NPASS Compound

Structure

NPC29389 OpenBabel07101718292D 37 41 0 0 1 0 0 0 0 0999 V2000 0.0922 -1.6794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3257 -0.1894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7345 2.6103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1443 1.8005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1707 3.4269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6144 3.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6510 3.1126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0423 3.5213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7158 -0.3194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0019 0.9996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7158 0.4007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1887 1.5423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5314 -0.3194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1682 0.2333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1769 2.3234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5142 0.3717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9972 -0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0922 -0.6794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6490 0.5469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8830 3.1346 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0032 2.6594 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1797 2.3981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5314 0.4007 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4140 1.3519 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5165 3.2912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6116 0.0929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1995 1.4728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0922 0.7608 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5633 0.8262 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9114 4.1342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0298 4.1288 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6934 -0.9038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1891 2.1163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0396 0.1407 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 -1.2017 0.6638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0939 2.9027 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 8 2 0 0 0 0 7 21 1 0 0 0 0 8 25 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 12 33 1 0 0 0 0 13 18 2 0 0 0 0 13 23 1 0 0 0 0 14 19 2 0 0 0 0 14 26 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 28 1 0 0 0 0 16 34 1 0 0 0 0 17 29 1 0 0 0 0 17 35 1 0 0 0 0 20 3 1 6 0 0 0 20 30 1 0 0 0 0 21 20 1 6 0 0 0 21 33 1 0 0 0 0 22 27 1 1 0 0 0 22 37 1 0 0 0 0 23 28 1 1 0 0 0 23 36 1 0 0 0 0 24 29 1 1 0 0 0 24 36 1 0 0 0 0 25 31 2 0 0 0 0 25 37 1 0 0 0 0 26 32 2 0 0 0 0 26 34 1 0 0 0 0 27 28 1 6 0 0 0 28 11 1 1 0 0 0 29 27 1 6 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.26
Volume:	521.861
LogP:	2.9
LogD:	1.752
LogS:	-4.432
# Rotatable Bonds:	1
TPSA:	103.82
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	7.145
Fsp3:	0.655
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.214
MDCK Permeability:	1.5549354429822415e-05
Pgp-inhibitor:	0.815
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.794

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.14
Plasma Protein Binding (PPB):	82.69097137451172%
Volume Distribution (VD):	1.911
Pgp-substrate:	5.464231014251709%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.736
CYP2C19-substrate:	0.643
CYP2C9-inhibitor:	0.898
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.855
CYP3A4-substrate:	0.657

ADMET: Excretion

Clearance (CL):	1.459
Half-life (T1/2):	0.715

ADMET: Toxicity

hERG Blockers:	0.675
Human Hepatotoxicity (H-HT):	0.749
Drug-inuced Liver Injury (DILI):	0.09
AMES Toxicity:	0.797
Rat Oral Acute Toxicity:	0.434
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.927
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.904

Download Data

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

Natural Product: NPC29389

Natural Product ID:	NPC29389
*Common Name:**	Roridin E
IUPAC Name:	n.a.
Synonyms:	Roridin E
Standard InCHIKey:	KEEQQEKLEZRLDS-FLGSVKSYSA-N
Standard InCHI:	InChI=1S/C29H38O8/c1-18-9-11-28-16-34-26(32)14-19(2)10-12-33-21(20(3)30)7-5-6-8-25(31)37-22-15-24(36-23(28)13-18)29(17-35-29)27(22,28)4/h5-8,13-14,20-24,30H,9-12,15-17H2,1-4H3/b7-5+,8-6-,19-14+/t20-,21-,22-,23-,24-,27-,28-,29+/m1/s1
SMILES:	C/C/1=CC(=O)OC[C@]23CCC(=C[C@H]2O[C@H]2[C@]4([C@]3(C)[C@H](OC(=O)/C=CC=C[C@@H](OCC1)[C@H](O)C)C2)CO4)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509175
PubChem CID:	44593339
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075777]
NPO29965	Myrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	Palau	n.a.	PMID[11277768]
NPO29965	Myrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027756]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[13678412]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21539317]
NPO7578	Trichoderma cornu-damae	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30457333]
NPO6563	Paramyrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117520]
NPO10303	Cercophora areolata	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792624]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29965	Myrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6563	Paramyrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7578	Trichoderma cornu-damae	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6563	Paramyrothecium roridum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10303	Cercophora areolata	Species	Lasiosphaeriaceae	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
EC50	4
IC50	10
Others	3

Activity Type	# Activity
Cell Line	11
NON-MOLECULAR	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.0003	ug.mL-1	PMID[464853]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.0002	ug.mL-1	PMID[464853]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	0.0005	ug.mL-1	PMID[464856]
NPT189	Cell Line	Vero	Chlorocebus aethiops	EC50	=	0.0004	ug.mL-1	PMID[464856]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	9700.0	nM	PMID[464857]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	=	0.02	nM	PMID[464858]
NPT2459	Cell Line	HCC70	Homo sapiens	IC50	=	0.02	nM	PMID[464858]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	0.03	nM	PMID[464858]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	0.05	nM	PMID[464858]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	540.0	nM	PMID[464859]
NPT2482	Cell Line	SW 1116	Homo sapiens	IC50	=	39.0	nM	PMID[464859]
NPT3095	Organism	Sordaria fimicola	Sordaria fimicola	Activity	=	100.0	%	PMID[464854]
NPT3096	Organism	Ascobolus	Ascobolus	Activity	=	100.0	%	PMID[464854]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	29.0	mm	PMID[464854]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.6	10'-10 uM	PMID[464855]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	EC50	=	0.00015	ug.mL-1	PMID[464856]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	0.0007	ug.mL-1	PMID[464856]

☑ 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 NPC29389 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	195
0.1-0.2	1121
0.2-0.3	4297
0.3-0.4	9603
0.4-0.5	13316
0.5-0.6	7939
0.6-0.7	5306
0.7-0.8	832
0.8-0.85	33
0.85-0.9	11
0.9-0.95	25
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469960
1.0	High Similarity	NPC265502
1.0	High Similarity	NPC93026
0.9898	High Similarity	NPC108682
0.9898	High Similarity	NPC469959
0.9898	High Similarity	NPC469957
0.9898	High Similarity	NPC472263
0.9485	High Similarity	NPC79631
0.9485	High Similarity	NPC98813
0.9485	High Similarity	NPC13743
0.9381	High Similarity	NPC65700
0.9327	High Similarity	NPC287075
0.9327	High Similarity	NPC101400
0.9327	High Similarity	NPC101965
0.9238	High Similarity	NPC305044
0.9238	High Similarity	NPC265290
0.9231	High Similarity	NPC313921
0.9231	High Similarity	NPC98038
0.9082	High Similarity	NPC476057
0.9082	High Similarity	NPC347923
0.9072	High Similarity	NPC240838
0.9	High Similarity	NPC26557
0.899	High Similarity	NPC274458
0.899	High Similarity	NPC474957
0.899	High Similarity	NPC79449
0.8911	High Similarity	NPC200672
0.8911	High Similarity	NPC252242
0.8911	High Similarity	NPC475956
0.8911	High Similarity	NPC214714
0.8889	High Similarity	NPC182811
0.8824	High Similarity	NPC260809
0.8824	High Similarity	NPC474783
0.8824	High Similarity	NPC232515
0.8774	High Similarity	NPC71680
0.8725	High Similarity	NPC475986
0.8692	High Similarity	NPC241477
0.8679	High Similarity	NPC41551
0.8679	High Similarity	NPC15551
0.8679	High Similarity	NPC50223
0.8636	High Similarity	NPC474286
0.8636	High Similarity	NPC475130
0.8393	Intermediate Similarity	NPC278681
0.8319	Intermediate Similarity	NPC112936
0.8304	Intermediate Similarity	NPC16701
0.8283	Intermediate Similarity	NPC197107
0.823	Intermediate Similarity	NPC213761
0.823	Intermediate Similarity	NPC35171
0.8214	Intermediate Similarity	NPC185287
0.8214	Intermediate Similarity	NPC157380
0.8208	Intermediate Similarity	NPC169843
0.8198	Intermediate Similarity	NPC216665
0.8174	Intermediate Similarity	NPC471082
0.8165	Intermediate Similarity	NPC181298
0.8113	Intermediate Similarity	NPC123505
0.8073	Intermediate Similarity	NPC475274
0.8073	Intermediate Similarity	NPC77089
0.8061	Intermediate Similarity	NPC61527
0.8058	Intermediate Similarity	NPC57664
0.8039	Intermediate Similarity	NPC469491
0.8036	Intermediate Similarity	NPC43213
0.8019	Intermediate Similarity	NPC470972
0.7981	Intermediate Similarity	NPC120299
0.7963	Intermediate Similarity	NPC470980
0.7944	Intermediate Similarity	NPC183570
0.7931	Intermediate Similarity	NPC312481
0.7921	Intermediate Similarity	NPC177668
0.7921	Intermediate Similarity	NPC3952
0.7913	Intermediate Similarity	NPC219656
0.7905	Intermediate Similarity	NPC475653
0.7885	Intermediate Similarity	NPC255410
0.787	Intermediate Similarity	NPC472822
0.7857	Intermediate Similarity	NPC186155
0.7857	Intermediate Similarity	NPC78673
0.7857	Intermediate Similarity	NPC160517
0.785	Intermediate Similarity	NPC11956
0.7845	Intermediate Similarity	NPC79579
0.7822	Intermediate Similarity	NPC133450
0.781	Intermediate Similarity	NPC475332
0.781	Intermediate Similarity	NPC205143
0.78	Intermediate Similarity	NPC199382
0.7797	Intermediate Similarity	NPC6193
0.7788	Intermediate Similarity	NPC171126
0.7788	Intermediate Similarity	NPC300710
0.7778	Intermediate Similarity	NPC23584
0.7778	Intermediate Similarity	NPC280566
0.7778	Intermediate Similarity	NPC233500
0.7768	Intermediate Similarity	NPC470076
0.7759	Intermediate Similarity	NPC270850
0.7759	Intermediate Similarity	NPC5292
0.7759	Intermediate Similarity	NPC305260
0.7757	Intermediate Similarity	NPC472554
0.7739	Intermediate Similarity	NPC203862
0.7736	Intermediate Similarity	NPC222303
0.7719	Intermediate Similarity	NPC106446
0.7714	Intermediate Similarity	NPC113433
0.7712	Intermediate Similarity	NPC115349
0.7712	Intermediate Similarity	NPC196130
0.7706	Intermediate Similarity	NPC200861
0.7699	Intermediate Similarity	NPC317460
0.7699	Intermediate Similarity	NPC328074
0.7699	Intermediate Similarity	NPC44537
0.7699	Intermediate Similarity	NPC321272
0.7699	Intermediate Similarity	NPC470025
0.7692	Intermediate Similarity	NPC256368
0.7692	Intermediate Similarity	NPC472467
0.7692	Intermediate Similarity	NPC281775
0.7685	Intermediate Similarity	NPC473596
0.7685	Intermediate Similarity	NPC472552
0.7679	Intermediate Similarity	NPC316708
0.7679	Intermediate Similarity	NPC238850
0.7679	Intermediate Similarity	NPC103491
0.7672	Intermediate Similarity	NPC153440
0.7672	Intermediate Similarity	NPC13710
0.7672	Intermediate Similarity	NPC475401
0.7667	Intermediate Similarity	NPC179261
0.7664	Intermediate Similarity	NPC130792
0.7664	Intermediate Similarity	NPC290802
0.7664	Intermediate Similarity	NPC227865
0.7664	Intermediate Similarity	NPC475053
0.7652	Intermediate Similarity	NPC470075
0.7647	Intermediate Similarity	NPC219804
0.7636	Intermediate Similarity	NPC82251
0.7636	Intermediate Similarity	NPC475290
0.7636	Intermediate Similarity	NPC220217
0.7636	Intermediate Similarity	NPC119855
0.7632	Intermediate Similarity	NPC470027
0.7632	Intermediate Similarity	NPC469496
0.7632	Intermediate Similarity	NPC469454
0.7632	Intermediate Similarity	NPC469463
0.7627	Intermediate Similarity	NPC473228
0.7627	Intermediate Similarity	NPC470829
0.7615	Intermediate Similarity	NPC474124
0.7611	Intermediate Similarity	NPC474750
0.7611	Intermediate Similarity	NPC470026
0.7611	Intermediate Similarity	NPC284162
0.7611	Intermediate Similarity	NPC262083
0.7611	Intermediate Similarity	NPC471484
0.7611	Intermediate Similarity	NPC17791
0.7611	Intermediate Similarity	NPC255401
0.7607	Intermediate Similarity	NPC304260
0.7607	Intermediate Similarity	NPC268326
0.7607	Intermediate Similarity	NPC153085
0.7607	Intermediate Similarity	NPC29639
0.7607	Intermediate Similarity	NPC477092
0.7607	Intermediate Similarity	NPC291820
0.7607	Intermediate Similarity	NPC81222
0.7607	Intermediate Similarity	NPC44899
0.7607	Intermediate Similarity	NPC5883
0.7593	Intermediate Similarity	NPC11974
0.7593	Intermediate Similarity	NPC475617
0.7593	Intermediate Similarity	NPC298233
0.7589	Intermediate Similarity	NPC75389
0.7586	Intermediate Similarity	NPC475305
0.7586	Intermediate Similarity	NPC290693
0.7573	Intermediate Similarity	NPC202886
0.7568	Intermediate Similarity	NPC470192
0.7568	Intermediate Similarity	NPC109376
0.7563	Intermediate Similarity	NPC107493
0.7563	Intermediate Similarity	NPC470265
0.7563	Intermediate Similarity	NPC23786
0.7551	Intermediate Similarity	NPC474894
0.7547	Intermediate Similarity	NPC173329
0.7547	Intermediate Similarity	NPC288350
0.7545	Intermediate Similarity	NPC474550
0.7545	Intermediate Similarity	NPC473577
0.7545	Intermediate Similarity	NPC272632
0.7545	Intermediate Similarity	NPC475585
0.7545	Intermediate Similarity	NPC473543
0.7544	Intermediate Similarity	NPC236217
0.7542	Intermediate Similarity	NPC107607
0.7542	Intermediate Similarity	NPC474585
0.7525	Intermediate Similarity	NPC137253
0.7525	Intermediate Similarity	NPC311163
0.7525	Intermediate Similarity	NPC477668
0.7523	Intermediate Similarity	NPC109195
0.7523	Intermediate Similarity	NPC476471
0.7523	Intermediate Similarity	NPC475038
0.7523	Intermediate Similarity	NPC475344
0.7522	Intermediate Similarity	NPC177047
0.7521	Intermediate Similarity	NPC218093
0.7521	Intermediate Similarity	NPC159499
0.75	Intermediate Similarity	NPC472468
0.75	Intermediate Similarity	NPC470024
0.75	Intermediate Similarity	NPC199428
0.75	Intermediate Similarity	NPC310341
0.75	Intermediate Similarity	NPC38855
0.75	Intermediate Similarity	NPC477749
0.75	Intermediate Similarity	NPC275060
0.75	Intermediate Similarity	NPC5311
0.75	Intermediate Similarity	NPC224660
0.75	Intermediate Similarity	NPC472825
0.75	Intermediate Similarity	NPC190286
0.75	Intermediate Similarity	NPC193382
0.75	Intermediate Similarity	NPC99620
0.75	Intermediate Similarity	NPC50124
0.748	Intermediate Similarity	NPC134902
0.7479	Intermediate Similarity	NPC310511
0.7479	Intermediate Similarity	NPC46570
0.7479	Intermediate Similarity	NPC475219
0.7479	Intermediate Similarity	NPC231518

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 NPC29389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1287
0.2-0.3	3837
0.3-0.4	2689
0.4-0.5	720
0.5-0.6	285
0.6-0.7	164
0.7-0.8	6
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
0.81	Intermediate Similarity	NPD7838	Discovery
0.7931	Intermediate Similarity	NPD7503	Approved
0.7573	Intermediate Similarity	NPD46	Approved
0.7573	Intermediate Similarity	NPD6698	Approved
0.7479	Intermediate Similarity	NPD8033	Approved
0.7431	Intermediate Similarity	NPD5344	Discontinued
0.7407	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD7328	Approved
0.7373	Intermediate Similarity	NPD7327	Approved
0.7339	Intermediate Similarity	NPD6648	Approved
0.7311	Intermediate Similarity	NPD7516	Approved
0.725	Intermediate Similarity	NPD8377	Approved
0.725	Intermediate Similarity	NPD8294	Approved
0.7217	Intermediate Similarity	NPD6371	Approved
0.7193	Intermediate Similarity	NPD6686	Approved
0.719	Intermediate Similarity	NPD8335	Approved
0.719	Intermediate Similarity	NPD8380	Approved
0.719	Intermediate Similarity	NPD8296	Approved
0.719	Intermediate Similarity	NPD8379	Approved
0.719	Intermediate Similarity	NPD8378	Approved
0.7143	Intermediate Similarity	NPD7115	Discovery
0.7105	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6053	Discontinued
0.7091	Intermediate Similarity	NPD7638	Approved
0.7027	Intermediate Similarity	NPD7640	Approved
0.7027	Intermediate Similarity	NPD7639	Approved
0.6967	Remote Similarity	NPD6319	Approved
0.696	Remote Similarity	NPD7507	Approved
0.6957	Remote Similarity	NPD6412	Phase 2
0.6952	Remote Similarity	NPD7524	Approved
0.6852	Remote Similarity	NPD7637	Suspended
0.6838	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8297	Approved
0.6797	Remote Similarity	NPD7319	Approved
0.6792	Remote Similarity	NPD4251	Approved
0.6792	Remote Similarity	NPD4250	Approved
0.6786	Remote Similarity	NPD4225	Approved
0.6765	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4820	Approved
0.6765	Remote Similarity	NPD4819	Approved
0.6765	Remote Similarity	NPD4821	Approved
0.6765	Remote Similarity	NPD4822	Approved
0.6759	Remote Similarity	NPD5785	Approved
0.675	Remote Similarity	NPD4632	Approved
0.6731	Remote Similarity	NPD6695	Phase 3
0.6698	Remote Similarity	NPD4249	Approved
0.6697	Remote Similarity	NPD7983	Approved
0.6692	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6051	Approved
0.664	Remote Similarity	NPD8513	Phase 3
0.664	Remote Similarity	NPD8517	Approved
0.664	Remote Similarity	NPD8516	Approved
0.664	Remote Similarity	NPD8515	Approved
0.6639	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7492	Approved
0.661	Remote Similarity	NPD6899	Approved
0.661	Remote Similarity	NPD6881	Approved
0.6583	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6649	Approved
0.6583	Remote Similarity	NPD6650	Approved
0.6569	Remote Similarity	NPD4271	Approved
0.6569	Remote Similarity	NPD4268	Approved
0.6562	Remote Similarity	NPD6616	Approved
0.656	Remote Similarity	NPD6054	Approved
0.6549	Remote Similarity	NPD6083	Phase 2
0.6549	Remote Similarity	NPD6084	Phase 2
0.6535	Remote Similarity	NPD7604	Phase 2
0.6529	Remote Similarity	NPD6882	Approved
0.6525	Remote Similarity	NPD5697	Approved
0.6512	Remote Similarity	NPD7078	Approved
0.65	Remote Similarity	NPD7290	Approved
0.65	Remote Similarity	NPD7102	Approved
0.65	Remote Similarity	NPD6883	Approved
0.6486	Remote Similarity	NPD5779	Approved
0.6486	Remote Similarity	NPD5778	Approved
0.6481	Remote Similarity	NPD7750	Discontinued
0.6466	Remote Similarity	NPD7632	Discontinued
0.6462	Remote Similarity	NPD7736	Approved
0.6457	Remote Similarity	NPD6370	Approved
0.6452	Remote Similarity	NPD6009	Approved
0.6449	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6869	Approved
0.6446	Remote Similarity	NPD8130	Phase 1
0.6446	Remote Similarity	NPD6617	Approved
0.6446	Remote Similarity	NPD6847	Approved
0.6442	Remote Similarity	NPD7514	Phase 3
0.6442	Remote Similarity	NPD6931	Approved
0.6442	Remote Similarity	NPD6930	Phase 2
0.6441	Remote Similarity	NPD6675	Approved
0.6441	Remote Similarity	NPD7128	Approved
0.6441	Remote Similarity	NPD6402	Approved
0.6441	Remote Similarity	NPD6008	Approved
0.6441	Remote Similarity	NPD5739	Approved
0.6417	Remote Similarity	NPD6373	Approved
0.6417	Remote Similarity	NPD6012	Approved
0.6417	Remote Similarity	NPD6014	Approved
0.6417	Remote Similarity	NPD6013	Approved
0.6417	Remote Similarity	NPD6372	Approved
0.6406	Remote Similarity	NPD7829	Approved
0.6406	Remote Similarity	NPD7830	Approved
0.6396	Remote Similarity	NPD5284	Approved
0.6396	Remote Similarity	NPD5281	Approved
0.6396	Remote Similarity	NPD6411	Approved
0.6387	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD8074	Phase 3
0.6381	Remote Similarity	NPD6902	Approved
0.6378	Remote Similarity	NPD6015	Approved
0.6378	Remote Similarity	NPD6016	Approved
0.6378	Remote Similarity	NPD5983	Phase 2
0.6373	Remote Similarity	NPD6933	Approved
0.6372	Remote Similarity	NPD5695	Phase 3
0.6364	Remote Similarity	NPD4634	Approved
0.6364	Remote Similarity	NPD1695	Approved
0.6346	Remote Similarity	NPD6929	Approved
0.6341	Remote Similarity	NPD8133	Approved
0.6333	Remote Similarity	NPD6011	Approved
0.6333	Remote Similarity	NPD7320	Approved
0.6328	Remote Similarity	NPD5988	Approved
0.6321	Remote Similarity	NPD6435	Approved
0.6321	Remote Similarity	NPD5209	Approved
0.6316	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6932	Approved
0.6308	Remote Similarity	NPD6336	Discontinued
0.6299	Remote Similarity	NPD6059	Approved
0.6296	Remote Similarity	NPD5363	Approved
0.6286	Remote Similarity	NPD7332	Phase 2
0.6269	Remote Similarity	NPD6845	Suspended
0.6262	Remote Similarity	NPD7154	Phase 3
0.6262	Remote Similarity	NPD5362	Discontinued
0.626	Remote Similarity	NPD8293	Discontinued
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD7087	Discontinued
0.625	Remote Similarity	NPD7145	Approved
0.6239	Remote Similarity	NPD6684	Approved
0.6239	Remote Similarity	NPD7521	Approved
0.6239	Remote Similarity	NPD7334	Approved
0.6239	Remote Similarity	NPD4159	Approved
0.6239	Remote Similarity	NPD7146	Approved
0.6239	Remote Similarity	NPD6409	Approved
0.6239	Remote Similarity	NPD5330	Approved
0.6228	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6101	Approved
0.6207	Remote Similarity	NPD5696	Approved
0.6195	Remote Similarity	NPD6399	Phase 3
0.619	Remote Similarity	NPD7505	Discontinued
0.619	Remote Similarity	NPD4195	Approved
0.6186	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5211	Phase 2
0.6183	Remote Similarity	NPD8273	Phase 1
0.6182	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6926	Approved
0.6176	Remote Similarity	NPD6924	Approved
0.6154	Remote Similarity	NPD5776	Phase 2
0.6154	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD5285	Approved
0.6154	Remote Similarity	NPD5286	Approved
0.6154	Remote Similarity	NPD6925	Approved
0.6147	Remote Similarity	NPD6893	Approved
0.6147	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD1694	Approved
0.614	Remote Similarity	NPD5282	Discontinued
0.6132	Remote Similarity	NPD5368	Approved
0.6126	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6903	Approved
0.6116	Remote Similarity	NPD6685	Approved
0.6111	Remote Similarity	NPD5332	Approved
0.6111	Remote Similarity	NPD5331	Approved
0.6106	Remote Similarity	NPD5694	Approved
0.6106	Remote Similarity	NPD6050	Approved
0.6106	Remote Similarity	NPD5693	Phase 1
0.6094	Remote Similarity	NPD7101	Approved
0.6094	Remote Similarity	NPD7100	Approved
0.6087	Remote Similarity	NPD5210	Approved
0.6087	Remote Similarity	NPD4629	Approved
0.6087	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5141	Approved
0.6075	Remote Similarity	NPD4790	Discontinued
0.6075	Remote Similarity	NPD5369	Approved
0.6071	Remote Similarity	NPD4753	Phase 2
0.6066	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD3666	Approved
0.6055	Remote Similarity	NPD3665	Phase 1
0.6055	Remote Similarity	NPD3133	Approved
0.605	Remote Similarity	NPD5224	Approved
0.605	Remote Similarity	NPD5225	Approved
0.605	Remote Similarity	NPD5226	Approved
0.605	Remote Similarity	NPD4633	Approved
0.6048	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6683	Phase 2
0.6034	Remote Similarity	NPD7839	Suspended
0.6033	Remote Similarity	NPD6640	Phase 3
0.6031	Remote Similarity	NPD7642	Approved
0.6019	Remote Similarity	NPD4270	Approved
0.6019	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4269	Approved
0.6018	Remote Similarity	NPD5207	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