NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.11
Volume:	261.435
LogP:	3.128
LogD:	3.405
LogS:	-2.857
# Rotatable Bonds:	4
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.869
Synthetic Accessibility Score:	1.915
Fsp3:	0.2
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:	-4.85
MDCK Permeability:	1.683893242443446e-05
Pgp-inhibitor:	0.169
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	94.74523162841797%
Volume Distribution (VD):	1.651
Pgp-substrate:	4.661269664764404%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.111
CYP2C9-inhibitor:	0.626
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.975
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.755
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	12.652
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.107
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.666
Skin Sensitization:	0.946
Carcinogencity:	0.096
Eye Corrosion:	0.436
Eye Irritation:	0.978
Respiratory Toxicity:	0.189

Download Data

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

Natural Product: NPC808

Natural Product ID:	NPC808
*Common Name:**	Stilbostemin A
IUPAC Name:	5-[2-(2-methoxyphenyl)ethyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	ZXGSOIIHJOKSSX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O3/c1-18-15-5-3-2-4-12(15)7-6-11-8-13(16)10-14(17)9-11/h2-5,8-10,16-17H,6-7H2,1H3
SMILES:	COc1ccccc1CCc1cc(cc(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464899
PubChem CID:	11806868
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
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	Leaves, rhizomes, and roots	southeast Thailand near Chonburi	2000-Feb, 2001-Jan	PMID[12088422]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	slowly dried tubers	Bangkok, Thailand	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	n.a.	Southeast Thailand near Chonburi, Khao Khieo, close to the Chanthathen waterfall and Sri Racha	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	leaf and root	n.a.	n.a.	Database[Title]

☑ 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
EC50	4
IC50	1
MIC	5
Others	6

Activity Type	# Activity
Organism	14
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3821	Organism	Alternaria citri	Alternaria citri	EC50	=	70.0	ug.mL-1	PMID[473871]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC50	>	200.0	ug.mL-1	PMID[473871]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	46.0	ug.mL-1	PMID[473871]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC50	>	200.0	ug.mL-1	PMID[473871]
NPT3821	Organism	Alternaria citri	Alternaria citri	EC90	>	200.0	ug ml-1	PMID[473871]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC90	>	200.0	ug ml-1	PMID[473871]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	>	200.0	ug ml-1	PMID[473871]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC90	>	200.0	ug ml-1	PMID[473871]
NPT3821	Organism	Alternaria citri	Alternaria citri	MIC	>	200.0	ug.mL-1	PMID[473871]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	MIC	>	200.0	ug.mL-1	PMID[473871]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	>	200.0	ug.mL-1	PMID[473871]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	>	200.0	ug.mL-1	PMID[473871]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	>	200.0	ug.mL-1	PMID[473871]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	Inhibition	=	30.0	%	PMID[473871]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[473872]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[473872]

☑ 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 NPC808 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	379
0.1-0.2	1908
0.2-0.3	5443
0.3-0.4	13534
0.4-0.5	3900
0.5-0.6	5175
0.6-0.7	7948
0.7-0.8	3520
0.8-0.85	618
0.85-0.9	210
0.9-0.95	48
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC150624
0.9817	High Similarity	NPC33270
0.9817	High Similarity	NPC69261
0.9727	High Similarity	NPC190514
0.9722	High Similarity	NPC276737
0.9722	High Similarity	NPC22610
0.964	High Similarity	NPC184302
0.9636	High Similarity	NPC244816
0.9636	High Similarity	NPC50521
0.9636	High Similarity	NPC221549
0.9633	High Similarity	NPC53906
0.9545	High Similarity	NPC141090
0.9459	High Similarity	NPC15860
0.9459	High Similarity	NPC127894
0.9459	High Similarity	NPC219070
0.9459	High Similarity	NPC470759
0.9459	High Similarity	NPC474933
0.9455	High Similarity	NPC167934
0.9386	High Similarity	NPC476633
0.9369	High Similarity	NPC85292
0.9369	High Similarity	NPC229147
0.9369	High Similarity	NPC54507
0.9369	High Similarity	NPC114064
0.9369	High Similarity	NPC203113
0.9352	High Similarity	NPC168657
0.9352	High Similarity	NPC94045
0.9304	High Similarity	NPC77789
0.9304	High Similarity	NPC18128
0.9298	High Similarity	NPC102639
0.9286	High Similarity	NPC195466
0.9279	High Similarity	NPC464
0.9279	High Similarity	NPC185541
0.9266	High Similarity	NPC296920
0.9266	High Similarity	NPC90520
0.9224	High Similarity	NPC121115
0.9204	High Similarity	NPC131118
0.9189	High Similarity	NPC180508
0.9189	High Similarity	NPC228287
0.9182	High Similarity	NPC280606
0.9174	High Similarity	NPC2682
0.9068	High Similarity	NPC105031
0.9068	High Similarity	NPC113495
0.9068	High Similarity	NPC105925
0.9052	High Similarity	NPC75713
0.9	High Similarity	NPC303521
0.8992	High Similarity	NPC223953
0.8992	High Similarity	NPC170485
0.8991	High Similarity	NPC75440
0.8991	High Similarity	NPC174981
0.8983	High Similarity	NPC138248
0.8983	High Similarity	NPC228503
0.8981	High Similarity	NPC164576
0.8974	High Similarity	NPC41562
0.8972	High Similarity	NPC102216
0.8966	High Similarity	NPC218753
0.8919	High Similarity	NPC255068
0.8917	High Similarity	NPC169474
0.8917	High Similarity	NPC293054
0.8917	High Similarity	NPC82679
0.8917	High Similarity	NPC246620
0.8917	High Similarity	NPC124452
0.8917	High Similarity	NPC324112
0.8917	High Similarity	NPC159968
0.8917	High Similarity	NPC282000
0.8917	High Similarity	NPC74817
0.8917	High Similarity	NPC236791
0.8917	High Similarity	NPC473221
0.8917	High Similarity	NPC236760
0.8909	High Similarity	NPC33728
0.8909	High Similarity	NPC19808
0.8908	High Similarity	NPC60885
0.8908	High Similarity	NPC278955
0.8908	High Similarity	NPC105718
0.8908	High Similarity	NPC234400
0.8899	High Similarity	NPC35543
0.8898	High Similarity	NPC136319
0.8898	High Similarity	NPC228922
0.8898	High Similarity	NPC233526
0.8898	High Similarity	NPC197757
0.8898	High Similarity	NPC282496
0.8898	High Similarity	NPC95168
0.8898	High Similarity	NPC474160
0.887	High Similarity	NPC63010
0.8843	High Similarity	NPC154866
0.8843	High Similarity	NPC266691
0.8833	High Similarity	NPC214406
0.8833	High Similarity	NPC82299
0.8833	High Similarity	NPC44748
0.8833	High Similarity	NPC78974
0.8833	High Similarity	NPC223136
0.8833	High Similarity	NPC103823
0.8833	High Similarity	NPC28730
0.8833	High Similarity	NPC18924
0.8824	High Similarity	NPC270030
0.8818	High Similarity	NPC245115
0.8814	High Similarity	NPC36016
0.8814	High Similarity	NPC100099
0.8796	High Similarity	NPC241891
0.8793	High Similarity	NPC137294
0.8793	High Similarity	NPC85895
0.8785	High Similarity	NPC100340
0.8785	High Similarity	NPC143659
0.8772	High Similarity	NPC232165
0.877	High Similarity	NPC212015
0.877	High Similarity	NPC190144
0.877	High Similarity	NPC471518
0.877	High Similarity	NPC471519
0.876	High Similarity	NPC252131
0.876	High Similarity	NPC266555
0.876	High Similarity	NPC53781
0.876	High Similarity	NPC46978
0.875	High Similarity	NPC224527
0.875	High Similarity	NPC233410
0.875	High Similarity	NPC165770
0.875	High Similarity	NPC225679
0.875	High Similarity	NPC82483
0.875	High Similarity	NPC203133
0.875	High Similarity	NPC193544
0.875	High Similarity	NPC131397
0.875	High Similarity	NPC476632
0.875	High Similarity	NPC117214
0.875	High Similarity	NPC299584
0.875	High Similarity	NPC208950
0.875	High Similarity	NPC298757
0.875	High Similarity	NPC116907
0.875	High Similarity	NPC221077
0.875	High Similarity	NPC472093
0.875	High Similarity	NPC4493
0.875	High Similarity	NPC57490
0.875	High Similarity	NPC476254
0.875	High Similarity	NPC251855
0.875	High Similarity	NPC17943
0.875	High Similarity	NPC265483
0.875	High Similarity	NPC475169
0.8739	High Similarity	NPC76465
0.8739	High Similarity	NPC84086
0.8739	High Similarity	NPC38761
0.8739	High Similarity	NPC82016
0.8729	High Similarity	NPC193364
0.8729	High Similarity	NPC54972
0.8729	High Similarity	NPC212965
0.8727	High Similarity	NPC233320
0.8718	High Similarity	NPC8283
0.8718	High Similarity	NPC474565
0.8718	High Similarity	NPC258979
0.8718	High Similarity	NPC93398
0.8716	High Similarity	NPC134829
0.8707	High Similarity	NPC74821
0.8699	High Similarity	NPC224157
0.8699	High Similarity	NPC51840
0.8699	High Similarity	NPC299221
0.8699	High Similarity	NPC126836
0.8699	High Similarity	NPC192687
0.8699	High Similarity	NPC254000
0.8699	High Similarity	NPC311680
0.8699	High Similarity	NPC234488
0.8689	High Similarity	NPC28765
0.8689	High Similarity	NPC63179
0.8689	High Similarity	NPC215300
0.8689	High Similarity	NPC38017
0.8678	High Similarity	NPC230479
0.8678	High Similarity	NPC26879
0.8678	High Similarity	NPC50315
0.8678	High Similarity	NPC283049
0.8673	High Similarity	NPC166995
0.8673	High Similarity	NPC43525
0.8667	High Similarity	NPC86502
0.8667	High Similarity	NPC197351
0.8667	High Similarity	NPC140521
0.8667	High Similarity	NPC246648
0.8667	High Similarity	NPC106914
0.8667	High Similarity	NPC134195
0.8667	High Similarity	NPC5796
0.8667	High Similarity	NPC206487
0.8655	High Similarity	NPC120638
0.8655	High Similarity	NPC57199
0.8655	High Similarity	NPC135414
0.8655	High Similarity	NPC474864
0.8655	High Similarity	NPC74137
0.8644	High Similarity	NPC277798
0.8644	High Similarity	NPC100108
0.8644	High Similarity	NPC166759
0.8636	High Similarity	NPC302681
0.8636	High Similarity	NPC109691
0.8636	High Similarity	NPC470700
0.8636	High Similarity	NPC39097
0.8636	High Similarity	NPC39664
0.8636	High Similarity	NPC113457
0.8636	High Similarity	NPC118286
0.8632	High Similarity	NPC295259
0.8632	High Similarity	NPC226629
0.8629	High Similarity	NPC472590
0.8629	High Similarity	NPC473309
0.8629	High Similarity	NPC232275
0.8629	High Similarity	NPC12275
0.8629	High Similarity	NPC15543
0.8629	High Similarity	NPC282508
0.8629	High Similarity	NPC45715
0.8629	High Similarity	NPC474356
0.8629	High Similarity	NPC471517

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 NPC808 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	1049
0.2-0.3	1494
0.3-0.4	2706
0.4-0.5	1741
0.5-0.6	1057
0.6-0.7	608
0.7-0.8	109
0.8-0.85	12
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8729	High Similarity	NPD1610	Phase 2
0.8707	High Similarity	NPD1548	Phase 1
0.8618	High Similarity	NPD4625	Phase 3
0.8583	High Similarity	NPD4749	Approved
0.8537	High Similarity	NPD4908	Phase 1
0.8468	Intermediate Similarity	NPD3027	Phase 3
0.844	Intermediate Similarity	NPD846	Approved
0.844	Intermediate Similarity	NPD940	Approved
0.8407	Intermediate Similarity	NPD4750	Phase 3
0.84	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8374	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8349	Intermediate Similarity	NPD1242	Phase 1
0.8306	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD6671	Approved
0.8268	Intermediate Similarity	NPD1613	Approved
0.8268	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.813	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD422	Phase 1
0.8016	Intermediate Similarity	NPD3018	Phase 2
0.8016	Intermediate Similarity	NPD2861	Phase 2
0.7984	Intermediate Similarity	NPD1240	Approved
0.7982	Intermediate Similarity	NPD844	Approved
0.7982	Intermediate Similarity	NPD968	Approved
0.7949	Intermediate Similarity	NPD228	Approved
0.7863	Intermediate Similarity	NPD1607	Approved
0.784	Intermediate Similarity	NPD2982	Phase 2
0.784	Intermediate Similarity	NPD2983	Phase 2
0.7833	Intermediate Similarity	NPD709	Approved
0.7829	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD6100	Approved
0.782	Intermediate Similarity	NPD6099	Approved
0.7818	Intermediate Similarity	NPD2860	Approved
0.7818	Intermediate Similarity	NPD2859	Approved
0.7815	Intermediate Similarity	NPD5283	Phase 1
0.7768	Intermediate Similarity	NPD3020	Approved
0.776	Intermediate Similarity	NPD2981	Phase 2
0.776	Intermediate Similarity	NPD2233	Approved
0.776	Intermediate Similarity	NPD2230	Approved
0.776	Intermediate Similarity	NPD2232	Approved
0.7759	Intermediate Similarity	NPD290	Approved
0.7748	Intermediate Similarity	NPD288	Approved
0.7744	Intermediate Similarity	NPD1510	Phase 2
0.7727	Intermediate Similarity	NPD2933	Approved
0.7727	Intermediate Similarity	NPD2934	Approved
0.771	Intermediate Similarity	NPD2238	Phase 2
0.7699	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4626	Approved
0.7656	Intermediate Similarity	NPD6584	Phase 3
0.7627	Intermediate Similarity	NPD5451	Approved
0.7619	Intermediate Similarity	NPD1608	Approved
0.7591	Intermediate Similarity	NPD3892	Phase 2
0.7578	Intermediate Similarity	NPD2797	Approved
0.7576	Intermediate Similarity	NPD4060	Phase 1
0.7556	Intermediate Similarity	NPD2935	Discontinued
0.7542	Intermediate Similarity	NPD2684	Approved
0.754	Intermediate Similarity	NPD1091	Approved
0.752	Intermediate Similarity	NPD1778	Approved
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6696	Suspended
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7447	Phase 1
0.7479	Intermediate Similarity	NPD3021	Approved
0.7479	Intermediate Similarity	NPD3022	Approved
0.7477	Intermediate Similarity	NPD845	Approved
0.7464	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4097	Suspended
0.746	Intermediate Similarity	NPD3496	Discontinued
0.7445	Intermediate Similarity	NPD1549	Phase 2
0.7445	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1651	Approved
0.7438	Intermediate Similarity	NPD7635	Approved
0.7429	Intermediate Similarity	NPD7212	Phase 2
0.7429	Intermediate Similarity	NPD7213	Phase 3
0.7426	Intermediate Similarity	NPD1551	Phase 2
0.7422	Intermediate Similarity	NPD1669	Approved
0.7422	Intermediate Similarity	NPD6583	Phase 3
0.7422	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD6582	Phase 2
0.7411	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD600	Approved
0.7405	Intermediate Similarity	NPD596	Approved
0.7398	Intermediate Similarity	NPD2557	Approved
0.7381	Intermediate Similarity	NPD2668	Approved
0.7381	Intermediate Similarity	NPD2667	Approved
0.7381	Intermediate Similarity	NPD17	Approved
0.7377	Intermediate Similarity	NPD1398	Phase 1
0.7372	Intermediate Similarity	NPD3540	Phase 1
0.7364	Intermediate Similarity	NPD1283	Approved
0.7344	Intermediate Similarity	NPD2231	Phase 2
0.7344	Intermediate Similarity	NPD2235	Phase 2
0.7338	Intermediate Similarity	NPD3750	Approved
0.7329	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD3847	Discontinued
0.7311	Intermediate Similarity	NPD2342	Discontinued
0.7305	Intermediate Similarity	NPD1511	Approved
0.7302	Intermediate Similarity	NPD5691	Approved
0.7302	Intermediate Similarity	NPD3444	Approved
0.7302	Intermediate Similarity	NPD3445	Approved
0.7302	Intermediate Similarity	NPD3443	Approved
0.7299	Intermediate Similarity	NPD2796	Approved
0.7299	Intermediate Similarity	NPD3539	Phase 1
0.7295	Intermediate Similarity	NPD5535	Approved
0.7295	Intermediate Similarity	NPD821	Approved
0.7295	Intermediate Similarity	NPD1138	Approved
0.7295	Intermediate Similarity	NPD7843	Approved
0.7293	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD9295	Approved
0.7266	Intermediate Similarity	NPD1611	Approved
0.7266	Intermediate Similarity	NPD5177	Phase 3
0.7266	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1934	Approved
0.7259	Intermediate Similarity	NPD5124	Phase 1
0.7259	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7157	Approved
0.7258	Intermediate Similarity	NPD6387	Discontinued
0.7252	Intermediate Similarity	NPD4624	Approved
0.7239	Intermediate Similarity	NPD839	Approved
0.7239	Intermediate Similarity	NPD840	Approved
0.7231	Intermediate Similarity	NPD3225	Approved
0.7226	Intermediate Similarity	NPD7033	Discontinued
0.7214	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1137	Approved
0.7213	Intermediate Similarity	NPD1139	Approved
0.7211	Intermediate Similarity	NPD2801	Approved
0.7203	Intermediate Similarity	NPD1512	Approved
0.72	Intermediate Similarity	NPD7340	Approved
0.7197	Intermediate Similarity	NPD1712	Approved
0.7193	Intermediate Similarity	NPD1809	Phase 2
0.719	Intermediate Similarity	NPD1792	Phase 2
0.7185	Intermediate Similarity	NPD1558	Phase 1
0.7176	Intermediate Similarity	NPD1203	Approved
0.7165	Intermediate Similarity	NPD5585	Approved
0.7165	Intermediate Similarity	NPD1357	Approved
0.7165	Intermediate Similarity	NPD3049	Approved
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7133	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1281	Approved
0.7123	Intermediate Similarity	NPD4380	Phase 2
0.7122	Intermediate Similarity	NPD5762	Approved
0.7122	Intermediate Similarity	NPD5763	Approved
0.7121	Intermediate Similarity	NPD3691	Phase 2
0.7121	Intermediate Similarity	NPD2798	Approved
0.7121	Intermediate Similarity	NPD3690	Phase 2
0.7114	Intermediate Similarity	NPD3882	Suspended
0.7109	Intermediate Similarity	NPD6516	Phase 2
0.7109	Intermediate Similarity	NPD5846	Approved
0.7103	Intermediate Similarity	NPD9089	Approved
0.7099	Intermediate Similarity	NPD8651	Approved
0.7099	Intermediate Similarity	NPD2922	Phase 1
0.7095	Intermediate Similarity	NPD7819	Suspended
0.7092	Intermediate Similarity	NPD7466	Approved
0.709	Intermediate Similarity	NPD7095	Approved
0.709	Intermediate Similarity	NPD1024	Discontinued
0.7087	Intermediate Similarity	NPD1182	Approved
0.7083	Intermediate Similarity	NPD1445	Approved
0.7083	Intermediate Similarity	NPD1444	Approved
0.708	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD111	Approved
0.7063	Intermediate Similarity	NPD3596	Phase 2
0.7063	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7041	Phase 2
0.7063	Intermediate Similarity	NPD9493	Approved
0.7063	Intermediate Similarity	NPD4357	Discontinued
0.7059	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD943	Approved
0.7059	Intermediate Similarity	NPD3620	Phase 2
0.705	Intermediate Similarity	NPD6032	Approved
0.7047	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6798	Discontinued
0.7029	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4536	Approved
0.7029	Intermediate Similarity	NPD4538	Approved
0.7029	Intermediate Similarity	NPD2200	Suspended
0.7027	Intermediate Similarity	NPD37	Approved
0.7023	Intermediate Similarity	NPD5327	Phase 3
0.7021	Intermediate Similarity	NPD1652	Phase 2
0.7021	Intermediate Similarity	NPD3060	Approved
0.7015	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD9093	Approved
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.7007	Intermediate Similarity	NPD5735	Approved
0.7	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9697	Approved
0.7	Intermediate Similarity	NPD1201	Approved
0.7	Intermediate Similarity	NPD7768	Phase 2
0.7	Intermediate Similarity	NPD1535	Discovery
0.6993	Remote Similarity	NPD7124	Phase 2
0.6993	Remote Similarity	NPD6232	Discontinued
0.6992	Remote Similarity	NPD7905	Discontinued
0.6986	Remote Similarity	NPD1653	Approved
0.6985	Remote Similarity	NPD7477	Discontinued
0.6978	Remote Similarity	NPD3748	Approved
0.6978	Remote Similarity	NPD4308	Phase 3
0.6977	Remote Similarity	NPD2554	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