NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.09
Volume:	216.831
LogP:	1.095
LogD:	1.27
LogS:	-3.935
# Rotatable Bonds:	0
TPSA:	42.31
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	3.271
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.786
MDCK Permeability:	2.1836083760717884e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.877
Plasma Protein Binding (PPB):	72.58111572265625%
Volume Distribution (VD):	1.313
Pgp-substrate:	24.274320602416992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.936
CYP1A2-substrate:	0.884
CYP2C19-inhibitor:	0.374
CYP2C19-substrate:	0.613
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.617
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.618
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	6.624
Half-life (T1/2):	0.357

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.781
Drug-inuced Liver Injury (DILI):	0.465
AMES Toxicity:	0.96
Rat Oral Acute Toxicity:	0.371
Maximum Recommended Daily Dose:	0.709
Skin Sensitization:	0.673
Carcinogencity:	0.968
Eye Corrosion:	0.004
Eye Irritation:	0.058
Respiratory Toxicity:	0.35

Download Data

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

Natural Product: NPC217021

Natural Product ID:	NPC217021
*Common Name:**	Damirone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NWBAIJSXHACZNH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H12N2O2/c1-13-4-3-7-6-14(2)11-10(7)8(13)5-9(15)12(11)16/h5-6H,3-4H2,1-2H3
SMILES:	CN1CCc2cn(C)c3c2C1=CC(=O)C3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559637
PubChem CID:	2946
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
NPO33311	spongosorite	Genus	Halichondriidae	Eukaryota	n.a.	southern australian	n.a.	PMID[19226152]
NPO33239	Higginsia	Genus	Stelligeridae	Eukaryota	n.a.	southern australian	n.a.	PMID[19226152]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[573724]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[573724]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[573724]

☑ 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 NPC217021 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	392
0.1-0.2	3586
0.2-0.3	16928
0.3-0.4	15273
0.4-0.5	3114
0.5-0.6	2191
0.6-0.7	1025
0.7-0.8	162
0.8-0.85	17
0.85-0.9	4
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470679
0.9514	High Similarity	NPC473878
0.9459	High Similarity	NPC470680
0.9459	High Similarity	NPC100104
0.9262	High Similarity	NPC474492
0.898	High Similarity	NPC100726
0.871	High Similarity	NPC274981
0.8667	High Similarity	NPC102664
0.8543	High Similarity	NPC123906
0.8497	Intermediate Similarity	NPC251391
0.8487	Intermediate Similarity	NPC471655
0.8366	Intermediate Similarity	NPC313889
0.8312	Intermediate Similarity	NPC70406
0.8165	Intermediate Similarity	NPC80681
0.8133	Intermediate Similarity	NPC182940
0.8117	Intermediate Similarity	NPC105811
0.8105	Intermediate Similarity	NPC467188
0.8098	Intermediate Similarity	NPC262338
0.8086	Intermediate Similarity	NPC70949
0.8046	Intermediate Similarity	NPC292361
0.8024	Intermediate Similarity	NPC73994
0.8012	Intermediate Similarity	NPC265100
0.8012	Intermediate Similarity	NPC83774
0.7917	Intermediate Similarity	NPC61011
0.7904	Intermediate Similarity	NPC157583
0.787	Intermediate Similarity	NPC191415
0.7862	Intermediate Similarity	NPC209362
0.7861	Intermediate Similarity	NPC268966
0.7848	Intermediate Similarity	NPC472260
0.7811	Intermediate Similarity	NPC79777
0.7811	Intermediate Similarity	NPC234403
0.7805	Intermediate Similarity	NPC114637
0.7784	Intermediate Similarity	NPC469529
0.7778	Intermediate Similarity	NPC46895
0.7763	Intermediate Similarity	NPC65408
0.775	Intermediate Similarity	NPC229055
0.773	Intermediate Similarity	NPC242116
0.7706	Intermediate Similarity	NPC477042
0.7702	Intermediate Similarity	NPC74357
0.7697	Intermediate Similarity	NPC167710
0.7692	Intermediate Similarity	NPC237188
0.7688	Intermediate Similarity	NPC469359
0.768	Intermediate Similarity	NPC106757
0.7674	Intermediate Similarity	NPC477003
0.7654	Intermediate Similarity	NPC213914
0.7596	Intermediate Similarity	NPC88115
0.7588	Intermediate Similarity	NPC284775
0.7557	Intermediate Similarity	NPC475874
0.7543	Intermediate Similarity	NPC474259
0.7543	Intermediate Similarity	NPC477415
0.7543	Intermediate Similarity	NPC23476
0.7532	Intermediate Similarity	NPC472288
0.753	Intermediate Similarity	NPC233380
0.7514	Intermediate Similarity	NPC81535
0.7514	Intermediate Similarity	NPC102755
0.75	Intermediate Similarity	NPC473628
0.75	Intermediate Similarity	NPC255909
0.7472	Intermediate Similarity	NPC216550
0.743	Intermediate Similarity	NPC326422
0.7425	Intermediate Similarity	NPC115232
0.7418	Intermediate Similarity	NPC474767
0.7417	Intermediate Similarity	NPC71236
0.7416	Intermediate Similarity	NPC476460
0.7403	Intermediate Similarity	NPC473814
0.7403	Intermediate Similarity	NPC78767
0.7401	Intermediate Similarity	NPC103119
0.7389	Intermediate Similarity	NPC93390
0.7381	Intermediate Similarity	NPC56233
0.7368	Intermediate Similarity	NPC139763
0.736	Intermediate Similarity	NPC469489
0.7348	Intermediate Similarity	NPC128244
0.7333	Intermediate Similarity	NPC304203
0.7333	Intermediate Similarity	NPC225622
0.7333	Intermediate Similarity	NPC221726
0.7333	Intermediate Similarity	NPC477414
0.733	Intermediate Similarity	NPC311282
0.7321	Intermediate Similarity	NPC42372
0.729	Intermediate Similarity	NPC291517
0.7288	Intermediate Similarity	NPC118084
0.7278	Intermediate Similarity	NPC41717
0.7268	Intermediate Similarity	NPC476143
0.7267	Intermediate Similarity	NPC293216
0.7258	Intermediate Similarity	NPC317701
0.7256	Intermediate Similarity	NPC281094
0.7237	Intermediate Similarity	NPC313823
0.7232	Intermediate Similarity	NPC133003
0.723	Intermediate Similarity	NPC265605
0.723	Intermediate Similarity	NPC48564
0.723	Intermediate Similarity	NPC182570
0.7228	Intermediate Similarity	NPC237414
0.7225	Intermediate Similarity	NPC151635
0.7216	Intermediate Similarity	NPC159125
0.7189	Intermediate Similarity	NPC121327
0.7166	Intermediate Similarity	NPC476252
0.716	Intermediate Similarity	NPC478184
0.7158	Intermediate Similarity	NPC472116
0.7143	Intermediate Similarity	NPC248462
0.7143	Intermediate Similarity	NPC473821
0.7135	Intermediate Similarity	NPC477004
0.7135	Intermediate Similarity	NPC123395
0.7128	Intermediate Similarity	NPC472259
0.7124	Intermediate Similarity	NPC471589
0.712	Intermediate Similarity	NPC74153
0.7112	Intermediate Similarity	NPC57398
0.7112	Intermediate Similarity	NPC143977
0.711	Intermediate Similarity	NPC477976
0.711	Intermediate Similarity	NPC252572
0.7083	Intermediate Similarity	NPC293487
0.7081	Intermediate Similarity	NPC477041
0.7081	Intermediate Similarity	NPC34837
0.7081	Intermediate Similarity	NPC477044
0.7079	Intermediate Similarity	NPC467063
0.7072	Intermediate Similarity	NPC324091
0.7069	Intermediate Similarity	NPC186068
0.7062	Intermediate Similarity	NPC470677
0.7059	Intermediate Similarity	NPC478182
0.7053	Intermediate Similarity	NPC475410
0.7053	Intermediate Similarity	NPC469577
0.7052	Intermediate Similarity	NPC249614
0.7039	Intermediate Similarity	NPC295158
0.7039	Intermediate Similarity	NPC282103
0.7037	Intermediate Similarity	NPC469563
0.7027	Intermediate Similarity	NPC106824
0.7021	Intermediate Similarity	NPC328318
0.7021	Intermediate Similarity	NPC328596
0.7018	Intermediate Similarity	NPC71132
0.7011	Intermediate Similarity	NPC135950
0.7007	Intermediate Similarity	NPC476566
0.7	Intermediate Similarity	NPC214106
0.7	Intermediate Similarity	NPC472065
0.6995	Remote Similarity	NPC47190
0.6989	Remote Similarity	NPC474916
0.6989	Remote Similarity	NPC84827
0.6989	Remote Similarity	NPC14113
0.6989	Remote Similarity	NPC145885
0.6983	Remote Similarity	NPC207851
0.6979	Remote Similarity	NPC61038
0.6978	Remote Similarity	NPC154339
0.6973	Remote Similarity	NPC102592
0.6973	Remote Similarity	NPC79356
0.6961	Remote Similarity	NPC473946
0.6959	Remote Similarity	NPC21174
0.6959	Remote Similarity	NPC271797
0.6959	Remote Similarity	NPC477413
0.6959	Remote Similarity	NPC110182
0.6957	Remote Similarity	NPC267343
0.6957	Remote Similarity	NPC269886
0.6957	Remote Similarity	NPC472295
0.6957	Remote Similarity	NPC472210
0.6957	Remote Similarity	NPC81802
0.6957	Remote Similarity	NPC247735
0.6954	Remote Similarity	NPC302647
0.6952	Remote Similarity	NPC284338
0.6952	Remote Similarity	NPC477045
0.6952	Remote Similarity	NPC103361
0.6949	Remote Similarity	NPC11126
0.6947	Remote Similarity	NPC327592
0.6933	Remote Similarity	NPC159630
0.6933	Remote Similarity	NPC230085
0.6927	Remote Similarity	NPC116555
0.6927	Remote Similarity	NPC469578
0.6911	Remote Similarity	NPC317373
0.6902	Remote Similarity	NPC472292
0.6901	Remote Similarity	NPC194881
0.6901	Remote Similarity	NPC478185
0.6897	Remote Similarity	NPC91895
0.6897	Remote Similarity	NPC32534
0.6895	Remote Similarity	NPC138562
0.6893	Remote Similarity	NPC64436
0.6884	Remote Similarity	NPC14686
0.6882	Remote Similarity	NPC472293
0.6879	Remote Similarity	NPC256893
0.6879	Remote Similarity	NPC478183
0.6875	Remote Similarity	NPC150259
0.6863	Remote Similarity	NPC27740
0.6859	Remote Similarity	NPC477043
0.6857	Remote Similarity	NPC273532
0.6856	Remote Similarity	NPC220594
0.6856	Remote Similarity	NPC469562
0.6855	Remote Similarity	NPC23215
0.6854	Remote Similarity	NPC126709
0.6854	Remote Similarity	NPC55772
0.6854	Remote Similarity	NPC248041
0.6854	Remote Similarity	NPC12649
0.6851	Remote Similarity	NPC474258
0.6848	Remote Similarity	NPC117244
0.6848	Remote Similarity	NPC138370
0.6848	Remote Similarity	NPC473763
0.6848	Remote Similarity	NPC114974
0.6846	Remote Similarity	NPC240136
0.6846	Remote Similarity	NPC297486
0.6846	Remote Similarity	NPC471402
0.6845	Remote Similarity	NPC227582
0.6845	Remote Similarity	NPC312860
0.6842	Remote Similarity	NPC329825
0.6842	Remote Similarity	NPC472062
0.6842	Remote Similarity	NPC472063
0.6842	Remote Similarity	NPC472069
0.6839	Remote Similarity	NPC143075
0.6839	Remote Similarity	NPC266249

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 NPC217021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	601
0.2-0.3	1033
0.3-0.4	2148
0.4-0.5	2712
0.5-0.6	1849
0.6-0.7	528
0.7-0.8	55
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
0.8095	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1270	Approved
0.7939	Intermediate Similarity	NPD4524	Discontinued
0.7866	Intermediate Similarity	NPD1343	Approved
0.7763	Intermediate Similarity	NPD201	Phase 2
0.7763	Intermediate Similarity	NPD200	Phase 2
0.7706	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4988	Discontinued
0.7607	Intermediate Similarity	NPD1630	Approved
0.753	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD272	Approved
0.7485	Intermediate Similarity	NPD2753	Discontinued
0.747	Intermediate Similarity	NPD1631	Approved
0.7436	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3238	Discontinued
0.7396	Intermediate Similarity	NPD1573	Approved
0.7396	Intermediate Similarity	NPD1575	Approved
0.7394	Intermediate Similarity	NPD2213	Approved
0.7394	Intermediate Similarity	NPD2214	Approved
0.7391	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4848	Phase 1
0.7273	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3476	Approved
0.7255	Intermediate Similarity	NPD3475	Approved
0.7246	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD460	Discontinued
0.723	Intermediate Similarity	NPD268	Approved
0.723	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD271	Approved
0.7216	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1643	Phase 3
0.72	Intermediate Similarity	NPD2481	Approved
0.72	Intermediate Similarity	NPD2479	Phase 3
0.7181	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2118	Approved
0.7171	Intermediate Similarity	NPD2119	Approved
0.7168	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1586	Approved
0.7135	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD1658	Discontinued
0.711	Intermediate Similarity	NPD750	Phase 2
0.7101	Intermediate Similarity	NPD5400	Approved
0.7098	Intermediate Similarity	NPD6787	Phase 2
0.7097	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3178	Discontinued
0.7053	Intermediate Similarity	NPD3905	Phase 3
0.7045	Intermediate Similarity	NPD1587	Approved
0.7043	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD2336	Approved
0.7026	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2879	Approved
0.7021	Intermediate Similarity	NPD2881	Approved
0.7006	Intermediate Similarity	NPD4030	Approved
0.7006	Intermediate Similarity	NPD4029	Approved
0.7006	Intermediate Similarity	NPD5473	Discontinued
0.7006	Intermediate Similarity	NPD4028	Approved
0.7	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4922	Phase 2
0.6983	Remote Similarity	NPD7564	Discontinued
0.6977	Remote Similarity	NPD6446	Discontinued
0.6973	Remote Similarity	NPD2290	Phase 3
0.6973	Remote Similarity	NPD2289	Phase 3
0.6968	Remote Similarity	NPD5017	Discontinued
0.6963	Remote Similarity	NPD3840	Phase 2
0.6963	Remote Similarity	NPD3839	Phase 2
0.6961	Remote Similarity	NPD2770	Discontinued
0.6948	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD991	Phase 2
0.6947	Remote Similarity	NPD3947	Discontinued
0.6947	Remote Similarity	NPD6987	Phase 1
0.6937	Remote Similarity	NPD2896	Discontinued
0.6935	Remote Similarity	NPD1952	Discontinued
0.6933	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5020	Approved
0.6909	Remote Similarity	NPD4547	Phase 3
0.6906	Remote Similarity	NPD5809	Phase 3
0.6902	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3942	Approved
0.6899	Remote Similarity	NPD3944	Approved
0.6893	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1600	Suspended
0.6883	Remote Similarity	NPD9583	Approved
0.6882	Remote Similarity	NPD2307	Discontinued
0.6882	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6999	Discontinued
0.686	Remote Similarity	NPD5088	Discontinued
0.6859	Remote Similarity	NPD4299	Phase 1
0.6853	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9599	Approved
0.6848	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2511	Approved
0.6839	Remote Similarity	NPD2509	Approved
0.6839	Remote Similarity	NPD2510	Approved
0.6837	Remote Similarity	NPD5888	Phase 2
0.6836	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7619	Phase 3
0.6828	Remote Similarity	NPD7618	Phase 3
0.6823	Remote Similarity	NPD2008	Discontinued
0.6821	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6152	Phase 1
0.6811	Remote Similarity	NPD3430	Approved
0.6811	Remote Similarity	NPD3431	Approved
0.6809	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1004	Phase 2
0.6807	Remote Similarity	NPD1005	Phase 2
0.6806	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1031	Discontinued
0.6792	Remote Similarity	NPD3385	Approved
0.6791	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.678	Remote Similarity	NPD482	Approved
0.6771	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4051	Discontinued
0.6768	Remote Similarity	NPD3394	Approved
0.6768	Remote Similarity	NPD3393	Approved
0.6768	Remote Similarity	NPD3389	Approved
0.6763	Remote Similarity	NPD3583	Phase 2
0.6761	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD9357	Approved
0.6748	Remote Similarity	NPD107	Approved
0.6742	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.673	Remote Similarity	NPD9100	Approved
0.6725	Remote Similarity	NPD4326	Phase 2
0.6722	Remote Similarity	NPD3927	Phase 2
0.672	Remote Similarity	NPD5505	Discontinued
0.6718	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD715	Phase 3
0.6708	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4703	Approved
0.6707	Remote Similarity	NPD1722	Approved
0.6707	Remote Similarity	NPD4702	Approved
0.6706	Remote Similarity	NPD2061	Approved
0.6705	Remote Similarity	NPD6771	Discontinued
0.6703	Remote Similarity	NPD721	Approved
0.6701	Remote Similarity	NPD1506	Discontinued
0.6701	Remote Similarity	NPD2411	Approved
0.6687	Remote Similarity	NPD2071	Approved
0.6687	Remote Similarity	NPD2074	Approved
0.6687	Remote Similarity	NPD2070	Approved
0.6687	Remote Similarity	NPD2073	Approved
0.6687	Remote Similarity	NPD2069	Approved
0.6687	Remote Similarity	NPD2068	Approved
0.6687	Remote Similarity	NPD2075	Approved
0.6687	Remote Similarity	NPD2072	Approved
0.6686	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2443	Approved
0.6667	Remote Similarity	NPD2006	Phase 2
0.6667	Remote Similarity	NPD6664	Approved
0.6667	Remote Similarity	NPD7666	Phase 3
0.6667	Remote Similarity	NPD7665	Phase 2
0.6667	Remote Similarity	NPD2430	Phase 2
0.6667	Remote Similarity	NPD1545	Discontinued
0.6667	Remote Similarity	NPD2442	Approved
0.665	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5016	Approved
0.6649	Remote Similarity	NPD7568	Phase 1
0.6647	Remote Similarity	NPD7469	Discontinued
0.6647	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3654	Approved
0.6634	Remote Similarity	NPD1996	Discontinued
0.663	Remote Similarity	NPD3315	Phase 3
0.6629	Remote Similarity	NPD2915	Discontinued
0.6627	Remote Similarity	NPD6017	Discontinued
0.6618	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD6954	Phase 2
0.6615	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD2096	Phase 2
0.6612	Remote Similarity	NPD2091	Phase 2
0.6612	Remote Similarity	NPD1096	Discontinued
0.6608	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2809	Approved
0.6607	Remote Similarity	NPD9271	Approved
0.6605	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2405	Phase 3
0.6596	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD3246	Discontinued
0.6592	Remote Similarity	NPD4883	Approved
0.6591	Remote Similarity	NPD5636	Discontinued
0.6587	Remote Similarity	NPD9074	Approved
0.6587	Remote Similarity	NPD9075	Approved
0.6585	Remote Similarity	NPD4804	Approved
0.6585	Remote Similarity	NPD786	Approved
0.658	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD8304	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