NPASS Compound

Structure

CID298072 OpenBabel06191716102D 56 64 0 0 1 0 0 0 0 0999 V2000 6.9700 1.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1149 0.0299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0967 -3.3562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7488 -1.7887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8567 -3.4832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0383 -1.2016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5663 -1.8628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7016 -0.4623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4737 -0.3188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2343 0.2320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7577 -1.7847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8930 -0.3841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5212 -0.9175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8291 0.6753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0160 -1.9690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5379 -1.6889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1003 0.8296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5691 1.1918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1836 -0.1771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3970 -2.5590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3494 1.8368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0895 0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5663 -2.3681 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9367 -1.5710 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9976 -2.5611 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4210 -1.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0415 -2.0008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3717 -1.4992 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1797 0.2426 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1171 0.9670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3019 0.9629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3031 -1.2922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0206 0.0002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3614 -2.5665 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4148 0.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3569 -0.7654 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9822 0.9328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8297 -2.3621 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3956 0.7163 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5880 0.6830 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9365 -0.3066 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3570 -1.9915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6342 -0.8431 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.2967 2.4371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6697 2.0224 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3285 -1.7462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9360 2.0533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8723 -2.9460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4845 0.4830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8260 -1.2975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3972 -1.9532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7099 1.0638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8091 0.4998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6341 -1.9918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0348 -0.3823 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 22 1 0 0 0 0 2 22 1 0 0 0 0 4 24 1 0 0 0 0 5 38 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 10 14 2 0 0 0 0 11 26 2 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 31 1 0 0 0 0 15 16 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 22 1 0 0 0 0 19 32 1 0 0 0 0 20 25 1 0 0 0 0 20 38 1 0 0 0 0 21 44 1 0 0 0 0 23 3 1 1 0 0 0 23 25 1 0 0 0 0 23 27 1 0 0 0 0 24 34 1 0 0 0 0 24 41 1 6 0 0 0 25 15 1 6 0 0 0 26 43 1 0 0 0 0 27 16 1 1 0 0 0 27 28 1 0 0 0 0 28 51 1 6 0 0 0 29 40 1 6 0 0 0 29 41 1 0 0 0 0 30 40 1 6 0 0 0 30 52 1 0 0 0 0 31 45 2 0 0 0 0 31 52 1 0 0 0 0 32 46 2 0 0 0 0 32 51 1 0 0 0 0 33 35 1 0 0 0 0 33 36 1 0 0 0 0 33 41 1 1 0 0 0 34 42 1 1 0 0 0 34 54 1 0 0 0 0 35 39 1 6 0 0 0 35 53 1 0 0 0 0 36 42 1 6 0 0 0 36 55 1 0 0 0 0 37 39 1 6 0 0 0 37 40 1 0 0 0 0 37 47 1 0 0 0 0 38 42 1 6 0 0 0 38 48 1 0 0 0 0 39 21 1 6 0 0 0 39 53 1 0 0 0 0 40 49 1 1 0 0 0 41 56 1 1 0 0 0 42 50 1 1 0 0 0 43 54 1 0 0 0 0 43 55 1 0 0 0 0 43 56 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	780.37
Volume:	771.093
LogP:	4.692
LogD:	3.518
LogS:	-4.15
# Rotatable Bonds:	6
TPSA:	193.97
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	10
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.216
Synthetic Accessibility Score:	7.825
Fsp3:	0.721
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:	-5.115
MDCK Permeability:	7.802072650520131e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.924
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.236
Plasma Protein Binding (PPB):	95.14476013183594%
Volume Distribution (VD):	0.879
Pgp-substrate:	2.4097583293914795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.35
CYP2C9-inhibitor:	0.184
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.443
CYP3A4-substrate:	0.483

ADMET: Excretion

Clearance (CL):	2.782
Half-life (T1/2):	0.784

ADMET: Toxicity

hERG Blockers:	0.517
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.284
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.581
Carcinogencity:	0.714
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC298072

Natural Product ID:	NPC298072
*Common Name:**	Rediocide E
IUPAC Name:	n.a.
Synonyms:	Rediocide E
Standard InCHIKey:	RTYNTVIIQWLHDN-WXDMZXKPSA-N
Standard InCHI:	InChI=1S/C43H56O13/c1-22(2)19-32(46)51-28-13-9-10-14-31(45)52-30-18-17-29-40(30,49)37(47)39(21-44)35(53-39)33-36-42(50,38(5,48)20-25-15-16-27(28)23(25)3)34-24(4)41(29,33)56-43(54-34,55-36)26-11-7-6-8-12-26/h6-14,22-25,27-30,33-37,44,47-50H,15-21H2,1-5H3/b13-9+,14-10+/t23-,24+,25+,27-,28-,29+,30-,33-,34-,35-,36+,37+,38+,39-,40+,41-,42-,43?/m0/s1
SMILES:	OC[C@]12O[C@H]1[C@@H]1[C@]34[C@H]5[C@@]([C@@H]2O)(O)[C@H](CC5)OC(=O)/C=C/C=C/[C@@H]([C@@H]2[C@H]([C@@H](C[C@@]([C@]5([C@@H]1OC(O3)(O[C@H]5[C@H]4C)c1ccccc1)O)(C)O)CC2)C)OC(=O)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505537
PubChem CID:	44575543
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	roots	Rat Buri Province, Thailand	1988-DEC	PMID[14987064]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[16204992]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17790	Trigonostemon reidioides	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	=	0.5	ppm	PMID[531697]

☑ 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 NPC298072 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	362
0.1-0.2	1318
0.2-0.3	2965
0.3-0.4	6377
0.4-0.5	11822
0.5-0.6	15130
0.6-0.7	3898
0.7-0.8	715
0.8-0.85	71
0.85-0.9	18
0.9-0.95	17
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC62792
0.9583	High Similarity	NPC478123
0.94	High Similarity	NPC478124
0.9301	High Similarity	NPC471139
0.9195	High Similarity	NPC475638
0.9195	High Similarity	NPC290683
0.9195	High Similarity	NPC475548
0.9139	High Similarity	NPC323356
0.9139	High Similarity	NPC471138
0.9139	High Similarity	NPC326328
0.9139	High Similarity	NPC309991
0.9085	High Similarity	NPC478125
0.9073	High Similarity	NPC319404
0.906	High Similarity	NPC471135
0.9007	High Similarity	NPC322048
0.9007	High Similarity	NPC318447
0.894	High Similarity	NPC323001
0.894	High Similarity	NPC326235
0.8699	High Similarity	NPC325078
0.8658	High Similarity	NPC312393
0.8616	High Similarity	NPC40138
0.8609	High Similarity	NPC476173
0.8608	High Similarity	NPC325732
0.8608	High Similarity	NPC324769
0.8581	High Similarity	NPC49297
0.8571	High Similarity	NPC154675
0.8535	High Similarity	NPC275477
0.8516	High Similarity	NPC181924
0.8491	Intermediate Similarity	NPC477491
0.8477	Intermediate Similarity	NPC327031
0.8462	Intermediate Similarity	NPC476784
0.8447	Intermediate Similarity	NPC477488
0.8421	Intermediate Similarity	NPC474564
0.8418	Intermediate Similarity	NPC477190
0.8418	Intermediate Similarity	NPC43304
0.8418	Intermediate Similarity	NPC477188
0.8375	Intermediate Similarity	NPC61891
0.8375	Intermediate Similarity	NPC473468
0.8375	Intermediate Similarity	NPC475567
0.8375	Intermediate Similarity	NPC473557
0.8366	Intermediate Similarity	NPC70236
0.8366	Intermediate Similarity	NPC476092
0.8366	Intermediate Similarity	NPC475218
0.8366	Intermediate Similarity	NPC475447
0.8365	Intermediate Similarity	NPC322420
0.8323	Intermediate Similarity	NPC146310
0.8323	Intermediate Similarity	NPC475531
0.8323	Intermediate Similarity	NPC475198
0.8323	Intermediate Similarity	NPC475175
0.8301	Intermediate Similarity	NPC76103
0.8289	Intermediate Similarity	NPC478263
0.8269	Intermediate Similarity	NPC469398
0.825	Intermediate Similarity	NPC66193
0.8247	Intermediate Similarity	NPC475417
0.8247	Intermediate Similarity	NPC475561
0.8224	Intermediate Similarity	NPC478264
0.8205	Intermediate Similarity	NPC472658
0.8205	Intermediate Similarity	NPC472657
0.8199	Intermediate Similarity	NPC471134
0.8194	Intermediate Similarity	NPC96308
0.8194	Intermediate Similarity	NPC469415
0.8176	Intermediate Similarity	NPC477623
0.817	Intermediate Similarity	NPC240115
0.8158	Intermediate Similarity	NPC34943
0.8153	Intermediate Similarity	NPC469422
0.8153	Intermediate Similarity	NPC471176
0.8129	Intermediate Similarity	NPC222102
0.8129	Intermediate Similarity	NPC303429
0.8075	Intermediate Similarity	NPC165234
0.8075	Intermediate Similarity	NPC475536
0.8052	Intermediate Similarity	NPC20255
0.8052	Intermediate Similarity	NPC473602
0.8038	Intermediate Similarity	NPC34066
0.8038	Intermediate Similarity	NPC251139
0.8026	Intermediate Similarity	NPC192658
0.8025	Intermediate Similarity	NPC475437
0.8025	Intermediate Similarity	NPC475300
0.8025	Intermediate Similarity	NPC475505
0.8025	Intermediate Similarity	NPC473797
0.8025	Intermediate Similarity	NPC473641
0.8025	Intermediate Similarity	NPC475464
0.8	Intermediate Similarity	NPC473760
0.7987	Intermediate Similarity	NPC472568
0.7987	Intermediate Similarity	NPC70344
0.7987	Intermediate Similarity	NPC472575
0.7987	Intermediate Similarity	NPC472572
0.7987	Intermediate Similarity	NPC473088
0.7987	Intermediate Similarity	NPC70403
0.7987	Intermediate Similarity	NPC470159
0.7987	Intermediate Similarity	NPC125882
0.7987	Intermediate Similarity	NPC470157
0.7987	Intermediate Similarity	NPC476973
0.7987	Intermediate Similarity	NPC200471
0.7987	Intermediate Similarity	NPC472571
0.7987	Intermediate Similarity	NPC177940
0.7987	Intermediate Similarity	NPC311825
0.7987	Intermediate Similarity	NPC471104
0.7987	Intermediate Similarity	NPC158663
0.7987	Intermediate Similarity	NPC171525
0.7987	Intermediate Similarity	NPC29704
0.7987	Intermediate Similarity	NPC469349
0.7987	Intermediate Similarity	NPC184817
0.7987	Intermediate Similarity	NPC96903
0.7987	Intermediate Similarity	NPC92867
0.7987	Intermediate Similarity	NPC174982
0.7974	Intermediate Similarity	NPC191387
0.7974	Intermediate Similarity	NPC131966
0.7961	Intermediate Similarity	NPC291599
0.7961	Intermediate Similarity	NPC118080
0.7961	Intermediate Similarity	NPC41481
0.7961	Intermediate Similarity	NPC87448
0.7961	Intermediate Similarity	NPC97947
0.7961	Intermediate Similarity	NPC472576
0.7961	Intermediate Similarity	NPC27377
0.7961	Intermediate Similarity	NPC16912
0.7935	Intermediate Similarity	NPC48599
0.7935	Intermediate Similarity	NPC209592
0.7925	Intermediate Similarity	NPC469456
0.7922	Intermediate Similarity	NPC11685
0.7922	Intermediate Similarity	NPC95810
0.7922	Intermediate Similarity	NPC475759
0.7922	Intermediate Similarity	NPC70716
0.7922	Intermediate Similarity	NPC188865
0.7922	Intermediate Similarity	NPC57628
0.7922	Intermediate Similarity	NPC95265
0.7922	Intermediate Similarity	NPC163719
0.7922	Intermediate Similarity	NPC476974
0.7922	Intermediate Similarity	NPC472569
0.7922	Intermediate Similarity	NPC241951
0.7922	Intermediate Similarity	NPC470152
0.7922	Intermediate Similarity	NPC25768
0.7922	Intermediate Similarity	NPC125106
0.7922	Intermediate Similarity	NPC472573
0.7922	Intermediate Similarity	NPC472570
0.7922	Intermediate Similarity	NPC475122
0.7914	Intermediate Similarity	NPC269668
0.7908	Intermediate Similarity	NPC34012
0.7908	Intermediate Similarity	NPC475513
0.7908	Intermediate Similarity	NPC473755
0.7898	Intermediate Similarity	NPC469448
0.7898	Intermediate Similarity	NPC31829
0.7895	Intermediate Similarity	NPC275592
0.7895	Intermediate Similarity	NPC473440
0.7895	Intermediate Similarity	NPC472547
0.7895	Intermediate Similarity	NPC162613
0.7895	Intermediate Similarity	NPC90614
0.7895	Intermediate Similarity	NPC97667
0.7895	Intermediate Similarity	NPC171207
0.7895	Intermediate Similarity	NPC87934
0.7895	Intermediate Similarity	NPC100913
0.7877	Intermediate Similarity	NPC58061
0.7871	Intermediate Similarity	NPC472556
0.7871	Intermediate Similarity	NPC251062
0.7871	Intermediate Similarity	NPC184464
0.7857	Intermediate Similarity	NPC91703
0.7857	Intermediate Similarity	NPC163087
0.7843	Intermediate Similarity	NPC266374
0.7834	Intermediate Similarity	NPC266265
0.7834	Intermediate Similarity	NPC476975
0.7834	Intermediate Similarity	NPC270590
0.7834	Intermediate Similarity	NPC301556
0.7834	Intermediate Similarity	NPC92293
0.7834	Intermediate Similarity	NPC471101
0.7829	Intermediate Similarity	NPC9905
0.7821	Intermediate Similarity	NPC474935
0.7812	Intermediate Similarity	NPC132599
0.7812	Intermediate Similarity	NPC473611
0.7812	Intermediate Similarity	NPC473632
0.7812	Intermediate Similarity	NPC469730
0.7812	Intermediate Similarity	NPC5115
0.7808	Intermediate Similarity	NPC476971
0.7808	Intermediate Similarity	NPC476972
0.7803	Intermediate Similarity	NPC186746
0.7799	Intermediate Similarity	NPC138641
0.7799	Intermediate Similarity	NPC233581
0.7799	Intermediate Similarity	NPC283875
0.7799	Intermediate Similarity	NPC22571
0.7799	Intermediate Similarity	NPC469648
0.7799	Intermediate Similarity	NPC469647
0.7799	Intermediate Similarity	NPC145649
0.7793	Intermediate Similarity	NPC284022
0.7792	Intermediate Similarity	NPC63737
0.7785	Intermediate Similarity	NPC476976
0.7785	Intermediate Similarity	NPC470245
0.7785	Intermediate Similarity	NPC473214
0.7778	Intermediate Similarity	NPC475613
0.7778	Intermediate Similarity	NPC469399
0.7771	Intermediate Similarity	NPC281717
0.7764	Intermediate Similarity	NPC11410
0.7763	Intermediate Similarity	NPC39549
0.7755	Intermediate Similarity	NPC175333
0.775	Intermediate Similarity	NPC469477
0.775	Intermediate Similarity	NPC133430
0.7748	Intermediate Similarity	NPC200154
0.7742	Intermediate Similarity	NPC477894
0.774	Intermediate Similarity	NPC476970
0.774	Intermediate Similarity	NPC475933
0.774	Intermediate Similarity	NPC470158
0.7736	Intermediate Similarity	NPC472398
0.7736	Intermediate Similarity	NPC470153

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 NPC298072 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	813
0.2-0.3	1928
0.3-0.4	3384
0.4-0.5	2044
0.5-0.6	591
0.6-0.7	99
0.7-0.8	3
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
0.7633	Intermediate Similarity	NPD7799	Discontinued
0.7386	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7236	Approved
0.7283	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7685	Pre-registration
0.7211	Intermediate Similarity	NPD5125	Phase 3
0.7211	Intermediate Similarity	NPD5126	Approved
0.7195	Intermediate Similarity	NPD7239	Suspended
0.7161	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7266	Discontinued
0.7075	Intermediate Similarity	NPD7741	Discontinued
0.6966	Remote Similarity	NPD8368	Discontinued
0.6944	Remote Similarity	NPD8407	Phase 2
0.6936	Remote Similarity	NPD8127	Discontinued
0.6932	Remote Similarity	NPD7228	Approved
0.6913	Remote Similarity	NPD8335	Approved
0.6913	Remote Similarity	NPD8380	Approved
0.6913	Remote Similarity	NPD8379	Approved
0.6913	Remote Similarity	NPD8296	Approved
0.6913	Remote Similarity	NPD8378	Approved
0.6894	Remote Similarity	NPD5763	Approved
0.6894	Remote Similarity	NPD5762	Approved
0.6892	Remote Similarity	NPD7516	Approved
0.6883	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD8294	Approved
0.6846	Remote Similarity	NPD8377	Approved
0.6824	Remote Similarity	NPD7327	Approved
0.6824	Remote Similarity	NPD7328	Approved
0.6807	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4967	Phase 2
0.6802	Remote Similarity	NPD7057	Phase 3
0.6802	Remote Similarity	NPD7058	Phase 2
0.6802	Remote Similarity	NPD4966	Approved
0.6802	Remote Similarity	NPD4965	Approved
0.68	Remote Similarity	NPD8033	Approved
0.6778	Remote Similarity	NPD7240	Approved
0.6752	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7199	Phase 2
0.6727	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD37	Approved
0.6724	Remote Similarity	NPD6234	Discontinued
0.6719	Remote Similarity	NPD7497	Discontinued
0.6713	Remote Similarity	NPD6685	Approved
0.6703	Remote Similarity	NPD8361	Approved
0.6703	Remote Similarity	NPD8435	Approved
0.6703	Remote Similarity	NPD8360	Approved
0.6689	Remote Similarity	NPD7503	Approved
0.6686	Remote Similarity	NPD8455	Phase 2
0.6685	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4198	Discontinued
0.6631	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8312	Approved
0.6612	Remote Similarity	NPD8313	Approved
0.6608	Remote Similarity	NPD7028	Phase 2
0.6605	Remote Similarity	NPD7097	Phase 1
0.6595	Remote Similarity	NPD8434	Phase 2
0.6585	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6004	Phase 3
0.6585	Remote Similarity	NPD6005	Phase 3
0.6585	Remote Similarity	NPD6002	Phase 3
0.6584	Remote Similarity	NPD5735	Approved
0.6573	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6663	Approved
0.6543	Remote Similarity	NPD6653	Approved
0.6527	Remote Similarity	NPD6190	Approved
0.6519	Remote Similarity	NPD5736	Approved
0.6516	Remote Similarity	NPD7507	Approved
0.6506	Remote Similarity	NPD6674	Discontinued
0.6505	Remote Similarity	NPD8150	Discontinued
0.6503	Remote Similarity	NPD5765	Approved
0.6497	Remote Similarity	NPD7319	Approved
0.6491	Remote Similarity	NPD1653	Approved
0.6486	Remote Similarity	NPD6912	Phase 3
0.6486	Remote Similarity	NPD969	Suspended
0.6477	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6273	Approved
0.6467	Remote Similarity	NPD8166	Discontinued
0.6464	Remote Similarity	NPD3751	Discontinued
0.6429	Remote Similarity	NPD5844	Phase 1
0.6429	Remote Similarity	NPD8320	Phase 1
0.6429	Remote Similarity	NPD8319	Approved
0.6425	Remote Similarity	NPD3787	Discontinued
0.642	Remote Similarity	NPD4140	Approved
0.6393	Remote Similarity	NPD7074	Phase 3
0.6392	Remote Similarity	NPD3094	Phase 2
0.6389	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.638	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.638	Remote Similarity	NPD5124	Phase 1
0.6373	Remote Similarity	NPD7700	Phase 2
0.6373	Remote Similarity	NPD7699	Phase 2
0.6369	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7961	Discontinued
0.6358	Remote Similarity	NPD2629	Approved
0.6352	Remote Similarity	NPD6085	Phase 2
0.6352	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7094	Approved
0.6333	Remote Similarity	NPD6858	Approved
0.6324	Remote Similarity	NPD6559	Discontinued
0.6324	Remote Similarity	NPD6765	Approved
0.6324	Remote Similarity	NPD6764	Approved
0.6321	Remote Similarity	NPD8485	Approved
0.6307	Remote Similarity	NPD5760	Phase 2
0.6307	Remote Similarity	NPD5761	Phase 2
0.6307	Remote Similarity	NPD7819	Suspended
0.6296	Remote Similarity	NPD7985	Registered
0.6294	Remote Similarity	NPD7680	Approved
0.6292	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.628	Remote Similarity	NPD6355	Discontinued
0.6276	Remote Similarity	NPD6647	Phase 2
0.6272	Remote Similarity	NPD4628	Phase 3
0.6257	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD7054	Approved
0.6242	Remote Similarity	NPD6353	Approved
0.6242	Remote Similarity	NPD3092	Approved
0.6236	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7999	Approved
0.6229	Remote Similarity	NPD4380	Phase 2
0.6221	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6534	Approved
0.6218	Remote Similarity	NPD6535	Approved
0.6216	Remote Similarity	NPD7472	Approved
0.6215	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD7435	Discontinued
0.6207	Remote Similarity	NPD8462	Phase 1
0.6203	Remote Similarity	NPD7808	Phase 3
0.6201	Remote Similarity	NPD7075	Discontinued
0.62	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6785	Approved
0.619	Remote Similarity	NPD6784	Approved
0.6188	Remote Similarity	NPD6362	Approved
0.6183	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD6648	Approved
0.6176	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD7458	Discontinued
0.6169	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8513	Phase 3
0.6154	Remote Similarity	NPD8515	Approved
0.6154	Remote Similarity	NPD8517	Approved
0.6154	Remote Similarity	NPD2424	Discontinued
0.6154	Remote Similarity	NPD8516	Approved
0.615	Remote Similarity	NPD7251	Discontinued
0.6146	Remote Similarity	NPD7930	Approved
0.6144	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD7008	Discontinued
0.6133	Remote Similarity	NPD5494	Approved
0.6131	Remote Similarity	NPD7137	Phase 2
0.6131	Remote Similarity	NPD7698	Approved
0.6131	Remote Similarity	NPD7696	Phase 3
0.6131	Remote Similarity	NPD7697	Approved
0.6125	Remote Similarity	NPD7736	Approved
0.6121	Remote Similarity	NPD3620	Phase 2
0.6121	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1652	Phase 2
0.6118	Remote Similarity	NPD8133	Approved
0.6117	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2861	Phase 2
0.6111	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD7874	Approved
0.6108	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD3818	Discontinued
0.6108	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5058	Phase 3
0.6104	Remote Similarity	NPD7115	Discovery
0.6098	Remote Similarity	NPD3764	Approved
0.6096	Remote Similarity	NPD6797	Phase 2
0.6089	Remote Similarity	NPD5402	Approved
0.6089	Remote Similarity	NPD7701	Phase 2
0.6082	Remote Similarity	NPD2575	Approved
0.608	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6823	Phase 2
0.6078	Remote Similarity	NPD7783	Phase 2
0.6078	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7033	Discontinued
0.6067	Remote Similarity	NPD2182	Approved
0.6062	Remote Similarity	NPD7078	Approved
0.6061	Remote Similarity	NPD6781	Approved
0.6061	Remote Similarity	NPD6776	Approved
0.6061	Remote Similarity	NPD6779	Approved
0.6061	Remote Similarity	NPD6778	Approved
0.6061	Remote Similarity	NPD6780	Approved
0.6061	Remote Similarity	NPD6782	Approved
0.6061	Remote Similarity	NPD6777	Approved
0.6059	Remote Similarity	NPD8151	Discontinued
0.6057	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD7473	Discontinued
0.6049	Remote Similarity	NPD5647	Approved
0.6038	Remote Similarity	NPD7492	Approved
0.6038	Remote Similarity	NPD1091	Approved
0.6037	Remote Similarity	NPD7095	Approved
0.6026	Remote Similarity	NPD2067	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data