NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	769.46
Volume:	799.754
LogP:	7.307
LogD:	4.923
LogS:	-2.657
# Rotatable Bonds:	29
TPSA:	200.4
# H-Bond Aceptor:	14
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.032
Synthetic Accessibility Score:	4.521
Fsp3:	0.659
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.343
MDCK Permeability:	4.52E-05
Pgp-inhibitor:	0.702
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.65
20% Bioavailability (F20%):	1
30% Bioavailability (F30%):	1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	98.30%
Volume Distribution (VD):	1.024
Pgp-substrate:	0.66%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.569
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.778
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.231
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.084

ADMET: Excretion

Clearance (CL):	3.418
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.821
Drug-inuced Liver Injury (DILI):	0.639
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.438
Skin Sensitization:	0.081
Carcinogencity:	0.08
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC477589

Natural Product ID:	NPC477589
*Common Name:**	Noccardimicin E
IUPAC Name:	[2-methyl-1-oxo-1-[(2-oxoazepan-3-yl)amino]hexadecan-3-yl] 6-[acetyl(hydroxy)amino]-2-[[2-(2-hydroxyphenyl)-1,3-oxazole-4-carbonyl]amino]hexanoate
Synonyms:	Noccardimicin E
Standard InCHIKey:	PIFYJYLXAXDUEB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C41H63N5O9/c1-4-5-6-7-8-9-10-11-12-13-14-25-36(29(2)37(49)43-32-22-17-19-26-42-38(32)50)55-41(52)33(23-18-20-27-46(53)30(3)47)44-39(51)34-28-54-40(45-34)31-21-15-16-24-35(31)48/h15-16,21,24,28-29,32-33,36,48,53H,4-14,17-20,22-23,25-27H2,1-3H3,(H,42,50)(H,43,49)(H,44,51)
SMILES:	CCCCCCCCCCCCCC(C(C)C(=O)NC1CCCCNC1=O)OC(=O)C(CCCCN(C(=O)C)O)NC(=O)C2=COC(=N2)C3=CC=CC=C3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	135466875
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides

*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
NPO33569	0cardia sp. TP-A0674	Species	0cardiaceae	Bacteria	n.a.	isolated from a soil sample collected at Keta, Ishikawa, Japan	n.a.	PMID[16038549]

☑ 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
IC50	1
Ki	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT264	Individual Protein	Muscarinic acetylcholine receptor M3	Homo sapiens	IC50	=	4560	nM	PMID[16038549]
NPT264	Individual Protein	Muscarinic acetylcholine receptor M3	Homo sapiens	Ki	=	970	nM	PMID[16038549]

☑ 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 NPC477589 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	330
0.1-0.2	2127
0.2-0.3	9879
0.3-0.4	7554
0.4-0.5	12724
0.5-0.6	9244
0.6-0.7	794
0.7-0.8	39
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477587
0.9718	High Similarity	NPC477585
0.9718	High Similarity	NPC477588
0.9718	High Similarity	NPC477590
0.9718	High Similarity	NPC477586
0.7851	Intermediate Similarity	NPC314633
0.7699	Intermediate Similarity	NPC316224
0.7598	Intermediate Similarity	NPC315804
0.7598	Intermediate Similarity	NPC313804
0.7543	Intermediate Similarity	NPC205372
0.7455	Intermediate Similarity	NPC472286
0.7455	Intermediate Similarity	NPC472287
0.7444	Intermediate Similarity	NPC317572
0.7403	Intermediate Similarity	NPC131885
0.7401	Intermediate Similarity	NPC269367
0.7388	Intermediate Similarity	NPC161801
0.7362	Intermediate Similarity	NPC97746
0.7277	Intermediate Similarity	NPC478141
0.7273	Intermediate Similarity	NPC16066
0.7253	Intermediate Similarity	NPC314270
0.725	Intermediate Similarity	NPC196718
0.725	Intermediate Similarity	NPC102593
0.7227	Intermediate Similarity	NPC186351
0.7227	Intermediate Similarity	NPC140296
0.722	Intermediate Similarity	NPC472284
0.7193	Intermediate Similarity	NPC316403
0.7149	Intermediate Similarity	NPC298436
0.7143	Intermediate Similarity	NPC476830
0.7143	Intermediate Similarity	NPC320394
0.7143	Intermediate Similarity	NPC146418
0.7137	Intermediate Similarity	NPC58209
0.7126	Intermediate Similarity	NPC160100
0.7119	Intermediate Similarity	NPC128115
0.7117	Intermediate Similarity	NPC230403
0.7109	Intermediate Similarity	NPC209981
0.7106	Intermediate Similarity	NPC309919
0.7106	Intermediate Similarity	NPC49195
0.7101	Intermediate Similarity	NPC476826
0.7101	Intermediate Similarity	NPC476831
0.7101	Intermediate Similarity	NPC476827
0.7094	Intermediate Similarity	NPC196449
0.7094	Intermediate Similarity	NPC314222
0.7092	Intermediate Similarity	NPC316110
0.7092	Intermediate Similarity	NPC313587
0.7092	Intermediate Similarity	NPC315893
0.7083	Intermediate Similarity	NPC476832
0.7083	Intermediate Similarity	NPC325683
0.7071	Intermediate Similarity	NPC477219
0.7054	Intermediate Similarity	NPC194740
0.7046	Intermediate Similarity	NPC54066
0.7042	Intermediate Similarity	NPC37924
0.7027	Intermediate Similarity	NPC470042
0.7016	Intermediate Similarity	NPC166712
0.7012	Intermediate Similarity	NPC476828
0.6988	Remote Similarity	NPC188400
0.698	Remote Similarity	NPC34770
0.6975	Remote Similarity	NPC150239
0.6975	Remote Similarity	NPC174760
0.697	Remote Similarity	NPC321428
0.6967	Remote Similarity	NPC322800
0.6967	Remote Similarity	NPC477218
0.6967	Remote Similarity	NPC168135
0.696	Remote Similarity	NPC220408
0.6955	Remote Similarity	NPC241025
0.6941	Remote Similarity	NPC472435
0.6938	Remote Similarity	NPC282346
0.6932	Remote Similarity	NPC72715
0.6926	Remote Similarity	NPC472436
0.6926	Remote Similarity	NPC315411
0.6926	Remote Similarity	NPC299035
0.6926	Remote Similarity	NPC14288
0.6926	Remote Similarity	NPC177432
0.692	Remote Similarity	NPC75179
0.6917	Remote Similarity	NPC203373
0.6901	Remote Similarity	NPC24370
0.6901	Remote Similarity	NPC319232
0.6891	Remote Similarity	NPC174576
0.6891	Remote Similarity	NPC247803
0.689	Remote Similarity	NPC181081
0.6885	Remote Similarity	NPC322135
0.6882	Remote Similarity	NPC101312
0.6872	Remote Similarity	NPC34580
0.6872	Remote Similarity	NPC124920
0.6872	Remote Similarity	NPC304307
0.6872	Remote Similarity	NPC118559
0.687	Remote Similarity	NPC284888
0.6866	Remote Similarity	NPC286195
0.6857	Remote Similarity	NPC217176
0.6854	Remote Similarity	NPC172355
0.6853	Remote Similarity	NPC208364
0.685	Remote Similarity	NPC165964
0.6849	Remote Similarity	NPC169402
0.6844	Remote Similarity	NPC100547
0.6835	Remote Similarity	NPC477979
0.6835	Remote Similarity	NPC50562
0.683	Remote Similarity	NPC144381
0.6829	Remote Similarity	NPC477516
0.6827	Remote Similarity	NPC474183
0.6822	Remote Similarity	NPC38237
0.6822	Remote Similarity	NPC474428
0.6816	Remote Similarity	NPC223409
0.6816	Remote Similarity	NPC95240
0.6807	Remote Similarity	NPC148183
0.6807	Remote Similarity	NPC67658
0.6807	Remote Similarity	NPC3207
0.6807	Remote Similarity	NPC152768
0.6805	Remote Similarity	NPC198503
0.6803	Remote Similarity	NPC261251
0.6803	Remote Similarity	NPC244536
0.6802	Remote Similarity	NPC323752
0.6802	Remote Similarity	NPC323198
0.6795	Remote Similarity	NPC129897
0.6793	Remote Similarity	NPC151781
0.6793	Remote Similarity	NPC74562
0.6793	Remote Similarity	NPC316181
0.6787	Remote Similarity	NPC184680
0.6783	Remote Similarity	NPC476829
0.6782	Remote Similarity	NPC471978
0.6765	Remote Similarity	NPC116238
0.6763	Remote Similarity	NPC469439
0.6762	Remote Similarity	NPC214142
0.6761	Remote Similarity	NPC54803
0.6761	Remote Similarity	NPC321592
0.676	Remote Similarity	NPC470784
0.676	Remote Similarity	NPC470785
0.6759	Remote Similarity	NPC180668
0.6759	Remote Similarity	NPC148896
0.6759	Remote Similarity	NPC471013
0.6758	Remote Similarity	NPC283152
0.6752	Remote Similarity	NPC315061
0.675	Remote Similarity	NPC184408
0.675	Remote Similarity	NPC303658
0.6745	Remote Similarity	NPC173250
0.6734	Remote Similarity	NPC220852
0.6733	Remote Similarity	NPC168922
0.6722	Remote Similarity	NPC168209
0.6721	Remote Similarity	NPC473449
0.6721	Remote Similarity	NPC179287
0.672	Remote Similarity	NPC6786
0.6718	Remote Similarity	NPC120513
0.6707	Remote Similarity	NPC33064
0.6707	Remote Similarity	NPC245055
0.6707	Remote Similarity	NPC182222
0.6706	Remote Similarity	NPC1608
0.6705	Remote Similarity	NPC471979
0.6705	Remote Similarity	NPC473833
0.6696	Remote Similarity	NPC194040
0.6695	Remote Similarity	NPC66191
0.6695	Remote Similarity	NPC314817
0.6695	Remote Similarity	NPC316297
0.6693	Remote Similarity	NPC67401
0.6681	Remote Similarity	NPC308137
0.6681	Remote Similarity	NPC264176
0.6681	Remote Similarity	NPC310211
0.668	Remote Similarity	NPC473187
0.668	Remote Similarity	NPC326930
0.668	Remote Similarity	NPC85879
0.668	Remote Similarity	NPC475301
0.668	Remote Similarity	NPC53255
0.6667	Remote Similarity	NPC74969
0.6654	Remote Similarity	NPC230683
0.6654	Remote Similarity	NPC13603
0.6654	Remote Similarity	NPC10904
0.6653	Remote Similarity	NPC470280
0.6653	Remote Similarity	NPC285343
0.6652	Remote Similarity	NPC315542
0.6641	Remote Similarity	NPC471015
0.664	Remote Similarity	NPC274640
0.664	Remote Similarity	NPC119134
0.6639	Remote Similarity	NPC220337
0.6639	Remote Similarity	NPC87413
0.6639	Remote Similarity	NPC175150
0.6639	Remote Similarity	NPC312645
0.6639	Remote Similarity	NPC187501
0.6639	Remote Similarity	NPC243633
0.6639	Remote Similarity	NPC23294
0.6636	Remote Similarity	NPC30527
0.6628	Remote Similarity	NPC258048
0.6627	Remote Similarity	NPC82472
0.6627	Remote Similarity	NPC472434
0.6626	Remote Similarity	NPC323969
0.6614	Remote Similarity	NPC272549
0.661	Remote Similarity	NPC53344
0.661	Remote Similarity	NPC193238
0.6607	Remote Similarity	NPC207851
0.6604	Remote Similarity	NPC100734
0.6604	Remote Similarity	NPC88923
0.6604	Remote Similarity	NPC315634
0.6601	Remote Similarity	NPC475816
0.66	Remote Similarity	NPC172222
0.66	Remote Similarity	NPC329631
0.66	Remote Similarity	NPC141053
0.6597	Remote Similarity	NPC303951
0.6591	Remote Similarity	NPC328928
0.659	Remote Similarity	NPC472589
0.659	Remote Similarity	NPC318068
0.6588	Remote Similarity	NPC291609
0.6587	Remote Similarity	NPC240384
0.6587	Remote Similarity	NPC15801
0.6586	Remote Similarity	NPC260434

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 NPC477589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	584
0.2-0.3	962
0.3-0.4	1664
0.4-0.5	2983
0.5-0.6	2418
0.6-0.7	320
0.7-0.8	21
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
0.8153	Intermediate Similarity	NPD6974	Phase 3
0.8009	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD7853	Phase 2
0.7876	Intermediate Similarity	NPD7180	Phase 3
0.7812	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4898	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD2779	Approved
0.7621	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD7031	Phase 1
0.7611	Intermediate Similarity	NPD3945	Discontinued
0.7521	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2778	Approved
0.75	Intermediate Similarity	NPD1638	Discovery
0.7489	Intermediate Similarity	NPD8479	Phase 2
0.7489	Intermediate Similarity	NPD5866	Approved
0.7479	Intermediate Similarity	NPD3263	Phase 3
0.7451	Intermediate Similarity	NPD5922	Phase 3
0.7436	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4394	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD8356	Approved
0.7325	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3392	Approved
0.7309	Intermediate Similarity	NPD6252	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD5532	Phase 2
0.7293	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6347	Phase 2
0.7284	Intermediate Similarity	NPD5443	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD1867	Approved
0.7277	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2951	Discontinued
0.7257	Intermediate Similarity	NPD5640	Discontinued
0.7254	Intermediate Similarity	NPD7417	Discontinued
0.7253	Intermediate Similarity	NPD5632	Approved
0.7227	Intermediate Similarity	NPD8430	Approved
0.7224	Intermediate Similarity	NPD7022	Phase 2
0.7222	Intermediate Similarity	NPD2884	Phase 1
0.7212	Intermediate Similarity	NPD5513	Phase 2
0.7181	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7490	Discontinued
0.7174	Intermediate Similarity	NPD2081	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD1505	Phase 2
0.7131	Intermediate Similarity	NPD5857	Phase 3
0.7126	Intermediate Similarity	NPD3801	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD8463	Approved
0.7095	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6716	Phase 1
0.7068	Intermediate Similarity	NPD5817	Discontinued
0.7061	Intermediate Similarity	NPD4368	Phase 2
0.7056	Intermediate Similarity	NPD6495	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5512	Phase 3
0.7052	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5293	Phase 2
0.7046	Intermediate Similarity	NPD5850	Phase 3
0.7034	Intermediate Similarity	NPD7395	Discontinued
0.7012	Intermediate Similarity	NPD7994	Phase 2
0.7008	Intermediate Similarity	NPD4373	Phase 2
0.7004	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5416	Discontinued
0.6992	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7796	Approved
0.6967	Remote Similarity	NPD7797	Approved
0.6966	Remote Similarity	NPD7069	Discontinued
0.696	Remote Similarity	NPD6874	Approved
0.6955	Remote Similarity	NPD4952	Phase 3
0.6948	Remote Similarity	NPD4322	Discontinued
0.694	Remote Similarity	NPD7467	Discontinued
0.6937	Remote Similarity	NPD2792	Approved
0.6926	Remote Similarity	NPD1467	Approved
0.6926	Remote Similarity	NPD1466	Phase 3
0.6891	Remote Similarity	NPD6198	Phase 1
0.6885	Remote Similarity	NPD5479	Discontinued
0.6885	Remote Similarity	NPD5924	Discontinued
0.688	Remote Similarity	NPD8117	Approved
0.688	Remote Similarity	NPD8116	Phase 3
0.6875	Remote Similarity	NPD4923	Phase 1
0.686	Remote Similarity	NPD3925	Approved
0.6848	Remote Similarity	NPD8255	Phase 2
0.6842	Remote Similarity	NPD772	Phase 3
0.6828	Remote Similarity	NPD6550	Discontinued
0.6826	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7605	Discovery
0.6816	Remote Similarity	NPD1659	Phase 1
0.6811	Remote Similarity	NPD8324	Phase 2
0.6811	Remote Similarity	NPD4369	Phase 2
0.681	Remote Similarity	NPD4467	Phase 2
0.681	Remote Similarity	NPD4465	Phase 2
0.6809	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3259	Approved
0.6803	Remote Similarity	NPD4086	Phase 1
0.6802	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7886	Phase 2
0.68	Remote Similarity	NPD7885	Phase 2
0.6786	Remote Similarity	NPD4334	Discontinued
0.6784	Remote Similarity	NPD5482	Discontinued
0.6781	Remote Similarity	NPD3507	Phase 2
0.6778	Remote Similarity	NPD4989	Phase 2
0.6773	Remote Similarity	NPD6790	Phase 1
0.6767	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4897	Phase 2
0.676	Remote Similarity	NPD6825	Phase 1
0.6752	Remote Similarity	NPD5429	Discontinued
0.675	Remote Similarity	NPD6568	Discontinued
0.6741	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5507	Approved
0.6736	Remote Similarity	NPD5506	Approved
0.6736	Remote Similarity	NPD7556	Discontinued
0.6732	Remote Similarity	NPD8359	Phase 2
0.6722	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6475	Phase 2
0.6708	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5256	Discontinued
0.6694	Remote Similarity	NPD7426	Phase 1
0.6693	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6321	Discontinued
0.6681	Remote Similarity	NPD4392	Phase 2
0.668	Remote Similarity	NPD8102	Discontinued
0.668	Remote Similarity	NPD4887	Discontinued
0.668	Remote Similarity	NPD8246	Approved
0.668	Remote Similarity	NPD8247	Approved
0.668	Remote Similarity	NPD3250	Phase 1
0.6667	Remote Similarity	NPD1768	Approved
0.6667	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6857	Phase 3
0.6667	Remote Similarity	NPD5488	Discontinued
0.6667	Remote Similarity	NPD7689	Approved
0.6653	Remote Similarity	NPD6962	Phase 2
0.6653	Remote Similarity	NPD3258	Approved
0.6641	Remote Similarity	NPD8370	Discontinued
0.6638	Remote Similarity	NPD3003	Approved
0.6638	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7318	Phase 3
0.6623	Remote Similarity	NPD4315	Phase 2
0.6623	Remote Similarity	NPD4372	Phase 1
0.6614	Remote Similarity	NPD3006	Discontinued
0.661	Remote Similarity	NPD7452	Approved
0.661	Remote Similarity	NPD7453	Approved
0.6607	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7803	Approved
0.6601	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6298	Discontinued
0.6597	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3351	Approved
0.6578	Remote Similarity	NPD7708	Approved
0.6576	Remote Similarity	NPD3328	Phase 2
0.6573	Remote Similarity	NPD5014	Discontinued
0.6571	Remote Similarity	NPD6209	Approved
0.6571	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.657	Remote Similarity	NPD1976	Approved
0.657	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD4130	Phase 3
0.6564	Remote Similarity	NPD1898	Discontinued
0.6562	Remote Similarity	NPD7967	Discontinued
0.6559	Remote Similarity	NPD8289	Discontinued
0.6558	Remote Similarity	NPD1955	Discontinued
0.6555	Remote Similarity	NPD5593	Approved
0.6555	Remote Similarity	NPD5594	Approved
0.6553	Remote Similarity	NPD6176	Phase 1
0.655	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD3154	Approved
0.6549	Remote Similarity	NPD1483	Discontinued
0.6549	Remote Similarity	NPD3153	Approved
0.6546	Remote Similarity	NPD5022	Discontinued
0.6543	Remote Similarity	NPD2011	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7878	Phase 2
0.6542	Remote Similarity	NPD7317	Phase 3
0.6541	Remote Similarity	NPD5450	Discontinued
0.654	Remote Similarity	NPD7956	Approved
0.654	Remote Similarity	NPD3350	Approved
0.654	Remote Similarity	NPD7955	Approved
0.654	Remote Similarity	NPD7043	Discontinued
0.654	Remote Similarity	NPD7222	Phase 2
0.6535	Remote Similarity	NPD4613	Phase 2
0.6533	Remote Similarity	NPD8459	Approved
0.6533	Remote Similarity	NPD8460	Approved
0.6532	Remote Similarity	NPD4328	Approved
0.6518	Remote Similarity	NPD4203	Approved
0.6518	Remote Similarity	NPD4204	Approved
0.6516	Remote Similarity	NPD6770	Approved
0.6516	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3243	Approved
0.6513	Remote Similarity	NPD6376	Discontinued
0.6512	Remote Similarity	NPD7996	Phase 2
0.65	Remote Similarity	NPD7470	Discontinued
0.6494	Remote Similarity	NPD6590	Discontinued
0.6492	Remote Similarity	NPD7603	Discontinued
0.6488	Remote Similarity	NPD5902	Approved
0.6488	Remote Similarity	NPD6169	Phase 1
0.6488	Remote Similarity	NPD3257	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