NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.07
Volume:	261.043
LogP:	1.304
LogD:	1.888
LogS:	-4.82
# Rotatable Bonds:	1
TPSA:	57.65
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	2.867
Fsp3:	0.067
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:	-4.918
MDCK Permeability:	3.263551479903981e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.407
Plasma Protein Binding (PPB):	83.5586929321289%
Volume Distribution (VD):	0.878
Pgp-substrate:	5.985265254974365%

ADMET: Metabolism

CYP1A2-inhibitor:	0.941
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.721
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.605
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.316
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	8.516
Half-life (T1/2):	0.667

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.527
AMES Toxicity:	0.983
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.076
Carcinogencity:	0.977
Eye Corrosion:	0.004
Eye Irritation:	0.878
Respiratory Toxicity:	0.389

Download Data

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

Natural Product: NPC274981

Natural Product ID:	NPC274981
*Common Name:**	Makaluvamine O
IUPAC Name:	n.a.
Synonyms:	Makaluvamine O
Standard InCHIKey:	FDGKQWLSJXEOPF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H7BrN2O2/c11-6-7-5-4(1-2-12-7)3-13-8(5)10(15)9(6)14/h3,12-13H,1-2H2
SMILES:	C1CNC2=C(C(=O)C(=O)c3c2c1c[nH]3)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511880
PubChem CID:	5323533
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001734] Pyrroloquinolines [CHEMONTID:0002829] Pyrrolo[4,3,2-de]quinolines

*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
NPO20958	Smenospongia aurea	Species	Thorectidae	Eukaryota	n.a.	Jamaican	n.a.	PMID[11975483]
NPO20958	Smenospongia aurea	Species	Thorectidae	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
IC50	1
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.94	ug.mL-1	PMID[501060]
NPT2	Others	Unspecified		Selectivity Index	>	5.1	n.a.	PMID[501060]

☑ 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 NPC274981 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	509
0.1-0.2	6448
0.2-0.3	20412
0.3-0.4	9977
0.4-0.5	2436
0.5-0.6	1965
0.6-0.7	788
0.7-0.8	139
0.8-0.85	12
0.85-0.9	5
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9408	High Similarity	NPC474492
0.9221	High Similarity	NPC470680
0.9221	High Similarity	NPC100104
0.8727	High Similarity	NPC234403
0.8727	High Similarity	NPC79777
0.871	High Similarity	NPC217021
0.871	High Similarity	NPC470679
0.8526	High Similarity	NPC471655
0.8526	High Similarity	NPC473878
0.8393	Intermediate Similarity	NPC182940
0.8364	Intermediate Similarity	NPC262338
0.8266	Intermediate Similarity	NPC473628
0.8182	Intermediate Similarity	NPC221726
0.8182	Intermediate Similarity	NPC225622
0.8182	Intermediate Similarity	NPC477414
0.8114	Intermediate Similarity	NPC475874
0.8113	Intermediate Similarity	NPC123906
0.8086	Intermediate Similarity	NPC74357
0.8075	Intermediate Similarity	NPC251391
0.805	Intermediate Similarity	NPC100726
0.8	Intermediate Similarity	NPC102664
0.7941	Intermediate Similarity	NPC186068
0.791	Intermediate Similarity	NPC268966
0.7845	Intermediate Similarity	NPC167710
0.784	Intermediate Similarity	NPC313889
0.7829	Intermediate Similarity	NPC477003
0.7816	Intermediate Similarity	NPC191415
0.7797	Intermediate Similarity	NPC474259
0.7797	Intermediate Similarity	NPC477415
0.7797	Intermediate Similarity	NPC23476
0.776	Intermediate Similarity	NPC477004
0.7759	Intermediate Similarity	NPC477042
0.7746	Intermediate Similarity	NPC284775
0.7742	Intermediate Similarity	NPC88115
0.773	Intermediate Similarity	NPC106757
0.7716	Intermediate Similarity	NPC105811
0.7702	Intermediate Similarity	NPC467188
0.7692	Intermediate Similarity	NPC233380
0.7692	Intermediate Similarity	NPC292361
0.7683	Intermediate Similarity	NPC70406
0.7663	Intermediate Similarity	NPC237414
0.7644	Intermediate Similarity	NPC477413
0.7588	Intermediate Similarity	NPC42372
0.7584	Intermediate Similarity	NPC474258
0.7582	Intermediate Similarity	NPC326422
0.7571	Intermediate Similarity	NPC102755
0.7569	Intermediate Similarity	NPC476460
0.7542	Intermediate Similarity	NPC469359
0.7528	Intermediate Similarity	NPC110158
0.7526	Intermediate Similarity	NPC143075
0.75	Intermediate Similarity	NPC213914
0.75	Intermediate Similarity	NPC473946
0.7486	Intermediate Similarity	NPC304203
0.7485	Intermediate Similarity	NPC229055
0.7485	Intermediate Similarity	NPC209362
0.7468	Intermediate Similarity	NPC291517
0.7389	Intermediate Similarity	NPC311282
0.7384	Intermediate Similarity	NPC115232
0.7384	Intermediate Similarity	NPC2414
0.7353	Intermediate Similarity	NPC80681
0.733	Intermediate Similarity	NPC293216
0.7316	Intermediate Similarity	NPC317701
0.7299	Intermediate Similarity	NPC70949
0.7273	Intermediate Similarity	NPC74153
0.7243	Intermediate Similarity	NPC216550
0.7225	Intermediate Similarity	NPC265100
0.7216	Intermediate Similarity	NPC302647
0.7204	Intermediate Similarity	NPC473821
0.7198	Intermediate Similarity	NPC133003
0.7194	Intermediate Similarity	NPC470702
0.7194	Intermediate Similarity	NPC473218
0.7191	Intermediate Similarity	NPC151635
0.7175	Intermediate Similarity	NPC252572
0.7167	Intermediate Similarity	NPC73994
0.7157	Intermediate Similarity	NPC470703
0.7151	Intermediate Similarity	NPC83774
0.7151	Intermediate Similarity	NPC157583
0.7143	Intermediate Similarity	NPC476143
0.7143	Intermediate Similarity	NPC477044
0.7143	Intermediate Similarity	NPC23215
0.7143	Intermediate Similarity	NPC477041
0.7135	Intermediate Similarity	NPC324091
0.7135	Intermediate Similarity	NPC154339
0.7127	Intermediate Similarity	NPC470677
0.7107	Intermediate Similarity	NPC110182
0.7081	Intermediate Similarity	NPC103119
0.7077	Intermediate Similarity	NPC116555
0.7072	Intermediate Similarity	NPC61011
0.7059	Intermediate Similarity	NPC47190
0.7056	Intermediate Similarity	NPC237188
0.7037	Intermediate Similarity	NPC79356
0.7037	Intermediate Similarity	NPC102592
0.7027	Intermediate Similarity	NPC278434
0.7021	Intermediate Similarity	NPC267343
0.7017	Intermediate Similarity	NPC55772
0.7016	Intermediate Similarity	NPC477045
0.7011	Intermediate Similarity	NPC473706
0.7	Intermediate Similarity	NPC78767
0.7	Intermediate Similarity	NPC473814
0.6989	Remote Similarity	NPC71132
0.6984	Remote Similarity	NPC202812
0.6974	Remote Similarity	NPC175602
0.6971	Remote Similarity	NPC214106
0.6971	Remote Similarity	NPC242116
0.6961	Remote Similarity	NPC14113
0.6961	Remote Similarity	NPC84827
0.6961	Remote Similarity	NPC145885
0.6959	Remote Similarity	NPC476252
0.6957	Remote Similarity	NPC46895
0.6957	Remote Similarity	NPC467063
0.6944	Remote Similarity	NPC149155
0.6944	Remote Similarity	NPC110500
0.6944	Remote Similarity	NPC203468
0.6927	Remote Similarity	NPC469976
0.6923	Remote Similarity	NPC126709
0.6923	Remote Similarity	NPC283219
0.6923	Remote Similarity	NPC477043
0.6923	Remote Similarity	NPC469563
0.6923	Remote Similarity	NPC11126
0.6923	Remote Similarity	NPC248041
0.6915	Remote Similarity	NPC138370
0.6911	Remote Similarity	NPC227582
0.6911	Remote Similarity	NPC174281
0.6911	Remote Similarity	NPC475286
0.691	Remote Similarity	NPC78020
0.6906	Remote Similarity	NPC267885
0.6895	Remote Similarity	NPC93390
0.6888	Remote Similarity	NPC82053
0.6875	Remote Similarity	NPC34837
0.6869	Remote Similarity	NPC61038
0.6868	Remote Similarity	NPC111275
0.6862	Remote Similarity	NPC469489
0.686	Remote Similarity	NPC472260
0.6859	Remote Similarity	NPC179701
0.6854	Remote Similarity	NPC114637
0.6853	Remote Similarity	NPC469577
0.6853	Remote Similarity	NPC475410
0.6851	Remote Similarity	NPC469529
0.6848	Remote Similarity	NPC105127
0.6848	Remote Similarity	NPC65408
0.6845	Remote Similarity	NPC190296
0.6842	Remote Similarity	NPC247735
0.6842	Remote Similarity	NPC81802
0.6842	Remote Similarity	NPC269886
0.6842	Remote Similarity	NPC472210
0.6842	Remote Similarity	NPC472295
0.6842	Remote Similarity	NPC88315
0.6839	Remote Similarity	NPC475914
0.6839	Remote Similarity	NPC474318
0.6839	Remote Similarity	NPC153123
0.6839	Remote Similarity	NPC74413
0.6839	Remote Similarity	NPC19696
0.6839	Remote Similarity	NPC136957
0.6839	Remote Similarity	NPC268744
0.6839	Remote Similarity	NPC201266
0.6839	Remote Similarity	NPC220797
0.6839	Remote Similarity	NPC474767
0.6836	Remote Similarity	NPC271797
0.6836	Remote Similarity	NPC21174
0.6828	Remote Similarity	NPC99939
0.6828	Remote Similarity	NPC308931
0.6823	Remote Similarity	NPC262898
0.6818	Remote Similarity	NPC469578
0.6818	Remote Similarity	NPC266249
0.6814	Remote Similarity	NPC269270
0.6809	Remote Similarity	NPC255909
0.6809	Remote Similarity	NPC209917
0.6806	Remote Similarity	NPC195239
0.6806	Remote Similarity	NPC157828
0.6804	Remote Similarity	NPC166209
0.6804	Remote Similarity	NPC269203
0.6804	Remote Similarity	NPC77241
0.6804	Remote Similarity	NPC252338
0.6804	Remote Similarity	NPC13456
0.6802	Remote Similarity	NPC472065
0.6791	Remote Similarity	NPC62749
0.6789	Remote Similarity	NPC472292
0.6788	Remote Similarity	NPC96102
0.6786	Remote Similarity	NPC101130
0.6786	Remote Similarity	NPC129412
0.6786	Remote Similarity	NPC114033
0.6786	Remote Similarity	NPC58268
0.678	Remote Similarity	NPC14686
0.6778	Remote Similarity	NPC471943
0.6774	Remote Similarity	NPC228835
0.6771	Remote Similarity	NPC128244
0.6771	Remote Similarity	NPC472293
0.6771	Remote Similarity	NPC11445
0.6766	Remote Similarity	NPC110126
0.6765	Remote Similarity	NPC314372
0.6765	Remote Similarity	NPC159856
0.6763	Remote Similarity	NPC229893
0.676	Remote Similarity	NPC474696
0.6758	Remote Similarity	NPC139763
0.6753	Remote Similarity	NPC284338
0.675	Remote Similarity	NPC469562
0.675	Remote Similarity	NPC123839
0.675	Remote Similarity	NPC220594
0.6747	Remote Similarity	NPC84911
0.674	Remote Similarity	NPC54214

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 NPC274981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	683
0.2-0.3	1209
0.3-0.4	2570
0.4-0.5	2679
0.5-0.6	1426
0.6-0.7	300
0.7-0.8	14
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
0.7458	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2214	Approved
0.7456	Intermediate Similarity	NPD2213	Approved
0.7238	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1270	Approved
0.7127	Intermediate Similarity	NPD3178	Discontinued
0.7112	Intermediate Similarity	NPD460	Discontinued
0.7102	Intermediate Similarity	NPD1343	Approved
0.7079	Intermediate Similarity	NPD4524	Discontinued
0.7072	Intermediate Similarity	NPD2481	Approved
0.7072	Intermediate Similarity	NPD2479	Phase 3
0.7065	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4922	Phase 2
0.703	Intermediate Similarity	NPD1996	Discontinued
0.6978	Remote Similarity	NPD5473	Discontinued
0.6947	Remote Similarity	NPD4848	Phase 1
0.6944	Remote Similarity	NPD482	Approved
0.6915	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1722	Approved
0.6872	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD201	Phase 2
0.6848	Remote Similarity	NPD200	Phase 2
0.6848	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4988	Discontinued
0.6832	Remote Similarity	NPD3393	Approved
0.6832	Remote Similarity	NPD3394	Approved
0.6832	Remote Similarity	NPD3389	Approved
0.6818	Remote Similarity	NPD2510	Approved
0.6818	Remote Similarity	NPD2509	Approved
0.6806	Remote Similarity	NPD7618	Phase 3
0.6806	Remote Similarity	NPD7619	Phase 3
0.6788	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2753	Discontinued
0.6774	Remote Similarity	NPD2096	Phase 2
0.6774	Remote Similarity	NPD2091	Phase 2
0.6751	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3238	Discontinued
0.672	Remote Similarity	NPD2094	Phase 2
0.672	Remote Similarity	NPD2092	Phase 2
0.672	Remote Similarity	NPD2095	Phase 2
0.6718	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD2008	Discontinued
0.6708	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD991	Phase 2
0.6684	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7564	Discontinued
0.6684	Remote Similarity	NPD2290	Phase 3
0.6684	Remote Similarity	NPD2289	Phase 3
0.6683	Remote Similarity	NPD1506	Discontinued
0.6667	Remote Similarity	NPD786	Approved
0.6667	Remote Similarity	NPD1630	Approved
0.6667	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6664	Approved
0.6629	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD272	Approved
0.6617	Remote Similarity	NPD1600	Suspended
0.6615	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD750	Phase 2
0.6611	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2411	Approved
0.6593	Remote Similarity	NPD1573	Approved
0.6593	Remote Similarity	NPD1575	Approved
0.6585	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4051	Discontinued
0.6576	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD2443	Approved
0.6567	Remote Similarity	NPD2442	Approved
0.6556	Remote Similarity	NPD1631	Approved
0.6556	Remote Similarity	NPD3583	Phase 2
0.6552	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3320	Approved
0.6543	Remote Similarity	NPD3318	Approved
0.6543	Remote Similarity	NPD3319	Phase 1
0.6541	Remote Similarity	NPD4075	Phase 2
0.6536	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD2408	Discontinued
0.6534	Remote Similarity	NPD2837	Discontinued
0.6531	Remote Similarity	NPD1982	Phase 1
0.6529	Remote Similarity	NPD9599	Approved
0.6513	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5901	Discontinued
0.65	Remote Similarity	NPD4299	Phase 1
0.65	Remote Similarity	NPD3947	Discontinued
0.6497	Remote Similarity	NPD2061	Approved
0.6489	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5888	Phase 2
0.6477	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6152	Phase 1
0.6467	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD3100	Discontinued
0.6456	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD1096	Discontinued
0.6418	Remote Similarity	NPD5426	Phase 3
0.6409	Remote Similarity	NPD5400	Approved
0.6407	Remote Similarity	NPD9100	Approved
0.6404	Remote Similarity	NPD6459	Phase 2
0.6398	Remote Similarity	NPD5065	Approved
0.6398	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4883	Approved
0.6393	Remote Similarity	NPD6446	Discontinued
0.6386	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3476	Approved
0.6386	Remote Similarity	NPD3475	Approved
0.6384	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5853	Phase 3
0.6378	Remote Similarity	NPD5855	Phase 3
0.6374	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD2070	Approved
0.6374	Remote Similarity	NPD2068	Approved
0.6374	Remote Similarity	NPD2069	Approved
0.6374	Remote Similarity	NPD2071	Approved
0.6373	Remote Similarity	NPD6068	Discontinued
0.6368	Remote Similarity	NPD4304	Discovery
0.6364	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD2640	Approved
0.6359	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD2641	Approved
0.6358	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.635	Remote Similarity	NPD5017	Discontinued
0.6349	Remote Similarity	NPD1643	Phase 3
0.6349	Remote Similarity	NPD3927	Phase 2
0.6349	Remote Similarity	NPD1618	Phase 2
0.6341	Remote Similarity	NPD9583	Approved
0.6335	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD268	Approved
0.6335	Remote Similarity	NPD271	Approved
0.6333	Remote Similarity	NPD5198	Approved
0.6333	Remote Similarity	NPD5199	Approved
0.6332	Remote Similarity	NPD2405	Phase 3
0.6332	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD6787	Phase 2
0.6328	Remote Similarity	NPD2172	Phase 1
0.6321	Remote Similarity	NPD2770	Discontinued
0.6321	Remote Similarity	NPD3961	Discontinued
0.6321	Remote Similarity	NPD3246	Discontinued
0.6319	Remote Similarity	NPD6771	Discontinued
0.6319	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2896	Discontinued
0.6313	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.631	Remote Similarity	NPD1586	Approved
0.6308	Remote Similarity	NPD2336	Approved
0.6308	Remote Similarity	NPD1658	Discontinued
0.6303	Remote Similarity	NPD2119	Approved
0.6303	Remote Similarity	NPD2118	Approved
0.63	Remote Similarity	NPD484	Approved
0.629	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD9392	Approved
0.6289	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD9396	Approved
0.6286	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD3323	Discontinued
0.6284	Remote Similarity	NPD1545	Discontinued
0.628	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7454	Approved
0.628	Remote Similarity	NPD7455	Approved
0.6277	Remote Similarity	NPD6044	Discontinued
0.6275	Remote Similarity	NPD3905	Phase 3
0.6275	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD1183	Approved
0.6269	Remote Similarity	NPD7026	Phase 2
0.6264	Remote Similarity	NPD1404	Approved
0.6264	Remote Similarity	NPD1403	Approved
0.6256	Remote Similarity	NPD4499	Approved
0.6256	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6376	Discontinued
0.6243	Remote Similarity	NPD107	Approved
0.6243	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD2881	Approved
0.6238	Remote Similarity	NPD2879	Approved
0.6237	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD3915	Approved
0.6232	Remote Similarity	NPD5475	Discontinued
0.6229	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6242	Discontinued
0.6223	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.622	Remote Similarity	NPD9357	Approved
0.6214	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD3077	Approved
0.6211	Remote Similarity	NPD1587	Approved
0.6211	Remote Similarity	NPD3078	Approved
0.6211	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD3079	Approved
0.6211	Remote Similarity	NPD3076	Approved
0.6205	Remote Similarity	NPD7175	Phase 1

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