity	NPC153617
0.7295	Intermediate Similarity	NPC469636
0.7295	Intermediate Similarity	NPC17417
0.7295	Intermediate Similarity	NPC10251
0.7293	Intermediate Similarity	NPC252114
0.7293	Intermediate Similarity	NPC471157
0.7293	Intermediate Similarity	NPC61181
0.7286	Intermediate Similarity	NPC220936
0.7286	Intermediate Similarity	NPC31745
0.7285	Intermediate Similarity	NPC165234
0.7285	Intermediate Similarity	NPC475536
0.7279	Intermediate Similarity	NPC478255
0.7273	Intermediate Similarity	NPC125053
0.7266	Intermediate Similarity	NPC64340
0.7266	Intermediate Similarity	NPC89324
0.726	Intermediate Similarity	NPC469415
0.726	Intermediate Similarity	NPC96599
0.726	Intermediate Similarity	NPC478242
0.7259	Intermediate Similarity	NPC475671
0.7259	Intermediate Similarity	NPC475508
0.7259	Intermediate Similarity	NPC475452
0.7258	Intermediate Similarity	NPC270699
0.7258	Intermediate Similarity	NPC82899
0.7254	Intermediate Similarity	NPC473792
0.7254	Intermediate Similarity	NPC473873
0.7252	Intermediate Similarity	NPC52097
0.7248	Intermediate Similarity	NPC477472
0.7248	Intermediate Similarity	NPC477470
0.7248	Intermediate Similarity	NPC477474
0.7246	Intermediate Similarity	NPC475262
0.7246	Intermediate Similarity	NPC290833
0.7246	Intermediate Similarity	NPC265459
0.7246	Intermediate Similarity	NPC34456
0.7239	Intermediate Similarity	NPC175333
0.7237	Intermediate Similarity	NPC475464
0.7237	Intermediate Similarity	NPC475505
0.7237	Intermediate Similarity	NPC473641
0.7237	Intermediate Similarity	NPC473797
0.7237	Intermediate Similarity	NPC475437
0.7237	Intermediate Similarity	NPC475300
0.7236	Intermediate Similarity	NPC196246
0.7236	Intermediate Similarity	NPC214067
0.723	Intermediate Similarity	NPC469398
0.723	Intermediate Similarity	NPC469456

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 NPC476096 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	745
0.2-0.3	1451
0.3-0.4	3274
0.4-0.5	2337
0.5-0.6	975
0.6-0.7	124
0.7-0.8	5
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
0.8015	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD2067	Discontinued
0.75	Intermediate Similarity	NPD7798	Approved
0.7295	Intermediate Similarity	NPD2182	Approved
0.7172	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6647	Phase 2
0.7163	Intermediate Similarity	NPD7266	Discontinued
0.704	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5909	Discontinued
0.6967	Remote Similarity	NPD164	Approved
0.6911	Remote Similarity	NPD5048	Discontinued
0.685	Remote Similarity	NPD969	Suspended
0.6833	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8455	Phase 2
0.678	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1238	Approved
0.6763	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6637	Approved
0.672	Remote Similarity	NPD6685	Approved
0.6696	Remote Similarity	NPD1282	Approved
0.6667	Remote Similarity	NPD7094	Approved
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD3672	Approved
0.6642	Remote Similarity	NPD5126	Approved
0.6642	Remote Similarity	NPD5125	Phase 3
0.6615	Remote Similarity	NPD6010	Discontinued
0.6606	Remote Similarity	NPD8313	Approved
0.6606	Remote Similarity	NPD8312	Approved
0.6565	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5926	Approved
0.6547	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7799	Discontinued
0.6535	Remote Similarity	NPD6686	Approved
0.6529	Remote Similarity	NPD1989	Approved
0.6513	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6190	Approved
0.6504	Remote Similarity	NPD2066	Phase 3
0.6503	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD7097	Phase 1
0.648	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5765	Approved
0.6462	Remote Similarity	NPD6912	Phase 3
0.6458	Remote Similarity	NPD1933	Approved
0.6456	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD6832	Phase 2
0.6443	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD2629	Approved
0.6423	Remote Similarity	NPD6287	Discontinued
0.6403	Remote Similarity	NPD5667	Approved
0.6402	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1932	Approved
0.6386	Remote Similarity	NPD8368	Discontinued
0.6386	Remote Similarity	NPD7685	Pre-registration
0.637	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.637	Remote Similarity	NPD9545	Approved
0.6364	Remote Similarity	NPD7472	Approved
0.6364	Remote Similarity	NPD1202	Approved
0.6357	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD7808	Phase 3
0.6339	Remote Similarity	NPD227	Approved
0.6339	Remote Similarity	NPD225	Approved
0.6337	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD6233	Phase 2
0.6319	Remote Similarity	NPD7961	Discontinued
0.6316	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD1091	Approved
0.6303	Remote Similarity	NPD689	Discontinued
0.6303	Remote Similarity	NPD5346	Phase 2
0.6303	Remote Similarity	NPD5347	Phase 2
0.6303	Remote Similarity	NPD7054	Approved
0.6299	Remote Similarity	NPD5403	Approved
0.6296	Remote Similarity	NPD2347	Approved
0.629	Remote Similarity	NPD9495	Approved
0.6287	Remote Similarity	NPD7251	Discontinued
0.6279	Remote Similarity	NPD1358	Approved
0.6275	Remote Similarity	NPD5401	Approved
0.6272	Remote Similarity	NPD8407	Phase 2
0.6271	Remote Similarity	NPD4793	Discontinued
0.6269	Remote Similarity	NPD4198	Discontinued
0.6266	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD7074	Phase 3
0.626	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7075	Discontinued
0.625	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7228	Approved
0.6241	Remote Similarity	NPD1241	Discontinued
0.6235	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD2329	Discontinued
0.6228	Remote Similarity	NPD6797	Phase 2
0.6226	Remote Similarity	NPD5402	Approved
0.6225	Remote Similarity	NPD4628	Phase 3
0.622	Remote Similarity	NPD1929	Approved
0.622	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.622	Remote Similarity	NPD1930	Approved
0.6209	Remote Similarity	NPD6799	Approved
0.6207	Remote Similarity	NPD7713	Phase 3
0.6204	Remote Similarity	NPD8515	Approved
0.6204	Remote Similarity	NPD8517	Approved
0.6204	Remote Similarity	NPD8516	Approved
0.6204	Remote Similarity	NPD8513	Phase 3
0.6203	Remote Similarity	NPD37	Approved
0.6198	Remote Similarity	NPD7609	Phase 3
0.619	Remote Similarity	NPD6559	Discontinued
0.619	Remote Similarity	NPD7240	Approved
0.6188	Remote Similarity	NPD4967	Phase 2
0.6188	Remote Similarity	NPD4966	Approved
0.6188	Remote Similarity	NPD4965	Approved
0.6186	Remote Similarity	NPD9257	Approved
0.6186	Remote Similarity	NPD9259	Approved
0.6183	Remote Similarity	NPD1317	Discontinued
0.6181	Remote Similarity	NPD6039	Approved
0.6176	Remote Similarity	NPD6065	Approved
0.6174	Remote Similarity	NPD226	Approved
0.6172	Remote Similarity	NPD1237	Approved
0.617	Remote Similarity	NPD2199	Approved
0.617	Remote Similarity	NPD2198	Approved
0.6164	Remote Similarity	NPD7819	Suspended
0.6159	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1653	Approved
0.6149	Remote Similarity	NPD2567	Approved
0.6149	Remote Similarity	NPD2569	Approved
0.6148	Remote Similarity	NPD3317	Approved
0.6148	Remote Similarity	NPD7631	Approved
0.6145	Remote Similarity	NPD3818	Discontinued
0.6144	Remote Similarity	NPD7236	Approved
0.614	Remote Similarity	NPD9490	Approved
0.6138	Remote Similarity	NPD6798	Discontinued
0.6138	Remote Similarity	NPD3764	Approved
0.6136	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD1087	Approved
0.6127	Remote Similarity	NPD3267	Approved
0.6127	Remote Similarity	NPD3266	Approved
0.6122	Remote Similarity	NPD230	Phase 1
0.6118	Remote Similarity	NPD8166	Discontinued
0.6116	Remote Similarity	NPD46	Approved
0.6116	Remote Similarity	NPD6698	Approved
0.6115	Remote Similarity	NPD7830	Approved
0.6115	Remote Similarity	NPD7458	Discontinued
0.6115	Remote Similarity	NPD7829	Approved
0.6111	Remote Similarity	NPD6234	Discontinued
0.6111	Remote Similarity	NPD2613	Approved
0.6104	Remote Similarity	NPD3950	Discontinued
0.6103	Remote Similarity	NPD4574	Approved
0.6103	Remote Similarity	NPD4576	Approved
0.6103	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD6801	Discontinued
0.6087	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD6085	Phase 2
0.6084	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD3134	Approved
0.6076	Remote Similarity	NPD4380	Phase 2
0.6071	Remote Similarity	NPD4807	Approved
0.6071	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4806	Approved
0.6069	Remote Similarity	NPD7008	Discontinued
0.6068	Remote Similarity	NPD9491	Approved
0.6067	Remote Similarity	NPD2796	Approved
0.6067	Remote Similarity	NPD7699	Phase 2
0.6067	Remote Similarity	NPD7700	Phase 2
0.6061	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4234	Approved
0.6061	Remote Similarity	NPD4233	Approved
0.6051	Remote Similarity	NPD7239	Suspended
0.6048	Remote Similarity	NPD1693	Approved
0.6044	Remote Similarity	NPD8320	Phase 1
0.6044	Remote Similarity	NPD8319	Approved
0.6043	Remote Similarity	NPD5306	Approved
0.6043	Remote Similarity	NPD5305	Approved
0.604	Remote Similarity	NPD4448	Approved
0.604	Remote Similarity	NPD4449	Approved
0.6039	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7411	Suspended
0.6038	Remote Similarity	NPD6386	Approved
0.6038	Remote Similarity	NPD6385	Approved
0.6036	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD800	Approved
0.6027	Remote Similarity	NPD3268	Approved
0.6027	Remote Similarity	NPD2313	Discontinued
0.6026	Remote Similarity	NPD4513	Discontinued
0.6025	Remote Similarity	NPD3817	Phase 2
0.6025	Remote Similarity	NPD5353	Approved
0.6024	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD2160	Approved
0.6014	Remote Similarity	NPD2628	Approved
0.6014	Remote Similarity	NPD2159	Approved
0.6014	Remote Similarity	NPD2627	Approved
0.6014	Remote Similarity	NPD7741	Discontinued
0.6014	Remote Similarity	NPD2626	Approved
0.6014	Remote Similarity	NPD2625	Approved
0.6014	Remote Similarity	NPD6355	Discontinued
0.6014	Remote Similarity	NPD2797	Approved
0.6013	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD2575	Approved
0.6013	Remote Similarity	NPD6398	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