NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	428.86
Volume:	268.775
LogP:	3.747
LogD:	3.028
LogS:	-4.508
# Rotatable Bonds:	5
TPSA:	30.49
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.72
Synthetic Accessibility Score:	2.783
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.66
MDCK Permeability:	1.3390747881203424e-05
Pgp-inhibitor:	0.15
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.716
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	96.4115982055664%
Volume Distribution (VD):	2.342
Pgp-substrate:	4.298118591308594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.928
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.178
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.795
CYP2D6-inhibitor:	0.235
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.355
CYP3A4-substrate:	0.708

ADMET: Excretion

Clearance (CL):	3.631
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.344
Human Hepatotoxicity (H-HT):	0.416
Drug-inuced Liver Injury (DILI):	0.107
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.539
Skin Sensitization:	0.797
Carcinogencity:	0.036
Eye Corrosion:	0.01
Eye Irritation:	0.019
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC79076

Natural Product ID:	NPC79076
*Common Name:**	Convolutamine H
IUPAC Name:	N-methyl-2-(2,3,4-tribromo-5,6-dimethoxyphenyl)ethanamine
Synonyms:	Convolutamine H
Standard InCHIKey:	TXBNYKFQXDKTHG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14Br3NO2/c1-15-5-4-6-7(12)8(13)9(14)11(17-3)10(6)16-2/h15H,4-5H2,1-3H3
SMILES:	CNCCc1c(c(c(c(c1OC)OC)Br)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446593
PubChem CID:	11812063
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004113] Methoxybenzenes [CHEMONTID:0004111] Dimethoxybenzenes

*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
NPO5804	Amathia convoluta	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088445]
NPO32745	amathia tortusa	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21705225]
NPO5804	Amathia convoluta	Species	Vesiculariidae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6229	Organism	Heteropogon contortus	Heteropogon contortus	LD99	=	0.2	ug ml-1	PMID[546270]
NPT4924	Organism	Haemonchus contortus	Haemonchus contortus	LD99	=	0.2	ug ml-1	PMID[546271]

☑ 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 NPC79076 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	350
0.1-0.2	4768
0.2-0.3	14244
0.3-0.4	9338
0.4-0.5	11582
0.5-0.6	2178
0.6-0.7	224
0.7-0.8	9
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8551	High Similarity	NPC135173
0.8252	Intermediate Similarity	NPC235633
0.7703	Intermediate Similarity	NPC470248
0.76	Intermediate Similarity	NPC470250
0.7467	Intermediate Similarity	NPC470249
0.7338	Intermediate Similarity	NPC470247
0.7292	Intermediate Similarity	NPC298486
0.7103	Intermediate Similarity	NPC211992
0.6993	Remote Similarity	NPC120075
0.6959	Remote Similarity	NPC272463
0.6954	Remote Similarity	NPC262641
0.6928	Remote Similarity	NPC160692
0.6923	Remote Similarity	NPC128877
0.6913	Remote Similarity	NPC110131
0.6867	Remote Similarity	NPC134219
0.6839	Remote Similarity	NPC470471
0.681	Remote Similarity	NPC226514
0.6792	Remote Similarity	NPC308571
0.6752	Remote Similarity	NPC470470
0.6752	Remote Similarity	NPC253429
0.6744	Remote Similarity	NPC191557
0.6687	Remote Similarity	NPC113862
0.6667	Remote Similarity	NPC140359
0.6667	Remote Similarity	NPC13020
0.6647	Remote Similarity	NPC135103
0.6646	Remote Similarity	NPC474673
0.6646	Remote Similarity	NPC76412
0.6645	Remote Similarity	NPC158078
0.6623	Remote Similarity	NPC105513
0.6623	Remote Similarity	NPC85049
0.6621	Remote Similarity	NPC50782
0.6604	Remote Similarity	NPC168680
0.6603	Remote Similarity	NPC303011
0.6581	Remote Similarity	NPC226493
0.6581	Remote Similarity	NPC160081
0.6566	Remote Similarity	NPC47672
0.6566	Remote Similarity	NPC469711
0.6564	Remote Similarity	NPC109346
0.6562	Remote Similarity	NPC470709
0.6556	Remote Similarity	NPC84606
0.6556	Remote Similarity	NPC129885
0.6548	Remote Similarity	NPC233926
0.6548	Remote Similarity	NPC156311
0.6543	Remote Similarity	NPC470472
0.6543	Remote Similarity	NPC78530
0.6525	Remote Similarity	NPC186469
0.6522	Remote Similarity	NPC64066
0.6522	Remote Similarity	NPC323204
0.6516	Remote Similarity	NPC160193
0.6503	Remote Similarity	NPC294249
0.6494	Remote Similarity	NPC291847
0.6494	Remote Similarity	NPC172403
0.649	Remote Similarity	NPC219444
0.6467	Remote Similarity	NPC227976
0.6463	Remote Similarity	NPC264379
0.6458	Remote Similarity	NPC21890
0.6438	Remote Similarity	NPC115803
0.6421	Remote Similarity	NPC156055
0.6405	Remote Similarity	NPC137117
0.6398	Remote Similarity	NPC271942
0.6391	Remote Similarity	NPC114124
0.6389	Remote Similarity	NPC475396
0.6376	Remote Similarity	NPC71186
0.6369	Remote Similarity	NPC326599
0.6369	Remote Similarity	NPC476570
0.6369	Remote Similarity	NPC152947
0.6369	Remote Similarity	NPC329595
0.6358	Remote Similarity	NPC160932
0.6353	Remote Similarity	NPC2295
0.6353	Remote Similarity	NPC477564
0.6341	Remote Similarity	NPC135349
0.6337	Remote Similarity	NPC474535
0.6327	Remote Similarity	NPC221301
0.6323	Remote Similarity	NPC43706
0.6313	Remote Similarity	NPC226001
0.6312	Remote Similarity	NPC245386
0.631	Remote Similarity	NPC207824
0.631	Remote Similarity	NPC473608
0.631	Remote Similarity	NPC60538
0.6306	Remote Similarity	NPC105702
0.6301	Remote Similarity	NPC475697
0.6299	Remote Similarity	NPC236265
0.6296	Remote Similarity	NPC40321
0.6292	Remote Similarity	NPC288747
0.6284	Remote Similarity	NPC162294
0.6282	Remote Similarity	NPC474147
0.6282	Remote Similarity	NPC13004
0.6282	Remote Similarity	NPC473708
0.628	Remote Similarity	NPC89341
0.6279	Remote Similarity	NPC203784
0.6279	Remote Similarity	NPC126519
0.6279	Remote Similarity	NPC170503
0.6278	Remote Similarity	NPC298981
0.6278	Remote Similarity	NPC207819
0.6278	Remote Similarity	NPC473462
0.6278	Remote Similarity	NPC110454
0.6278	Remote Similarity	NPC126128
0.6273	Remote Similarity	NPC301050
0.6273	Remote Similarity	NPC131204
0.6273	Remote Similarity	NPC7018
0.6267	Remote Similarity	NPC85276
0.6258	Remote Similarity	NPC220311
0.6242	Remote Similarity	NPC150929
0.6235	Remote Similarity	NPC76213
0.6235	Remote Similarity	NPC277669
0.6234	Remote Similarity	NPC217277
0.6228	Remote Similarity	NPC71629
0.6228	Remote Similarity	NPC296085
0.6222	Remote Similarity	NPC469979
0.6218	Remote Similarity	NPC301713
0.6216	Remote Similarity	NPC80337
0.6216	Remote Similarity	NPC473892
0.6216	Remote Similarity	NPC475658
0.6213	Remote Similarity	NPC258222
0.6211	Remote Similarity	NPC11147
0.618	Remote Similarity	NPC477255
0.6178	Remote Similarity	NPC153990
0.6175	Remote Similarity	NPC74618
0.6175	Remote Similarity	NPC301941
0.6175	Remote Similarity	NPC214188
0.6173	Remote Similarity	NPC42793
0.6173	Remote Similarity	NPC167944
0.6173	Remote Similarity	NPC231884
0.6169	Remote Similarity	NPC47790
0.6169	Remote Similarity	NPC229213
0.6167	Remote Similarity	NPC225130
0.6159	Remote Similarity	NPC314682
0.6154	Remote Similarity	NPC475120
0.6154	Remote Similarity	NPC42383
0.6154	Remote Similarity	NPC142776
0.615	Remote Similarity	NPC230539
0.6149	Remote Similarity	NPC244890
0.6149	Remote Similarity	NPC59387
0.6145	Remote Similarity	NPC261940
0.6145	Remote Similarity	NPC184632
0.6139	Remote Similarity	NPC55113
0.6138	Remote Similarity	NPC97811
0.6135	Remote Similarity	NPC213471
0.6129	Remote Similarity	NPC471591
0.6129	Remote Similarity	NPC473572
0.6129	Remote Similarity	NPC474169
0.6129	Remote Similarity	NPC249113
0.6127	Remote Similarity	NPC80129
0.6127	Remote Similarity	NPC187022
0.6125	Remote Similarity	NPC93882
0.6125	Remote Similarity	NPC130595
0.6125	Remote Similarity	NPC118419
0.6121	Remote Similarity	NPC474915
0.6121	Remote Similarity	NPC188163
0.6121	Remote Similarity	NPC328750
0.6121	Remote Similarity	NPC213206
0.6121	Remote Similarity	NPC474128
0.6115	Remote Similarity	NPC475361
0.6104	Remote Similarity	NPC173511
0.6104	Remote Similarity	NPC88733
0.6102	Remote Similarity	NPC124433
0.6102	Remote Similarity	NPC293871
0.6099	Remote Similarity	NPC475615
0.6098	Remote Similarity	NPC210086
0.6096	Remote Similarity	NPC473409
0.6096	Remote Similarity	NPC141405
0.6096	Remote Similarity	NPC82741
0.6095	Remote Similarity	NPC51957
0.6095	Remote Similarity	NPC106295
0.6095	Remote Similarity	NPC476144
0.6095	Remote Similarity	NPC210437
0.6095	Remote Similarity	NPC476151
0.6095	Remote Similarity	NPC16107
0.6092	Remote Similarity	NPC160931
0.6092	Remote Similarity	NPC37205
0.6092	Remote Similarity	NPC190931
0.6087	Remote Similarity	NPC285078
0.6087	Remote Similarity	NPC313737
0.6087	Remote Similarity	NPC6854
0.6085	Remote Similarity	NPC102245
0.6084	Remote Similarity	NPC474851
0.6084	Remote Similarity	NPC474850
0.6084	Remote Similarity	NPC292792
0.6082	Remote Similarity	NPC13397
0.608	Remote Similarity	NPC38980
0.6075	Remote Similarity	NPC259071
0.6075	Remote Similarity	NPC77435
0.6071	Remote Similarity	NPC145304
0.6067	Remote Similarity	NPC39103
0.6067	Remote Similarity	NPC2770
0.6066	Remote Similarity	NPC290534
0.6065	Remote Similarity	NPC116562
0.6061	Remote Similarity	NPC59661
0.6059	Remote Similarity	NPC7467
0.6059	Remote Similarity	NPC59907
0.6059	Remote Similarity	NPC37144
0.6051	Remote Similarity	NPC141739
0.6051	Remote Similarity	NPC136112
0.6049	Remote Similarity	NPC163560
0.6049	Remote Similarity	NPC218530
0.6048	Remote Similarity	NPC476567
0.6048	Remote Similarity	NPC136860
0.6048	Remote Similarity	NPC128019
0.6043	Remote Similarity	NPC144823
0.6043	Remote Similarity	NPC174607

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 NPC79076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	1192
0.2-0.3	2284
0.3-0.4	3182
0.4-0.5	1664
0.5-0.6	557
0.6-0.7	48
0.7-0.8	0
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
0.6863	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4010	Discontinued
0.6744	Remote Similarity	NPD6688	Approved
0.6744	Remote Similarity	NPD6687	Approved
0.6667	Remote Similarity	NPD595	Approved
0.6667	Remote Similarity	NPD593	Approved
0.6624	Remote Similarity	NPD2653	Approved
0.6489	Remote Similarity	NPD8095	Phase 1
0.6485	Remote Similarity	NPD1424	Approved
0.6481	Remote Similarity	NPD3060	Approved
0.6481	Remote Similarity	NPD4162	Approved
0.6452	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD1009	Approved
0.6369	Remote Similarity	NPD5718	Phase 2
0.6347	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.631	Remote Similarity	NPD6031	Approved
0.631	Remote Similarity	NPD6030	Approved
0.6298	Remote Similarity	NPD1298	Discontinued
0.6287	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD2245	Discovery
0.6226	Remote Similarity	NPD3530	Approved
0.6226	Remote Similarity	NPD3532	Approved
0.6226	Remote Similarity	NPD3531	Approved
0.6225	Remote Similarity	NPD3049	Approved
0.622	Remote Similarity	NPD7153	Discontinued
0.6213	Remote Similarity	NPD5976	Discontinued
0.6184	Remote Similarity	NPD2554	Approved
0.6184	Remote Similarity	NPD2556	Approved
0.6176	Remote Similarity	NPD3687	Approved
0.6176	Remote Similarity	NPD3686	Approved
0.6173	Remote Similarity	NPD6895	Approved
0.6173	Remote Similarity	NPD6896	Approved
0.6154	Remote Similarity	NPD2184	Approved
0.6154	Remote Similarity	NPD2183	Approved
0.6139	Remote Similarity	NPD596	Approved
0.6139	Remote Similarity	NPD600	Approved
0.6127	Remote Similarity	NPD7298	Approved
0.6125	Remote Similarity	NPD2674	Phase 3
0.6121	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4584	Approved
0.6092	Remote Similarity	NPD4585	Approved
0.6084	Remote Similarity	NPD5177	Phase 3
0.6084	Remote Similarity	NPD9244	Approved
0.6062	Remote Similarity	NPD1336	Approved
0.6051	Remote Similarity	NPD1794	Approved
0.6036	Remote Similarity	NPD1774	Approved
0.6025	Remote Similarity	NPD840	Approved
0.6025	Remote Similarity	NPD839	Approved
0.6013	Remote Similarity	NPD9621	Approved
0.6013	Remote Similarity	NPD9620	Approved
0.6013	Remote Similarity	NPD9619	Approved
0.6012	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2978	Approved
0.6	Remote Similarity	NPD9718	Approved
0.6	Remote Similarity	NPD2977	Approved
0.5987	Remote Similarity	NPD9615	Approved
0.5987	Remote Similarity	NPD9613	Approved
0.5987	Remote Similarity	NPD9616	Approved
0.5987	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD2922	Phase 1
0.5963	Remote Similarity	NPD3144	Approved
0.5963	Remote Similarity	NPD3145	Approved
0.5952	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD1341	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD3055	Approved
0.5949	Remote Similarity	NPD3053	Approved
0.5948	Remote Similarity	NPD316	Approved
0.5943	Remote Similarity	NPD5720	Discontinued
0.5939	Remote Similarity	NPD2155	Approved
0.5939	Remote Similarity	NPD2154	Approved
0.5939	Remote Similarity	NPD2156	Approved
0.5922	Remote Similarity	NPD1411	Approved
0.5917	Remote Similarity	NPD5241	Discontinued
0.5915	Remote Similarity	NPD2986	Phase 2
0.5915	Remote Similarity	NPD2989	Phase 2
0.5912	Remote Similarity	NPD7905	Discontinued
0.5907	Remote Similarity	NPD2804	Phase 1
0.5904	Remote Similarity	NPD2161	Phase 2
0.5886	Remote Similarity	NPD5310	Approved
0.5886	Remote Similarity	NPD5311	Approved
0.5882	Remote Similarity	NPD3337	Discontinued
0.5882	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7124	Phase 2
0.5879	Remote Similarity	NPD6111	Discontinued
0.5872	Remote Similarity	NPD1351	Approved
0.5872	Remote Similarity	NPD1349	Approved
0.5872	Remote Similarity	NPD1350	Approved
0.5867	Remote Similarity	NPD9379	Approved
0.5867	Remote Similarity	NPD9377	Approved
0.5864	Remote Similarity	NPD598	Approved
0.5864	Remote Similarity	NPD601	Approved
0.5864	Remote Similarity	NPD597	Approved
0.586	Remote Similarity	NPD2230	Approved
0.586	Remote Similarity	NPD2233	Approved
0.586	Remote Similarity	NPD2232	Approved
0.5849	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD1818	Approved
0.5849	Remote Similarity	NPD1820	Approved
0.5849	Remote Similarity	NPD1819	Approved
0.5849	Remote Similarity	NPD1817	Approved
0.5844	Remote Similarity	NPD2486	Discontinued
0.5838	Remote Similarity	NPD3639	Approved
0.5838	Remote Similarity	NPD3640	Phase 3
0.5838	Remote Similarity	NPD3641	Approved
0.5828	Remote Similarity	NPD1136	Approved
0.5828	Remote Similarity	NPD1130	Approved
0.5828	Remote Similarity	NPD3163	Approved
0.5828	Remote Similarity	NPD1132	Approved
0.5828	Remote Similarity	NPD3162	Approved
0.5824	Remote Similarity	NPD2677	Approved
0.5823	Remote Similarity	NPD2429	Approved
0.5823	Remote Similarity	NPD1420	Approved
0.5823	Remote Similarity	NPD2428	Approved
0.5823	Remote Similarity	NPD1421	Approved
0.5813	Remote Similarity	NPD558	Phase 2
0.5801	Remote Similarity	NPD6107	Approved
0.58	Remote Similarity	NPD228	Approved
0.5793	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD2563	Approved
0.5787	Remote Similarity	NPD2560	Approved
0.578	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.578	Remote Similarity	NPD52	Approved
0.578	Remote Similarity	NPD7526	Approved
0.5774	Remote Similarity	NPD1375	Discontinued
0.5771	Remote Similarity	NPD4017	Approved
0.5769	Remote Similarity	NPD2667	Approved
0.5769	Remote Similarity	NPD4166	Phase 2
0.5769	Remote Similarity	NPD2668	Approved
0.5767	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD5722	Discontinued
0.5759	Remote Similarity	NPD2235	Phase 2
0.5759	Remote Similarity	NPD2231	Phase 2
0.5754	Remote Similarity	NPD6788	Approved
0.5754	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD4083	Discontinued
0.5732	Remote Similarity	NPD3294	Phase 2
0.573	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD5283	Phase 1
0.5724	Remote Similarity	NPD592	Approved
0.5724	Remote Similarity	NPD594	Approved
0.5723	Remote Similarity	NPD3157	Approved
0.5723	Remote Similarity	NPD3158	Phase 1
0.5714	Remote Similarity	NPD3156	Discontinued
0.5714	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4210	Discontinued
0.5706	Remote Similarity	NPD3167	Approved
0.5706	Remote Similarity	NPD4772	Phase 2
0.5706	Remote Similarity	NPD4773	Phase 2
0.5706	Remote Similarity	NPD3164	Approved
0.5706	Remote Similarity	NPD3165	Approved
0.5706	Remote Similarity	NPD4236	Phase 3
0.5706	Remote Similarity	NPD1024	Discontinued
0.5706	Remote Similarity	NPD3166	Approved
0.5706	Remote Similarity	NPD4237	Approved
0.5706	Remote Similarity	NPD5061	Approved
0.5706	Remote Similarity	NPD5062	Approved
0.5698	Remote Similarity	NPD3122	Phase 3
0.5697	Remote Similarity	NPD2238	Phase 2
0.5697	Remote Similarity	NPD3061	Approved
0.5697	Remote Similarity	NPD3059	Approved
0.5697	Remote Similarity	NPD3062	Approved
0.569	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.5677	Remote Similarity	NPD1103	Approved
0.5677	Remote Similarity	NPD1102	Approved
0.5673	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD6331	Phase 2
0.5671	Remote Similarity	NPD1039	Discontinued
0.5671	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD9381	Approved
0.5669	Remote Similarity	NPD9384	Approved
0.5657	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.565	Remote Similarity	NPD6875	Approved
0.565	Remote Similarity	NPD4179	Approved
0.565	Remote Similarity	NPD6876	Approved
0.565	Remote Similarity	NPD4180	Approved
0.5647	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.564	Remote Similarity	NPD3692	Discontinued
0.564	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.564	Remote Similarity	NPD5160	Discontinued
0.5638	Remote Similarity	NPD6297	Approved
0.5636	Remote Similarity	NPD4475	Approved
0.5636	Remote Similarity	NPD4474	Approved
0.5636	Remote Similarity	NPD1423	Approved
0.5629	Remote Similarity	NPD817	Approved
0.5629	Remote Similarity	NPD3052	Approved
0.5629	Remote Similarity	NPD823	Approved
0.5629	Remote Similarity	NPD5314	Approved
0.5629	Remote Similarity	NPD3054	Approved
0.5629	Remote Similarity	NPD2492	Phase 1
0.5625	Remote Similarity	NPD1669	Approved
0.5625	Remote Similarity	NPD9622	Approved
0.5621	Remote Similarity	NPD3175	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