NPASS Compound

Structure

NPC13743 OpenBabel07101718322D 40 44 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 5.6427 4.0851 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 4.7912 4.6095 0.0000 C 0 0 0 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 4.8195 5.6091 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 3.9114 4.1342 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 19 1 0 0 0 0 2 20 1 0 0 0 0 4 22 1 0 0 0 0 5 29 1 0 0 0 0 6 7 1 0 0 0 0 6 8 2 0 0 0 0 7 9 2 0 0 0 0 8 23 1 0 0 0 0 9 27 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 13 35 1 0 0 0 0 14 19 2 0 0 0 0 14 25 1 0 0 0 0 15 20 2 0 0 0 0 15 28 1 0 0 0 0 16 24 1 0 0 0 0 16 26 1 0 0 0 0 17 30 1 0 0 0 0 17 36 1 0 0 0 0 18 31 1 0 0 0 0 18 37 1 0 0 0 0 21 3 1 6 0 0 0 21 38 1 0 0 0 0 22 32 2 0 0 0 0 22 38 1 0 0 0 0 23 21 1 6 0 0 0 23 35 1 0 0 0 0 24 29 1 1 0 0 0 24 40 1 0 0 0 0 25 30 1 1 0 0 0 25 39 1 0 0 0 0 26 31 1 1 0 0 0 26 39 1 0 0 0 0 27 33 2 0 0 0 0 27 40 1 0 0 0 0 28 34 2 0 0 0 0 28 36 1 0 0 0 0 29 30 1 6 0 0 0 30 12 1 1 0 0 0 31 29 1 6 0 0 0 31 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	556.27
Volume:	562.607
LogP:	3.873
LogD:	2.756
LogS:	-4.85
# Rotatable Bonds:	3
TPSA:	109.89
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.213
Synthetic Accessibility Score:	7.179
Fsp3:	0.645
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:	-5.033
MDCK Permeability:	1.690242970653344e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.949
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.919

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	87.2437515258789%
Volume Distribution (VD):	2.045
Pgp-substrate:	6.267740726470947%

ADMET: Metabolism

CYP1A2-inhibitor:	0.082
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.863
CYP2C19-substrate:	0.289
CYP2C9-inhibitor:	0.924
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.813
CYP3A4-substrate:	0.674

ADMET: Excretion

Clearance (CL):	2.046
Half-life (T1/2):	0.668

ADMET: Toxicity

hERG Blockers:	0.317
Human Hepatotoxicity (H-HT):	0.796
Drug-inuced Liver Injury (DILI):	0.725
AMES Toxicity:	0.982
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.965
Carcinogencity:	0.099
Eye Corrosion:	0.004
Eye Irritation:	0.103
Respiratory Toxicity:	0.303

Download Data

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

Natural Product: NPC13743

Natural Product ID:	NPC13743
*Common Name:**	Roridin E Acetate
IUPAC Name:	n.a.
Synonyms:	Roridin E Acetate
Standard InCHIKey:	UMMRHXXIVGSHOW-JOAVBITDSA-N
Standard InCHI:	InChI=1S/C31H40O9/c1-19-10-12-30-17-36-28(34)15-20(2)11-13-35-23(21(3)38-22(4)32)8-6-7-9-27(33)40-24-16-26(39-25(30)14-19)31(18-37-31)29(24,30)5/h6-9,14-15,21,23-26H,10-13,16-18H2,1-5H3/b8-6+,9-7-,20-15+/t21-,23-,24-,25-,26-,29-,30-,31+/m1/s1
SMILES:	CC1=C[C@@H]2[C@@]3(CC1)COC(=O)/C=C(C)/CCO[C@H](/C=C/C=CC(=O)O[C@@H]1C[C@H]([C@@]4(CO4)[C@@]31C)O2)[C@@H](C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452441
PubChem CID:	44558998
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]
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]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	0.014	ug.mL-1	PMID[450025]
NPT189	Cell Line	Vero	Chlorocebus aethiops	EC50	=	0.0041	ug.mL-1	PMID[450025]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	EC50	=	0.00006	ug.mL-1	PMID[450025]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	0.015	ug.mL-1	PMID[450025]

☑ 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 NPC13743 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	228
0.1-0.2	1276
0.2-0.3	4816
0.3-0.4	12492
0.4-0.5	11792
0.5-0.6	7805
0.6-0.7	3793
0.7-0.8	428
0.8-0.85	19
0.85-0.9	25
0.9-0.95	20
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC98813
0.9485	High Similarity	NPC93026
0.9485	High Similarity	NPC469960
0.9485	High Similarity	NPC29389
0.9485	High Similarity	NPC265502
0.9388	High Similarity	NPC469957
0.9388	High Similarity	NPC108682
0.9388	High Similarity	NPC469959
0.9388	High Similarity	NPC472263
0.8969	High Similarity	NPC79631
0.8866	High Similarity	NPC65700
0.8846	High Similarity	NPC287075
0.8846	High Similarity	NPC101400
0.8846	High Similarity	NPC101965
0.8762	High Similarity	NPC305044
0.8762	High Similarity	NPC265290
0.875	High Similarity	NPC98038
0.875	High Similarity	NPC313921
0.8614	High Similarity	NPC169843
0.8571	High Similarity	NPC347923
0.8571	High Similarity	NPC476057
0.8557	High Similarity	NPC240838
0.85	High Similarity	NPC26557
0.8485	Intermediate Similarity	NPC79449
0.8485	Intermediate Similarity	NPC274458
0.8485	Intermediate Similarity	NPC474957
0.8416	Intermediate Similarity	NPC252242
0.8416	Intermediate Similarity	NPC200672
0.8416	Intermediate Similarity	NPC475956
0.8416	Intermediate Similarity	NPC214714
0.8396	Intermediate Similarity	NPC241477
0.8384	Intermediate Similarity	NPC182811
0.8381	Intermediate Similarity	NPC15551
0.8333	Intermediate Similarity	NPC260809
0.8333	Intermediate Similarity	NPC232515
0.8333	Intermediate Similarity	NPC474783
0.8302	Intermediate Similarity	NPC71680
0.8235	Intermediate Similarity	NPC475986
0.8208	Intermediate Similarity	NPC41551
0.8208	Intermediate Similarity	NPC50223
0.8182	Intermediate Similarity	NPC474286
0.8182	Intermediate Similarity	NPC475130
0.81	Intermediate Similarity	NPC113433
0.8081	Intermediate Similarity	NPC281775
0.8018	Intermediate Similarity	NPC16701
0.7961	Intermediate Similarity	NPC298233
0.7946	Intermediate Similarity	NPC278681
0.7946	Intermediate Similarity	NPC213761
0.7946	Intermediate Similarity	NPC35171
0.7928	Intermediate Similarity	NPC157380
0.7925	Intermediate Similarity	NPC470192
0.7917	Intermediate Similarity	NPC137253
0.7876	Intermediate Similarity	NPC112936
0.781	Intermediate Similarity	NPC123505
0.7807	Intermediate Similarity	NPC312481
0.7778	Intermediate Similarity	NPC197107
0.7778	Intermediate Similarity	NPC475274
0.7768	Intermediate Similarity	NPC185287
0.7748	Intermediate Similarity	NPC43213
0.7748	Intermediate Similarity	NPC216665
0.7739	Intermediate Similarity	NPC471082
0.7732	Intermediate Similarity	NPC61527
0.7706	Intermediate Similarity	NPC181298
0.7672	Intermediate Similarity	NPC6193
0.7642	Intermediate Similarity	NPC280566
0.7642	Intermediate Similarity	NPC183570
0.7636	Intermediate Similarity	NPC475495
0.7615	Intermediate Similarity	NPC77089
0.7593	Intermediate Similarity	NPC471601
0.7573	Intermediate Similarity	NPC194132
0.7573	Intermediate Similarity	NPC209297
0.7573	Intermediate Similarity	NPC475380
0.7573	Intermediate Similarity	NPC57664
0.7568	Intermediate Similarity	NPC477093
0.7568	Intermediate Similarity	NPC473522
0.7568	Intermediate Similarity	NPC475277
0.7549	Intermediate Similarity	NPC471994
0.7549	Intermediate Similarity	NPC469491
0.7549	Intermediate Similarity	NPC166143
0.7549	Intermediate Similarity	NPC120351
0.7549	Intermediate Similarity	NPC140277
0.7547	Intermediate Similarity	NPC470972
0.7547	Intermediate Similarity	NPC471993
0.7547	Intermediate Similarity	NPC11956
0.7545	Intermediate Similarity	NPC238850
0.7526	Intermediate Similarity	NPC78673
0.7526	Intermediate Similarity	NPC160517
0.7526	Intermediate Similarity	NPC186155
0.7524	Intermediate Similarity	NPC290802
0.7522	Intermediate Similarity	NPC470793
0.75	Intermediate Similarity	NPC470980
0.75	Intermediate Similarity	NPC120299
0.75	Intermediate Similarity	NPC475446
0.75	Intermediate Similarity	NPC171126
0.75	Intermediate Similarity	NPC311241
0.7478	Intermediate Similarity	NPC270850
0.7478	Intermediate Similarity	NPC219656
0.7478	Intermediate Similarity	NPC5292
0.7478	Intermediate Similarity	NPC305260
0.7477	Intermediate Similarity	NPC23584
0.7477	Intermediate Similarity	NPC262083
0.7477	Intermediate Similarity	NPC471484
0.7476	Intermediate Similarity	NPC281134
0.7475	Intermediate Similarity	NPC199382
0.7474	Intermediate Similarity	NPC474739
0.7453	Intermediate Similarity	NPC472554
0.7447	Intermediate Similarity	NPC474005
0.7429	Intermediate Similarity	NPC124181
0.7429	Intermediate Similarity	NPC475653
0.7429	Intermediate Similarity	NPC72647
0.7429	Intermediate Similarity	NPC107806
0.7426	Intermediate Similarity	NPC3952
0.7426	Intermediate Similarity	NPC177668
0.7419	Intermediate Similarity	NPC301525
0.7414	Intermediate Similarity	NPC79579
0.7411	Intermediate Similarity	NPC44537
0.7407	Intermediate Similarity	NPC272632
0.7407	Intermediate Similarity	NPC472822
0.7404	Intermediate Similarity	NPC255410
0.7391	Intermediate Similarity	NPC153440
0.7387	Intermediate Similarity	NPC103491
0.7383	Intermediate Similarity	NPC78127
0.7383	Intermediate Similarity	NPC471757
0.7383	Intermediate Similarity	NPC472552
0.7374	Intermediate Similarity	NPC261253
0.7374	Intermediate Similarity	NPC204048
0.7374	Intermediate Similarity	NPC474045
0.7358	Intermediate Similarity	NPC227865
0.7353	Intermediate Similarity	NPC221282
0.735	Intermediate Similarity	NPC310511
0.735	Intermediate Similarity	NPC233500
0.734	Intermediate Similarity	NPC186109
0.7339	Intermediate Similarity	NPC119855
0.7339	Intermediate Similarity	NPC220217
0.7333	Intermediate Similarity	NPC153559
0.7333	Intermediate Similarity	NPC100912
0.7333	Intermediate Similarity	NPC47834
0.7333	Intermediate Similarity	NPC475332
0.7333	Intermediate Similarity	NPC205143
0.7328	Intermediate Similarity	NPC472667
0.7328	Intermediate Similarity	NPC81222
0.7328	Intermediate Similarity	NPC291820
0.7327	Intermediate Similarity	NPC133450
0.7327	Intermediate Similarity	NPC177141
0.7321	Intermediate Similarity	NPC284162
0.7321	Intermediate Similarity	NPC255401
0.7321	Intermediate Similarity	NPC470076
0.7321	Intermediate Similarity	NPC474750
0.7321	Intermediate Similarity	NPC17791
0.7315	Intermediate Similarity	NPC85742
0.7308	Intermediate Similarity	NPC300710
0.7304	Intermediate Similarity	NPC203862
0.7304	Intermediate Similarity	NPC475305
0.73	Intermediate Similarity	NPC476600
0.7297	Intermediate Similarity	NPC471934
0.7297	Intermediate Similarity	NPC75389
0.729	Intermediate Similarity	NPC146822
0.7288	Intermediate Similarity	NPC115349
0.7288	Intermediate Similarity	NPC196130
0.7281	Intermediate Similarity	NPC106446
0.7273	Intermediate Similarity	NPC109376
0.7265	Intermediate Similarity	NPC4548
0.7265	Intermediate Similarity	NPC107607
0.7265	Intermediate Similarity	NPC474585
0.7264	Intermediate Similarity	NPC222303
0.7264	Intermediate Similarity	NPC473307
0.7257	Intermediate Similarity	NPC470025
0.7257	Intermediate Similarity	NPC321272
0.7257	Intermediate Similarity	NPC150228
0.7257	Intermediate Similarity	NPC214005
0.7257	Intermediate Similarity	NPC328074
0.7257	Intermediate Similarity	NPC317460
0.7255	Intermediate Similarity	NPC475748
0.725	Intermediate Similarity	NPC179261
0.7248	Intermediate Similarity	NPC473543
0.7248	Intermediate Similarity	NPC165969
0.7248	Intermediate Similarity	NPC200861
0.7241	Intermediate Similarity	NPC473720
0.7241	Intermediate Similarity	NPC475401
0.7241	Intermediate Similarity	NPC470420
0.7241	Intermediate Similarity	NPC13710
0.7241	Intermediate Similarity	NPC218093
0.7238	Intermediate Similarity	NPC288350
0.7238	Intermediate Similarity	NPC171598
0.7238	Intermediate Similarity	NPC173329
0.7232	Intermediate Similarity	NPC316708
0.7228	Intermediate Similarity	NPC93411
0.7228	Intermediate Similarity	NPC473879
0.7228	Intermediate Similarity	NPC470612
0.7228	Intermediate Similarity	NPC470613
0.7227	Intermediate Similarity	NPC219804
0.7222	Intermediate Similarity	NPC49393
0.7222	Intermediate Similarity	NPC109195
0.7222	Intermediate Similarity	NPC476471
0.7222	Intermediate Similarity	NPC475344
0.7222	Intermediate Similarity	NPC473596
0.7222	Intermediate Similarity	NPC475038
0.7222	Intermediate Similarity	NPC105725
0.7217	Intermediate Similarity	NPC470075
0.7217	Intermediate Similarity	NPC190286

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 NPC13743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1374
0.2-0.3	4112
0.3-0.4	2501
0.4-0.5	583
0.5-0.6	279
0.6-0.7	112
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
0.76	Intermediate Similarity	NPD7838	Discovery
0.75	Intermediate Similarity	NPD7503	Approved
0.7358	Intermediate Similarity	NPD6648	Approved
0.7103	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD46	Approved
0.7087	Intermediate Similarity	NPD6698	Approved
0.7059	Intermediate Similarity	NPD8033	Approved
0.699	Remote Similarity	NPD6051	Approved
0.6972	Remote Similarity	NPD5344	Discontinued
0.6949	Remote Similarity	NPD7328	Approved
0.6949	Remote Similarity	NPD7327	Approved
0.6891	Remote Similarity	NPD7516	Approved
0.6833	Remote Similarity	NPD8294	Approved
0.6833	Remote Similarity	NPD8377	Approved
0.6814	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6053	Discontinued
0.6789	Remote Similarity	NPD7638	Approved
0.6783	Remote Similarity	NPD6371	Approved
0.6777	Remote Similarity	NPD8378	Approved
0.6777	Remote Similarity	NPD8296	Approved
0.6777	Remote Similarity	NPD8380	Approved
0.6777	Remote Similarity	NPD8335	Approved
0.6777	Remote Similarity	NPD8379	Approved
0.6754	Remote Similarity	NPD6686	Approved
0.6727	Remote Similarity	NPD7639	Approved
0.6727	Remote Similarity	NPD7640	Approved
0.6726	Remote Similarity	NPD6008	Approved
0.6723	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5209	Approved
0.6562	Remote Similarity	NPD7260	Phase 2
0.656	Remote Similarity	NPD7507	Approved
0.6557	Remote Similarity	NPD6319	Approved
0.6542	Remote Similarity	NPD7637	Suspended
0.6538	Remote Similarity	NPD7521	Approved
0.6538	Remote Similarity	NPD6684	Approved
0.6538	Remote Similarity	NPD5330	Approved
0.6538	Remote Similarity	NPD7334	Approved
0.6538	Remote Similarity	NPD7146	Approved
0.6538	Remote Similarity	NPD6409	Approved
0.6525	Remote Similarity	NPD8297	Approved
0.6522	Remote Similarity	NPD6412	Phase 2
0.6522	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4250	Approved
0.6476	Remote Similarity	NPD4251	Approved
0.6476	Remote Similarity	NPD7524	Approved
0.6449	Remote Similarity	NPD5785	Approved
0.6442	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD1694	Approved
0.6436	Remote Similarity	NPD4819	Approved
0.6436	Remote Similarity	NPD4821	Approved
0.6436	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4822	Approved
0.6436	Remote Similarity	NPD4820	Approved
0.6415	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6903	Approved
0.641	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6695	Phase 3
0.6406	Remote Similarity	NPD7319	Approved
0.6389	Remote Similarity	NPD5693	Phase 1
0.6389	Remote Similarity	NPD5694	Approved
0.6389	Remote Similarity	NPD6050	Approved
0.6381	Remote Similarity	NPD4249	Approved
0.6349	Remote Similarity	NPD7492	Approved
0.6346	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4225	Approved
0.6333	Remote Similarity	NPD4632	Approved
0.6325	Remote Similarity	NPD6881	Approved
0.6325	Remote Similarity	NPD6899	Approved
0.6311	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6650	Approved
0.6303	Remote Similarity	NPD6649	Approved
0.6299	Remote Similarity	NPD6616	Approved
0.6296	Remote Similarity	NPD5207	Approved
0.6296	Remote Similarity	NPD5692	Phase 3
0.629	Remote Similarity	NPD6054	Approved
0.627	Remote Similarity	NPD7604	Phase 2
0.6263	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD6882	Approved
0.624	Remote Similarity	NPD8513	Phase 3
0.624	Remote Similarity	NPD8516	Approved
0.624	Remote Similarity	NPD8515	Approved
0.624	Remote Similarity	NPD8517	Approved
0.6239	Remote Similarity	NPD7983	Approved
0.6239	Remote Similarity	NPD5281	Approved
0.6239	Remote Similarity	NPD5284	Approved
0.6239	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD4271	Approved
0.6238	Remote Similarity	NPD4268	Approved
0.6237	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7290	Approved
0.6218	Remote Similarity	NPD6883	Approved
0.6218	Remote Similarity	NPD7102	Approved
0.6216	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5695	Phase 3
0.6204	Remote Similarity	NPD6673	Approved
0.6204	Remote Similarity	NPD6080	Approved
0.6204	Remote Similarity	NPD6904	Approved
0.6202	Remote Similarity	NPD7736	Approved
0.619	Remote Similarity	NPD6370	Approved
0.6182	Remote Similarity	NPD5779	Approved
0.6182	Remote Similarity	NPD5778	Approved
0.6179	Remote Similarity	NPD6009	Approved
0.6174	Remote Similarity	NPD7632	Discontinued
0.6168	Remote Similarity	NPD7750	Discontinued
0.6167	Remote Similarity	NPD6617	Approved
0.6167	Remote Similarity	NPD6869	Approved
0.6167	Remote Similarity	NPD6847	Approved
0.6167	Remote Similarity	NPD8130	Phase 1
0.6167	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD5739	Approved
0.6154	Remote Similarity	NPD7128	Approved
0.6154	Remote Similarity	NPD6675	Approved
0.6136	Remote Similarity	NPD6845	Suspended
0.6134	Remote Similarity	NPD6012	Approved
0.6134	Remote Similarity	NPD6372	Approved
0.6134	Remote Similarity	NPD6014	Approved
0.6134	Remote Similarity	NPD6013	Approved
0.6134	Remote Similarity	NPD6373	Approved
0.6132	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6931	Approved
0.6117	Remote Similarity	NPD6930	Phase 2
0.6117	Remote Similarity	NPD7514	Phase 3
0.6111	Remote Similarity	NPD6672	Approved
0.6111	Remote Similarity	NPD5983	Phase 2
0.6111	Remote Similarity	NPD6016	Approved
0.6111	Remote Similarity	NPD6015	Approved
0.6111	Remote Similarity	NPD5737	Approved
0.6091	Remote Similarity	NPD6411	Approved
0.6063	Remote Similarity	NPD5988	Approved
0.6058	Remote Similarity	NPD6902	Approved
0.6053	Remote Similarity	NPD5696	Approved
0.605	Remote Similarity	NPD6011	Approved
0.605	Remote Similarity	NPD7320	Approved
0.6047	Remote Similarity	NPD6336	Discontinued
0.6036	Remote Similarity	NPD6399	Phase 3
0.6032	Remote Similarity	NPD6059	Approved
0.6019	Remote Similarity	NPD4195	Approved
0.6019	Remote Similarity	NPD6929	Approved
0.6016	Remote Similarity	NPD7829	Approved
0.6016	Remote Similarity	NPD7830	Approved
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD6435	Approved
0.6	Remote Similarity	NPD8074	Phase 3
0.5982	Remote Similarity	NPD5282	Discontinued
0.5981	Remote Similarity	NPD5363	Approved
0.598	Remote Similarity	NPD6932	Approved
0.5966	Remote Similarity	NPD5701	Approved
0.5965	Remote Similarity	NPD5959	Approved
0.5963	Remote Similarity	NPD5208	Approved
0.5962	Remote Similarity	NPD7332	Phase 2
0.595	Remote Similarity	NPD4634	Approved
0.5946	Remote Similarity	NPD7087	Discontinued
0.5943	Remote Similarity	NPD5362	Discontinued
0.5943	Remote Similarity	NPD7154	Phase 3
0.5935	Remote Similarity	NPD8133	Approved
0.5929	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5654	Approved
0.5926	Remote Similarity	NPD6098	Approved
0.5922	Remote Similarity	NPD7145	Approved
0.5909	Remote Similarity	NPD6101	Approved
0.5909	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD5211	Phase 2
0.5882	Remote Similarity	NPD6933	Approved
0.5877	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5286	Approved
0.5862	Remote Similarity	NPD4696	Approved
0.5862	Remote Similarity	NPD5285	Approved
0.5842	Remote Similarity	NPD6924	Approved
0.5842	Remote Similarity	NPD6926	Approved
0.5841	Remote Similarity	NPD6001	Approved
0.5833	Remote Similarity	NPD6685	Approved
0.5833	Remote Similarity	NPD6893	Approved
0.5827	Remote Similarity	NPD7101	Approved
0.5827	Remote Similarity	NPD7100	Approved
0.5825	Remote Similarity	NPD6925	Approved
0.5825	Remote Similarity	NPD5776	Phase 2
0.5812	Remote Similarity	NPD4159	Approved
0.581	Remote Similarity	NPD5368	Approved
0.5802	Remote Similarity	NPD8273	Phase 1
0.5798	Remote Similarity	NPD5141	Approved
0.5794	Remote Similarity	NPD7505	Discontinued
0.5794	Remote Similarity	NPD5331	Approved
0.5794	Remote Similarity	NPD5332	Approved
0.5789	Remote Similarity	NPD4629	Approved
0.5789	Remote Similarity	NPD5210	Approved
0.5772	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4753	Phase 2
0.5763	Remote Similarity	NPD5225	Approved
0.5763	Remote Similarity	NPD4633	Approved
0.5763	Remote Similarity	NPD5226	Approved
0.5763	Remote Similarity	NPD5224	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