NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	231.09
Volume:	231.92
LogP:	1.728
LogD:	1.515
LogS:	-2.322
# Rotatable Bonds:	1
TPSA:	65.62
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.705
Synthetic Accessibility Score:	2.637
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.856
MDCK Permeability:	1.5628738765371963e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.904

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	94.25995635986328%
Volume Distribution (VD):	0.658
Pgp-substrate:	4.136921405792236%

ADMET: Metabolism

CYP1A2-inhibitor:	0.869
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.179
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.533
CYP2C9-substrate:	0.806
CYP2D6-inhibitor:	0.635
CYP2D6-substrate:	0.737
CYP3A4-inhibitor:	0.438
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	8.337
Half-life (T1/2):	0.848

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.691
AMES Toxicity:	0.79
Rat Oral Acute Toxicity:	0.212
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.573
Carcinogencity:	0.891
Eye Corrosion:	0.003
Eye Irritation:	0.379
Respiratory Toxicity:	0.24

Download Data

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

Natural Product: NPC171372

Natural Product ID:	NPC171372
*Common Name:**	(8S)-2-Hydroxy-1-(4-Hydroxyphenyl)-5,6,7,8-Tetrahydropyrrolizin-3-One
IUPAC Name:	(8S)-2-hydroxy-1-(4-hydroxyphenyl)-5,6,7,8-tetrahydropyrrolizin-3-one
Synonyms:	7a(S)-p-hydroxyphenopyrrozin
Standard InCHIKey:	KFPFLSSRTQAZQF-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C13H13NO3/c15-9-5-3-8(4-6-9)11-10-2-1-7-14(10)13(17)12(11)16/h3-6,10,15-16H,1-2,7H2/t10-/m0/s1
SMILES:	Oc1ccc(cc1)C1=C(O)C(=O)N2[C@H]1CCC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479677
PubChem CID:	11687274
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000219] Pyrrolizines

*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
NPO33326	chromocleista sp.	Species	Aspergillaceae	Eukaryota	n.a.	Gulf of Mexico	n.a.	PMID[16643030]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	25.0	ug.mL-1	PMID[504206]

☑ 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 NPC171372 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	204
0.1-0.2	1691
0.2-0.3	7986
0.3-0.4	9622
0.4-0.5	13896
0.5-0.6	7886
0.6-0.7	1305
0.7-0.8	104
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8346	Intermediate Similarity	NPC109580
0.8102	Intermediate Similarity	NPC251439
0.797	Intermediate Similarity	NPC120251
0.7883	Intermediate Similarity	NPC242159
0.7883	Intermediate Similarity	NPC313694
0.7868	Intermediate Similarity	NPC473360
0.7797	Intermediate Similarity	NPC155847
0.7797	Intermediate Similarity	NPC289381
0.777	Intermediate Similarity	NPC476989
0.7769	Intermediate Similarity	NPC268348
0.7744	Intermediate Similarity	NPC218323
0.7519	Intermediate Similarity	NPC307020
0.7518	Intermediate Similarity	NPC257390
0.7518	Intermediate Similarity	NPC150712
0.75	Intermediate Similarity	NPC16188
0.7481	Intermediate Similarity	NPC305717
0.7464	Intermediate Similarity	NPC208757
0.7424	Intermediate Similarity	NPC56634
0.7379	Intermediate Similarity	NPC125852
0.7377	Intermediate Similarity	NPC178902
0.7365	Intermediate Similarity	NPC261934
0.7365	Intermediate Similarity	NPC56685
0.7365	Intermediate Similarity	NPC262166
0.7365	Intermediate Similarity	NPC202198
0.7365	Intermediate Similarity	NPC5194
0.7364	Intermediate Similarity	NPC10286
0.7364	Intermediate Similarity	NPC213
0.7347	Intermediate Similarity	NPC473491
0.7308	Intermediate Similarity	NPC188867
0.7308	Intermediate Similarity	NPC106551
0.7308	Intermediate Similarity	NPC281686
0.7299	Intermediate Similarity	NPC17374
0.7297	Intermediate Similarity	NPC233702
0.7287	Intermediate Similarity	NPC118202
0.7273	Intermediate Similarity	NPC319950
0.7273	Intermediate Similarity	NPC125732
0.7244	Intermediate Similarity	NPC474149
0.7241	Intermediate Similarity	NPC266741
0.7231	Intermediate Similarity	NPC317254
0.7222	Intermediate Similarity	NPC153690
0.7214	Intermediate Similarity	NPC328070
0.7203	Intermediate Similarity	NPC238412
0.7203	Intermediate Similarity	NPC471201
0.72	Intermediate Similarity	NPC231705
0.7192	Intermediate Similarity	NPC81026
0.7176	Intermediate Similarity	NPC82963
0.7165	Intermediate Similarity	NPC290566
0.7165	Intermediate Similarity	NPC145638
0.7165	Intermediate Similarity	NPC258056
0.7153	Intermediate Similarity	NPC231572
0.7152	Intermediate Similarity	NPC244509
0.7143	Intermediate Similarity	NPC239697
0.7143	Intermediate Similarity	NPC142297
0.7133	Intermediate Similarity	NPC473052
0.7133	Intermediate Similarity	NPC473055
0.7121	Intermediate Similarity	NPC311737
0.7121	Intermediate Similarity	NPC38458
0.7113	Intermediate Similarity	NPC273907
0.7113	Intermediate Similarity	NPC118099
0.7113	Intermediate Similarity	NPC474787
0.7113	Intermediate Similarity	NPC293377
0.7113	Intermediate Similarity	NPC475318
0.7113	Intermediate Similarity	NPC49577
0.7113	Intermediate Similarity	NPC76785
0.7113	Intermediate Similarity	NPC9687
0.7113	Intermediate Similarity	NPC475598
0.7113	Intermediate Similarity	NPC474811
0.7113	Intermediate Similarity	NPC90194
0.7113	Intermediate Similarity	NPC474855
0.7113	Intermediate Similarity	NPC260045
0.7113	Intermediate Similarity	NPC476102
0.7113	Intermediate Similarity	NPC79465
0.7113	Intermediate Similarity	NPC151706
0.7111	Intermediate Similarity	NPC27581
0.7111	Intermediate Similarity	NPC474862
0.7111	Intermediate Similarity	NPC142577
0.7087	Intermediate Similarity	NPC24101
0.7087	Intermediate Similarity	NPC96224
0.7086	Intermediate Similarity	NPC39431
0.7083	Intermediate Similarity	NPC193528
0.7083	Intermediate Similarity	NPC248505
0.7083	Intermediate Similarity	NPC95366
0.7083	Intermediate Similarity	NPC322526
0.7073	Intermediate Similarity	NPC29601
0.7073	Intermediate Similarity	NPC214200
0.7073	Intermediate Similarity	NPC228400
0.7071	Intermediate Similarity	NPC474087
0.7059	Intermediate Similarity	NPC326349
0.7059	Intermediate Similarity	NPC323336
0.7054	Intermediate Similarity	NPC269340
0.705	Intermediate Similarity	NPC66177
0.705	Intermediate Similarity	NPC268763
0.705	Intermediate Similarity	NPC8305
0.7039	Intermediate Similarity	NPC476268
0.7032	Intermediate Similarity	NPC241794
0.7015	Intermediate Similarity	NPC283760
0.7014	Intermediate Similarity	NPC145446
0.7014	Intermediate Similarity	NPC137172
0.7013	Intermediate Similarity	NPC244336
0.7006	Intermediate Similarity	NPC469479
0.7	Intermediate Similarity	NPC181709
0.7	Intermediate Similarity	NPC124802
0.6992	Remote Similarity	NPC137096
0.6978	Remote Similarity	NPC476353
0.6972	Remote Similarity	NPC217574
0.696	Remote Similarity	NPC135784
0.696	Remote Similarity	NPC470202
0.696	Remote Similarity	NPC68055
0.6959	Remote Similarity	NPC473804
0.6959	Remote Similarity	NPC297322
0.6944	Remote Similarity	NPC96406
0.6942	Remote Similarity	NPC32977
0.6942	Remote Similarity	NPC81010
0.694	Remote Similarity	NPC142638
0.694	Remote Similarity	NPC317784
0.694	Remote Similarity	NPC85276
0.6939	Remote Similarity	NPC204546
0.6929	Remote Similarity	NPC296712
0.6928	Remote Similarity	NPC256689
0.6928	Remote Similarity	NPC123011
0.6918	Remote Similarity	NPC469505
0.6917	Remote Similarity	NPC45040
0.6913	Remote Similarity	NPC119569
0.6911	Remote Similarity	NPC107619
0.6894	Remote Similarity	NPC142599
0.6891	Remote Similarity	NPC123273
0.6891	Remote Similarity	NPC258219
0.6891	Remote Similarity	NPC242240
0.6891	Remote Similarity	NPC318325
0.689	Remote Similarity	NPC39822
0.6887	Remote Similarity	NPC324081
0.6885	Remote Similarity	NPC286006
0.6879	Remote Similarity	NPC283079
0.6879	Remote Similarity	NPC478147
0.6875	Remote Similarity	NPC103947
0.6875	Remote Similarity	NPC328419
0.6875	Remote Similarity	NPC193673
0.6875	Remote Similarity	NPC45783
0.6875	Remote Similarity	NPC159150
0.6875	Remote Similarity	NPC94280
0.687	Remote Similarity	NPC146422
0.6864	Remote Similarity	NPC23167
0.6855	Remote Similarity	NPC141957
0.6855	Remote Similarity	NPC302597
0.685	Remote Similarity	NPC303141
0.6849	Remote Similarity	NPC252107
0.6842	Remote Similarity	NPC160179
0.6838	Remote Similarity	NPC175313
0.6838	Remote Similarity	NPC321133
0.6833	Remote Similarity	NPC300017
0.6831	Remote Similarity	NPC126859
0.6831	Remote Similarity	NPC259665
0.6831	Remote Similarity	NPC89769
0.6813	Remote Similarity	NPC129486
0.6813	Remote Similarity	NPC33507
0.6807	Remote Similarity	NPC25493
0.6807	Remote Similarity	NPC113460
0.6806	Remote Similarity	NPC266425
0.6806	Remote Similarity	NPC243404
0.6803	Remote Similarity	NPC128062
0.6803	Remote Similarity	NPC151715
0.68	Remote Similarity	NPC83790
0.68	Remote Similarity	NPC128237
0.6797	Remote Similarity	NPC469539
0.6797	Remote Similarity	NPC469540
0.6792	Remote Similarity	NPC61004
0.6788	Remote Similarity	NPC326079
0.6788	Remote Similarity	NPC473051
0.6788	Remote Similarity	NPC473050
0.6781	Remote Similarity	NPC99078
0.678	Remote Similarity	NPC197783
0.6777	Remote Similarity	NPC304541
0.6774	Remote Similarity	NPC201967
0.6774	Remote Similarity	NPC471073
0.6774	Remote Similarity	NPC270811
0.6774	Remote Similarity	NPC260000
0.6772	Remote Similarity	NPC304761
0.6772	Remote Similarity	NPC150254
0.6772	Remote Similarity	NPC147000
0.6772	Remote Similarity	NPC226778
0.6769	Remote Similarity	NPC79543
0.6761	Remote Similarity	NPC325651
0.6759	Remote Similarity	NPC167096
0.6759	Remote Similarity	NPC470441
0.6755	Remote Similarity	NPC9373
0.6752	Remote Similarity	NPC265146
0.675	Remote Similarity	NPC328649
0.675	Remote Similarity	NPC280347
0.675	Remote Similarity	NPC177420
0.6748	Remote Similarity	NPC274678
0.6748	Remote Similarity	NPC246679
0.6748	Remote Similarity	NPC26244
0.6746	Remote Similarity	NPC329375
0.6738	Remote Similarity	NPC323775
0.6738	Remote Similarity	NPC236347
0.6736	Remote Similarity	NPC118419
0.6735	Remote Similarity	NPC220923
0.673	Remote Similarity	NPC472923
0.673	Remote Similarity	NPC63931
0.6728	Remote Similarity	NPC328494

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 NPC171372 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	581
0.2-0.3	935
0.3-0.4	1924
0.4-0.5	3141
0.5-0.6	1960
0.6-0.7	434
0.7-0.8	27
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
0.763	Intermediate Similarity	NPD4207	Discontinued
0.7519	Intermediate Similarity	NPD317	Approved
0.7519	Intermediate Similarity	NPD4659	Approved
0.7519	Intermediate Similarity	NPD318	Approved
0.748	Intermediate Similarity	NPD2228	Approved
0.748	Intermediate Similarity	NPD2234	Approved
0.748	Intermediate Similarity	NPD2229	Approved
0.7459	Intermediate Similarity	NPD9610	Approved
0.7459	Intermediate Similarity	NPD9608	Approved
0.7407	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4103	Phase 2
0.7385	Intermediate Similarity	NPD856	Approved
0.7385	Intermediate Similarity	NPD16	Approved
0.7339	Intermediate Similarity	NPD1445	Approved
0.7339	Intermediate Similarity	NPD1444	Approved
0.7328	Intermediate Similarity	NPD5304	Approved
0.7328	Intermediate Similarity	NPD5303	Approved
0.7313	Intermediate Similarity	NPD2561	Approved
0.7313	Intermediate Similarity	NPD2562	Approved
0.7308	Intermediate Similarity	NPD9568	Approved
0.7171	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1792	Phase 2
0.7154	Intermediate Similarity	NPD1793	Approved
0.7154	Intermediate Similarity	NPD1791	Approved
0.7154	Intermediate Similarity	NPD855	Approved
0.7154	Intermediate Similarity	NPD854	Approved
0.7153	Intermediate Similarity	NPD1133	Approved
0.7153	Intermediate Similarity	NPD1134	Approved
0.7153	Intermediate Similarity	NPD1135	Approved
0.7153	Intermediate Similarity	NPD1129	Approved
0.7153	Intermediate Similarity	NPD1131	Approved
0.7143	Intermediate Similarity	NPD4093	Discontinued
0.7099	Intermediate Similarity	NPD255	Approved
0.7099	Intermediate Similarity	NPD256	Approved
0.7095	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD316	Approved
0.7068	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4212	Discontinued
0.705	Intermediate Similarity	NPD3635	Approved
0.705	Intermediate Similarity	NPD3636	Approved
0.705	Intermediate Similarity	NPD3637	Approved
0.702	Intermediate Similarity	NPD1670	Discontinued
0.7	Intermediate Similarity	NPD3595	Approved
0.7	Intermediate Similarity	NPD3594	Approved
0.6992	Remote Similarity	NPD9613	Approved
0.6992	Remote Similarity	NPD9615	Approved
0.6992	Remote Similarity	NPD9616	Approved
0.6963	Remote Similarity	NPD1751	Approved
0.696	Remote Similarity	NPD3682	Approved
0.696	Remote Similarity	NPD3680	Approved
0.6954	Remote Similarity	NPD7303	Discontinued
0.6943	Remote Similarity	NPD2098	Approved
0.6929	Remote Similarity	NPD4208	Discontinued
0.6906	Remote Similarity	NPD3055	Approved
0.6906	Remote Similarity	NPD3053	Approved
0.6901	Remote Similarity	NPD601	Approved
0.6901	Remote Similarity	NPD598	Approved
0.6901	Remote Similarity	NPD597	Approved
0.6897	Remote Similarity	NPD743	Approved
0.6894	Remote Similarity	NPD9614	Approved
0.6894	Remote Similarity	NPD9618	Approved
0.6889	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1755	Approved
0.6879	Remote Similarity	NPD2606	Approved
0.6879	Remote Similarity	NPD2605	Approved
0.687	Remote Similarity	NPD9379	Approved
0.687	Remote Similarity	NPD9377	Approved
0.6867	Remote Similarity	NPD3141	Discontinued
0.6853	Remote Similarity	NPD1136	Approved
0.6853	Remote Similarity	NPD5745	Approved
0.6853	Remote Similarity	NPD1132	Approved
0.6853	Remote Similarity	NPD1130	Approved
0.6838	Remote Similarity	NPD2667	Approved
0.6838	Remote Similarity	NPD2668	Approved
0.6831	Remote Similarity	NPD5156	Approved
0.6831	Remote Similarity	NPD5155	Approved
0.6828	Remote Similarity	NPD823	Approved
0.6828	Remote Similarity	NPD817	Approved
0.6815	Remote Similarity	NPD2097	Approved
0.6803	Remote Similarity	NPD1725	Approved
0.68	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7131	Phase 3
0.6792	Remote Similarity	NPD8303	Discontinued
0.6788	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3554	Approved
0.6781	Remote Similarity	NPD3552	Approved
0.6781	Remote Similarity	NPD3555	Approved
0.6781	Remote Similarity	NPD3553	Approved
0.6772	Remote Similarity	NPD311	Approved
0.6772	Remote Similarity	NPD314	Approved
0.6772	Remote Similarity	NPD10	Approved
0.6772	Remote Similarity	NPD310	Approved
0.6772	Remote Similarity	NPD315	Approved
0.6772	Remote Similarity	NPD309	Approved
0.677	Remote Similarity	NPD4652	Approved
0.6763	Remote Similarity	NPD1420	Approved
0.6763	Remote Similarity	NPD1421	Approved
0.6757	Remote Similarity	NPD4725	Approved
0.6757	Remote Similarity	NPD4726	Approved
0.6757	Remote Similarity	NPD4721	Approved
0.675	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.675	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2859	Approved
0.6748	Remote Similarity	NPD2860	Approved
0.6739	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD9619	Approved
0.6738	Remote Similarity	NPD599	Approved
0.6738	Remote Similarity	NPD9621	Approved
0.6738	Remote Similarity	NPD9620	Approved
0.6738	Remote Similarity	NPD602	Approved
0.6736	Remote Similarity	NPD6405	Approved
0.6736	Remote Similarity	NPD6407	Approved
0.6736	Remote Similarity	NPD829	Discontinued
0.6735	Remote Similarity	NPD1753	Discontinued
0.6733	Remote Similarity	NPD5481	Discontinued
0.6714	Remote Similarity	NPD5310	Approved
0.6714	Remote Similarity	NPD2079	Discontinued
0.6714	Remote Similarity	NPD5311	Approved
0.6713	Remote Similarity	NPD3136	Phase 2
0.6713	Remote Similarity	NPD5746	Approved
0.6712	Remote Similarity	NPD3052	Approved
0.6712	Remote Similarity	NPD2568	Approved
0.6712	Remote Similarity	NPD3054	Approved
0.6712	Remote Similarity	NPD2492	Phase 1
0.6708	Remote Similarity	NPD2890	Approved
0.6708	Remote Similarity	NPD2017	Approved
0.6708	Remote Similarity	NPD2889	Approved
0.6708	Remote Similarity	NPD2888	Approved
0.6693	Remote Similarity	NPD3681	Approved
0.6693	Remote Similarity	NPD3683	Approved
0.669	Remote Similarity	NPD9569	Approved
0.6667	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3123	Discovery
0.6667	Remote Similarity	NPD2934	Approved
0.6667	Remote Similarity	NPD4621	Approved
0.6667	Remote Similarity	NPD2933	Approved
0.6667	Remote Similarity	NPD4619	Approved
0.6667	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3536	Discontinued
0.6667	Remote Similarity	NPD3421	Phase 3
0.6645	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6583	Phase 3
0.6643	Remote Similarity	NPD9622	Approved
0.6643	Remote Similarity	NPD6582	Phase 2
0.6626	Remote Similarity	NPD5137	Approved
0.6623	Remote Similarity	NPD6676	Phase 2
0.6621	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD7086	Phase 2
0.662	Remote Similarity	NPD858	Approved
0.662	Remote Similarity	NPD859	Approved
0.662	Remote Similarity	NPD7451	Discontinued
0.6614	Remote Similarity	NPD4818	Approved
0.6614	Remote Similarity	NPD4817	Approved
0.661	Remote Similarity	NPD111	Approved
0.66	Remote Similarity	NPD7037	Approved
0.6599	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD196	Phase 1
0.6594	Remote Similarity	NPD9384	Approved
0.6594	Remote Similarity	NPD9381	Approved
0.6591	Remote Similarity	NPD4253	Approved
0.6591	Remote Similarity	NPD4254	Approved
0.6587	Remote Similarity	NPD3020	Approved
0.6577	Remote Similarity	NPD7450	Phase 2
0.6575	Remote Similarity	NPD3059	Approved
0.6575	Remote Similarity	NPD3062	Approved
0.6575	Remote Similarity	NPD6346	Approved
0.6575	Remote Similarity	NPD3061	Approved
0.6573	Remote Similarity	NPD3663	Approved
0.6573	Remote Similarity	NPD3664	Approved
0.6573	Remote Similarity	NPD3662	Phase 3
0.6573	Remote Similarity	NPD3661	Approved
0.6569	Remote Similarity	NPD1759	Phase 1
0.6565	Remote Similarity	NPD4717	Approved
0.6565	Remote Similarity	NPD4718	Approved
0.6565	Remote Similarity	NPD4720	Approved
0.6562	Remote Similarity	NPD4656	Approved
0.6562	Remote Similarity	NPD4229	Approved
0.6562	Remote Similarity	NPD4231	Approved
0.6562	Remote Similarity	NPD4658	Approved
0.6558	Remote Similarity	NPD2874	Phase 2
0.6556	Remote Similarity	NPD4236	Phase 3
0.6556	Remote Similarity	NPD4237	Approved
0.6554	Remote Similarity	NPD6636	Phase 3
0.6552	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1330	Phase 2
0.6552	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2626	Approved
0.6549	Remote Similarity	NPD2627	Approved
0.6549	Remote Similarity	NPD2159	Approved
0.6549	Remote Similarity	NPD2160	Approved
0.6549	Remote Similarity	NPD2625	Approved
0.6549	Remote Similarity	NPD2628	Approved
0.6536	Remote Similarity	NPD6609	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