NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.16
Volume:	291.884
LogP:	2.421
LogD:	2.373
LogS:	-0.75
# Rotatable Bonds:	3
TPSA:	36.36
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.925
Synthetic Accessibility Score:	2.469
Fsp3:	0.353
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.759
MDCK Permeability:	2.378936369495932e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	79.0542221069336%
Volume Distribution (VD):	2.016
Pgp-substrate:	23.848716735839844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.537
CYP1A2-substrate:	0.909
CYP2C19-inhibitor:	0.814
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.592
CYP2D6-inhibitor:	0.955
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.674

ADMET: Excretion

Clearance (CL):	20.653
Half-life (T1/2):	0.836

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.551
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.839
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.898
Carcinogencity:	0.159
Eye Corrosion:	0.041
Eye Irritation:	0.175
Respiratory Toxicity:	0.849

Download Data

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

Natural Product: NPC124542

Natural Product ID:	NPC124542
*Common Name:**	(2S)-N-Hydroxybenzylanabasine
IUPAC Name:	2-[[(2S)-2-pyridin-3-ylpiperidin-1-yl]methyl]phenol
Synonyms:
Standard InCHIKey:	QKGCWXDVBXIISA-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C17H20N2O/c20-17-9-2-1-6-15(17)13-19-11-4-3-8-16(19)14-7-5-10-18-12-14/h1-2,5-7,9-10,12,16,20H,3-4,8,11,13H2/t16-/m0/s1
SMILES:	Oc1ccccc1CN1CCCC[C@H]1c1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386319
PubChem CID:	29955678
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000195] Piperidines [CHEMONTID:0003087] Benzylpiperidines [CHEMONTID:0002622] N-benzylpiperidines

*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
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23734721]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15986	Alangium chinense	Species	Cornaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	6700.0	nM	PMID[508200]

☑ 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 NPC124542 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	462
0.1-0.2	4189
0.2-0.3	12635
0.3-0.4	8953
0.4-0.5	10908
0.5-0.6	3900
0.6-0.7	1431
0.7-0.8	210
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471177
1.0	High Similarity	NPC59779
0.9735	High Similarity	NPC471178
0.8679	High Similarity	NPC97367
0.8447	Intermediate Similarity	NPC473057
0.8148	Intermediate Similarity	NPC84508
0.8121	Intermediate Similarity	NPC108469
0.8098	Intermediate Similarity	NPC25899
0.8049	Intermediate Similarity	NPC48192
0.8047	Intermediate Similarity	NPC203754
0.8047	Intermediate Similarity	NPC150048
0.8024	Intermediate Similarity	NPC314940
0.8024	Intermediate Similarity	NPC473764
0.7921	Intermediate Similarity	NPC329541
0.7867	Intermediate Similarity	NPC471311
0.7867	Intermediate Similarity	NPC471313
0.7798	Intermediate Similarity	NPC98187
0.7778	Intermediate Similarity	NPC324611
0.7765	Intermediate Similarity	NPC324149
0.7748	Intermediate Similarity	NPC212125
0.7733	Intermediate Similarity	NPC151489
0.7719	Intermediate Similarity	NPC471294
0.7688	Intermediate Similarity	NPC475070
0.7688	Intermediate Similarity	NPC329708
0.7688	Intermediate Similarity	NPC47059
0.7688	Intermediate Similarity	NPC264166
0.7688	Intermediate Similarity	NPC274291
0.7688	Intermediate Similarity	NPC165349
0.7688	Intermediate Similarity	NPC118832
0.7684	Intermediate Similarity	NPC171171
0.7673	Intermediate Similarity	NPC60553
0.7662	Intermediate Similarity	NPC256893
0.7661	Intermediate Similarity	NPC252590
0.7644	Intermediate Similarity	NPC232340
0.7634	Intermediate Similarity	NPC200836
0.7632	Intermediate Similarity	NPC306397
0.7624	Intermediate Similarity	NPC289786
0.7619	Intermediate Similarity	NPC177404
0.7614	Intermediate Similarity	NPC133306
0.7614	Intermediate Similarity	NPC220765
0.76	Intermediate Similarity	NPC271792
0.7598	Intermediate Similarity	NPC472289
0.7592	Intermediate Similarity	NPC202605
0.7592	Intermediate Similarity	NPC112206
0.7571	Intermediate Similarity	NPC204717
0.7569	Intermediate Similarity	NPC99666
0.7566	Intermediate Similarity	NPC477111
0.7553	Intermediate Similarity	NPC477113
0.7548	Intermediate Similarity	NPC174421
0.7542	Intermediate Similarity	NPC46580
0.7541	Intermediate Similarity	NPC242209
0.7528	Intermediate Similarity	NPC314002
0.7516	Intermediate Similarity	NPC165370
0.7515	Intermediate Similarity	NPC47298
0.7515	Intermediate Similarity	NPC315214
0.7514	Intermediate Similarity	NPC259545
0.7486	Intermediate Similarity	NPC96890
0.7486	Intermediate Similarity	NPC184964
0.7485	Intermediate Similarity	NPC161292
0.7471	Intermediate Similarity	NPC32028
0.7471	Intermediate Similarity	NPC159319
0.7469	Intermediate Similarity	NPC471323
0.7468	Intermediate Similarity	NPC29702
0.7459	Intermediate Similarity	NPC3715
0.7456	Intermediate Similarity	NPC131718
0.7447	Intermediate Similarity	NPC53144
0.7438	Intermediate Similarity	NPC280853
0.7434	Intermediate Similarity	NPC476322
0.743	Intermediate Similarity	NPC295158
0.7421	Intermediate Similarity	NPC471312
0.7407	Intermediate Similarity	NPC16452
0.7407	Intermediate Similarity	NPC36229
0.7407	Intermediate Similarity	NPC470500
0.7407	Intermediate Similarity	NPC476581
0.7405	Intermediate Similarity	NPC224928
0.7405	Intermediate Similarity	NPC77555
0.7394	Intermediate Similarity	NPC211813
0.7391	Intermediate Similarity	NPC285016
0.7391	Intermediate Similarity	NPC245657
0.7386	Intermediate Similarity	NPC146373
0.7386	Intermediate Similarity	NPC245244
0.7386	Intermediate Similarity	NPC166424
0.738	Intermediate Similarity	NPC249040
0.7378	Intermediate Similarity	NPC220523
0.7375	Intermediate Similarity	NPC471596
0.7372	Intermediate Similarity	NPC69914
0.7366	Intermediate Similarity	NPC192315
0.7365	Intermediate Similarity	NPC26872
0.736	Intermediate Similarity	NPC266551
0.736	Intermediate Similarity	NPC161887
0.736	Intermediate Similarity	NPC219963
0.7356	Intermediate Similarity	NPC121658
0.7356	Intermediate Similarity	NPC14651
0.7351	Intermediate Similarity	NPC473053
0.7347	Intermediate Similarity	NPC476041
0.7347	Intermediate Similarity	NPC304926
0.7341	Intermediate Similarity	NPC44161
0.7337	Intermediate Similarity	NPC106937
0.7337	Intermediate Similarity	NPC26850
0.7337	Intermediate Similarity	NPC129721
0.7333	Intermediate Similarity	NPC237740
0.7326	Intermediate Similarity	NPC476167
0.7321	Intermediate Similarity	NPC63562
0.7315	Intermediate Similarity	NPC240136
0.7315	Intermediate Similarity	NPC297486
0.7315	Intermediate Similarity	NPC471402
0.7313	Intermediate Similarity	NPC214980
0.7312	Intermediate Similarity	NPC90229
0.7312	Intermediate Similarity	NPC473814
0.7312	Intermediate Similarity	NPC78767
0.7308	Intermediate Similarity	NPC476131
0.7306	Intermediate Similarity	NPC5145
0.7305	Intermediate Similarity	NPC153769
0.7299	Intermediate Similarity	NPC164664
0.7299	Intermediate Similarity	NPC476518
0.7299	Intermediate Similarity	NPC126481
0.7297	Intermediate Similarity	NPC93390
0.7296	Intermediate Similarity	NPC477110
0.7284	Intermediate Similarity	NPC318935
0.7283	Intermediate Similarity	NPC56170
0.7283	Intermediate Similarity	NPC195268
0.7283	Intermediate Similarity	NPC133140
0.7267	Intermediate Similarity	NPC102423
0.7267	Intermediate Similarity	NPC91958
0.7263	Intermediate Similarity	NPC470474
0.7256	Intermediate Similarity	NPC471598
0.7255	Intermediate Similarity	NPC290094
0.7251	Intermediate Similarity	NPC322976
0.7251	Intermediate Similarity	NPC63338
0.7251	Intermediate Similarity	NPC324203
0.7249	Intermediate Similarity	NPC31930
0.7247	Intermediate Similarity	NPC164340
0.7237	Intermediate Similarity	NPC48564
0.7237	Intermediate Similarity	NPC265605
0.7237	Intermediate Similarity	NPC182570
0.7235	Intermediate Similarity	NPC132680
0.7235	Intermediate Similarity	NPC269919
0.7234	Intermediate Similarity	NPC287437
0.7234	Intermediate Similarity	NPC476578
0.7234	Intermediate Similarity	NPC476582
0.7234	Intermediate Similarity	NPC4071
0.7219	Intermediate Similarity	NPC156704
0.7219	Intermediate Similarity	NPC74153
0.7216	Intermediate Similarity	NPC111624
0.7216	Intermediate Similarity	NPC474409
0.7216	Intermediate Similarity	NPC85273
0.7213	Intermediate Similarity	NPC32771
0.7204	Intermediate Similarity	NPC146724
0.7202	Intermediate Similarity	NPC18348
0.7195	Intermediate Similarity	NPC470404
0.7195	Intermediate Similarity	NPC470394
0.7195	Intermediate Similarity	NPC470403
0.7191	Intermediate Similarity	NPC283152
0.719	Intermediate Similarity	NPC329825
0.7189	Intermediate Similarity	NPC471448
0.7172	Intermediate Similarity	NPC469727
0.7171	Intermediate Similarity	NPC201508
0.7168	Intermediate Similarity	NPC476446
0.7168	Intermediate Similarity	NPC469813
0.7168	Intermediate Similarity	NPC78375
0.716	Intermediate Similarity	NPC471594
0.7152	Intermediate Similarity	NPC315320
0.7151	Intermediate Similarity	NPC42979
0.7151	Intermediate Similarity	NPC473821
0.7151	Intermediate Similarity	NPC72980
0.7143	Intermediate Similarity	NPC328029
0.7143	Intermediate Similarity	NPC53069
0.7143	Intermediate Similarity	NPC202768
0.7143	Intermediate Similarity	NPC296482
0.7135	Intermediate Similarity	NPC288943
0.7135	Intermediate Similarity	NPC224764
0.7128	Intermediate Similarity	NPC309845
0.7127	Intermediate Similarity	NPC48938
0.7121	Intermediate Similarity	NPC183407
0.712	Intermediate Similarity	NPC183805
0.712	Intermediate Similarity	NPC470678
0.7119	Intermediate Similarity	NPC313791
0.7115	Intermediate Similarity	NPC169625
0.7115	Intermediate Similarity	NPC202957
0.7111	Intermediate Similarity	NPC222592
0.7111	Intermediate Similarity	NPC168486
0.7108	Intermediate Similarity	NPC6215
0.7108	Intermediate Similarity	NPC470395
0.7105	Intermediate Similarity	NPC315491
0.7105	Intermediate Similarity	NPC45459
0.7101	Intermediate Similarity	NPC255800
0.7101	Intermediate Similarity	NPC96584
0.71	Intermediate Similarity	NPC193267
0.71	Intermediate Similarity	NPC213530
0.7099	Intermediate Similarity	NPC251722
0.7099	Intermediate Similarity	NPC314102
0.7098	Intermediate Similarity	NPC472111
0.7098	Intermediate Similarity	NPC474145
0.7098	Intermediate Similarity	NPC476121
0.7098	Intermediate Similarity	NPC475841
0.7098	Intermediate Similarity	NPC476124
0.7095	Intermediate Similarity	NPC326575
0.7093	Intermediate Similarity	NPC113812
0.7088	Intermediate Similarity	NPC207851
0.7083	Intermediate Similarity	NPC475774

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 NPC124542 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	678
0.2-0.3	853
0.3-0.4	896
0.4-0.5	2665
0.5-0.6	2710
0.6-0.7	948
0.7-0.8	163
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8618	High Similarity	NPD3813	Approved
0.8608	High Similarity	NPD5255	Approved
0.8519	High Similarity	NPD6872	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD4375	Approved
0.8176	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD925	Approved
0.8171	Intermediate Similarity	NPD926	Approved
0.8101	Intermediate Similarity	NPD4702	Approved
0.8101	Intermediate Similarity	NPD4703	Approved
0.8072	Intermediate Similarity	NPD2781	Approved
0.807	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD6569	Phase 2
0.8065	Intermediate Similarity	NPD1649	Discontinued
0.8061	Intermediate Similarity	NPD2780	Approved
0.8061	Intermediate Similarity	NPD2782	Approved
0.8059	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD4044	Discontinued
0.8012	Intermediate Similarity	NPD424	Approved
0.8012	Intermediate Similarity	NPD425	Approved
0.7965	Intermediate Similarity	NPD3386	Phase 2
0.7956	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7469	Discontinued
0.7882	Intermediate Similarity	NPD5065	Approved
0.7869	Intermediate Similarity	NPD3931	Approved
0.7869	Intermediate Similarity	NPD3928	Approved
0.7821	Intermediate Similarity	NPD6361	Phase 2
0.7821	Intermediate Similarity	NPD4551	Phase 2
0.7816	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9690	Approved
0.7771	Intermediate Similarity	NPD9705	Discontinued
0.7771	Intermediate Similarity	NPD112	Approved
0.776	Intermediate Similarity	NPD6389	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2582	Approved
0.7758	Intermediate Similarity	NPD2581	Approved
0.7748	Intermediate Similarity	NPD9284	Approved
0.7742	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD3717	Discontinued
0.773	Intermediate Similarity	NPD2882	Phase 1
0.7722	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4021	Phase 2
0.7688	Intermediate Similarity	NPD4035	Approved
0.7688	Intermediate Similarity	NPD32	Approved
0.7688	Intermediate Similarity	NPD4034	Approved
0.7688	Intermediate Similarity	NPD4033	Approved
0.7688	Intermediate Similarity	NPD4038	Approved
0.7688	Intermediate Similarity	NPD4036	Approved
0.7688	Intermediate Similarity	NPD31	Approved
0.7688	Intermediate Similarity	NPD4037	Approved
0.7688	Intermediate Similarity	NPD4122	Approved
0.7688	Intermediate Similarity	NPD4039	Approved
0.7661	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5862	Discovery
0.7632	Intermediate Similarity	NPD9080	Approved
0.763	Intermediate Similarity	NPD5100	Phase 3
0.7627	Intermediate Similarity	NPD3082	Discontinued
0.7622	Intermediate Similarity	NPD3262	Approved
0.7606	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD7948	Phase 1
0.7596	Intermediate Similarity	NPD2952	Discontinued
0.7595	Intermediate Similarity	NPD2896	Discontinued
0.7593	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6159	Phase 2
0.7586	Intermediate Similarity	NPD1032	Phase 2
0.7584	Intermediate Similarity	NPD4921	Phase 3
0.7584	Intermediate Similarity	NPD4919	Phase 3
0.7584	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3395	Approved
0.7582	Intermediate Similarity	NPD3396	Approved
0.7581	Intermediate Similarity	NPD6975	Discontinued
0.7569	Intermediate Similarity	NPD4372	Phase 1
0.7541	Intermediate Similarity	NPD3477	Phase 2
0.7541	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4889	Approved
0.7515	Intermediate Similarity	NPD1685	Approved
0.7515	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1684	Approved
0.7515	Intermediate Similarity	NPD6158	Phase 2
0.7514	Intermediate Similarity	NPD2334	Discontinued
0.7486	Intermediate Similarity	NPD3039	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1352	Discontinued
0.7459	Intermediate Similarity	NPD8063	Discontinued
0.7457	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2511	Approved
0.7452	Intermediate Similarity	NPD3942	Approved
0.7452	Intermediate Similarity	NPD3944	Approved
0.7444	Intermediate Similarity	NPD1034	Phase 3
0.7444	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4989	Phase 2
0.7436	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD9695	Approved
0.7421	Intermediate Similarity	NPD9506	Approved
0.7418	Intermediate Similarity	NPD4148	Approved
0.7403	Intermediate Similarity	NPD2119	Approved
0.7403	Intermediate Similarity	NPD2118	Approved
0.7401	Intermediate Similarity	NPD2600	Approved
0.7401	Intermediate Similarity	NPD2599	Approved
0.7401	Intermediate Similarity	NPD2601	Approved
0.7394	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3017	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7112	Discontinued
0.7375	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2616	Phase 3
0.7371	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2615	Phase 3
0.7363	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3321	Discontinued
0.7363	Intermediate Similarity	NPD1213	Phase 3
0.7356	Intermediate Similarity	NPD2123	Phase 3
0.7348	Intermediate Similarity	NPD8020	Approved
0.7348	Intermediate Similarity	NPD2383	Phase 1
0.7348	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8021	Approved
0.7337	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4528	Approved
0.7337	Intermediate Similarity	NPD802	Phase 2
0.7337	Intermediate Similarity	NPD4529	Approved
0.7337	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4526	Approved
0.7337	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5999	Phase 2
0.7322	Intermediate Similarity	NPD6022	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3330	Phase 1
0.7314	Intermediate Similarity	NPD2077	Approved
0.7314	Intermediate Similarity	NPD2076	Approved
0.7305	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD991	Phase 2
0.7283	Intermediate Similarity	NPD3924	Approved
0.7283	Intermediate Similarity	NPD3922	Approved
0.7283	Intermediate Similarity	NPD3923	Approved
0.7283	Intermediate Similarity	NPD3921	Approved
0.7278	Intermediate Similarity	NPD6026	Approved
0.7273	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD3439	Approved
0.7267	Intermediate Similarity	NPD5925	Phase 1
0.7267	Intermediate Similarity	NPD5088	Discontinued
0.7263	Intermediate Similarity	NPD8408	Discontinued
0.7263	Intermediate Similarity	NPD5513	Phase 2
0.7263	Intermediate Similarity	NPD4203	Approved
0.7263	Intermediate Similarity	NPD4204	Approved
0.7261	Intermediate Similarity	NPD3475	Approved
0.7261	Intermediate Similarity	NPD3476	Approved
0.7258	Intermediate Similarity	NPD2482	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD268	Approved
0.7237	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD271	Approved
0.7235	Intermediate Similarity	NPD9382	Approved
0.7235	Intermediate Similarity	NPD9383	Approved
0.7235	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD2382	Approved
0.7232	Intermediate Similarity	NPD2381	Approved
0.7232	Intermediate Similarity	NPD2380	Approved
0.7209	Intermediate Similarity	NPD8026	Phase 1
0.7195	Intermediate Similarity	NPD3525	Discontinued
0.7191	Intermediate Similarity	NPD4072	Approved
0.7191	Intermediate Similarity	NPD4071	Approved
0.7189	Intermediate Similarity	NPD3404	Approved
0.7189	Intermediate Similarity	NPD9689	Approved
0.7189	Intermediate Similarity	NPD6887	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3575	Approved
0.7186	Intermediate Similarity	NPD3576	Approved
0.7178	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6281	Approved
0.7167	Intermediate Similarity	NPD1570	Approved
0.7165	Intermediate Similarity	NPD4437	Phase 3
0.716	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD2993	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD9206	Approved
0.7152	Intermediate Similarity	NPD9207	Approved
0.7143	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5555	Phase 1
0.7143	Intermediate Similarity	NPD3815	Phase 1
0.7143	Intermediate Similarity	NPD3816	Phase 1
0.7143	Intermediate Similarity	NPD4548	Discontinued
0.7143	Intermediate Similarity	NPD7069	Discontinued
0.7135	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD2959	Phase 3
0.7125	Intermediate Similarity	NPD4028	Approved
0.7125	Intermediate Similarity	NPD4030	Approved
0.7125	Intermediate Similarity	NPD4029	Approved
0.7121	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1599	Approved
0.7118	Intermediate Similarity	NPD2809	Approved
0.7113	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4998	Phase 3
0.7112	Intermediate Similarity	NPD4999	Phase 3
0.7105	Intermediate Similarity	NPD484	Approved
0.7104	Intermediate Similarity	NPD7758	Approved
0.7104	Intermediate Similarity	NPD7757	Approved
0.71	Intermediate Similarity	NPD6500	Approved
0.71	Intermediate Similarity	NPD6501	Approved
0.7097	Intermediate Similarity	NPD2127	Suspended
0.7095	Intermediate Similarity	NPD8122	Approved
0.7095	Intermediate Similarity	NPD8123	Approved
0.7093	Intermediate Similarity	NPD3433	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