NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	316.01
Volume:	247.592
LogP:	-0.172
LogD:	0.907
LogS:	-1.773
# Rotatable Bonds:	4
TPSA:	91.42
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.727
Synthetic Accessibility Score:	3.457
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.43
MDCK Permeability:	2.2195104975253344e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.791

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.78
Plasma Protein Binding (PPB):	42.865325927734375%
Volume Distribution (VD):	0.466
Pgp-substrate:	70.86656951904297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.887
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.333
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	2.798
Half-life (T1/2):	0.819

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.219
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.388
Carcinogencity:	0.159
Eye Corrosion:	0.008
Eye Irritation:	0.177
Respiratory Toxicity:	0.219

Download Data

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

Natural Product: NPC77061

Natural Product ID:	NPC77061
*Common Name:**	Damipipecolin
IUPAC Name:	(2R,4R)-4-(4-bromo-1H-pyrrole-2-carbonyl)oxypiperidine-2-carboxylic acid
Synonyms:	damipipecolin
Standard InCHIKey:	NDJQQEYLUZNTCW-HTQZYQBOSA-N
Standard InCHI:	InChI=1S/C11H13BrN2O4/c12-6-3-9(14-5-6)11(17)18-7-1-2-13-8(4-7)10(15)16/h3,5,7-8,13-14H,1-2,4H2,(H,15,16)/t7-,8-/m1/s1
SMILES:	C1CN[C@H](C[C@@H]1OC(=O)c1cc(c[nH]1)Br)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL239967
PubChem CID:	16742594
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0002404] Alpha amino acids [CHEMONTID:0004145] D-alpha-amino acids

*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
NPO15231	Axinella damicornis	Species	Axinellidae	Eukaryota	n.a.	Mediterranean	n.a.	PMID[17582775]
NPO15231	Axinella damicornis	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	10

Activity Type	# Activity
Others	10

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Activity	=	11.2	%	PMID[483392]
NPT2	Others	Unspecified	Activity	=	29.7	%	PMID[483392]
NPT2	Others	Unspecified	Activity	=	38.0	%	PMID[483392]
NPT2	Others	Unspecified	Activity	=	71.6	%	PMID[483392]
NPT2	Others	Unspecified	Activity	=	83.3	%	PMID[483392]
NPT2	Others	Unspecified	Activity	=	90.5	%	PMID[483392]
NPT2	Others	Unspecified	Activity	=	96.6	%	PMID[483392]
NPT2	Others	Unspecified	Activity	=	105.9	%	PMID[483392]
NPT2	Others	Unspecified	Activity	=	114.1	%	PMID[483392]
NPT2	Others	Unspecified	Activity	=	70.4	%	PMID[483392]

☑ 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 NPC77061 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	322
0.1-0.2	4326
0.2-0.3	14311
0.3-0.4	16788
0.4-0.5	3433
0.5-0.6	2504
0.6-0.7	956
0.7-0.8	55
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8057	Intermediate Similarity	NPC33229
0.791	Intermediate Similarity	NPC142688
0.7772	Intermediate Similarity	NPC302647
0.7684	Intermediate Similarity	NPC52110
0.7614	Intermediate Similarity	NPC302159
0.7582	Intermediate Similarity	NPC473706
0.7556	Intermediate Similarity	NPC298288
0.7538	Intermediate Similarity	NPC103361
0.7487	Intermediate Similarity	NPC273532
0.744	Intermediate Similarity	NPC118940
0.7424	Intermediate Similarity	NPC135950
0.7371	Intermediate Similarity	NPC311282
0.7363	Intermediate Similarity	NPC75135
0.7348	Intermediate Similarity	NPC109158
0.7343	Intermediate Similarity	NPC123839
0.7333	Intermediate Similarity	NPC13432
0.732	Intermediate Similarity	NPC207851
0.7317	Intermediate Similarity	NPC82053
0.7273	Intermediate Similarity	NPC474383
0.7259	Intermediate Similarity	NPC75544
0.7246	Intermediate Similarity	NPC266249
0.7234	Intermediate Similarity	NPC41717
0.723	Intermediate Similarity	NPC168209
0.7222	Intermediate Similarity	NPC469489
0.7204	Intermediate Similarity	NPC477979
0.7192	Intermediate Similarity	NPC123395
0.7188	Intermediate Similarity	NPC476419
0.7173	Intermediate Similarity	NPC80528
0.7172	Intermediate Similarity	NPC209917
0.713	Intermediate Similarity	NPC175150
0.713	Intermediate Similarity	NPC243633
0.7129	Intermediate Similarity	NPC109922
0.7123	Intermediate Similarity	NPC153452
0.712	Intermediate Similarity	NPC249614
0.7102	Intermediate Similarity	NPC328029
0.71	Intermediate Similarity	NPC138370
0.7089	Intermediate Similarity	NPC36405
0.7081	Intermediate Similarity	NPC474236
0.7077	Intermediate Similarity	NPC317010
0.7075	Intermediate Similarity	NPC89508
0.7056	Intermediate Similarity	NPC312645
0.7056	Intermediate Similarity	NPC472285
0.7045	Intermediate Similarity	NPC23215
0.7045	Intermediate Similarity	NPC291517
0.7044	Intermediate Similarity	NPC179701
0.7027	Intermediate Similarity	NPC107287
0.7023	Intermediate Similarity	NPC469717
0.701	Intermediate Similarity	NPC262898
0.7005	Intermediate Similarity	NPC27296
0.7	Intermediate Similarity	NPC476524
0.6983	Remote Similarity	NPC85443
0.6981	Remote Similarity	NPC82370
0.6965	Remote Similarity	NPC83111
0.695	Remote Similarity	NPC278434
0.6948	Remote Similarity	NPC207020
0.6943	Remote Similarity	NPC253810
0.6939	Remote Similarity	NPC283219
0.6935	Remote Similarity	NPC312860
0.6935	Remote Similarity	NPC476423
0.6927	Remote Similarity	NPC90019
0.6919	Remote Similarity	NPC476525
0.6898	Remote Similarity	NPC263455
0.6897	Remote Similarity	NPC476516
0.689	Remote Similarity	NPC165599
0.6885	Remote Similarity	NPC260041
0.6872	Remote Similarity	NPC244741
0.6869	Remote Similarity	NPC275292
0.6869	Remote Similarity	NPC243381
0.6864	Remote Similarity	NPC229893
0.686	Remote Similarity	NPC474767
0.6856	Remote Similarity	NPC54214
0.6853	Remote Similarity	NPC248041
0.6853	Remote Similarity	NPC126709
0.6837	Remote Similarity	NPC229348
0.6833	Remote Similarity	NPC212766
0.6833	Remote Similarity	NPC289423
0.6828	Remote Similarity	NPC15801
0.6814	Remote Similarity	NPC182222
0.6811	Remote Similarity	NPC112741
0.6806	Remote Similarity	NPC50562
0.6796	Remote Similarity	NPC292361
0.6792	Remote Similarity	NPC316403
0.6786	Remote Similarity	NPC203468
0.6786	Remote Similarity	NPC110500
0.6786	Remote Similarity	NPC149155
0.678	Remote Similarity	NPC88315
0.678	Remote Similarity	NPC473821
0.6778	Remote Similarity	NPC472288
0.6777	Remote Similarity	NPC132539
0.6774	Remote Similarity	NPC67658
0.6768	Remote Similarity	NPC276540
0.6768	Remote Similarity	NPC233050
0.6763	Remote Similarity	NPC74153
0.6762	Remote Similarity	NPC57398
0.6756	Remote Similarity	NPC260434
0.6753	Remote Similarity	NPC316224
0.6751	Remote Similarity	NPC267885
0.6748	Remote Similarity	NPC202812
0.6739	Remote Similarity	NPC37473
0.6737	Remote Similarity	NPC475870
0.6733	Remote Similarity	NPC112489
0.6733	Remote Similarity	NPC46022
0.6733	Remote Similarity	NPC235684
0.6703	Remote Similarity	NPC167400
0.6696	Remote Similarity	NPC192712
0.6695	Remote Similarity	NPC216369
0.6684	Remote Similarity	NPC274981
0.6684	Remote Similarity	NPC169586
0.6683	Remote Similarity	NPC295158
0.6683	Remote Similarity	NPC141454
0.6682	Remote Similarity	NPC74360
0.6682	Remote Similarity	NPC476874
0.6681	Remote Similarity	NPC267853
0.6667	Remote Similarity	NPC45459
0.6667	Remote Similarity	NPC315491
0.6667	Remote Similarity	NPC473628
0.6667	Remote Similarity	NPC46811
0.6667	Remote Similarity	NPC470894
0.6652	Remote Similarity	NPC476517
0.6652	Remote Similarity	NPC244897
0.665	Remote Similarity	NPC315555
0.6649	Remote Similarity	NPC213914
0.6649	Remote Similarity	NPC471655
0.6649	Remote Similarity	NPC212742
0.6636	Remote Similarity	NPC321428
0.6634	Remote Similarity	NPC154339
0.6634	Remote Similarity	NPC475874
0.6633	Remote Similarity	NPC111275
0.6633	Remote Similarity	NPC14113
0.6633	Remote Similarity	NPC84827
0.6633	Remote Similarity	NPC145885
0.6632	Remote Similarity	NPC209362
0.6622	Remote Similarity	NPC2395
0.662	Remote Similarity	NPC477043
0.662	Remote Similarity	NPC470505
0.6618	Remote Similarity	NPC267343
0.6618	Remote Similarity	NPC192306
0.6617	Remote Similarity	NPC71037
0.6616	Remote Similarity	NPC37268
0.6615	Remote Similarity	NPC474492
0.6611	Remote Similarity	NPC150592
0.661	Remote Similarity	NPC313823
0.6608	Remote Similarity	NPC315062
0.6606	Remote Similarity	NPC315804
0.6606	Remote Similarity	NPC317752
0.6606	Remote Similarity	NPC313804
0.6602	Remote Similarity	NPC114974
0.6601	Remote Similarity	NPC282103
0.6601	Remote Similarity	NPC280290
0.6594	Remote Similarity	NPC316411
0.6589	Remote Similarity	NPC472286
0.6589	Remote Similarity	NPC472287
0.6588	Remote Similarity	NPC214428
0.6582	Remote Similarity	NPC78020
0.6579	Remote Similarity	NPC200553
0.6579	Remote Similarity	NPC279189
0.6575	Remote Similarity	NPC478157
0.6574	Remote Similarity	NPC472752
0.6574	Remote Similarity	NPC478158
0.6571	Remote Similarity	NPC477044
0.6571	Remote Similarity	NPC67288
0.6571	Remote Similarity	NPC477041
0.6564	Remote Similarity	NPC233380
0.6562	Remote Similarity	NPC64216
0.6562	Remote Similarity	NPC138018
0.6561	Remote Similarity	NPC281049
0.6561	Remote Similarity	NPC174576
0.656	Remote Similarity	NPC318299
0.6558	Remote Similarity	NPC156044
0.6557	Remote Similarity	NPC9635
0.6556	Remote Similarity	NPC20021
0.6552	Remote Similarity	NPC469814
0.6552	Remote Similarity	NPC284678
0.6549	Remote Similarity	NPC244536
0.6542	Remote Similarity	NPC473239
0.654	Remote Similarity	NPC477045
0.6538	Remote Similarity	NPC29702
0.6535	Remote Similarity	NPC472861
0.6535	Remote Similarity	NPC184932
0.6533	Remote Similarity	NPC235885
0.653	Remote Similarity	NPC472291
0.6526	Remote Similarity	NPC193761
0.6524	Remote Similarity	NPC78767
0.6524	Remote Similarity	NPC473814
0.6524	Remote Similarity	NPC156704
0.6522	Remote Similarity	NPC174489
0.6522	Remote Similarity	NPC210123
0.652	Remote Similarity	NPC241025
0.6517	Remote Similarity	NPC55772
0.6513	Remote Similarity	NPC476418
0.6513	Remote Similarity	NPC162268
0.6513	Remote Similarity	NPC206148
0.6512	Remote Similarity	NPC309498
0.6507	Remote Similarity	NPC93390
0.6504	Remote Similarity	NPC319232
0.6504	Remote Similarity	NPC24370
0.6503	Remote Similarity	NPC114310
0.6502	Remote Similarity	NPC469358
0.6502	Remote Similarity	NPC54066
0.6498	Remote Similarity	NPC472070

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 NPC77061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	613
0.2-0.3	1135
0.3-0.4	2289
0.4-0.5	2878
0.5-0.6	1787
0.6-0.7	271
0.7-0.8	8
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
0.7766	Intermediate Similarity	NPD3178	Discontinued
0.7524	Intermediate Similarity	NPD1996	Discontinued
0.7409	Intermediate Similarity	NPD1096	Discontinued
0.7389	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2509	Approved
0.7246	Intermediate Similarity	NPD2510	Approved
0.717	Intermediate Similarity	NPD3389	Approved
0.717	Intermediate Similarity	NPD3393	Approved
0.717	Intermediate Similarity	NPD3394	Approved
0.7022	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD820	Phase 3
0.6901	Remote Similarity	NPD7470	Discontinued
0.6891	Remote Similarity	NPD565	Phase 2
0.687	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3947	Discontinued
0.6842	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5475	Discontinued
0.6811	Remote Similarity	NPD9271	Approved
0.6802	Remote Similarity	NPD8289	Discontinued
0.6786	Remote Similarity	NPD482	Approved
0.6784	Remote Similarity	NPD5891	Approved
0.6772	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3794	Approved
0.6759	Remote Similarity	NPD3795	Approved
0.6752	Remote Similarity	NPD5482	Discontinued
0.6732	Remote Similarity	NPD6665	Discontinued
0.6712	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD9075	Approved
0.6703	Remote Similarity	NPD9074	Approved
0.6698	Remote Similarity	NPD5901	Discontinued
0.6698	Remote Similarity	NPD7396	Approved
0.6682	Remote Similarity	NPD6770	Approved
0.6667	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2094	Phase 2
0.6667	Remote Similarity	NPD2092	Phase 2
0.6667	Remote Similarity	NPD484	Approved
0.6667	Remote Similarity	NPD2095	Phase 2
0.6667	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4376	Phase 3
0.6634	Remote Similarity	NPD2091	Phase 2
0.6634	Remote Similarity	NPD2096	Phase 2
0.6618	Remote Similarity	NPD4529	Approved
0.6618	Remote Similarity	NPD4526	Approved
0.6618	Remote Similarity	NPD4528	Approved
0.6615	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3280	Approved
0.6576	Remote Similarity	NPD107	Approved
0.6565	Remote Similarity	NPD3006	Discontinued
0.6564	Remote Similarity	NPD1659	Phase 1
0.6561	Remote Similarity	NPD1623	Approved
0.6558	Remote Similarity	NPD3371	Approved
0.6555	Remote Similarity	NPD2290	Phase 3
0.6555	Remote Similarity	NPD2289	Phase 3
0.6549	Remote Similarity	NPD4086	Phase 1
0.6541	Remote Similarity	NPD4805	Approved
0.6494	Remote Similarity	NPD7853	Phase 2
0.649	Remote Similarity	NPD5450	Discontinued
0.6486	Remote Similarity	NPD5632	Approved
0.6484	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD750	Phase 2
0.648	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD4301	Approved
0.6468	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD5003	Discontinued
0.6444	Remote Similarity	NPD8356	Approved
0.6443	Remote Similarity	NPD604	Clinical (unspecified phase)
0.644	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.644	Remote Similarity	NPD510	Phase 1
0.6432	Remote Similarity	NPD4804	Approved
0.6429	Remote Similarity	NPD1631	Approved
0.6425	Remote Similarity	NPD2547	Discontinued
0.6422	Remote Similarity	NPD4506	Discontinued
0.6422	Remote Similarity	NPD6529	Discontinued
0.6416	Remote Similarity	NPD6173	Approved
0.6416	Remote Similarity	NPD6753	Phase 1
0.6416	Remote Similarity	NPD6752	Phase 1
0.6415	Remote Similarity	NPD772	Phase 3
0.6409	Remote Similarity	NPD5866	Approved
0.6404	Remote Similarity	NPD1643	Phase 3
0.6404	Remote Similarity	NPD9510	Approved
0.6395	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD8063	Discontinued
0.6392	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD2581	Approved
0.6392	Remote Similarity	NPD2582	Approved
0.6384	Remote Similarity	NPD7404	Approved
0.6382	Remote Similarity	NPD1575	Approved
0.6382	Remote Similarity	NPD1573	Approved
0.6381	Remote Similarity	NPD1173	Approved
0.6368	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3915	Approved
0.636	Remote Similarity	NPD5640	Discontinued
0.6359	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7010	Phase 3
0.6335	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD3918	Approved
0.6335	Remote Similarity	NPD3917	Approved
0.6332	Remote Similarity	NPD8430	Approved
0.633	Remote Similarity	NPD1392	Approved
0.6316	Remote Similarity	NPD2564	Approved
0.6316	Remote Similarity	NPD2565	Phase 2
0.6311	Remote Similarity	NPD3569	Discontinued
0.6301	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD9364	Phase 2
0.6298	Remote Similarity	NPD9363	Approved
0.6293	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD9362	Approved
0.6287	Remote Similarity	NPD5065	Approved
0.6284	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD7957	Phase 1
0.6283	Remote Similarity	NPD7180	Phase 3
0.6276	Remote Similarity	NPD1630	Approved
0.6274	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD8072	Approved
0.6267	Remote Similarity	NPD6176	Phase 1
0.6263	Remote Similarity	NPD5088	Discontinued
0.6262	Remote Similarity	NPD5596	Phase 2
0.625	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.625	Remote Similarity	NPD706	Phase 1
0.625	Remote Similarity	NPD7727	Phase 2
0.6244	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD9506	Approved
0.6233	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD3945	Discontinued
0.6221	Remote Similarity	NPD8073	Approved
0.622	Remote Similarity	NPD1034	Phase 3
0.622	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6217	Remote Similarity	NPD7603	Discontinued
0.6216	Remote Similarity	NPD5416	Discontinued
0.6211	Remote Similarity	NPD6242	Discontinued
0.621	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7001	Phase 3
0.6209	Remote Similarity	NPD4699	Discontinued
0.6208	Remote Similarity	NPD8468	Phase 2
0.6207	Remote Similarity	NPD158	Discontinued
0.6207	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD5149	Phase 2
0.6205	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD4427	Phase 2
0.619	Remote Similarity	NPD7994	Phase 2
0.6186	Remote Similarity	NPD946	Discontinued
0.6186	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.618	Remote Similarity	NPD7688	Phase 1
0.6179	Remote Similarity	NPD981	Phase 2
0.6178	Remote Similarity	NPD8160	Phase 2
0.6175	Remote Similarity	NPD5017	Discontinued
0.6168	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD1618	Phase 2
0.6164	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD1418	Phase 2
0.6162	Remote Similarity	NPD687	Clinical (unspecified phase)
0.616	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD2076	Approved
0.6158	Remote Similarity	NPD2077	Approved
0.6157	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.615	Remote Similarity	NPD1038	Approved
0.615	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD4417	Approved
0.6139	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6137	Remote Similarity	NPD5022	Discontinued
0.6136	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7970	Approved
0.6132	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4500	Approved
0.6129	Remote Similarity	NPD4501	Approved
0.6123	Remote Similarity	NPD4429	Discontinued
0.6123	Remote Similarity	NPD5948	Phase 2
0.6121	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD1587	Approved
0.6116	Remote Similarity	NPD8096	Phase 3
0.6116	Remote Similarity	NPD8097	Phase 3
0.6114	Remote Similarity	NPD7233	Approved
0.6114	Remote Similarity	NPD6068	Discontinued
0.6114	Remote Similarity	NPD7234	Approved
0.6108	Remote Similarity	NPD9548	Phase 2
0.6106	Remote Similarity	NPD3353	Approved
0.6106	Remote Similarity	NPD5612	Discontinued
0.6101	Remote Similarity	NPD7817	Phase 1
0.6099	Remote Similarity	NPD9080	Approved
0.6099	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD2831	Approved
0.6091	Remote Similarity	NPD944	Approved
0.6079	Remote Similarity	NPD8326	Phase 3
0.6079	Remote Similarity	NPD7823	Clinical (unspecified phase)

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