NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	265.07
Volume:	267.342
LogP:	3.478
LogD:	3.102
LogS:	-6.002
# Rotatable Bonds:	1
TPSA:	61.55
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	2.224
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.838
MDCK Permeability:	2.2892993001732975e-05
Pgp-inhibitor:	0.033
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.821

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.674
Plasma Protein Binding (PPB):	96.66796875%
Volume Distribution (VD):	0.88
Pgp-substrate:	2.0509698390960693%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.222
CYP2C19-inhibitor:	0.827
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.536
CYP2C9-substrate:	0.84
CYP2D6-inhibitor:	0.946
CYP2D6-substrate:	0.666
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.084

ADMET: Excretion

Clearance (CL):	13.872
Half-life (T1/2):	0.111

ADMET: Toxicity

hERG Blockers:	0.351
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.713
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.265
Skin Sensitization:	0.709
Carcinogencity:	0.938
Eye Corrosion:	0.004
Eye Irritation:	0.427
Respiratory Toxicity:	0.666

Download Data

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

Natural Product: NPC16436

Natural Product ID:	NPC16436
*Common Name:**	Aristolamide Ii
IUPAC Name:	naphtho[2,1-g][1,3]benzodioxole-5-carboxamide
Synonyms:	Aristolamide Ii
Standard InCHIKey:	MOCSPCCAGNSGTH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H11NO3/c17-16(18)12-7-13-15(20-8-19-13)14-10-4-2-1-3-9(10)5-6-11(12)14/h1-7H,8H2,(H2,17,18)
SMILES:	OC(=N)c1cc2OCOc2c2c1ccc1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1684819
PubChem CID:	51346765
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[12880323]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20097074]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21353775]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[534764]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.11	ug.mL-1	PMID[534764]

☑ 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 NPC16436 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	384
0.1-0.2	1940
0.2-0.3	6188
0.3-0.4	12329
0.4-0.5	4883
0.5-0.6	7793
0.6-0.7	7625
0.7-0.8	1523
0.8-0.85	30
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC77359
0.8429	Intermediate Similarity	NPC100129
0.8414	Intermediate Similarity	NPC254610
0.8312	Intermediate Similarity	NPC474442
0.8289	Intermediate Similarity	NPC211296
0.8264	Intermediate Similarity	NPC228843
0.8231	Intermediate Similarity	NPC266006
0.8176	Intermediate Similarity	NPC105847
0.8176	Intermediate Similarity	NPC218131
0.8176	Intermediate Similarity	NPC77572
0.8176	Intermediate Similarity	NPC243759
0.816	Intermediate Similarity	NPC474051
0.8158	Intermediate Similarity	NPC33832
0.8146	Intermediate Similarity	NPC145304
0.8138	Intermediate Similarity	NPC97316
0.8138	Intermediate Similarity	NPC227002
0.8133	Intermediate Similarity	NPC191231
0.8121	Intermediate Similarity	NPC12668
0.8121	Intermediate Similarity	NPC308768
0.8108	Intermediate Similarity	NPC266453
0.8108	Intermediate Similarity	NPC200935
0.8108	Intermediate Similarity	NPC230919
0.8108	Intermediate Similarity	NPC196420
0.8108	Intermediate Similarity	NPC151656
0.8101	Intermediate Similarity	NPC109765
0.8095	Intermediate Similarity	NPC69213
0.8058	Intermediate Similarity	NPC183262
0.8054	Intermediate Similarity	NPC243996
0.8054	Intermediate Similarity	NPC220344
0.8054	Intermediate Similarity	NPC275061
0.8054	Intermediate Similarity	NPC132804
0.805	Intermediate Similarity	NPC202495
0.8028	Intermediate Similarity	NPC17348
0.8013	Intermediate Similarity	NPC175838
0.8	Intermediate Similarity	NPC296742
0.8	Intermediate Similarity	NPC112676
0.7987	Intermediate Similarity	NPC116019
0.7987	Intermediate Similarity	NPC242715
0.7987	Intermediate Similarity	NPC22902
0.7987	Intermediate Similarity	NPC56329
0.7945	Intermediate Similarity	NPC149337
0.7945	Intermediate Similarity	NPC471983
0.7941	Intermediate Similarity	NPC224293
0.7933	Intermediate Similarity	NPC53722
0.7933	Intermediate Similarity	NPC201404
0.7933	Intermediate Similarity	NPC290714
0.7919	Intermediate Similarity	NPC30632
0.7919	Intermediate Similarity	NPC143139
0.7919	Intermediate Similarity	NPC205442
0.7919	Intermediate Similarity	NPC202846
0.7917	Intermediate Similarity	NPC21563
0.7917	Intermediate Similarity	NPC177167
0.7905	Intermediate Similarity	NPC160697
0.7905	Intermediate Similarity	NPC471942
0.7898	Intermediate Similarity	NPC18614
0.7895	Intermediate Similarity	NPC230538
0.7895	Intermediate Similarity	NPC103637
0.7895	Intermediate Similarity	NPC41782
0.7895	Intermediate Similarity	NPC133934
0.7895	Intermediate Similarity	NPC183709
0.7895	Intermediate Similarity	NPC229172
0.7895	Intermediate Similarity	NPC36531
0.7895	Intermediate Similarity	NPC184684
0.7895	Intermediate Similarity	NPC184641
0.7891	Intermediate Similarity	NPC303144
0.7891	Intermediate Similarity	NPC259742
0.7891	Intermediate Similarity	NPC147616
0.7891	Intermediate Similarity	NPC219671
0.7891	Intermediate Similarity	NPC471505
0.7891	Intermediate Similarity	NPC104077
0.7887	Intermediate Similarity	NPC249788
0.7881	Intermediate Similarity	NPC165026
0.7881	Intermediate Similarity	NPC73505
0.7881	Intermediate Similarity	NPC34431
0.7881	Intermediate Similarity	NPC295719
0.7877	Intermediate Similarity	NPC184814
0.7862	Intermediate Similarity	NPC38017
0.7862	Intermediate Similarity	NPC23012
0.7862	Intermediate Similarity	NPC215300
0.7857	Intermediate Similarity	NPC476301
0.7857	Intermediate Similarity	NPC43508
0.7853	Intermediate Similarity	NPC22130
0.7853	Intermediate Similarity	NPC116838
0.7853	Intermediate Similarity	NPC198796
0.7852	Intermediate Similarity	NPC108198
0.7852	Intermediate Similarity	NPC200557
0.7852	Intermediate Similarity	NPC111655
0.7852	Intermediate Similarity	NPC241241
0.7852	Intermediate Similarity	NPC10314
0.7852	Intermediate Similarity	NPC158142
0.7852	Intermediate Similarity	NPC69029
0.7852	Intermediate Similarity	NPC294884
0.7848	Intermediate Similarity	NPC118332
0.7843	Intermediate Similarity	NPC324962
0.7843	Intermediate Similarity	NPC265154
0.7838	Intermediate Similarity	NPC58585
0.7834	Intermediate Similarity	NPC24425
0.7834	Intermediate Similarity	NPC52475
0.7815	Intermediate Similarity	NPC79622
0.7815	Intermediate Similarity	NPC212942
0.7815	Intermediate Similarity	NPC29868
0.7815	Intermediate Similarity	NPC292487
0.78	Intermediate Similarity	NPC197166
0.7793	Intermediate Similarity	NPC53781
0.7792	Intermediate Similarity	NPC121661
0.7792	Intermediate Similarity	NPC217635
0.7792	Intermediate Similarity	NPC172171
0.7792	Intermediate Similarity	NPC471667
0.7792	Intermediate Similarity	NPC79429
0.7792	Intermediate Similarity	NPC239254
0.7792	Intermediate Similarity	NPC73467
0.7785	Intermediate Similarity	NPC185680
0.7785	Intermediate Similarity	NPC170779
0.7785	Intermediate Similarity	NPC256776
0.7785	Intermediate Similarity	NPC125649
0.7785	Intermediate Similarity	NPC145722
0.7785	Intermediate Similarity	NPC90083
0.7785	Intermediate Similarity	NPC311256
0.7784	Intermediate Similarity	NPC477558
0.7778	Intermediate Similarity	NPC253878
0.7778	Intermediate Similarity	NPC302506
0.777	Intermediate Similarity	NPC189482
0.777	Intermediate Similarity	NPC106739
0.7763	Intermediate Similarity	NPC284464
0.7756	Intermediate Similarity	NPC31325
0.7756	Intermediate Similarity	NPC224674
0.7756	Intermediate Similarity	NPC275284
0.7756	Intermediate Similarity	NPC213074
0.7756	Intermediate Similarity	NPC114505
0.7756	Intermediate Similarity	NPC15956
0.7756	Intermediate Similarity	NPC193473
0.7755	Intermediate Similarity	NPC63574
0.7755	Intermediate Similarity	NPC143483
0.7748	Intermediate Similarity	NPC25111
0.7748	Intermediate Similarity	NPC73535
0.7748	Intermediate Similarity	NPC6262
0.7748	Intermediate Similarity	NPC272157
0.7748	Intermediate Similarity	NPC201145
0.7748	Intermediate Similarity	NPC90615
0.7742	Intermediate Similarity	NPC475868
0.7742	Intermediate Similarity	NPC110763
0.7742	Intermediate Similarity	NPC166506
0.7742	Intermediate Similarity	NPC286245
0.7742	Intermediate Similarity	NPC180953
0.7742	Intermediate Similarity	NPC189239
0.7742	Intermediate Similarity	NPC272619
0.7742	Intermediate Similarity	NPC197352
0.774	Intermediate Similarity	NPC147247
0.774	Intermediate Similarity	NPC472968
0.774	Intermediate Similarity	NPC246974
0.7738	Intermediate Similarity	NPC265383
0.7736	Intermediate Similarity	NPC21902
0.7733	Intermediate Similarity	NPC313081
0.7733	Intermediate Similarity	NPC18576
0.7733	Intermediate Similarity	NPC474139
0.7733	Intermediate Similarity	NPC142547
0.7733	Intermediate Similarity	NPC135777
0.773	Intermediate Similarity	NPC103916
0.7724	Intermediate Similarity	NPC213711
0.7724	Intermediate Similarity	NPC40352
0.7724	Intermediate Similarity	NPC274356
0.7718	Intermediate Similarity	NPC112237
0.7718	Intermediate Similarity	NPC26394
0.7718	Intermediate Similarity	NPC471390
0.7718	Intermediate Similarity	NPC196937
0.7718	Intermediate Similarity	NPC471391
0.7714	Intermediate Similarity	NPC29472
0.7712	Intermediate Similarity	NPC471414
0.7697	Intermediate Similarity	NPC6369
0.7697	Intermediate Similarity	NPC30951
0.7697	Intermediate Similarity	NPC9068
0.7697	Intermediate Similarity	NPC184613
0.7692	Intermediate Similarity	NPC30462
0.7692	Intermediate Similarity	NPC252286
0.7692	Intermediate Similarity	NPC126291
0.7692	Intermediate Similarity	NPC260118
0.7692	Intermediate Similarity	NPC154971
0.7682	Intermediate Similarity	NPC114155
0.7682	Intermediate Similarity	NPC32189
0.7682	Intermediate Similarity	NPC300846
0.7682	Intermediate Similarity	NPC68292
0.7682	Intermediate Similarity	NPC476639
0.7677	Intermediate Similarity	NPC164183
0.7677	Intermediate Similarity	NPC253015
0.7677	Intermediate Similarity	NPC179521
0.7677	Intermediate Similarity	NPC471065
0.7677	Intermediate Similarity	NPC327623
0.7671	Intermediate Similarity	NPC471986
0.7671	Intermediate Similarity	NPC157740
0.7671	Intermediate Similarity	NPC191302
0.7671	Intermediate Similarity	NPC99798
0.7667	Intermediate Similarity	NPC49603
0.7667	Intermediate Similarity	NPC141023
0.7667	Intermediate Similarity	NPC47181
0.7667	Intermediate Similarity	NPC187616
0.7667	Intermediate Similarity	NPC193026
0.7667	Intermediate Similarity	NPC103967
0.7662	Intermediate Similarity	NPC470917
0.7662	Intermediate Similarity	NPC186033
0.7662	Intermediate Similarity	NPC60249

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 NPC16436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	936
0.2-0.3	1275
0.3-0.4	2858
0.4-0.5	2058
0.5-0.6	1179
0.6-0.7	533
0.7-0.8	37
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
0.8151	Intermediate Similarity	NPD4097	Suspended
0.7756	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1558	Phase 1
0.7622	Intermediate Similarity	NPD3705	Approved
0.7613	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6674	Discontinued
0.7578	Intermediate Similarity	NPD37	Approved
0.7439	Intermediate Similarity	NPD4966	Approved
0.7439	Intermediate Similarity	NPD4967	Phase 2
0.7439	Intermediate Similarity	NPD4965	Approved
0.7405	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5111	Phase 2
0.74	Intermediate Similarity	NPD5110	Phase 2
0.74	Intermediate Similarity	NPD5109	Approved
0.7394	Intermediate Similarity	NPD5604	Discontinued
0.7349	Intermediate Similarity	NPD6234	Discontinued
0.7338	Intermediate Similarity	NPD4108	Discontinued
0.7273	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD709	Approved
0.7244	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6232	Discontinued
0.7219	Intermediate Similarity	NPD4625	Phase 3
0.7215	Intermediate Similarity	NPD6331	Phase 2
0.719	Intermediate Similarity	NPD3620	Phase 2
0.719	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4005	Discontinued
0.7172	Intermediate Similarity	NPD1357	Approved
0.7162	Intermediate Similarity	NPD1669	Approved
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4626	Approved
0.7114	Intermediate Similarity	NPD2922	Phase 1
0.7113	Intermediate Similarity	NPD5283	Phase 1
0.7108	Intermediate Similarity	NPD2977	Approved
0.7108	Intermediate Similarity	NPD5929	Approved
0.7108	Intermediate Similarity	NPD2978	Approved
0.7105	Intermediate Similarity	NPD3027	Phase 3
0.7099	Intermediate Similarity	NPD4319	Phase 2
0.7093	Intermediate Similarity	NPD7473	Discontinued
0.7086	Intermediate Similarity	NPD2861	Phase 2
0.7086	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1613	Approved
0.7078	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7228	Approved
0.705	Intermediate Similarity	NPD2342	Discontinued
0.7047	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4123	Phase 3
0.7025	Intermediate Similarity	NPD1375	Discontinued
0.7019	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5844	Phase 1
0.7007	Intermediate Similarity	NPD2286	Discontinued
0.7	Intermediate Similarity	NPD6696	Suspended
0.7	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1283	Approved
0.6987	Remote Similarity	NPD2157	Approved
0.6982	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2808	Discontinued
0.6981	Remote Similarity	NPD7037	Approved
0.6972	Remote Similarity	NPD228	Approved
0.6968	Remote Similarity	NPD4060	Phase 1
0.6948	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7020	Approved
0.6933	Remote Similarity	NPD7019	Approved
0.6933	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3657	Discovery
0.6919	Remote Similarity	NPD3051	Approved
0.6906	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5125	Phase 3
0.6892	Remote Similarity	NPD5126	Approved
0.6879	Remote Similarity	NPD2969	Approved
0.6879	Remote Similarity	NPD2970	Approved
0.6872	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4357	Discontinued
0.6867	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2677	Approved
0.6852	Remote Similarity	NPD5241	Discontinued
0.6848	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2122	Discontinued
0.6842	Remote Similarity	NPD5709	Phase 3
0.6839	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3060	Approved
0.6826	Remote Similarity	NPD4675	Approved
0.6826	Remote Similarity	NPD4678	Approved
0.6826	Remote Similarity	NPD7028	Phase 2
0.6824	Remote Similarity	NPD5691	Approved
0.6824	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1651	Approved
0.6818	Remote Similarity	NPD4908	Phase 1
0.6807	Remote Similarity	NPD2883	Discontinued
0.6805	Remote Similarity	NPD8455	Phase 2
0.6802	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6746	Phase 2
0.6802	Remote Similarity	NPD4666	Phase 3
0.68	Remote Similarity	NPD1281	Approved
0.68	Remote Similarity	NPD1610	Phase 2
0.68	Remote Similarity	NPD1611	Approved
0.6798	Remote Similarity	NPD7240	Approved
0.6797	Remote Similarity	NPD4624	Approved
0.6797	Remote Similarity	NPD6584	Phase 3
0.6795	Remote Similarity	NPD2674	Phase 3
0.6791	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7003	Approved
0.6784	Remote Similarity	NPD4055	Discovery
0.6772	Remote Similarity	NPD6823	Phase 2
0.6772	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2563	Approved
0.6765	Remote Similarity	NPD2560	Approved
0.6761	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1840	Phase 2
0.6755	Remote Similarity	NPD2232	Approved
0.6755	Remote Similarity	NPD2233	Approved
0.6755	Remote Similarity	NPD2230	Approved
0.6753	Remote Similarity	NPD1712	Approved
0.6753	Remote Similarity	NPD3018	Phase 2
0.675	Remote Similarity	NPD2161	Phase 2
0.6748	Remote Similarity	NPD2219	Phase 1
0.6747	Remote Similarity	NPD5976	Discontinued
0.6743	Remote Similarity	NPD27	Approved
0.6743	Remote Similarity	NPD2489	Approved
0.6742	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7007	Discovery
0.6728	Remote Similarity	NPD4237	Approved
0.6728	Remote Similarity	NPD5177	Phase 3
0.6728	Remote Similarity	NPD4236	Phase 3
0.6725	Remote Similarity	NPD7773	Phase 2
0.6722	Remote Similarity	NPD4578	Approved
0.6722	Remote Similarity	NPD4577	Approved
0.6709	Remote Similarity	NPD5735	Approved
0.6707	Remote Similarity	NPD5058	Phase 3
0.6706	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6559	Discontinued
0.669	Remote Similarity	NPD7635	Approved
0.6689	Remote Similarity	NPD1091	Approved
0.6688	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4110	Phase 3
0.6687	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7833	Phase 2
0.6686	Remote Similarity	NPD6072	Discontinued
0.6686	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7831	Phase 2
0.6667	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD6387	Discontinued
0.6649	Remote Similarity	NPD8151	Discontinued
0.6648	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3382	Approved
0.6647	Remote Similarity	NPD5722	Discontinued
0.6647	Remote Similarity	NPD3383	Approved
0.6647	Remote Similarity	NPD3384	Approved
0.6646	Remote Similarity	NPD2979	Phase 3
0.6646	Remote Similarity	NPD4140	Approved
0.6646	Remote Similarity	NPD2238	Phase 2
0.6644	Remote Similarity	NPD1548	Phase 1
0.663	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6071	Discontinued
0.6627	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD3145	Approved
0.6624	Remote Similarity	NPD3144	Approved
0.6622	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4663	Approved
0.6608	Remote Similarity	NPD5772	Approved
0.6608	Remote Similarity	NPD5773	Approved
0.6607	Remote Similarity	NPD1653	Approved
0.6605	Remote Similarity	NPD5763	Approved
0.6605	Remote Similarity	NPD5762	Approved
0.6605	Remote Similarity	NPD7266	Discontinued
0.6601	Remote Similarity	NPD2982	Phase 2
0.6601	Remote Similarity	NPD2983	Phase 2
0.6601	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4749	Approved
0.6601	Remote Similarity	NPD6583	Phase 3
0.6601	Remote Similarity	NPD6582	Phase 2
0.6601	Remote Similarity	NPD5327	Phase 3
0.6587	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD52	Approved
0.6587	Remote Similarity	NPD7526	Approved
0.6584	Remote Similarity	NPD2155	Approved
0.6584	Remote Similarity	NPD2154	Approved
0.6584	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2156	Approved
0.6582	Remote Similarity	NPD7477	Discontinued
0.6576	Remote Similarity	NPD7906	Approved
0.6571	Remote Similarity	NPD8127	Discontinued
0.6568	Remote Similarity	NPD3226	Approved
0.6566	Remote Similarity	NPD6087	Phase 1
0.6564	Remote Similarity	NPD7153	Discontinued
0.6564	Remote Similarity	NPD1372	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