NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.13
Volume:	278.731
LogP:	3.609
LogD:	3.634
LogS:	-3.874
# Rotatable Bonds:	5
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.895
Synthetic Accessibility Score:	1.823
Fsp3:	0.25
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:	-4.878
MDCK Permeability:	1.6958047126536258e-05
Pgp-inhibitor:	0.483
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.309
30% Bioavailability (F30%):	0.449

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.246
Plasma Protein Binding (PPB):	96.91815948486328%
Volume Distribution (VD):	2.213
Pgp-substrate:	1.995865821838379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.582
CYP2C9-inhibitor:	0.685
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.971
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.881
CYP3A4-substrate:	0.432

ADMET: Excretion

Clearance (CL):	11.511
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.237
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.751
Skin Sensitization:	0.934
Carcinogencity:	0.113
Eye Corrosion:	0.362
Eye Irritation:	0.964
Respiratory Toxicity:	0.18

Download Data

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

Natural Product: NPC33270

Natural Product ID:	NPC33270
*Common Name:**	Stilbosteminn
IUPAC Name:	3-methoxy-5-[2-(2-methoxyphenyl)ethyl]phenol
Synonyms:	stilbostemin N
Standard InCHIKey:	CTQWBUQUEQSOJO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18O3/c1-18-15-10-12(9-14(17)11-15)7-8-13-5-3-4-6-16(13)19-2/h3-6,9-11,17H,7-8H2,1-2H3
SMILES:	COc1cc(CCc2ccccc2OC)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1761959
PubChem CID:	23630996
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679323]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[16643052]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	Roots; Stems; Tubers	n.a.	n.a.	PMID[16872143]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[18452334]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21353549]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21902195]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21902195]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	root	n.a.	PMID[21902195]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	104.6	%	PMID[569803]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	103.7	%	PMID[569803]

☑ 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 NPC33270 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	321
0.1-0.2	1785
0.2-0.3	5002
0.3-0.4	13572
0.4-0.5	4222
0.5-0.6	4806
0.6-0.7	7902
0.7-0.8	4038
0.8-0.85	679
0.85-0.9	276
0.9-0.95	71
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC69261
0.9908	High Similarity	NPC150624
0.982	High Similarity	NPC184302
0.9817	High Similarity	NPC808
0.9817	High Similarity	NPC53906
0.973	High Similarity	NPC190514
0.9725	High Similarity	NPC276737
0.9725	High Similarity	NPC22610
0.964	High Similarity	NPC221549
0.964	High Similarity	NPC470759
0.964	High Similarity	NPC50521
0.964	High Similarity	NPC127894
0.964	High Similarity	NPC15860
0.964	High Similarity	NPC219070
0.964	High Similarity	NPC474933
0.964	High Similarity	NPC244816
0.9561	High Similarity	NPC476633
0.955	High Similarity	NPC54507
0.955	High Similarity	NPC85292
0.955	High Similarity	NPC229147
0.955	High Similarity	NPC114064
0.955	High Similarity	NPC141090
0.9478	High Similarity	NPC18128
0.9478	High Similarity	NPC77789
0.9474	High Similarity	NPC102639
0.9459	High Similarity	NPC167934
0.9459	High Similarity	NPC185541
0.9459	High Similarity	NPC464
0.9381	High Similarity	NPC131118
0.9375	High Similarity	NPC203113
0.9369	High Similarity	NPC180508
0.9369	High Similarity	NPC228287
0.9358	High Similarity	NPC2682
0.9358	High Similarity	NPC168657
0.9358	High Similarity	NPC94045
0.9292	High Similarity	NPC195466
0.9237	High Similarity	NPC105031
0.9237	High Similarity	NPC105925
0.9237	High Similarity	NPC113495
0.9224	High Similarity	NPC75713
0.9189	High Similarity	NPC280606
0.916	High Similarity	NPC170485
0.9138	High Similarity	NPC218753
0.9099	High Similarity	NPC296920
0.9099	High Similarity	NPC90520
0.9083	High Similarity	NPC82679
0.9083	High Similarity	NPC246620
0.9083	High Similarity	NPC293054
0.9083	High Similarity	NPC282000
0.9083	High Similarity	NPC169474
0.9083	High Similarity	NPC473221
0.9083	High Similarity	NPC236760
0.9083	High Similarity	NPC324112
0.9083	High Similarity	NPC236791
0.9083	High Similarity	NPC124452
0.9083	High Similarity	NPC159968
0.9083	High Similarity	NPC74817
0.9083	High Similarity	NPC35543
0.9076	High Similarity	NPC60885
0.9076	High Similarity	NPC234400
0.9068	High Similarity	NPC474160
0.9068	High Similarity	NPC233526
0.9068	High Similarity	NPC95168
0.9068	High Similarity	NPC282496
0.9068	High Similarity	NPC136319
0.9068	High Similarity	NPC121115
0.9009	High Similarity	NPC303521
0.9008	High Similarity	NPC266691
0.9	High Similarity	NPC103823
0.9	High Similarity	NPC214406
0.9	High Similarity	NPC223953
0.9	High Similarity	NPC44748
0.9	High Similarity	NPC18924
0.9	High Similarity	NPC223136
0.9	High Similarity	NPC245115
0.9	High Similarity	NPC82299
0.9	High Similarity	NPC28730
0.9	High Similarity	NPC78974
0.8992	High Similarity	NPC228503
0.8992	High Similarity	NPC270030
0.8992	High Similarity	NPC138248
0.8991	High Similarity	NPC164576
0.8983	High Similarity	NPC36016
0.8983	High Similarity	NPC100099
0.8966	High Similarity	NPC137294
0.8966	High Similarity	NPC85895
0.8934	High Similarity	NPC471519
0.8934	High Similarity	NPC190144
0.8934	High Similarity	NPC471518
0.8929	High Similarity	NPC255068
0.8926	High Similarity	NPC46978
0.8919	High Similarity	NPC19808
0.8919	High Similarity	NPC33728
0.8919	High Similarity	NPC82016
0.8917	High Similarity	NPC17943
0.8917	High Similarity	NPC265483
0.8917	High Similarity	NPC208950
0.8917	High Similarity	NPC82483
0.8917	High Similarity	NPC299584
0.8917	High Similarity	NPC475169
0.8917	High Similarity	NPC203133
0.8917	High Similarity	NPC116907
0.8917	High Similarity	NPC298757
0.8917	High Similarity	NPC233410
0.8917	High Similarity	NPC105718
0.8917	High Similarity	NPC476254
0.8917	High Similarity	NPC57490
0.8917	High Similarity	NPC117214
0.8917	High Similarity	NPC193544
0.8917	High Similarity	NPC278955
0.8917	High Similarity	NPC131397
0.8917	High Similarity	NPC472093
0.8917	High Similarity	NPC251855
0.8917	High Similarity	NPC221077
0.8908	High Similarity	NPC38761
0.8908	High Similarity	NPC76465
0.8898	High Similarity	NPC212965
0.8898	High Similarity	NPC54972
0.8862	High Similarity	NPC51840
0.8862	High Similarity	NPC254000
0.8862	High Similarity	NPC126836
0.8862	High Similarity	NPC224157
0.8862	High Similarity	NPC234488
0.8862	High Similarity	NPC299221
0.8862	High Similarity	NPC192687
0.8862	High Similarity	NPC311680
0.8852	High Similarity	NPC28765
0.8852	High Similarity	NPC215300
0.8852	High Similarity	NPC154866
0.8843	High Similarity	NPC230479
0.8843	High Similarity	NPC50315
0.8843	High Similarity	NPC283049
0.8843	High Similarity	NPC26879
0.8833	High Similarity	NPC106914
0.8833	High Similarity	NPC140521
0.8833	High Similarity	NPC134195
0.8833	High Similarity	NPC197351
0.8833	High Similarity	NPC86502
0.8833	High Similarity	NPC246648
0.8829	High Similarity	NPC75440
0.8829	High Similarity	NPC174981
0.8824	High Similarity	NPC120638
0.8824	High Similarity	NPC474864
0.8824	High Similarity	NPC74137
0.8824	High Similarity	NPC41562
0.8814	High Similarity	NPC166759
0.8807	High Similarity	NPC241891
0.8807	High Similarity	NPC102216
0.8803	High Similarity	NPC295259
0.879	High Similarity	NPC474356
0.879	High Similarity	NPC282508
0.879	High Similarity	NPC471517
0.879	High Similarity	NPC15543
0.879	High Similarity	NPC12275
0.879	High Similarity	NPC45715
0.879	High Similarity	NPC472590
0.879	High Similarity	NPC473309
0.878	High Similarity	NPC212015
0.878	High Similarity	NPC16577
0.878	High Similarity	NPC469963
0.878	High Similarity	NPC10225
0.878	High Similarity	NPC58164
0.878	High Similarity	NPC222108
0.878	High Similarity	NPC469951
0.878	High Similarity	NPC96719
0.877	High Similarity	NPC252131
0.877	High Similarity	NPC242032
0.877	High Similarity	NPC266555
0.877	High Similarity	NPC53781
0.877	High Similarity	NPC127587
0.8761	High Similarity	NPC165770
0.8761	High Similarity	NPC225679
0.8761	High Similarity	NPC224527
0.8761	High Similarity	NPC4493
0.8761	High Similarity	NPC476632
0.876	High Similarity	NPC285040
0.876	High Similarity	NPC188022
0.876	High Similarity	NPC102540
0.876	High Similarity	NPC249836
0.876	High Similarity	NPC17809
0.876	High Similarity	NPC103420
0.875	High Similarity	NPC197757
0.875	High Similarity	NPC96940
0.875	High Similarity	NPC228922
0.875	High Similarity	NPC84086
0.8739	High Similarity	NPC193364
0.8729	High Similarity	NPC93398
0.8729	High Similarity	NPC258979
0.8729	High Similarity	NPC8283
0.8729	High Similarity	NPC474565
0.8727	High Similarity	NPC134829
0.872	High Similarity	NPC218884
0.872	High Similarity	NPC6451
0.8718	High Similarity	NPC74821
0.8718	High Similarity	NPC63010
0.8699	High Similarity	NPC38664
0.8699	High Similarity	NPC206615
0.8699	High Similarity	NPC38017
0.8699	High Similarity	NPC274717
0.8699	High Similarity	NPC98631

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 NPC33270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	1050
0.2-0.3	1464
0.3-0.4	2696
0.4-0.5	1791
0.5-0.6	1059
0.6-0.7	632
0.7-0.8	121
0.8-0.85	12
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.878	High Similarity	NPD4625	Phase 3
0.875	High Similarity	NPD4749	Approved
0.8739	High Similarity	NPD1610	Phase 2
0.8718	High Similarity	NPD1548	Phase 1
0.8699	High Similarity	NPD4908	Phase 1
0.8629	High Similarity	NPD3027	Phase 3
0.856	High Similarity	NPD4907	Clinical (unspecified phase)
0.8537	High Similarity	NPD6917	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD4750	Phase 3
0.8413	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.832	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD6671	Approved
0.8288	Intermediate Similarity	NPD940	Approved
0.8288	Intermediate Similarity	NPD846	Approved
0.8281	Intermediate Similarity	NPD1613	Approved
0.8281	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD1242	Phase 1
0.8175	Intermediate Similarity	NPD3018	Phase 2
0.8175	Intermediate Similarity	NPD2861	Phase 2
0.8145	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.813	Intermediate Similarity	NPD422	Phase 1
0.8	Intermediate Similarity	NPD2983	Phase 2
0.8	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD2982	Phase 2
0.7984	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD6099	Approved
0.797	Intermediate Similarity	NPD6100	Approved
0.792	Intermediate Similarity	NPD2981	Phase 2
0.7879	Intermediate Similarity	NPD1607	Approved
0.7845	Intermediate Similarity	NPD968	Approved
0.7838	Intermediate Similarity	NPD2859	Approved
0.7838	Intermediate Similarity	NPD844	Approved
0.7838	Intermediate Similarity	NPD2860	Approved
0.7833	Intermediate Similarity	NPD5283	Phase 1
0.7815	Intermediate Similarity	NPD228	Approved
0.7788	Intermediate Similarity	NPD3020	Approved
0.7778	Intermediate Similarity	NPD2232	Approved
0.7778	Intermediate Similarity	NPD2233	Approved
0.7778	Intermediate Similarity	NPD2230	Approved
0.7761	Intermediate Similarity	NPD1510	Phase 2
0.7748	Intermediate Similarity	NPD2933	Approved
0.7748	Intermediate Similarity	NPD2934	Approved
0.7737	Intermediate Similarity	NPD3892	Phase 2
0.7727	Intermediate Similarity	NPD2238	Phase 2
0.7705	Intermediate Similarity	NPD709	Approved
0.768	Intermediate Similarity	NPD4626	Approved
0.7674	Intermediate Similarity	NPD6584	Phase 3
0.7656	Intermediate Similarity	NPD6696	Suspended
0.7647	Intermediate Similarity	NPD5451	Approved
0.7643	Intermediate Similarity	NPD7447	Phase 1
0.7643	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD1608	Approved
0.7627	Intermediate Similarity	NPD290	Approved
0.7611	Intermediate Similarity	NPD288	Approved
0.7609	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2797	Approved
0.7594	Intermediate Similarity	NPD4060	Phase 1
0.7574	Intermediate Similarity	NPD2935	Discontinued
0.7571	Intermediate Similarity	NPD7213	Phase 3
0.7571	Intermediate Similarity	NPD7212	Phase 2
0.7565	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD2684	Approved
0.7559	Intermediate Similarity	NPD1091	Approved
0.754	Intermediate Similarity	NPD1778	Approved
0.7518	Intermediate Similarity	NPD3540	Phase 1
0.7518	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD3022	Approved
0.7482	Intermediate Similarity	NPD3750	Approved
0.7481	Intermediate Similarity	NPD4097	Suspended
0.748	Intermediate Similarity	NPD3496	Discontinued
0.7466	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1549	Phase 2
0.7464	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7635	Approved
0.7445	Intermediate Similarity	NPD2796	Approved
0.7445	Intermediate Similarity	NPD1551	Phase 2
0.7445	Intermediate Similarity	NPD3539	Phase 1
0.7442	Intermediate Similarity	NPD6583	Phase 3
0.7442	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6582	Phase 2
0.7419	Intermediate Similarity	NPD2557	Approved
0.741	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5124	Phase 1
0.7407	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD2667	Approved
0.7402	Intermediate Similarity	NPD17	Approved
0.7402	Intermediate Similarity	NPD2668	Approved
0.7397	Intermediate Similarity	NPD1934	Approved
0.7385	Intermediate Similarity	NPD3225	Approved
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7364	Intermediate Similarity	NPD2235	Phase 2
0.7364	Intermediate Similarity	NPD2231	Phase 2
0.7357	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2801	Approved
0.7345	Intermediate Similarity	NPD845	Approved
0.7344	Intermediate Similarity	NPD3847	Discontinued
0.7333	Intermediate Similarity	NPD2342	Discontinued
0.7324	Intermediate Similarity	NPD1511	Approved
0.7323	Intermediate Similarity	NPD3444	Approved
0.7323	Intermediate Similarity	NPD3445	Approved
0.7323	Intermediate Similarity	NPD3443	Approved
0.7323	Intermediate Similarity	NPD1651	Approved
0.7323	Intermediate Similarity	NPD5691	Approved
0.7317	Intermediate Similarity	NPD5535	Approved
0.7317	Intermediate Similarity	NPD7843	Approved
0.7313	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD1669	Approved
0.7293	Intermediate Similarity	NPD596	Approved
0.7293	Intermediate Similarity	NPD600	Approved
0.7286	Intermediate Similarity	NPD5177	Phase 3
0.7281	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7157	Approved
0.728	Intermediate Similarity	NPD6387	Discontinued
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4624	Approved
0.7273	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4380	Phase 2
0.7258	Intermediate Similarity	NPD1398	Phase 1
0.7252	Intermediate Similarity	NPD1283	Approved
0.7252	Intermediate Similarity	NPD8651	Approved
0.7248	Intermediate Similarity	NPD3882	Suspended
0.7234	Intermediate Similarity	NPD7466	Approved
0.723	Intermediate Similarity	NPD7819	Suspended
0.7222	Intermediate Similarity	NPD7340	Approved
0.7222	Intermediate Similarity	NPD1512	Approved
0.7206	Intermediate Similarity	NPD1558	Phase 1
0.7203	Intermediate Similarity	NPD4357	Discontinued
0.7188	Intermediate Similarity	NPD5585	Approved
0.7188	Intermediate Similarity	NPD3049	Approved
0.7183	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD1138	Approved
0.7177	Intermediate Similarity	NPD821	Approved
0.7174	Intermediate Similarity	NPD2200	Suspended
0.7165	Intermediate Similarity	NPD5536	Phase 2
0.7162	Intermediate Similarity	NPD37	Approved
0.7154	Intermediate Similarity	NPD1611	Approved
0.7143	Intermediate Similarity	NPD3690	Phase 2
0.7143	Intermediate Similarity	NPD9295	Approved
0.7143	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD3691	Phase 2
0.7133	Intermediate Similarity	NPD7768	Phase 2
0.7133	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7124	Phase 2
0.7132	Intermediate Similarity	NPD6516	Phase 2
0.7132	Intermediate Similarity	NPD839	Approved
0.7132	Intermediate Similarity	NPD840	Approved
0.7132	Intermediate Similarity	NPD5846	Approved
0.7124	Intermediate Similarity	NPD6232	Discontinued
0.7122	Intermediate Similarity	NPD3748	Approved
0.7121	Intermediate Similarity	NPD2922	Phase 1
0.7111	Intermediate Similarity	NPD7095	Approved
0.7105	Intermediate Similarity	NPD6746	Phase 2
0.7101	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1139	Approved
0.7097	Intermediate Similarity	NPD1137	Approved
0.7095	Intermediate Similarity	NPD7411	Suspended
0.7095	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1712	Approved
0.7087	Intermediate Similarity	NPD3596	Phase 2
0.7086	Intermediate Similarity	NPD7075	Discontinued
0.7086	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7041	Phase 2
0.7083	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6799	Approved
0.708	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3620	Phase 2
0.7075	Intermediate Similarity	NPD4005	Discontinued
0.7073	Intermediate Similarity	NPD1792	Phase 2
0.7071	Intermediate Similarity	NPD6032	Approved
0.7069	Intermediate Similarity	NPD1809	Phase 2
0.7068	Intermediate Similarity	NPD1203	Approved
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7054	Intermediate Similarity	NPD1357	Approved
0.705	Intermediate Similarity	NPD4538	Approved
0.705	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6111	Discontinued
0.705	Intermediate Similarity	NPD4536	Approved
0.7045	Intermediate Similarity	NPD5327	Phase 3
0.7042	Intermediate Similarity	NPD1652	Phase 2
0.7042	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3060	Approved
0.7039	Intermediate Similarity	NPD6234	Discontinued
0.7037	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2533	Approved
0.7034	Intermediate Similarity	NPD2532	Approved
0.7034	Intermediate Similarity	NPD2534	Approved
0.7032	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6166	Phase 2
0.7029	Intermediate Similarity	NPD6355	Discontinued
0.7029	Intermediate Similarity	NPD5735	Approved
0.7027	Intermediate Similarity	NPD4675	Approved
0.7027	Intermediate Similarity	NPD4678	Approved

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