NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.12
Volume:	252.645
LogP:	3.489
LogD:	3.626
LogS:	-3.065
# Rotatable Bonds:	3
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.847
Synthetic Accessibility Score:	1.879
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:	-4.719
MDCK Permeability:	2.0501278413576074e-05
Pgp-inhibitor:	0.139
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.17
Plasma Protein Binding (PPB):	97.6003189086914%
Volume Distribution (VD):	1.105
Pgp-substrate:	2.0348033905029297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.127
CYP2C9-inhibitor:	0.765
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.944
CYP2D6-substrate:	0.857
CYP3A4-inhibitor:	0.4
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	13.764
Half-life (T1/2):	0.86

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.161
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.525
Skin Sensitization:	0.946
Carcinogencity:	0.066
Eye Corrosion:	0.652
Eye Irritation:	0.986
Respiratory Toxicity:	0.124

Download Data

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

Natural Product: NPC174981

Natural Product ID:	NPC174981
*Common Name:**	Stilbostemin B
IUPAC Name:	2-methyl-5-(2-phenylethyl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	ZGLHZPWZOCCDAY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O2/c1-11-14(16)9-13(10-15(11)17)8-7-12-5-3-2-4-6-12/h2-6,9-10,16-17H,7-8H2,1H3
SMILES:	Cc1c(cc(CCc2ccccc2)cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464662
PubChem CID:	10376477
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]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12104	Stemona cf. pierrei	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10580	Herba glechomae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO12104	Stemona cf. pierrei	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	leaf and root	n.a.	n.a.	Database[Title]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25902	Glechoma grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10316	Glechoma longituba	Species	Lamiaceae	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
EC50	5
IC50	1
MIC	5
Others	6

Activity Type	# Activity
Organism	15
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3821	Organism	Alternaria citri	Alternaria citri	EC50	=	5.0	ug.mL-1	PMID[573650]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC50	=	16.0	ug.mL-1	PMID[573650]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	3.0	ug.mL-1	PMID[573650]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	EC50	=	10.0	ug.mL-1	PMID[573650]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC50	=	15.0	ug.mL-1	PMID[573650]
NPT3821	Organism	Alternaria citri	Alternaria citri	EC90	>	200.0	ug ml-1	PMID[573650]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC90	>	200.0	ug ml-1	PMID[573650]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	371.0	ug ml-1	PMID[573650]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	EC90	>	200.0	ug ml-1	PMID[573650]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC90	>	200.0	ug ml-1	PMID[573650]
NPT3821	Organism	Alternaria citri	Alternaria citri	MIC	=	200.0	ug.mL-1	PMID[573650]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	MIC	>	200.0	ug.mL-1	PMID[573650]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	100.0	ug.mL-1	PMID[573650]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	>	200.0	ug.mL-1	PMID[573650]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	>	200.0	ug.mL-1	PMID[573650]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[573651]
NPT2	Others	Unspecified		Inhibition	=	10.0	%	PMID[573651]

☑ 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 NPC174981 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	355
0.1-0.2	1963
0.2-0.3	5752
0.3-0.4	13660
0.4-0.5	4652
0.5-0.6	7742
0.6-0.7	6500
0.7-0.8	1705
0.8-0.85	222
0.85-0.9	85
0.9-0.95	52
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9901	High Similarity	NPC19808
0.9901	High Similarity	NPC33728
0.9709	High Similarity	NPC224527
0.9615	High Similarity	NPC166995
0.96	High Similarity	NPC244513
0.96	High Similarity	NPC227458
0.96	High Similarity	NPC102216
0.96	High Similarity	NPC218879
0.9524	High Similarity	NPC117846
0.951	High Similarity	NPC204901
0.951	High Similarity	NPC158253
0.951	High Similarity	NPC232523
0.9505	High Similarity	NPC37802
0.9412	High Similarity	NPC12640
0.9412	High Similarity	NPC99836
0.9412	High Similarity	NPC201662
0.9406	High Similarity	NPC241891
0.94	High Similarity	NPC143659
0.94	High Similarity	NPC100340
0.9346	High Similarity	NPC246760
0.9346	High Similarity	NPC84999
0.934	High Similarity	NPC23804
0.934	High Similarity	NPC261343
0.9333	High Similarity	NPC225679
0.9333	High Similarity	NPC4493
0.9333	High Similarity	NPC165770
0.9333	High Similarity	NPC476632
0.9327	High Similarity	NPC186385
0.9327	High Similarity	NPC299568
0.9314	High Similarity	NPC134829
0.9245	High Similarity	NPC43525
0.9223	High Similarity	NPC302681
0.9223	High Similarity	NPC39097
0.9223	High Similarity	NPC39664
0.9223	High Similarity	NPC470700
0.9223	High Similarity	NPC118286
0.9223	High Similarity	NPC109691
0.9216	High Similarity	NPC30506
0.9216	High Similarity	NPC119860
0.9135	High Similarity	NPC54844
0.9126	High Similarity	NPC292452
0.9126	High Similarity	NPC474839
0.9126	High Similarity	NPC246056
0.9118	High Similarity	NPC94351
0.9118	High Similarity	NPC168303
0.9118	High Similarity	NPC71002
0.9118	High Similarity	NPC249828
0.9118	High Similarity	NPC146798
0.9118	High Similarity	NPC85479
0.9118	High Similarity	NPC106396
0.9118	High Similarity	NPC222522
0.9118	High Similarity	NPC53051
0.9118	High Similarity	NPC313030
0.9118	High Similarity	NPC24404
0.9118	High Similarity	NPC242342
0.9118	High Similarity	NPC302219
0.9109	High Similarity	NPC10588
0.9109	High Similarity	NPC166761
0.91	High Similarity	NPC291789
0.9091	High Similarity	NPC190514
0.9091	High Similarity	NPC144343
0.9074	High Similarity	NPC107240
0.9048	High Similarity	NPC63698
0.9048	High Similarity	NPC61885
0.9038	High Similarity	NPC248904
0.902	High Similarity	NPC147310
0.902	High Similarity	NPC192032
0.902	High Similarity	NPC72947
0.902	High Similarity	NPC137415
0.902	High Similarity	NPC166313
0.902	High Similarity	NPC11280
0.902	High Similarity	NPC24407
0.902	High Similarity	NPC294186
0.902	High Similarity	NPC284011
0.9009	High Similarity	NPC184302
0.9	High Similarity	NPC470760
0.8991	High Similarity	NPC808
0.8981	High Similarity	NPC319803
0.8962	High Similarity	NPC202647
0.8922	High Similarity	NPC248573
0.8922	High Similarity	NPC161571
0.8922	High Similarity	NPC275053
0.8919	High Similarity	NPC48781
0.8919	High Similarity	NPC9592
0.8909	High Similarity	NPC150624
0.8909	High Similarity	NPC115808
0.8899	High Similarity	NPC249270
0.8879	High Similarity	NPC224870
0.885	High Similarity	NPC24125
0.8839	High Similarity	NPC191866
0.8829	High Similarity	NPC33270
0.8829	High Similarity	NPC69261
0.8824	High Similarity	NPC80027
0.8818	High Similarity	NPC232165
0.8807	High Similarity	NPC263753
0.8774	High Similarity	NPC61033
0.8774	High Similarity	NPC305603
0.8761	High Similarity	NPC69006
0.875	High Similarity	NPC168393
0.875	High Similarity	NPC206
0.8738	High Similarity	NPC72729
0.8727	High Similarity	NPC22610
0.8727	High Similarity	NPC276737
0.8725	High Similarity	NPC79241
0.8725	High Similarity	NPC6597
0.8704	High Similarity	NPC475018
0.87	High Similarity	NPC295295
0.8696	High Similarity	NPC77789
0.8696	High Similarity	NPC18128
0.8661	High Similarity	NPC221549
0.8661	High Similarity	NPC277588
0.8661	High Similarity	NPC244816
0.8661	High Similarity	NPC50521
0.8649	High Similarity	NPC53906
0.8641	High Similarity	NPC299762
0.8641	High Similarity	NPC33675
0.8627	High Similarity	NPC312132
0.8627	High Similarity	NPC259512
0.8624	High Similarity	NPC151537
0.8624	High Similarity	NPC268032
0.8614	High Similarity	NPC76938
0.8609	High Similarity	NPC39029
0.86	High Similarity	NPC231150
0.8598	High Similarity	NPC66834
0.8596	High Similarity	NPC223451
0.8571	High Similarity	NPC471228
0.8571	High Similarity	NPC235762
0.8571	High Similarity	NPC141090
0.8558	High Similarity	NPC174911
0.8545	High Similarity	NPC473521
0.8534	High Similarity	NPC122175
0.8529	High Similarity	NPC274678
0.8529	High Similarity	NPC32714
0.8522	High Similarity	NPC218753
0.8519	High Similarity	NPC306295
0.8509	High Similarity	NPC121866
0.8509	High Similarity	NPC217174
0.8505	High Similarity	NPC67250
0.8496	Intermediate Similarity	NPC219070
0.8496	Intermediate Similarity	NPC15860
0.8496	Intermediate Similarity	NPC127894
0.8496	Intermediate Similarity	NPC470759
0.8496	Intermediate Similarity	NPC474933
0.8491	Intermediate Similarity	NPC238696
0.8491	Intermediate Similarity	NPC475225
0.8482	Intermediate Similarity	NPC167934
0.8476	Intermediate Similarity	NPC477685
0.8476	Intermediate Similarity	NPC12221
0.8476	Intermediate Similarity	NPC252105
0.8475	Intermediate Similarity	NPC105031
0.8448	Intermediate Similarity	NPC237667
0.8448	Intermediate Similarity	NPC476633
0.844	Intermediate Similarity	NPC58865
0.8431	Intermediate Similarity	NPC128062
0.8426	Intermediate Similarity	NPC176527
0.8411	Intermediate Similarity	NPC47284
0.8411	Intermediate Similarity	NPC471350
0.8411	Intermediate Similarity	NPC117115
0.8407	Intermediate Similarity	NPC85292
0.8407	Intermediate Similarity	NPC114064
0.8407	Intermediate Similarity	NPC54507
0.8407	Intermediate Similarity	NPC229147
0.8407	Intermediate Similarity	NPC203113
0.839	Intermediate Similarity	NPC174729
0.839	Intermediate Similarity	NPC224342
0.839	Intermediate Similarity	NPC139774
0.8381	Intermediate Similarity	NPC48730
0.8381	Intermediate Similarity	NPC294741
0.8381	Intermediate Similarity	NPC129373
0.8381	Intermediate Similarity	NPC248396
0.8378	Intermediate Similarity	NPC46940
0.8365	Intermediate Similarity	NPC152097
0.8365	Intermediate Similarity	NPC156313
0.8364	Intermediate Similarity	NPC168657
0.8364	Intermediate Similarity	NPC94045
0.8362	Intermediate Similarity	NPC102639
0.835	Intermediate Similarity	NPC26244
0.8349	Intermediate Similarity	NPC105727
0.8349	Intermediate Similarity	NPC114392
0.8349	Intermediate Similarity	NPC34864
0.8349	Intermediate Similarity	NPC95344
0.8349	Intermediate Similarity	NPC58427
0.8348	Intermediate Similarity	NPC85895
0.8348	Intermediate Similarity	NPC137294
0.8333	Intermediate Similarity	NPC46978
0.8333	Intermediate Similarity	NPC306884
0.8333	Intermediate Similarity	NPC236760
0.8333	Intermediate Similarity	NPC94139
0.8333	Intermediate Similarity	NPC195466
0.8333	Intermediate Similarity	NPC53740
0.8333	Intermediate Similarity	NPC147284
0.8333	Intermediate Similarity	NPC271440
0.8333	Intermediate Similarity	NPC310456
0.8333	Intermediate Similarity	NPC473221
0.8333	Intermediate Similarity	NPC162314
0.8333	Intermediate Similarity	NPC3358
0.8333	Intermediate Similarity	NPC210497
0.8319	Intermediate Similarity	NPC464
0.8319	Intermediate Similarity	NPC185541
0.8319	Intermediate Similarity	NPC472893

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 NPC174981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	1046
0.2-0.3	1363
0.3-0.4	3036
0.4-0.5	1779
0.5-0.6	1102
0.6-0.7	384
0.7-0.8	51
0.8-0.85	11
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9327	High Similarity	NPD4750	Phase 3
0.902	High Similarity	NPD940	Approved
0.902	High Similarity	NPD846	Approved
0.8922	High Similarity	NPD1242	Phase 1
0.89	High Similarity	NPD844	Approved
0.8627	High Similarity	NPD288	Approved
0.835	Intermediate Similarity	NPD2859	Approved
0.835	Intermediate Similarity	NPD2860	Approved
0.8286	Intermediate Similarity	NPD3020	Approved
0.8252	Intermediate Similarity	NPD2933	Approved
0.8252	Intermediate Similarity	NPD2934	Approved
0.8214	Intermediate Similarity	NPD7635	Approved
0.8208	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8197	Intermediate Similarity	NPD4625	Phase 3
0.8151	Intermediate Similarity	NPD4749	Approved
0.8091	Intermediate Similarity	NPD2342	Discontinued
0.7981	Intermediate Similarity	NPD845	Approved
0.7946	Intermediate Similarity	NPD3021	Approved
0.7946	Intermediate Similarity	NPD3022	Approved
0.7905	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD1610	Phase 2
0.7805	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD1548	Phase 1
0.7698	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD4908	Phase 1
0.768	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1809	Phase 2
0.7632	Intermediate Similarity	NPD1792	Phase 2
0.7619	Intermediate Similarity	NPD3027	Phase 3
0.76	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD9089	Approved
0.7559	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD111	Approved
0.7542	Intermediate Similarity	NPD6671	Approved
0.7541	Intermediate Similarity	NPD1201	Approved
0.7522	Intermediate Similarity	NPD1444	Approved
0.7522	Intermediate Similarity	NPD1445	Approved
0.75	Intermediate Similarity	NPD9093	Approved
0.7481	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD497	Approved
0.7458	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1613	Approved
0.7442	Intermediate Similarity	NPD943	Approved
0.7424	Intermediate Similarity	NPD6100	Approved
0.7424	Intermediate Similarity	NPD6099	Approved
0.7398	Intermediate Similarity	NPD422	Phase 1
0.7373	Intermediate Similarity	NPD495	Approved
0.7373	Intermediate Similarity	NPD498	Approved
0.7373	Intermediate Similarity	NPD496	Approved
0.7364	Intermediate Similarity	NPD9273	Approved
0.7355	Intermediate Similarity	NPD3091	Approved
0.7333	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1607	Approved
0.7302	Intermediate Similarity	NPD1470	Approved
0.728	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD3092	Approved
0.7236	Intermediate Similarity	NPD4059	Approved
0.7236	Intermediate Similarity	NPD3019	Approved
0.7236	Intermediate Similarity	NPD2286	Discontinued
0.7236	Intermediate Similarity	NPD2932	Approved
0.7232	Intermediate Similarity	NPD3028	Approved
0.7227	Intermediate Similarity	NPD2229	Approved
0.7227	Intermediate Similarity	NPD2228	Approved
0.7227	Intermediate Similarity	NPD2234	Approved
0.7213	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2568	Approved
0.7188	Intermediate Similarity	NPD3018	Phase 2
0.7188	Intermediate Similarity	NPD2861	Phase 2
0.7177	Intermediate Similarity	NPD1981	Approved
0.7177	Intermediate Similarity	NPD1980	Approved
0.7177	Intermediate Similarity	NPD1983	Approved
0.7176	Intermediate Similarity	NPD1240	Approved
0.7174	Intermediate Similarity	NPD7390	Discontinued
0.717	Intermediate Similarity	NPD9094	Approved
0.7165	Intermediate Similarity	NPD3094	Phase 2
0.7165	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4093	Discontinued
0.7109	Intermediate Similarity	NPD599	Approved
0.7109	Intermediate Similarity	NPD859	Approved
0.7109	Intermediate Similarity	NPD602	Approved
0.7109	Intermediate Similarity	NPD858	Approved
0.7107	Intermediate Similarity	NPD709	Approved
0.7105	Intermediate Similarity	NPD9500	Approved
0.7097	Intermediate Similarity	NPD4626	Approved
0.7097	Intermediate Similarity	NPD4589	Approved
0.7097	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1751	Approved
0.7087	Intermediate Similarity	NPD6696	Suspended
0.708	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5303	Approved
0.7073	Intermediate Similarity	NPD5304	Approved
0.7069	Intermediate Similarity	NPD968	Approved
0.7059	Intermediate Similarity	NPD228	Approved
0.7045	Intermediate Similarity	NPD1555	Discontinued
0.7037	Intermediate Similarity	NPD5408	Approved
0.7037	Intermediate Similarity	NPD5406	Approved
0.7037	Intermediate Similarity	NPD5405	Approved
0.7037	Intermediate Similarity	NPD5404	Approved
0.7025	Intermediate Similarity	NPD1791	Approved
0.7025	Intermediate Similarity	NPD1793	Approved
0.7023	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD2982	Phase 2
0.7008	Intermediate Similarity	NPD2983	Phase 2
0.6984	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6407	Approved
0.697	Remote Similarity	NPD6405	Approved
0.6963	Remote Similarity	NPD1510	Phase 2
0.696	Remote Similarity	NPD3095	Discontinued
0.696	Remote Similarity	NPD1778	Approved
0.6957	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1398	Phase 1
0.6942	Remote Similarity	NPD5283	Phase 1
0.694	Remote Similarity	NPD4097	Suspended
0.6935	Remote Similarity	NPD7330	Discontinued
0.693	Remote Similarity	NPD1616	Discontinued
0.6929	Remote Similarity	NPD2233	Approved
0.6929	Remote Similarity	NPD2981	Phase 2
0.6929	Remote Similarity	NPD2232	Approved
0.6929	Remote Similarity	NPD1608	Approved
0.6929	Remote Similarity	NPD2230	Approved
0.6917	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2238	Phase 2
0.6912	Remote Similarity	NPD1551	Phase 2
0.6911	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1164	Approved
0.6899	Remote Similarity	NPD1135	Approved
0.6899	Remote Similarity	NPD1134	Approved
0.6899	Remote Similarity	NPD1129	Approved
0.6899	Remote Similarity	NPD1131	Approved
0.6899	Remote Similarity	NPD2797	Approved
0.6899	Remote Similarity	NPD1133	Approved
0.6897	Remote Similarity	NPD9608	Approved
0.6897	Remote Similarity	NPD9610	Approved
0.6891	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD9614	Approved
0.6885	Remote Similarity	NPD9618	Approved
0.688	Remote Similarity	NPD1651	Approved
0.6875	Remote Similarity	NPD4659	Approved
0.6864	Remote Similarity	NPD290	Approved
0.686	Remote Similarity	NPD9379	Approved
0.686	Remote Similarity	NPD9377	Approved
0.685	Remote Similarity	NPD1611	Approved
0.6846	Remote Similarity	NPD6584	Phase 3
0.6835	Remote Similarity	NPD3892	Phase 2
0.6833	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1283	Approved
0.6807	Remote Similarity	NPD9266	Approved
0.6807	Remote Similarity	NPD74	Approved
0.6803	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.68	Remote Similarity	NPD9087	Approved
0.68	Remote Similarity	NPD1759	Phase 1
0.6797	Remote Similarity	NPD2561	Approved
0.6797	Remote Similarity	NPD2562	Approved
0.6794	Remote Similarity	NPD5736	Approved
0.6791	Remote Similarity	NPD4060	Phase 1
0.6788	Remote Similarity	NPD2935	Discontinued
0.6774	Remote Similarity	NPD7340	Approved
0.6774	Remote Similarity	NPD9493	Approved
0.6769	Remote Similarity	NPD3055	Approved
0.6769	Remote Similarity	NPD4103	Phase 2
0.6769	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3053	Approved
0.6765	Remote Similarity	NPD3552	Approved
0.6765	Remote Similarity	NPD3553	Approved
0.6765	Remote Similarity	NPD3555	Approved
0.6765	Remote Similarity	NPD3554	Approved
0.6763	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7447	Phase 1
0.6761	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5451	Approved
0.6746	Remote Similarity	NPD5691	Approved
0.6744	Remote Similarity	NPD1755	Approved
0.6739	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD9264	Approved
0.6723	Remote Similarity	NPD9267	Approved
0.6723	Remote Similarity	NPD9263	Approved
0.672	Remote Similarity	NPD9615	Approved
0.672	Remote Similarity	NPD9616	Approved
0.672	Remote Similarity	NPD9613	Approved
0.672	Remote Similarity	NPD16	Approved
0.672	Remote Similarity	NPD1758	Phase 1
0.672	Remote Similarity	NPD856	Approved
0.6719	Remote Similarity	NPD1091	Approved
0.6718	Remote Similarity	NPD2195	Approved
0.6718	Remote Similarity	NPD2194	Approved
0.6715	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3750	Approved
0.6699	Remote Similarity	NPD9088	Approved
0.6693	Remote Similarity	NPD17	Approved
0.6693	Remote Similarity	NPD9381	Approved
0.6693	Remote Similarity	NPD9384	Approved
0.6692	Remote Similarity	NPD5310	Approved
0.6692	Remote Similarity	NPD5311	Approved
0.6692	Remote Similarity	NPD5155	Approved
0.6692	Remote Similarity	NPD5156	Approved
0.6691	Remote Similarity	NPD970	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