NPASS Compound

Structure

CID304110 OpenBabel06191716112D 45 50 0 0 1 0 0 0 0 0999 V2000 2.5471 -4.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -3.4314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0373 2.3196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0569 2.3196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9433 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3962 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3962 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -3.4314 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6981 -2.9412 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9433 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9433 -3.4314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6981 0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8490 -0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0943 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -1.9608 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3962 0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3962 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8490 -0.4902 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 2.5471 -1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9433 -4.4118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2452 -0.4902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9433 1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2452 -1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2452 1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 35 1 0 0 0 0 4 35 1 0 0 0 0 6 37 1 0 0 0 0 8 11 1 0 0 0 0 8 25 2 0 0 0 0 9 12 2 0 0 0 0 9 25 1 0 0 0 0 10 15 2 0 0 0 0 10 25 1 0 0 0 0 11 26 2 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 27 2 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 19 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 38 1 0 0 0 0 19 39 1 0 0 0 0 20 21 1 0 0 0 0 20 37 1 0 0 0 0 21 39 1 0 0 0 0 22 28 1 0 0 0 0 22 36 1 0 0 0 0 23 1 1 1 0 0 0 23 24 1 0 0 0 0 24 2 1 6 0 0 0 24 32 1 0 0 0 0 26 40 1 0 0 0 0 27 32 1 0 0 0 0 27 37 1 0 0 0 0 28 33 1 0 0 0 0 28 41 1 1 0 0 0 29 35 1 0 0 0 0 29 36 1 6 0 0 0 30 36 1 6 0 0 0 30 38 1 0 0 0 0 31 42 2 0 0 0 0 31 45 1 0 0 0 0 32 39 1 1 0 0 0 33 35 1 0 0 0 0 33 45 1 6 0 0 0 34 43 2 0 0 0 0 34 44 1 0 0 0 0 36 5 1 6 0 0 0 37 38 1 6 0 0 0 38 7 1 6 0 0 0 39 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.39
Volume:	666.047
LogP:	7.144
LogD:	5.491
LogS:	-4.645
# Rotatable Bonds:	5
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.179
Synthetic Accessibility Score:	5.067
Fsp3:	0.692
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:	-5.544
MDCK Permeability:	2.121872421412263e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.688

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	100.08853912353516%
Volume Distribution (VD):	0.491
Pgp-substrate:	3.011129856109619%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.303
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.633
CYP2C9-inhibitor:	0.249
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.429

ADMET: Excretion

Clearance (CL):	2.068
Half-life (T1/2):	0.13

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.205
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.156
Carcinogencity:	0.049
Eye Corrosion:	0.007
Eye Irritation:	0.021
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC304110

Natural Product ID:	NPC304110
*Common Name:**	3Beta-O-Trans-P-Coumaroyl-2Alpha-Hydroxy-12-Ursen-28-Oic Acid
IUPAC Name:	(1S,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-11-hydroxy-10-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	FEVUQLLYZLSRLB-SVRRIJHPSA-N
Standard InCHI:	InChI=1S/C39H54O6/c1-23-16-19-39(34(43)44)21-20-37(6)27(32(39)24(23)2)13-14-30-36(5)22-28(41)33(35(3,4)29(36)17-18-38(30,37)7)45-31(42)15-10-25-8-11-26(40)12-9-25/h8-13,15,23-24,28-30,32-33,40-41H,14,16-22H2,1-7H3,(H,43,44)/b15-10+/t23-,24+,28-,29+,30-,32+,33+,36+,37-,38-,39+/m1/s1
SMILES:	O=C(O[C@H]1[C@H](O)C[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@@H](C)[C@H](C)CC1)C(=O)O)C)C)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507062
PubChem CID:	14335960
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO12610	Diospyros dendo	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441080]
NPO7437	Lonchocarpus costaricensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26254	Fagus crenata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25776	Buddleja scordioides	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12610	Diospyros dendo	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26412	Streptomyces tauricus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1305	Eriophyllum confertiflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26873	Echinochloa crus-galli	Species	Poaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	Inhibition	=	35.0	%	PMID[516869]

☑ 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 NPC304110 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	312
0.1-0.2	1234
0.2-0.3	2421
0.3-0.4	4752
0.4-0.5	9011
0.5-0.6	11046
0.6-0.7	11810
0.7-0.8	1905
0.8-0.85	78
0.85-0.9	56
0.9-0.95	42
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC27518
0.9779	High Similarity	NPC25491
0.9699	High Similarity	NPC249817
0.9627	High Similarity	NPC22676
0.9627	High Similarity	NPC198621
0.9627	High Similarity	NPC216940
0.9627	High Similarity	NPC475482
0.9624	High Similarity	NPC477874
0.9624	High Similarity	NPC173569
0.9562	High Similarity	NPC477873
0.9562	High Similarity	NPC469447
0.9424	High Similarity	NPC53520
0.9328	High Similarity	NPC475346
0.9328	High Similarity	NPC475627
0.9328	High Similarity	NPC18982
0.9328	High Similarity	NPC475457
0.9301	High Similarity	NPC118033
0.9275	High Similarity	NPC472801
0.9275	High Similarity	NPC172311
0.927	High Similarity	NPC182249
0.927	High Similarity	NPC248287
0.927	High Similarity	NPC234548
0.9236	High Similarity	NPC475579
0.9236	High Similarity	NPC473773
0.922	High Similarity	NPC8102
0.922	High Similarity	NPC66894
0.9203	High Similarity	NPC470617
0.9203	High Similarity	NPC271494
0.9203	High Similarity	NPC473591
0.9203	High Similarity	NPC155192
0.9203	High Similarity	NPC470616
0.9173	High Similarity	NPC86257
0.9167	High Similarity	NPC473680
0.9167	High Similarity	NPC475311
0.9167	High Similarity	NPC473579
0.9167	High Similarity	NPC475454
0.913	High Similarity	NPC139243
0.913	High Similarity	NPC116742
0.9097	High Similarity	NPC327962
0.9058	High Similarity	NPC471152
0.9007	High Similarity	NPC252133
0.8978	High Similarity	NPC11266
0.8958	High Similarity	NPC325032
0.8958	High Similarity	NPC477483
0.8947	High Similarity	NPC190849
0.8947	High Similarity	NPC171007
0.8944	High Similarity	NPC26045
0.8936	High Similarity	NPC35212
0.8913	High Similarity	NPC472804
0.8913	High Similarity	NPC43353
0.8912	High Similarity	NPC105942
0.8912	High Similarity	NPC205392
0.8881	High Similarity	NPC307205
0.8873	High Similarity	NPC235557
0.8873	High Similarity	NPC310621
0.8872	High Similarity	NPC137416
0.8865	High Similarity	NPC473612
0.8792	High Similarity	NPC472807
0.8767	High Similarity	NPC279442
0.8705	High Similarity	NPC194970
0.8657	High Similarity	NPC265413
0.8657	High Similarity	NPC10154
0.863	High Similarity	NPC472937
0.863	High Similarity	NPC472938
0.863	High Similarity	NPC472936
0.8613	High Similarity	NPC475138
0.8581	High Similarity	NPC145527
0.8581	High Similarity	NPC208785
0.8581	High Similarity	NPC470619
0.8581	High Similarity	NPC470618
0.8562	High Similarity	NPC320734
0.8531	High Similarity	NPC471875
0.8519	High Similarity	NPC474532
0.8514	High Similarity	NPC473719
0.8506	High Similarity	NPC266365
0.85	High Similarity	NPC476282
0.8456	Intermediate Similarity	NPC472939
0.8425	Intermediate Similarity	NPC477207
0.8414	Intermediate Similarity	NPC477468
0.8408	Intermediate Similarity	NPC200726
0.8389	Intermediate Similarity	NPC298647
0.8389	Intermediate Similarity	NPC273358
0.8389	Intermediate Similarity	NPC477206
0.8367	Intermediate Similarity	NPC271607
0.8367	Intermediate Similarity	NPC235195
0.8367	Intermediate Similarity	NPC280717
0.8367	Intermediate Similarity	NPC19862
0.8357	Intermediate Similarity	NPC243305
0.8356	Intermediate Similarity	NPC204644
0.8354	Intermediate Similarity	NPC177362
0.8345	Intermediate Similarity	NPC470035
0.8333	Intermediate Similarity	NPC76032
0.8333	Intermediate Similarity	NPC132723
0.8322	Intermediate Similarity	NPC32017
0.8322	Intermediate Similarity	NPC96930
0.8313	Intermediate Similarity	NPC469774
0.8313	Intermediate Similarity	NPC469775
0.8313	Intermediate Similarity	NPC469773
0.8313	Intermediate Similarity	NPC469778
0.8313	Intermediate Similarity	NPC469776
0.8313	Intermediate Similarity	NPC100925
0.8313	Intermediate Similarity	NPC469772
0.8313	Intermediate Similarity	NPC295941
0.8313	Intermediate Similarity	NPC469777
0.8313	Intermediate Similarity	NPC32723
0.8313	Intermediate Similarity	NPC135334
0.8302	Intermediate Similarity	NPC202428
0.8302	Intermediate Similarity	NPC266545
0.8289	Intermediate Similarity	NPC475595
0.8289	Intermediate Similarity	NPC83663
0.8289	Intermediate Similarity	NPC475162
0.8289	Intermediate Similarity	NPC473544
0.8289	Intermediate Similarity	NPC475216
0.8289	Intermediate Similarity	NPC475145
0.8289	Intermediate Similarity	NPC266084
0.8267	Intermediate Similarity	NPC292206
0.8261	Intermediate Similarity	NPC473220
0.8261	Intermediate Similarity	NPC470753
0.8255	Intermediate Similarity	NPC470330
0.8252	Intermediate Similarity	NPC103082
0.8252	Intermediate Similarity	NPC279463
0.825	Intermediate Similarity	NPC472803
0.8235	Intermediate Similarity	NPC478058
0.8231	Intermediate Similarity	NPC184935
0.8219	Intermediate Similarity	NPC3218
0.8214	Intermediate Similarity	NPC131684
0.8188	Intermediate Similarity	NPC275576
0.8188	Intermediate Similarity	NPC470765
0.8187	Intermediate Similarity	NPC471870
0.8182	Intermediate Similarity	NPC477896
0.8176	Intermediate Similarity	NPC472556
0.8176	Intermediate Similarity	NPC471876
0.8163	Intermediate Similarity	NPC91703
0.8163	Intermediate Similarity	NPC2681
0.8163	Intermediate Similarity	NPC272907
0.8158	Intermediate Similarity	NPC119252
0.8151	Intermediate Similarity	NPC224491
0.8146	Intermediate Similarity	NPC46549
0.8146	Intermediate Similarity	NPC264229
0.8141	Intermediate Similarity	NPC471750
0.8133	Intermediate Similarity	NPC92293
0.8133	Intermediate Similarity	NPC301556
0.8133	Intermediate Similarity	NPC270590
0.8133	Intermediate Similarity	NPC471101
0.8133	Intermediate Similarity	NPC266265
0.8129	Intermediate Similarity	NPC169913
0.8125	Intermediate Similarity	NPC472372
0.8125	Intermediate Similarity	NPC472374
0.8112	Intermediate Similarity	NPC203486
0.8108	Intermediate Similarity	NPC475122
0.8108	Intermediate Similarity	NPC477209
0.8105	Intermediate Similarity	NPC48671
0.8099	Intermediate Similarity	NPC18798
0.8092	Intermediate Similarity	NPC116292
0.8092	Intermediate Similarity	NPC87630
0.8092	Intermediate Similarity	NPC162569
0.8092	Intermediate Similarity	NPC179128
0.8092	Intermediate Similarity	NPC35160
0.8092	Intermediate Similarity	NPC267469
0.8086	Intermediate Similarity	NPC13989
0.8085	Intermediate Similarity	NPC30174
0.8085	Intermediate Similarity	NPC288290
0.8074	Intermediate Similarity	NPC42657
0.8069	Intermediate Similarity	NPC39549
0.8069	Intermediate Similarity	NPC476699
0.8067	Intermediate Similarity	NPC258856
0.8067	Intermediate Similarity	NPC470038
0.8067	Intermediate Similarity	NPC75295
0.8067	Intermediate Similarity	NPC281717
0.8056	Intermediate Similarity	NPC471913
0.8056	Intermediate Similarity	NPC477893
0.8054	Intermediate Similarity	NPC469349
0.8054	Intermediate Similarity	NPC96447
0.8054	Intermediate Similarity	NPC472571
0.8054	Intermediate Similarity	NPC472568
0.8054	Intermediate Similarity	NPC474599
0.8054	Intermediate Similarity	NPC177940
0.8054	Intermediate Similarity	NPC471104
0.8054	Intermediate Similarity	NPC174982
0.8054	Intermediate Similarity	NPC29704
0.8054	Intermediate Similarity	NPC70403
0.8054	Intermediate Similarity	NPC472575
0.8054	Intermediate Similarity	NPC472572
0.8054	Intermediate Similarity	NPC473088
0.8054	Intermediate Similarity	NPC96903
0.8054	Intermediate Similarity	NPC158663
0.8054	Intermediate Similarity	NPC200471
0.8054	Intermediate Similarity	NPC171525
0.8054	Intermediate Similarity	NPC470157
0.8054	Intermediate Similarity	NPC184817
0.8054	Intermediate Similarity	NPC470159
0.8054	Intermediate Similarity	NPC476973
0.8052	Intermediate Similarity	NPC474534
0.8052	Intermediate Similarity	NPC471874
0.8052	Intermediate Similarity	NPC474533
0.805	Intermediate Similarity	NPC161151
0.8042	Intermediate Similarity	NPC165612
0.8041	Intermediate Similarity	NPC472410
0.8039	Intermediate Similarity	NPC140133
0.8039	Intermediate Similarity	NPC261659

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 NPC304110 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	806
0.2-0.3	1459
0.3-0.4	2591
0.4-0.5	2212
0.5-0.6	1303
0.6-0.7	486
0.7-0.8	27
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9348	High Similarity	NPD8166	Discontinued
0.8099	Intermediate Similarity	NPD6663	Approved
0.8092	Intermediate Similarity	NPD7458	Discontinued
0.8071	Intermediate Similarity	NPD5736	Approved
0.8041	Intermediate Similarity	NPD7003	Approved
0.8038	Intermediate Similarity	NPD8127	Discontinued
0.7895	Intermediate Similarity	NPD6273	Approved
0.78	Intermediate Similarity	NPD4628	Phase 3
0.7626	Intermediate Similarity	NPD3019	Approved
0.7626	Intermediate Similarity	NPD2932	Approved
0.7619	Intermediate Similarity	NPD6355	Discontinued
0.7574	Intermediate Similarity	NPD2629	Approved
0.7534	Intermediate Similarity	NPD6798	Discontinued
0.7517	Intermediate Similarity	NPD7097	Phase 1
0.7516	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD8032	Phase 2
0.7483	Intermediate Similarity	NPD7266	Discontinued
0.7468	Intermediate Similarity	NPD7236	Approved
0.7466	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7095	Approved
0.7451	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4110	Phase 3
0.7451	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4140	Approved
0.7432	Intermediate Similarity	NPD4060	Phase 1
0.7415	Intermediate Similarity	NPD3764	Approved
0.7412	Intermediate Similarity	NPD8313	Approved
0.7412	Intermediate Similarity	NPD8312	Approved
0.7405	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3092	Approved
0.7384	Intermediate Similarity	NPD8150	Discontinued
0.7365	Intermediate Similarity	NPD7228	Approved
0.7357	Intermediate Similarity	NPD3091	Approved
0.7347	Intermediate Similarity	NPD7008	Discontinued
0.7329	Intermediate Similarity	NPD8455	Phase 2
0.7326	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3620	Phase 2
0.7312	Intermediate Similarity	NPD6677	Suspended
0.731	Intermediate Similarity	NPD3094	Phase 2
0.7303	Intermediate Similarity	NPD5405	Approved
0.7303	Intermediate Similarity	NPD5404	Approved
0.7303	Intermediate Similarity	NPD5406	Approved
0.7303	Intermediate Similarity	NPD5408	Approved
0.7267	Intermediate Similarity	NPD37	Approved
0.7266	Intermediate Similarity	NPD4198	Discontinued
0.7261	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6234	Discontinued
0.725	Intermediate Similarity	NPD7028	Phase 2
0.7248	Intermediate Similarity	NPD6233	Phase 2
0.7241	Intermediate Similarity	NPD1283	Approved
0.7239	Intermediate Similarity	NPD4967	Phase 2
0.7239	Intermediate Similarity	NPD4966	Approved
0.7239	Intermediate Similarity	NPD7768	Phase 2
0.7239	Intermediate Similarity	NPD4965	Approved
0.7233	Intermediate Similarity	NPD7239	Suspended
0.7219	Intermediate Similarity	NPD5844	Phase 1
0.7203	Intermediate Similarity	NPD3023	Approved
0.7203	Intermediate Similarity	NPD3026	Approved
0.7192	Intermediate Similarity	NPD2797	Approved
0.719	Intermediate Similarity	NPD2438	Suspended
0.719	Intermediate Similarity	NPD2935	Discontinued
0.7184	Intermediate Similarity	NPD8434	Phase 2
0.7183	Intermediate Similarity	NPD3025	Approved
0.7183	Intermediate Similarity	NPD3024	Approved
0.7179	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5735	Approved
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7134	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4626	Approved
0.7133	Intermediate Similarity	NPD3095	Discontinued
0.7124	Intermediate Similarity	NPD2799	Discontinued
0.7122	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3750	Approved
0.7113	Intermediate Similarity	NPD9545	Approved
0.7097	Intermediate Similarity	NPD4534	Discontinued
0.7091	Intermediate Similarity	NPD7075	Discontinued
0.7089	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2979	Phase 3
0.7081	Intermediate Similarity	NPD3455	Phase 2
0.7073	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5951	Approved
0.7067	Intermediate Similarity	NPD3268	Approved
0.7063	Intermediate Similarity	NPD5691	Approved
0.7055	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6858	Approved
0.705	Intermediate Similarity	NPD7094	Approved
0.7044	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4380	Phase 2
0.7035	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1281	Approved
0.7021	Intermediate Similarity	NPD7157	Approved
0.702	Intermediate Similarity	NPD4062	Phase 3
0.7014	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7819	Suspended
0.7012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD8651	Approved
0.7007	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7473	Discontinued
0.6994	Remote Similarity	NPD7240	Approved
0.6993	Remote Similarity	NPD6653	Approved
0.697	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1470	Approved
0.6957	Remote Similarity	NPD3022	Approved
0.6957	Remote Similarity	NPD3021	Approved
0.6941	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5327	Phase 3
0.6937	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6599	Discontinued
0.6928	Remote Similarity	NPD230	Phase 1
0.6923	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD6232	Discontinued
0.6919	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1201	Approved
0.6913	Remote Similarity	NPD5647	Approved
0.6908	Remote Similarity	NPD7961	Discontinued
0.6897	Remote Similarity	NPD7685	Pre-registration
0.6879	Remote Similarity	NPD5958	Discontinued
0.6875	Remote Similarity	NPD7390	Discontinued
0.6871	Remote Similarity	NPD3972	Approved
0.6864	Remote Similarity	NPD7199	Phase 2
0.6863	Remote Similarity	NPD826	Approved
0.6863	Remote Similarity	NPD825	Approved
0.686	Remote Similarity	NPD7799	Discontinued
0.6859	Remote Similarity	NPD4477	Approved
0.6859	Remote Similarity	NPD2531	Phase 2
0.6859	Remote Similarity	NPD6099	Approved
0.6859	Remote Similarity	NPD6100	Approved
0.6859	Remote Similarity	NPD4476	Approved
0.6853	Remote Similarity	NPD9493	Approved
0.6848	Remote Similarity	NPD6801	Discontinued
0.6846	Remote Similarity	NPD1164	Approved
0.6842	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6166	Phase 2
0.6842	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5909	Discontinued
0.6835	Remote Similarity	NPD6674	Discontinued
0.6828	Remote Similarity	NPD5585	Approved
0.6828	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7497	Discontinued
0.6828	Remote Similarity	NPD1651	Approved
0.6826	Remote Similarity	NPD7058	Phase 2
0.6826	Remote Similarity	NPD7057	Phase 3
0.6821	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3300	Phase 2
0.6812	Remote Similarity	NPD1358	Approved
0.6809	Remote Similarity	NPD7843	Approved
0.6807	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2798	Approved
0.6797	Remote Similarity	NPD7715	Approved
0.6797	Remote Similarity	NPD7714	Approved
0.6795	Remote Similarity	NPD3748	Approved
0.6795	Remote Similarity	NPD4308	Phase 3
0.6791	Remote Similarity	NPD3020	Approved
0.6791	Remote Similarity	NPD8320	Phase 1
0.6791	Remote Similarity	NPD8319	Approved
0.6788	Remote Similarity	NPD7411	Suspended
0.6788	Remote Similarity	NPD6873	Phase 2
0.6786	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7074	Phase 3
0.6781	Remote Similarity	NPD1778	Approved
0.6781	Remote Similarity	NPD4059	Approved
0.6781	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6353	Approved
0.6772	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3226	Approved
0.6765	Remote Similarity	NPD6647	Phase 2
0.6765	Remote Similarity	NPD6959	Discontinued
0.6763	Remote Similarity	NPD3751	Discontinued
0.6761	Remote Similarity	NPD1241	Discontinued
0.6759	Remote Similarity	NPD1894	Discontinued
0.6759	Remote Similarity	NPD7741	Discontinued
0.6757	Remote Similarity	NPD1608	Approved
0.6755	Remote Similarity	NPD9494	Approved
0.6748	Remote Similarity	NPD5403	Approved
0.6748	Remote Similarity	NPD7427	Discontinued
0.6747	Remote Similarity	NPD1934	Approved
0.6739	Remote Similarity	NPD3134	Approved
0.6737	Remote Similarity	NPD8151	Discontinued
0.6735	Remote Similarity	NPD3847	Discontinued
0.6735	Remote Similarity	NPD3496	Discontinued
0.6733	Remote Similarity	NPD3267	Approved
0.6733	Remote Similarity	NPD3266	Approved
0.6732	Remote Similarity	NPD7985	Registered
0.6732	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2313	Discontinued
0.6732	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7054	Approved
0.6722	Remote Similarity	NPD8360	Approved
0.6722	Remote Similarity	NPD8361	Approved

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