NPASS Compound

Structure

NPC474303 OpenBabel07101718252D 49 51 0 0 1 0 0 0 0 0999 V2000 3.4258 -5.6197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2901 -6.7554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3860 0.1920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5786 1.8070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1624 -2.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9266 0.4603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7137 -1.4424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2070 -4.5320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6260 -3.2370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9703 -3.8927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6857 -1.4871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7900 -1.7270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9257 -0.5914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1343 -1.0714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2700 0.0643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1940 -1.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1940 -2.1940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1928 0.9070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5301 -5.8597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7303 -0.4636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1150 1.0039 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2667 -2.1940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0196 0.6531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8180 -1.6824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4157 -5.0120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3743 -0.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8030 -0.4636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4921 0.1568 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2667 -1.2667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8030 -2.9970 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -3.4606 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9273 -3.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9273 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8744 -5.2040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0629 1.1357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7303 -2.9970 0.0000 C 0 0 0 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 2.7331 1.5350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3380 -3.4737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1757 -5.9077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1673 -4.3563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9787 -5.4440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3029 2.0313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1417 -0.9164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3991 -0.0360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1624 -1.0267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2400 -4.3563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1144 -4.3084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1673 0.8957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 5 22 2 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 9 36 1 0 0 0 0 10 36 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 26 2 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 36 1 0 0 0 0 18 21 1 0 0 0 0 18 37 1 0 0 0 0 19 34 1 0 0 0 0 20 3 1 6 0 0 0 20 33 1 0 0 0 0 21 4 1 6 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 22 30 1 0 0 0 0 23 38 2 0 0 0 0 23 45 1 0 0 0 0 24 39 2 0 0 0 0 24 46 1 0 0 0 0 25 40 2 0 0 0 0 25 47 1 0 0 0 0 26 35 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 27 37 1 6 0 0 0 28 45 1 6 0 0 0 29 46 1 1 0 0 0 30 31 1 0 0 0 0 30 48 1 1 0 0 0 31 32 1 0 0 0 0 31 47 1 1 0 0 0 32 36 1 0 0 0 0 32 41 2 0 0 0 0 33 37 1 6 0 0 0 33 49 1 0 0 0 0 34 42 2 0 0 0 0 34 48 1 0 0 0 0 35 43 2 0 0 0 0 35 49 1 0 0 0 0 37 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	684.31
Volume:	699.32
LogP:	4.03
LogD:	2.287
LogS:	-4.369
# Rotatable Bonds:	12
TPSA:	168.8
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.246
Synthetic Accessibility Score:	5.684
Fsp3:	0.568
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:	-5.143
MDCK Permeability:	9.725932613946497e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.299
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	84.4100112915039%
Volume Distribution (VD):	2.321
Pgp-substrate:	8.580322265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.224
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.819
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	3.536
Half-life (T1/2):	0.385

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.992
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.781
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.069
Carcinogencity:	0.136
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.853

Download Data

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

Natural Product: NPC474303

Natural Product ID:	NPC474303
*Common Name:**	Tuckeyanol B
IUPAC Name:	[(1S,2S,3aR,4S,5S,6E,10R,11R,13R,13aR)-1,10,13-triacetyloxy-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-11-(2-methylpropanoyloxy)-9-oxo-2,3,4,5,10,11,13,13a-octahydro-1H-cyclopenta[12]annulen-4-yl] benzoate
Synonyms:	Tuckeyanol B
Standard InCHIKey:	UAJPJVYIJSOQMI-WKDKTOFFSA-N
Standard InCHI:	InChI=1S/C37H48O12/c1-19(2)34(42)48-30-22(5)29(46-24(7)39)27-28(45-23(6)38)21(4)18-37(27,44)33(49-35(43)26-14-12-11-13-15-26)20(3)16-17-36(9,10)32(41)31(30)47-25(8)40/h11-17,19-21,27-31,33,44H,5,18H2,1-4,6-10H3/b17-16+/t20-,21-,27+,28-,29-,30+,31+,33-,37+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@@H](C)C[C@]2([C@H]1[C@@H](OC(=O)C)C(=C)[C@@H](OC(=O)C(C)C)[C@@H](OC(=O)C)C(=O)C(/C=C/[C@@H]([C@@H]2OC(=O)c1ccccc1)C)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464933
PubChem CID:	44588951
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002877] Jatrophane and cyclojatrophane diterpenoids

*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
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18824363]
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[6736971]
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	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
Others	8

Activity Type	# Activity
Individual Protein	4
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	25.0	n.a.	PMID[483395]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	347.6	n.a.	PMID[483395]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	97.3	n.a.	PMID[483395]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	1353.2	n.a.	PMID[483395]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ID50	=	19.4	ug ml-1	PMID[483395]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ID50	=	12.0	ug ml-1	PMID[483395]
NPT35	Others	n.a.		LogP	=	4.0	n.a.	PMID[483395]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	FICI	=	0.25	n.a.	PMID[483395]

☑ 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 NPC474303 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	290
0.1-0.2	977
0.2-0.3	2330
0.3-0.4	5528
0.4-0.5	10347
0.5-0.6	12142
0.6-0.7	9684
0.7-0.8	1166
0.8-0.85	89
0.85-0.9	43
0.9-0.95	64
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475413
0.9851	High Similarity	NPC45307
0.985	High Similarity	NPC473497
0.9635	High Similarity	NPC170668
0.9624	High Similarity	NPC86772
0.9565	High Similarity	NPC205389
0.9552	High Similarity	NPC325805
0.9552	High Similarity	NPC272523
0.9545	High Similarity	NPC472250
0.9474	High Similarity	NPC475262
0.9474	High Similarity	NPC265459
0.9474	High Similarity	NPC79699
0.9474	High Similarity	NPC290833
0.9429	High Similarity	NPC477099
0.9429	High Similarity	NPC25484
0.9429	High Similarity	NPC477097
0.9429	High Similarity	NPC477101
0.9429	High Similarity	NPC232583
0.9403	High Similarity	NPC194769
0.9403	High Similarity	NPC285221
0.9394	High Similarity	NPC233860
0.9328	High Similarity	NPC472247
0.9323	High Similarity	NPC472248
0.9275	High Similarity	NPC82467
0.9275	High Similarity	NPC477096
0.9275	High Similarity	NPC477094
0.927	High Similarity	NPC242355
0.9254	High Similarity	NPC28836
0.9248	High Similarity	NPC239358
0.9231	High Similarity	NPC477098
0.9231	High Similarity	NPC477100
0.9197	High Similarity	NPC475660
0.9185	High Similarity	NPC200154
0.9185	High Similarity	NPC270364
0.9137	High Similarity	NPC153214
0.9111	High Similarity	NPC153617
0.9111	High Similarity	NPC311492
0.9104	High Similarity	NPC233692
0.9098	High Similarity	NPC272946
0.9078	High Similarity	NPC477095
0.9051	High Similarity	NPC27721
0.8993	High Similarity	NPC187566
0.8986	High Similarity	NPC473301
0.8986	High Similarity	NPC276652
0.8978	High Similarity	NPC202729
0.8971	High Similarity	NPC477368
0.8955	High Similarity	NPC475508
0.8921	High Similarity	NPC251294
0.8905	High Similarity	NPC232888
0.8905	High Similarity	NPC477367
0.8897	High Similarity	NPC477364
0.8857	High Similarity	NPC473654
0.8844	High Similarity	NPC70344
0.8832	High Similarity	NPC477359
0.8815	High Similarity	NPC42234
0.88	High Similarity	NPC55744
0.8759	High Similarity	NPC125033
0.8696	High Similarity	NPC324898
0.8696	High Similarity	NPC298547
0.8696	High Similarity	NPC134937
0.8686	High Similarity	NPC477360
0.8667	High Similarity	NPC472707
0.8633	High Similarity	NPC279637
0.8633	High Similarity	NPC149401
0.8593	High Similarity	NPC472706
0.8571	High Similarity	NPC477358
0.8571	High Similarity	NPC51602
0.854	High Similarity	NPC3450
0.854	High Similarity	NPC122504
0.854	High Similarity	NPC475452
0.854	High Similarity	NPC475671
0.8511	High Similarity	NPC327511
0.8511	High Similarity	NPC205305
0.8507	High Similarity	NPC472704
0.8483	Intermediate Similarity	NPC25043
0.8483	Intermediate Similarity	NPC134131
0.8483	Intermediate Similarity	NPC127857
0.8451	Intermediate Similarity	NPC53361
0.8451	Intermediate Similarity	NPC121268
0.8446	Intermediate Similarity	NPC471103
0.8433	Intermediate Similarity	NPC472703
0.84	Intermediate Similarity	NPC469456
0.84	Intermediate Similarity	NPC473670
0.84	Intermediate Similarity	NPC21410
0.84	Intermediate Similarity	NPC282239
0.8394	Intermediate Similarity	NPC477370
0.8382	Intermediate Similarity	NPC477366
0.8382	Intermediate Similarity	NPC477363
0.8378	Intermediate Similarity	NPC112216
0.8378	Intermediate Similarity	NPC7095
0.837	Intermediate Similarity	NPC477362
0.837	Intermediate Similarity	NPC8990
0.8345	Intermediate Similarity	NPC95449
0.8344	Intermediate Similarity	NPC217091
0.8344	Intermediate Similarity	NPC106895
0.8344	Intermediate Similarity	NPC11410
0.8333	Intermediate Similarity	NPC37968
0.8322	Intermediate Similarity	NPC306799
0.8322	Intermediate Similarity	NPC101043
0.8321	Intermediate Similarity	NPC477365
0.8321	Intermediate Similarity	NPC477357
0.8311	Intermediate Similarity	NPC60509
0.8311	Intermediate Similarity	NPC81698
0.8311	Intermediate Similarity	NPC250046
0.831	Intermediate Similarity	NPC217673
0.831	Intermediate Similarity	NPC52523
0.8309	Intermediate Similarity	NPC477369
0.8289	Intermediate Similarity	NPC472393
0.8278	Intermediate Similarity	NPC251139
0.8276	Intermediate Similarity	NPC475135
0.8276	Intermediate Similarity	NPC472546
0.8276	Intermediate Similarity	NPC182869
0.8276	Intermediate Similarity	NPC192658
0.8264	Intermediate Similarity	NPC162613
0.8264	Intermediate Similarity	NPC87934
0.8255	Intermediate Similarity	NPC161239
0.8255	Intermediate Similarity	NPC198455
0.8255	Intermediate Similarity	NPC165260
0.8247	Intermediate Similarity	NPC329997
0.8235	Intermediate Similarity	NPC471102
0.8231	Intermediate Similarity	NPC471100
0.8231	Intermediate Similarity	NPC471107
0.8219	Intermediate Similarity	NPC191387
0.8219	Intermediate Similarity	NPC131966
0.8212	Intermediate Similarity	NPC237549
0.8212	Intermediate Similarity	NPC77719
0.8212	Intermediate Similarity	NPC1173
0.8212	Intermediate Similarity	NPC472030
0.8212	Intermediate Similarity	NPC265395
0.8212	Intermediate Similarity	NPC473414
0.8212	Intermediate Similarity	NPC249471
0.8212	Intermediate Similarity	NPC257213
0.8212	Intermediate Similarity	NPC256142
0.8212	Intermediate Similarity	NPC472022
0.8212	Intermediate Similarity	NPC304876
0.8212	Intermediate Similarity	NPC472005
0.8212	Intermediate Similarity	NPC158333
0.8212	Intermediate Similarity	NPC219419
0.8212	Intermediate Similarity	NPC242262
0.8207	Intermediate Similarity	NPC266374
0.82	Intermediate Similarity	NPC161955
0.8194	Intermediate Similarity	NPC9905
0.8176	Intermediate Similarity	NPC312393
0.8176	Intermediate Similarity	NPC477737
0.8176	Intermediate Similarity	NPC478263
0.8163	Intermediate Similarity	NPC34943
0.8158	Intermediate Similarity	NPC473611
0.8158	Intermediate Similarity	NPC228204
0.8158	Intermediate Similarity	NPC26033
0.8158	Intermediate Similarity	NPC472549
0.8158	Intermediate Similarity	NPC112523
0.8158	Intermediate Similarity	NPC259144
0.8158	Intermediate Similarity	NPC114357
0.8158	Intermediate Similarity	NPC155329
0.8158	Intermediate Similarity	NPC114410
0.8151	Intermediate Similarity	NPC63737
0.8146	Intermediate Similarity	NPC469647
0.8146	Intermediate Similarity	NPC469648
0.8146	Intermediate Similarity	NPC138641
0.8146	Intermediate Similarity	NPC22571
0.8146	Intermediate Similarity	NPC283875
0.8133	Intermediate Similarity	NPC473214
0.8133	Intermediate Similarity	NPC470245
0.8133	Intermediate Similarity	NPC254558
0.8121	Intermediate Similarity	NPC327031
0.8108	Intermediate Similarity	NPC471162
0.8108	Intermediate Similarity	NPC478264
0.8092	Intermediate Similarity	NPC11588
0.8092	Intermediate Similarity	NPC134685
0.8092	Intermediate Similarity	NPC229545
0.8092	Intermediate Similarity	NPC248265
0.8082	Intermediate Similarity	NPC16912
0.8079	Intermediate Similarity	NPC472398
0.8079	Intermediate Similarity	NPC470153
0.8069	Intermediate Similarity	NPC170718
0.8067	Intermediate Similarity	NPC476975
0.8067	Intermediate Similarity	NPC473215
0.8054	Intermediate Similarity	NPC20255
0.8054	Intermediate Similarity	NPC240115
0.8054	Intermediate Similarity	NPC475552
0.8054	Intermediate Similarity	NPC473602
0.8052	Intermediate Similarity	NPC469771
0.805	Intermediate Similarity	NPC40138
0.8043	Intermediate Similarity	NPC246166
0.8041	Intermediate Similarity	NPC80895
0.8041	Intermediate Similarity	NPC471912
0.8039	Intermediate Similarity	NPC473632
0.8039	Intermediate Similarity	NPC469730
0.8039	Intermediate Similarity	NPC132599
0.8038	Intermediate Similarity	NPC324769
0.8038	Intermediate Similarity	NPC325732
0.8027	Intermediate Similarity	NPC51181
0.8027	Intermediate Similarity	NPC183540
0.8026	Intermediate Similarity	NPC477905
0.8026	Intermediate Similarity	NPC233581
0.8026	Intermediate Similarity	NPC472548
0.8026	Intermediate Similarity	NPC145649
0.8014	Intermediate Similarity	NPC472547
0.8014	Intermediate Similarity	NPC473440
0.8014	Intermediate Similarity	NPC82712

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 NPC474303 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	708
0.2-0.3	1720
0.3-0.4	2835
0.4-0.5	2215
0.5-0.6	1087
0.6-0.7	316
0.7-0.8	28
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8231	Intermediate Similarity	NPD7236	Approved
0.8176	Intermediate Similarity	NPD7799	Discontinued
0.8099	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7239	Suspended
0.7676	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7058	Phase 2
0.761	Intermediate Similarity	NPD7057	Phase 3
0.75	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD8368	Discontinued
0.7412	Intermediate Similarity	NPD8407	Phase 2
0.7296	Intermediate Similarity	NPD6599	Discontinued
0.7293	Intermediate Similarity	NPD6685	Approved
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.7267	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2629	Approved
0.7239	Intermediate Similarity	NPD7075	Discontinued
0.7225	Intermediate Similarity	NPD8434	Phase 2
0.7206	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4198	Discontinued
0.7192	Intermediate Similarity	NPD6085	Phase 2
0.7192	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7961	Discontinued
0.7162	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8435	Approved
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7134	Intermediate Similarity	NPD6799	Approved
0.7132	Intermediate Similarity	NPD2067	Discontinued
0.7089	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5765	Approved
0.7059	Intermediate Similarity	NPD2182	Approved
0.7045	Intermediate Similarity	NPD8360	Approved
0.7045	Intermediate Similarity	NPD8361	Approved
0.7042	Intermediate Similarity	NPD7741	Discontinued
0.7035	Intermediate Similarity	NPD6764	Approved
0.7035	Intermediate Similarity	NPD6765	Approved
0.7029	Intermediate Similarity	NPD6912	Phase 3
0.7029	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6801	Discontinued
0.6974	Remote Similarity	NPD6355	Discontinued
0.6968	Remote Similarity	NPD6002	Phase 3
0.6968	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6005	Phase 3
0.6968	Remote Similarity	NPD6004	Phase 3
0.6968	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5647	Approved
0.6951	Remote Similarity	NPD5760	Phase 2
0.6951	Remote Similarity	NPD5761	Phase 2
0.694	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD8150	Discontinued
0.6928	Remote Similarity	NPD6653	Approved
0.6923	Remote Similarity	NPD9545	Approved
0.6909	Remote Similarity	NPD3817	Phase 2
0.6906	Remote Similarity	NPD8485	Approved
0.6899	Remote Similarity	NPD6190	Approved
0.6894	Remote Similarity	NPD5403	Approved
0.6886	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6785	Approved
0.6875	Remote Similarity	NPD6784	Approved
0.6875	Remote Similarity	NPD5401	Approved
0.6859	Remote Similarity	NPD5762	Approved
0.6859	Remote Similarity	NPD5763	Approved
0.6848	Remote Similarity	NPD7819	Suspended
0.6815	Remote Similarity	NPD6647	Phase 2
0.6812	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5402	Approved
0.6795	Remote Similarity	NPD7137	Phase 2
0.6793	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4380	Phase 2
0.6765	Remote Similarity	NPD164	Approved
0.6763	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD230	Phase 1
0.6752	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7094	Approved
0.6738	Remote Similarity	NPD6858	Approved
0.6735	Remote Similarity	NPD6287	Discontinued
0.6735	Remote Similarity	NPD4807	Approved
0.6735	Remote Similarity	NPD4806	Approved
0.673	Remote Similarity	NPD2575	Approved
0.6728	Remote Similarity	NPD6273	Approved
0.6715	Remote Similarity	NPD5048	Discontinued
0.6712	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5306	Approved
0.6712	Remote Similarity	NPD5305	Approved
0.6711	Remote Similarity	NPD7008	Discontinued
0.6706	Remote Similarity	NPD8127	Discontinued
0.6689	Remote Similarity	NPD3661	Approved
0.6689	Remote Similarity	NPD3664	Approved
0.6689	Remote Similarity	NPD3662	Phase 3
0.6689	Remote Similarity	NPD3663	Approved
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD6362	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD969	Suspended
0.6667	Remote Similarity	NPD3882	Suspended
0.6642	Remote Similarity	NPD1237	Approved
0.6642	Remote Similarity	NPD9495	Approved
0.6627	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7305	Phase 1
0.6624	Remote Similarity	NPD7033	Discontinued
0.6607	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7458	Discontinued
0.6596	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1238	Approved
0.6584	Remote Similarity	NPD2354	Approved
0.6584	Remote Similarity	NPD3887	Approved
0.658	Remote Similarity	NPD8462	Phase 1
0.6575	Remote Similarity	NPD6319	Approved
0.6573	Remote Similarity	NPD2650	Approved
0.6573	Remote Similarity	NPD2652	Approved
0.6569	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1930	Approved
0.6569	Remote Similarity	NPD1929	Approved
0.6564	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2532	Approved
0.6564	Remote Similarity	NPD2534	Approved
0.6564	Remote Similarity	NPD2533	Approved
0.6564	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4136	Approved
0.6554	Remote Similarity	NPD4135	Approved
0.6554	Remote Similarity	NPD4106	Approved
0.6552	Remote Similarity	NPD9493	Approved
0.6549	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD6832	Phase 2
0.6532	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5951	Approved
0.6527	Remote Similarity	NPD7411	Suspended
0.6522	Remote Similarity	NPD8166	Discontinued
0.6519	Remote Similarity	NPD2799	Discontinued
0.6517	Remote Similarity	NPD7808	Phase 3
0.6516	Remote Similarity	NPD6233	Phase 2
0.6516	Remote Similarity	NPD6663	Approved
0.6508	Remote Similarity	NPD7497	Discontinued
0.65	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6166	Phase 2
0.6494	Remote Similarity	NPD7095	Approved
0.649	Remote Similarity	NPD5667	Approved
0.6488	Remote Similarity	NPD1934	Approved
0.6486	Remote Similarity	NPD5126	Approved
0.6486	Remote Similarity	NPD5125	Phase 3
0.648	Remote Similarity	NPD8313	Approved
0.648	Remote Similarity	NPD8312	Approved
0.6478	Remote Similarity	NPD2796	Approved
0.6474	Remote Similarity	NPD8320	Phase 1
0.6474	Remote Similarity	NPD8319	Approved
0.6471	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5736	Approved
0.6471	Remote Similarity	NPD5204	Approved
0.6471	Remote Similarity	NPD2066	Phase 3
0.6467	Remote Similarity	NPD1608	Approved
0.6463	Remote Similarity	NPD7009	Phase 2
0.6461	Remote Similarity	NPD7251	Discontinued
0.6458	Remote Similarity	NPD6010	Discontinued
0.6457	Remote Similarity	NPD7473	Discontinued
0.6456	Remote Similarity	NPD2569	Approved
0.6456	Remote Similarity	NPD2567	Approved
0.6452	Remote Similarity	NPD6798	Discontinued
0.6452	Remote Similarity	NPD2313	Discontinued
0.645	Remote Similarity	NPD7972	Discontinued
0.645	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8297	Approved
0.6425	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3818	Discontinued
0.642	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4102	Approved
0.6419	Remote Similarity	NPD4105	Approved
0.6418	Remote Similarity	NPD1693	Approved
0.6415	Remote Similarity	NPD1510	Phase 2
0.6408	Remote Similarity	NPD6371	Approved
0.6407	Remote Similarity	NPD3226	Approved
0.6405	Remote Similarity	NPD2798	Approved
0.6404	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6797	Phase 2
0.64	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5958	Discontinued
0.6398	Remote Similarity	NPD1549	Phase 2
0.6398	Remote Similarity	NPD4534	Discontinued
0.6395	Remote Similarity	NPD7610	Discontinued
0.6395	Remote Similarity	NPD919	Approved
0.6392	Remote Similarity	NPD6651	Approved
0.6386	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1876	Approved
0.6375	Remote Similarity	NPD2935	Discontinued
0.6374	Remote Similarity	NPD7768	Phase 2
0.6369	Remote Similarity	NPD1240	Approved
0.6364	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5494	Approved
0.6358	Remote Similarity	NPD3972	Approved
0.6358	Remote Similarity	NPD9717	Approved
0.6358	Remote Similarity	NPD2800	Approved
0.6358	Remote Similarity	NPD6637	Approved
0.6348	Remote Similarity	NPD7074	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