NPASS Compound

Structure

CID214142 OpenBabel06191716002D 48 50 0 0 1 0 0 0 0 0999 V2000 -2.0706 -10.7066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4556 -11.2313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7767 -7.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1593 -11.7560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4738 -6.4522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8268 -4.7912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6305 -1.2833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6305 -0.3030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7815 -1.7735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7815 0.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8359 -2.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1889 -0.7407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7948 -2.6055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1479 -0.9445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8087 -9.5703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4237 -9.0456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8063 -10.0951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6059 -3.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2710 -0.3330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7677 -9.7741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1527 -10.2989 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1207 -8.1132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4623 -10.8236 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5148 -6.2483 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5329 -1.4692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4509 -1.8769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9324 -1.2833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9324 -0.3030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5739 -1.2654 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5649 -3.6550 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9270 0.3956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5763 -0.7932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1617 -7.9093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2209 -2.9264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2118 -5.3159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5567 -0.7932 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8588 -6.9769 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9179 -1.9940 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8678 -4.5874 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4213 -10.6198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4098 -2.0807 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6240 1.3280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8860 0.1917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5057 -8.6379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1799 -3.1302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2529 -5.1121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 6 41 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 27 2 0 0 0 0 10 29 2 0 0 0 0 11 13 1 0 0 0 0 11 25 2 0 0 0 0 12 14 2 0 0 0 0 12 25 1 0 0 0 0 13 26 2 0 0 0 0 14 26 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 28 1 0 0 0 0 19 32 1 0 0 0 0 21 2 1 1 0 0 0 22 3 1 6 0 0 0 22 34 1 0 0 0 0 23 4 1 1 0 0 0 23 42 1 0 0 0 0 24 5 1 1 0 0 0 24 36 1 0 0 0 0 24 38 1 0 0 0 0 25 30 1 0 0 0 0 26 43 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 28 33 2 0 0 0 0 29 39 1 0 0 0 0 30 19 1 1 0 0 0 30 40 1 0 0 0 0 31 18 1 1 0 0 0 31 35 1 0 0 0 0 31 41 1 0 0 0 0 32 44 2 0 0 0 0 32 45 1 0 0 0 0 33 37 1 0 0 0 0 33 39 1 0 0 0 0 34 38 2 3 0 0 0 34 46 1 0 0 0 0 35 40 2 3 0 0 0 35 47 1 0 0 0 0 36 41 1 0 0 0 0 36 48 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	726.26
Volume:	698.707
LogP:	4.462
LogD:	3.601
LogS:	-3.731
# Rotatable Bonds:	19
TPSA:	172.06
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.11
Synthetic Accessibility Score:	4.624
Fsp3:	0.444
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:	-5.624
MDCK Permeability:	5.431759291241178e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.873
Human Intestinal Absorption (HIA):	0.225
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.056

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	98.30144500732422%
Volume Distribution (VD):	0.182
Pgp-substrate:	1.8870049715042114%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.173
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.82
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.228
CYP3A4-inhibitor:	0.893
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	2.945
Half-life (T1/2):	0.884

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.595
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.084
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC214142

Natural Product ID:	NPC214142
*Common Name:**	Jasplakinolide Z1
IUPAC Name:	(3R)-3-[[(2R)-3-(2-bromo-1H-indol-3-yl)-2-[[(2S)-2-[[(E,2S,6R,8S)-8-hydroxy-2,4,6-trimethylnon-4-enoyl]amino]propanoyl]-methylamino]propanoyl]amino]-3-(4-hydroxyphenyl)propanoic acid
Synonyms:	(+)-Jasplakinolide Z1; Jasplakinolide Z1
Standard InCHIKey:	PPXQSUWEWPAOGM-DHKPLNAMSA-N
Standard InCHI:	InChI=1S/C36H47BrN4O7/c1-20(15-21(2)17-23(4)42)16-22(3)34(46)38-24(5)36(48)41(6)31(18-28-27-9-7-8-10-29(27)39-33(28)37)35(47)40-30(19-32(44)45)25-11-13-26(43)14-12-25/h7-15,21-24,30-31,39,42-43H,16-19H2,1-6H3,(H,38,46)(H,40,47)(H,44,45)/b20-15+/t21-,22-,23-,24-,30+,31+/m0/s1
SMILES:	C/C(=C[C@H](C)C[C@H](C)O)/C[C@H](C)C(=N[C@@H](C)C(=O)N(C)[C@H](Cc1c2ccccc2[nH]c1Br)C(=N[C@H](CC(=O)O)c1ccc(cc1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1765401
PubChem CID:	54587134
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001939] Peptoid-peptide hybrids

*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
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.tet.2007.03.162]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.tet.2008.05.037]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.tet.2008.10.076]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075778]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	Fiji (S 1822.28', E 17758.87')	2000-FEB	PMID[21241058]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21241058]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26883470]
NPO11484	Jaspis splendens	Species	Ancorinidae	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
GI50	7
Others	1

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	13700.0	nM	PMID[470698]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	2500.0	nM	PMID[470698]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	=	1760.0	nM	PMID[470698]
NPT380	Cell Line	U-251	Homo sapiens	GI50	=	600.0	nM	PMID[470698]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	120.0	nM	PMID[470698]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	18800.0	nM	PMID[470698]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	=	280.0	nM	PMID[470698]
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	30.0	%	PMID[470699]

☑ 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 NPC214142 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	310
0.1-0.2	1860
0.2-0.3	12197
0.3-0.4	11315
0.4-0.5	10919
0.5-0.6	3525
0.6-0.7	2068
0.7-0.8	470
0.8-0.85	9
0.85-0.9	4
0.9-0.95	4
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.995	High Similarity	NPC261251
0.9901	High Similarity	NPC100547
0.9852	High Similarity	NPC223409
0.9852	High Similarity	NPC95240
0.9852	High Similarity	NPC322135
0.9851	High Similarity	NPC124920
0.9851	High Similarity	NPC34580
0.9851	High Similarity	NPC304307
0.9851	High Similarity	NPC118559
0.9804	High Similarity	NPC14288
0.9756	High Similarity	NPC54803
0.9756	High Similarity	NPC321592
0.9614	High Similarity	NPC284888
0.9567	High Similarity	NPC245055
0.9567	High Similarity	NPC33064
0.9431	High Similarity	NPC82472
0.9356	High Similarity	NPC74969
0.9048	High Similarity	NPC24370
0.9048	High Similarity	NPC319232
0.8889	High Similarity	NPC272549
0.8796	High Similarity	NPC323752
0.8796	High Similarity	NPC323198
0.875	High Similarity	NPC181081
0.845	Intermediate Similarity	NPC243716
0.8235	Intermediate Similarity	NPC326363
0.8116	Intermediate Similarity	NPC306376
0.8089	Intermediate Similarity	NPC325976
0.8082	Intermediate Similarity	NPC473317
0.8034	Intermediate Similarity	NPC314882
0.8028	Intermediate Similarity	NPC303658
0.8018	Intermediate Similarity	NPC28945
0.8018	Intermediate Similarity	NPC330009
0.8009	Intermediate Similarity	NPC476098
0.7973	Intermediate Similarity	NPC125597
0.7965	Intermediate Similarity	NPC220852
0.786	Intermediate Similarity	NPC285343
0.7854	Intermediate Similarity	NPC469928
0.7851	Intermediate Similarity	NPC315467
0.7826	Intermediate Similarity	NPC470784
0.7824	Intermediate Similarity	NPC478006
0.7824	Intermediate Similarity	NPC478158
0.7808	Intermediate Similarity	NPC478157
0.7799	Intermediate Similarity	NPC276517
0.7788	Intermediate Similarity	NPC33949
0.7788	Intermediate Similarity	NPC194740
0.7764	Intermediate Similarity	NPC153400
0.7746	Intermediate Similarity	NPC478009
0.7717	Intermediate Similarity	NPC75634
0.7706	Intermediate Similarity	NPC184680
0.7703	Intermediate Similarity	NPC281049
0.77	Intermediate Similarity	NPC249040
0.7672	Intermediate Similarity	NPC470785
0.7664	Intermediate Similarity	NPC314056
0.7661	Intermediate Similarity	NPC162860
0.7658	Intermediate Similarity	NPC305984
0.765	Intermediate Similarity	NPC270918
0.7639	Intermediate Similarity	NPC475816
0.7636	Intermediate Similarity	NPC207020
0.7629	Intermediate Similarity	NPC184225
0.7617	Intermediate Similarity	NPC315491
0.7617	Intermediate Similarity	NPC45459
0.7613	Intermediate Similarity	NPC322064
0.7602	Intermediate Similarity	NPC478010
0.759	Intermediate Similarity	NPC478011
0.7581	Intermediate Similarity	NPC475506
0.7577	Intermediate Similarity	NPC21638
0.7576	Intermediate Similarity	NPC473105
0.7571	Intermediate Similarity	NPC478013
0.7569	Intermediate Similarity	NPC88008
0.7569	Intermediate Similarity	NPC54420
0.7566	Intermediate Similarity	NPC220851
0.7566	Intermediate Similarity	NPC470501
0.756	Intermediate Similarity	NPC314176
0.7546	Intermediate Similarity	NPC155143
0.7546	Intermediate Similarity	NPC476874
0.7545	Intermediate Similarity	NPC473041
0.7534	Intermediate Similarity	NPC39679
0.7534	Intermediate Similarity	NPC152768
0.7534	Intermediate Similarity	NPC148183
0.7532	Intermediate Similarity	NPC474192
0.7532	Intermediate Similarity	NPC475720
0.7531	Intermediate Similarity	NPC477635
0.7531	Intermediate Similarity	NPC477630
0.7523	Intermediate Similarity	NPC469592
0.7523	Intermediate Similarity	NPC471080
0.7522	Intermediate Similarity	NPC470502
0.752	Intermediate Similarity	NPC321939
0.7512	Intermediate Similarity	NPC72980
0.7512	Intermediate Similarity	NPC165599
0.7511	Intermediate Similarity	NPC315804
0.7511	Intermediate Similarity	NPC313804
0.7511	Intermediate Similarity	NPC477549
0.75	Intermediate Similarity	NPC471944
0.7488	Intermediate Similarity	NPC293917
0.7477	Intermediate Similarity	NPC470500
0.7467	Intermediate Similarity	NPC469594
0.7466	Intermediate Similarity	NPC5145
0.7464	Intermediate Similarity	NPC94752
0.7456	Intermediate Similarity	NPC470503
0.7455	Intermediate Similarity	NPC183407
0.7454	Intermediate Similarity	NPC49196
0.7454	Intermediate Similarity	NPC313985
0.7454	Intermediate Similarity	NPC195461
0.7454	Intermediate Similarity	NPC249150
0.7454	Intermediate Similarity	NPC79129
0.7454	Intermediate Similarity	NPC81654
0.745	Intermediate Similarity	NPC478012
0.7444	Intermediate Similarity	NPC54744
0.7442	Intermediate Similarity	NPC473640
0.7442	Intermediate Similarity	NPC50503
0.7432	Intermediate Similarity	NPC23294
0.7427	Intermediate Similarity	NPC219336
0.7421	Intermediate Similarity	NPC223791
0.7421	Intermediate Similarity	NPC107077
0.7416	Intermediate Similarity	NPC94943
0.7409	Intermediate Similarity	NPC244741
0.7403	Intermediate Similarity	NPC311906
0.7397	Intermediate Similarity	NPC473376
0.7395	Intermediate Similarity	NPC156704
0.7395	Intermediate Similarity	NPC262898
0.7393	Intermediate Similarity	NPC213629
0.7393	Intermediate Similarity	NPC175474
0.7391	Intermediate Similarity	NPC91179
0.7389	Intermediate Similarity	NPC96321
0.7389	Intermediate Similarity	NPC264285
0.7387	Intermediate Similarity	NPC303951
0.7382	Intermediate Similarity	NPC200553
0.7382	Intermediate Similarity	NPC279189
0.7382	Intermediate Similarity	NPC89987
0.738	Intermediate Similarity	NPC64216
0.7379	Intermediate Similarity	NPC183662
0.7379	Intermediate Similarity	NPC15573
0.7379	Intermediate Similarity	NPC217372
0.7373	Intermediate Similarity	NPC474183
0.7373	Intermediate Similarity	NPC213308
0.7371	Intermediate Similarity	NPC99666
0.7368	Intermediate Similarity	NPC190007
0.7368	Intermediate Similarity	NPC60621
0.7366	Intermediate Similarity	NPC477610
0.7361	Intermediate Similarity	NPC102008
0.7361	Intermediate Similarity	NPC52557
0.7354	Intermediate Similarity	NPC87413
0.7349	Intermediate Similarity	NPC179701
0.7347	Intermediate Similarity	NPC475746
0.7345	Intermediate Similarity	NPC312645
0.7342	Intermediate Similarity	NPC476116
0.7336	Intermediate Similarity	NPC478141
0.733	Intermediate Similarity	NPC53344
0.7328	Intermediate Similarity	NPC471762
0.7327	Intermediate Similarity	NPC100321
0.7324	Intermediate Similarity	NPC117244
0.7324	Intermediate Similarity	NPC473763
0.7321	Intermediate Similarity	NPC212535
0.7319	Intermediate Similarity	NPC97902
0.7317	Intermediate Similarity	NPC216369
0.7309	Intermediate Similarity	NPC471304
0.7308	Intermediate Similarity	NPC469896
0.7306	Intermediate Similarity	NPC193761
0.7304	Intermediate Similarity	NPC51388
0.7301	Intermediate Similarity	NPC3207
0.7297	Intermediate Similarity	NPC210828
0.7297	Intermediate Similarity	NPC475910
0.7297	Intermediate Similarity	NPC86834
0.7293	Intermediate Similarity	NPC474896
0.7289	Intermediate Similarity	NPC89508
0.7288	Intermediate Similarity	NPC162002
0.7285	Intermediate Similarity	NPC277350
0.7284	Intermediate Similarity	NPC186351
0.7284	Intermediate Similarity	NPC470126
0.7281	Intermediate Similarity	NPC171317
0.7277	Intermediate Similarity	NPC320968
0.7269	Intermediate Similarity	NPC293151
0.7264	Intermediate Similarity	NPC46580
0.7261	Intermediate Similarity	NPC16352
0.7261	Intermediate Similarity	NPC31097
0.7261	Intermediate Similarity	NPC469734
0.726	Intermediate Similarity	NPC300183
0.7259	Intermediate Similarity	NPC477633
0.7257	Intermediate Similarity	NPC50562
0.7257	Intermediate Similarity	NPC118228
0.7257	Intermediate Similarity	NPC477979
0.7257	Intermediate Similarity	NPC15801
0.7253	Intermediate Similarity	NPC253580
0.7252	Intermediate Similarity	NPC183777
0.7246	Intermediate Similarity	NPC174489
0.7244	Intermediate Similarity	NPC12344
0.724	Intermediate Similarity	NPC475070
0.724	Intermediate Similarity	NPC242872
0.724	Intermediate Similarity	NPC470505
0.724	Intermediate Similarity	NPC125181
0.724	Intermediate Similarity	NPC263117
0.7235	Intermediate Similarity	NPC141454
0.7235	Intermediate Similarity	NPC243834
0.7235	Intermediate Similarity	NPC70956
0.7234	Intermediate Similarity	NPC63031
0.7233	Intermediate Similarity	NPC474409
0.7232	Intermediate Similarity	NPC234999
0.723	Intermediate Similarity	NPC111602
0.723	Intermediate Similarity	NPC102338
0.723	Intermediate Similarity	NPC63199

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 NPC214142 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	532
0.2-0.3	828
0.3-0.4	1357
0.4-0.5	2550
0.5-0.6	2744
0.6-0.7	877
0.7-0.8	84
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8538	High Similarity	NPD8405	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7603	Discontinued
0.7834	Intermediate Similarity	NPD7470	Discontinued
0.7725	Intermediate Similarity	NPD7948	Phase 1
0.7617	Intermediate Similarity	NPD484	Approved
0.7596	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD7944	Discontinued
0.7457	Intermediate Similarity	NPD4885	Approved
0.7456	Intermediate Similarity	NPD7716	Approved
0.7456	Intermediate Similarity	NPD7717	Approved
0.7455	Intermediate Similarity	NPD2916	Discontinued
0.7454	Intermediate Similarity	NPD4601	Approved
0.7454	Intermediate Similarity	NPD4600	Approved
0.7444	Intermediate Similarity	NPD3243	Approved
0.7422	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD8322	Phase 2
0.7395	Intermediate Similarity	NPD5003	Discontinued
0.7389	Intermediate Similarity	NPD7878	Phase 2
0.7376	Intermediate Similarity	NPD6376	Discontinued
0.7361	Intermediate Similarity	NPD53	Approved
0.7361	Intermediate Similarity	NPD7778	Approved
0.7361	Intermediate Similarity	NPD7777	Approved
0.7336	Intermediate Similarity	NPD8356	Approved
0.7333	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8093	Discontinued
0.7318	Intermediate Similarity	NPD8272	Phase 2
0.7285	Intermediate Similarity	NPD3003	Approved
0.7284	Intermediate Similarity	NPD8430	Approved
0.7277	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD8016	Phase 3
0.7269	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD2383	Phase 1
0.7257	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8114	Approved
0.724	Intermediate Similarity	NPD8115	Approved
0.724	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5632	Approved
0.7236	Intermediate Similarity	NPD8255	Phase 2
0.7232	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7224	Intermediate Similarity	NPD8463	Approved
0.7222	Intermediate Similarity	NPD8363	Approved
0.7222	Intermediate Similarity	NPD8364	Approved
0.722	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7853	Phase 2
0.7208	Intermediate Similarity	NPD6517	Phase 3
0.7207	Intermediate Similarity	NPD7957	Phase 1
0.7207	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6176	Phase 1
0.7182	Intermediate Similarity	NPD7817	Phase 1
0.7181	Intermediate Similarity	NPD4897	Phase 2
0.7176	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2175	Phase 3
0.7169	Intermediate Similarity	NPD2176	Approved
0.7169	Intermediate Similarity	NPD2177	Approved
0.7168	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD5612	Discontinued
0.7137	Intermediate Similarity	NPD8094	Discontinued
0.7137	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4500	Approved
0.7136	Intermediate Similarity	NPD4501	Approved
0.713	Intermediate Similarity	NPD6665	Discontinued
0.7119	Intermediate Similarity	NPD8106	Phase 2
0.7117	Intermediate Similarity	NPD8072	Approved
0.7116	Intermediate Similarity	NPD4499	Approved
0.711	Intermediate Similarity	NPD5512	Phase 3
0.7104	Intermediate Similarity	NPD7727	Phase 2
0.7104	Intermediate Similarity	NPD4511	Phase 1
0.7103	Intermediate Similarity	NPD4948	Discontinued
0.7091	Intermediate Similarity	NPD3814	Phase 1
0.7087	Intermediate Similarity	NPD2844	Phase 3
0.7085	Intermediate Similarity	NPD5901	Discontinued
0.708	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD8460	Approved
0.7077	Intermediate Similarity	NPD8459	Approved
0.7076	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2094	Phase 2
0.7075	Intermediate Similarity	NPD2092	Phase 2
0.7075	Intermediate Similarity	NPD2095	Phase 2
0.707	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5658	Approved
0.7064	Intermediate Similarity	NPD3259	Approved
0.7064	Intermediate Similarity	NPD7994	Phase 2
0.7062	Intermediate Similarity	NPD6452	Discontinued
0.7056	Intermediate Similarity	NPD7194	Discontinued
0.7054	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD1326	Approved
0.7053	Intermediate Similarity	NPD1325	Approved
0.7048	Intermediate Similarity	NPD5939	Approved
0.7048	Intermediate Similarity	NPD5936	Approved
0.7045	Intermediate Similarity	NPD7946	Pre-registration
0.7042	Intermediate Similarity	NPD2091	Phase 2
0.7042	Intermediate Similarity	NPD2096	Phase 2
0.704	Intermediate Similarity	NPD7955	Approved
0.704	Intermediate Similarity	NPD7956	Approved
0.7037	Intermediate Similarity	NPD2564	Approved
0.7037	Intermediate Similarity	NPD2565	Phase 2
0.7033	Intermediate Similarity	NPD482	Approved
0.7031	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5902	Approved
0.7031	Intermediate Similarity	NPD5903	Approved
0.7031	Intermediate Similarity	NPD7970	Approved
0.7027	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7452	Approved
0.7022	Intermediate Similarity	NPD7453	Approved
0.7022	Intermediate Similarity	NPD7222	Phase 2
0.7021	Intermediate Similarity	NPD7711	Discontinued
0.702	Intermediate Similarity	NPD8358	Approved
0.7014	Intermediate Similarity	NPD8395	Approved
0.7014	Intermediate Similarity	NPD8396	Approved
0.7014	Intermediate Similarity	NPD1768	Approved
0.7009	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8098	Approved
0.7008	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5507	Approved
0.6996	Remote Similarity	NPD8073	Approved
0.6996	Remote Similarity	NPD6716	Phase 1
0.6996	Remote Similarity	NPD5506	Approved
0.6995	Remote Similarity	NPD5596	Phase 2
0.6988	Remote Similarity	NPD8467	Approved
0.6988	Remote Similarity	NPD8427	Approved
0.6988	Remote Similarity	NPD8466	Approved
0.6988	Remote Similarity	NPD8465	Approved
0.6988	Remote Similarity	NPD8428	Approved
0.6988	Remote Similarity	NPD8429	Approved
0.6987	Remote Similarity	NPD7558	Phase 2
0.6987	Remote Similarity	NPD7790	Approved
0.6987	Remote Similarity	NPD4373	Phase 2
0.6987	Remote Similarity	NPD7952	Approved
0.6987	Remote Similarity	NPD7950	Approved
0.6987	Remote Similarity	NPD7953	Approved
0.6987	Remote Similarity	NPD7789	Approved
0.6987	Remote Similarity	NPD7951	Approved
0.6987	Remote Similarity	NPD7791	Approved
0.6986	Remote Similarity	NPD7618	Phase 3
0.6986	Remote Similarity	NPD4418	Discontinued
0.6986	Remote Similarity	NPD7619	Phase 3
0.6981	Remote Similarity	NPD5445	Approved
0.6981	Remote Similarity	NPD5899	Approved
0.6981	Remote Similarity	NPD5897	Approved
0.6981	Remote Similarity	NPD5898	Approved
0.698	Remote Similarity	NPD8359	Phase 2
0.6978	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7688	Phase 1
0.6974	Remote Similarity	NPD4502	Phase 2
0.6966	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.696	Remote Similarity	NPD4520	Approved
0.6957	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7426	Phase 1
0.6949	Remote Similarity	NPD8289	Discontinued
0.6947	Remote Similarity	NPD6290	Phase 2
0.6946	Remote Similarity	NPD7797	Approved
0.6946	Remote Similarity	NPD7796	Approved
0.6944	Remote Similarity	NPD7708	Approved
0.6943	Remote Similarity	NPD8096	Phase 3
0.6943	Remote Similarity	NPD8097	Phase 3
0.6937	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7181	Phase 3
0.6933	Remote Similarity	NPD4952	Phase 3
0.6933	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7726	Phase 1
0.692	Remote Similarity	NPD8247	Approved
0.692	Remote Similarity	NPD7731	Approved
0.692	Remote Similarity	NPD8292	Phase 2
0.692	Remote Similarity	NPD4086	Phase 1
0.692	Remote Similarity	NPD7730	Approved
0.692	Remote Similarity	NPD8246	Approved
0.691	Remote Similarity	NPD6770	Approved
0.6909	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD750	Phase 2
0.6904	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD8403	Phase 1
0.6903	Remote Similarity	NPD7001	Phase 3
0.6902	Remote Similarity	NPD7803	Approved
0.6897	Remote Similarity	NPD5164	Discontinued
0.6895	Remote Similarity	NPD5482	Discontinued
0.6892	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7781	Approved
0.6891	Remote Similarity	NPD7780	Approved
0.6891	Remote Similarity	NPD5559	Phase 2
0.6889	Remote Similarity	NPD6991	Approved
0.6882	Remote Similarity	NPD8425	Approved
0.6882	Remote Similarity	NPD8426	Approved
0.6878	Remote Similarity	NPD3263	Phase 3
0.6875	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6985	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